Abstract: The present disclosure provides a compound of formula I, its derivatives, salts, stereoisomers, or regio-isomers thereof, useful as intermediates in preparation of sulfonamide or sulfonyl urea growth regulators or herbicides. The present disclosure further provides process for preparing compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof.
TECHNICAL FIELD
The present disclosure relates to substituted pyrazole compounds as intermediates, its derivatives, salts, stereo-isomers or regio-isomers thereof, which are useful in the preparation of sulfonamide or sulfonyl urea growth regulators or herbicides.
The present disclosure also relates to methods for the preparation of such intermediates.
BACKGROUND
Sulfonamide or sulfonyl urea growth regulators or herbicides are a more recent class of chemical compounds that function by inhibiting the action of a plant enzyme, stopping plant growth, and eventually killing the plant. These are well known as being highly beneficial for controlling undesirable vegetation in agronomically desirable crops.
3The sulfonamide herbicides are reported to be prepared by various ways in the art. EP0204513 B1, which is incorporated in its entirety by reference, describes the method for preparation of such sulfonylureas and sulfonylthioureas herbicide from sulfonyl isocyanate or isocyanate intermediates with an appropriate heterocyclic amines. The patent document further discloses the preparation of the sulfonyl isocyanate intermediates by reacting appropriate sulfonamide with phosgene in presence of n-butyl isocyanate and 1,4-diazabicyclo[2.2.2]octane. Further, sulfonyl thioisocyanates are reported to be prepared by reacting corresponding sulfonamides with carbon disulphide and potassium hydroxide to form dipotassium salt which on treatment with phosgene provides the isothiocyanate intermediates.
The patent US4650892 discloses a process of preparation of sulfonamide herbicides using aromatic sulfonyl chlorides and sulfonamides.
One type of sulfonamide herbicides is Azimsulfuron or N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1 -methyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-sulfonamide , which is well known and has been found to be particularly useful as post emergent herbicides when used against sensitive weeds. Azimsulfuron affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS).
In view of the importance of the emerging sulfonamide or sulfonyl urea growth regulators or herbicides, there remains a need for developing new intermediates and viable processes for their synthesis that can be successfully used in the preparation of these herbicidal compounds.
SUMMARY
The present disclosure relates to substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I
wherein:
R1 is selected from -SH, -SCH2Ph, -SR or -S-SR1'; where R is a CM alkyl and R1' is a group of formula II, where * denotes the point of attachment
R2 is selected from a straight chain or a branched C1.7 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, F, I, NO2, CN, C1-5 alkyl, phenyl, or a C1-C4 alkoxy; and R3 is selected from a straight chain or a branched chain C1.7 alkyl, or a C1-C 14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from Ci, Br, F, I, C1-5 alkyl, phenyl or a C1-C4 alkoxy.
The present disclosure further provides a process for preparing substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I.
These and other features, aspects, and advantages of the present disclosure will become better understood with reference to the following description. This statement is provided to introduce a selection of concepts in a simplified form. This statement is not intended to identify key features or essential features of the subject matter, nor is it intended to be used to limit the scope of the subject matter.
DETAILED DESCRIPTION
Definitions
In the structural formulae given herein and throughout the present disclosure, the following terms have the indicated meaning, unless specifically stated otherwise.
The term "optionally substituted" as used herein means that the group in question is either unsubstituted or substituted with one or more of the substituents specified. When the group in question is substituted with more than one substituent, the substituent may be same or different.
"Halo" or "Halogen", alone or in combination with any other term means halogens such as chloro (CI), bromo (Br), fluoro (F) and iodo (I).
The term "C1.7 alkyl" refers to a monoradical branched or unbranched saturated hydrocarbon chain having 1, 2, 3, 4, 5, 6 or 7 carbon atoms. This term is exemplified by groups such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-hexyl, n-heptyl, and the like which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, I, NO2, CN, C1.5 alkyl, phenyl or a C1-C4 alkoxy.
The term " C6-C14 aryl" refers to an aromatic carbocyclic group of 6 to 14 carbon atoms having a single ring (e.g. phenyl) or multiple rings (e.g. biphenyl), or multiple condensed (fused) rings (e.g. naphthyl or anthranyl). Preferred aryls include phenyl, naphthyl and the like which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, I, C1.5 alkyl, phenyl or a C1-C4 alkoxy.
The compounds described herein may contain one or more chiral centers and/or double bonds and therefore, may exist as stereo-isomers, such as geometric isomers, enantiomers or diastereomers. Accordingly, the chemical structures depicted herein encompass all possible enantiomers and stereo-isomers of the illustrated or identified compounds including the stereo-isomerically pure form (e.g., geometrically pure, enantiomerically pure or diastereomerically pure) and enantiomeric and stereo-isomeric mixtures. Enantiomeric and stereo-isomeric mixtures can be resolved into their component enantiomers or stereo-isomers using separation techniques or chiral synthesis techniques well known to the person skilled in the art. The compounds may also exist in several tautomeric forms including the enol form, the keto form and mixtures thereof. Accordingly, the chemical structures depicted herein encompass all possible tautomeric forms of the illustrated or identified compounds.
In the compounds described herein the variable, R2, can be attached at 1 or 2 position and therefore, may exist as regio-isomers. Regio-isomers are produced as a result of the different outcomes of chemical reactions in which there are different orientations or sites to choose from. Accordingly, the chemical structures depicted herein encompass all possible regio-isomers forms of the illustrated or identified compounds.
The present disclosure will be described more fully hereinafter. Indeed, the invention can be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. As used in the specification, and in the appended claims, the singular forms "a", "an", "the", include plural referents unless the context clearly dictates otherwise.
The present disclosure provides pyrazole intermediates, its derivatives, salts, stereo-isomers or regio-isomers thereof, which are expected to be a useful intermediate in the preparation of herbicidal sulfonamide. The novel intermediates are useful either as an active ingredient for agrochemical, especially as herbicides or act as precursors for the synthesis of active ingredients.
Accordingly, the present disclosure provide substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I
wherein:
R; is selected from -SH, -SCH2Ph, -SR or -S-SR,'; where R is a CM alkyl and R1' is a group of formula II where * denotes the point of attachment
R.2 is selected from a straight chain or a branched C1-7 alkyl;
wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, F, I, NO2, CN, C1.5 alkyl, phenyl, or a C1-C4 alkoxy; and R3 is selected from a straight chain or a branched chain C1.7 alkyl, or a C1-Cu aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one
or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is
optionally substituted with one or more substituent independently selected from CI, Br, F, I,
C1.5 alkyl, phenyl or a C1-C4 alkoxy.
An embodiment of the present disclosure provides substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I wherein:
R.! is selected from -SH, -SCH2Ph, -SR or -S-SRi'; where R is a CM alkyl and Ri' is a group of formula II where * denotes the point of attachment
R.2 is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from Br, NO2, CN, C1.2 alkyl, or a C1-C2 alkoxy; and
R3 is selected from a straight chain or a branched chain Q.4 alkyl, or a phenyl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1.2 alkyl, or a C1-C2 alkoxy.
Another embodiment of the present disclosure provides substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I
wherein:
R1 is -SH;
R2 is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, NO2, CN, C1.2 alkyl, or a C1-C2 alkoxy; and R3 is selected from a straight chain or a branched chain CM alkyl or a phenyl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or a C1-C4 alkoxy.
Yet another embodiment of the present disclosure provides substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I
wherein:
R.2 is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, NO2, CN, Q.2 alkyl, or a C1-C2 alkoxy; and R3 is selected from a straight chain or a branched chain CM alkyl or a C6 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituent phenyl group; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or a C1-C4 alkoxy. Still another embodiment of the present disclosure provides substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I
wherein:
R1 is -S-SR1'; where R1' is a group of formula II where * denotes the point of attachment
R.2 is selected from a C1-3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and the substituent
when present in the phenyl group is one or more substituent independently selected
from CI, Br, N02, CN, Ci.2 alkyl, or a C1-C2 alkoxy; and R3 is selected from a straight chain or a branched chain CM alkyl or a C6 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1.2 alkyl, phenyl or a C1-C4 alkoxy.
Further an embodiment of the present disclosure provides a substituted pyrazole compound, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I, selected from:
1 -methyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -methyl-4-(l -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -ethyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -ethyl-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-methylpropyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5 -thiol; 1 -(2-methylpropyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -benzyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -benzyl-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-methyl-2H-tetrazol-5-yl)-l -phenyl-1 H-pyrazole-5-thiol; 4-( 1 -methyl-2H-tetrazol-5-yl)-l -phenyl-1 H-pyrazole-5-thiol; 1 -(2-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2-chlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-chlorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1-(2,3-dichlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,4-dichlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(2,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-(l -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-(2-methyl-2H-tetrazoI-5-yl)-1 H-pyrazole-5-thiol; l-(2,6-dichlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3,4-dichlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-(l -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2-bromophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-(l -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2-fluorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,4-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,5-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
l-(2-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(2-ethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(4-methoxyphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2-methylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-methylphenyl)-4-(l -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-methylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-methylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-l-methyl-lH-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazole-5-thiol; 1 -ethyl-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -ethyl-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol; 1-benzyl-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -benzyl-4-( i -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-l-phenyl-lH-pyrazole-5-thiol; 4-(l -ethyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol; 1 -(2-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-chlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5 -thiol; 1 -(4-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-chlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,3-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,3-dichlorophenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,4-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-l H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-l H-pyrazole-5-thiol;
1 -(3,4-dichlorophenyl)-4-(2-efhyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3,4-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2-bromophenyI)-4-(l-ethyl-2H-tetrazol-5-yI)-lH-pyrazoIe-5-thiol; 1 -(3-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3-bromophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1-(4-bromophenyl)-4-( 1-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,4-dimethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2-ethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(4-ethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-(l -ethyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-(2-ethyl-2H-tetrazol-5-yl)-l-(4-methylphenyl)-lH-pyrazole-5-thiol;
4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
1 -methyl-4-[2-( 1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -methyl-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-ethyl-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -ethyl-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
1 -benzyl-4-[2-(l -methylethyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol;
1 -benzyl-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol;
4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2-chlorophenyl)-4-[l-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3-chlorophenyl)-4-[2-(l -methyl ethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,4-dichlorophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,5-dichlorophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl] -1 H-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3,4-dichlorophenyl)-4- [2-( 1 -methylethyl)-2H-tetrazol-5 -yl] -1 H-pyrazole-5 -thiol;
1 -(3,4-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3,5-dichlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3,5-dichlorophenyl)-4-[l-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2-bromophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2-bromophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3-bromophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-bromophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol;
1 -(4-bromophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thioI; 1 -(4-fluorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-fluorophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[2-(l –methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol; l-(2,5-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,4-dimethylphenyl)-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-[2-(l -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-ethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 4-[2-(l -methylethyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-l -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-l-(4-methylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(2-methylpropyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-methylpropyl)-l H-pyrazole-5-thiol;
1 -benzyl-4-(2-benzyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -benzyl-4-( 1 -benzyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-phenyl-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(3-chlorophenyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(3 -chlorophenyl)-1 H-pyrazole-5 -thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,3-dichlorophenyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2,3-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,4-dichlorophenyl)-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,5-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,6-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-(l -benzyl-2H-tetrazol-5-yl)-1 -(2,6-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,4-dichlorophenyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(3,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(2-bromophenyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3 -bromophenyl)-1 H-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(3-bromophenyl)-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-bromophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(4-bromophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-(l -benzyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,3-dimethylphenyl)-lH-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,3-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,4-dimethylphenyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,5-dimethylphenyl)-lH-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1-(2,6-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2,6-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,4-dimethylphenyl)-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,5-dimethylphenyl)-lH-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol; 4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -methyl-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -methyl-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-ethyl-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-ylJ-1 -ethyl-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol; l-benzyl-4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -benzyl-4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-ylJ-1 -phenyl-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yll-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3-chlorophenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-chlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,3-dichlorophenyl)-l H-pyrazole-5-thiol; 4-[ 1-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,3-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,6-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,6-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,4-dichlorophenyl)-lH-pyrazole-5-thiol; 4-f 1 -(4-bromobenzyl)-2H-tetrazol-5-ylj-1 -(3,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,5-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3-bromophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3-bromophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-bromophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-bromophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-fluorophenyl)-lH-pyrazole-5-thiol; 4-[2-(l-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-fluorophenyl)-lH-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-fluorophenyl)-lH-pyrazole-5-thiol; 4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-fluorophenyl)-lH-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,3-dimethylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,3-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,6-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,6-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,4-dimethylphenyl)-lH-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,5-dimethylphenyl)-lH-pyrazole-5-thiol;
4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,5-dimethylphenyl)-lH-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-ethylphenyl)-lH-pyrazole-5-thiol;
4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-ethylphenyl)-lH-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazoI-5-yl]-l-(4-ethylphenyl)-lH-pyrazole-5-thiol;
4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-ethylphenyl)-l H-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-methoxyphenyl)-lH-pyrazole-5-thiol;
4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
4-{[5-(l-methyl-5-sulfanyl-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
4- {[5-(l -methyl-5-sulfanyl-l H-pyrazol-4-yl)-1 H-tetrazol-1 -yl]methyl}benzonitrile;
4-{[5-(l-ethyl-5-sulfanyl-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
4- {[5-( 1 -ethyl-5-sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yl]methyl}benzonitrile;
4-({5-[l -(2-methylpropyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-({5-[l-(2-methylpropyl)-5-sulfanyl-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)benzonitrile;
4-{[5-(l-benzyl-5-sulfanyl-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
4- {[5-(l -benzyl-5-sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yl]methyl}benzonitrile;
4-{[5-(l-phenyl-5-sulfanyl-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
4- {[5-(l -phenyl-5-sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yl]methyl} benzonitrile;
4-({5-[l-(2-chlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2-chlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-({5-[l-(3-chlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(3-chlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-({5-[l-(4-chlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-chlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1-(2,3-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,3-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-({5-[l-(2,4-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5-[ 1 -(2,4-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,5-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,5-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-({5-[l-(2,6-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,6-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-({5-[l-(3,4-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(3,4-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl] -1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-({5-[l-(3,5-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(3,5-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1 -(2-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-({5-[l-(3-bromophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(3-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-( {5-[ l -(4-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-({5-[l -(4-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-( {5-[ 1 -(4-fluorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl) benzonitrile;
4-( {5-[ 1 -(4-fluorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-({5-[l-(2-fluorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2-fluorophenyl)-5-sulfanyl-l H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-({5-[l-(2,3-dimethylphenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,3-dimethylphenyl)-5-sulfanyl-l H-pyrazoI-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-( {5-[ 1 -(2,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl) benzonitrile;
4-( {5-[ 1 -(2,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl] -1 H-tetrazol-1 –y1} methyl) benzonitrile;
4-( {5-[ 1 -(2,5-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl) benzonitrile;
4-( {5-[ 1 -(2,5-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,6-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2,6-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1-(3,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl) benzonitrile;
4-( {5-[ 1 -(3,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl] -1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-( {5-[ 1 -(3,5-dimethylphenyl)-5-sulfanyl-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5-[ 1 -(3,5-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-( {5-[ 1 -(2-ethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(2-ethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1 -(4-ethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[ 1 -(4-ethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-l H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[ 1 -(4-methoxyphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5-[ 1 -(4-methoxyphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-( {5-[ 1 -(2-methylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl) benzonitrile;
4-( {5-[ 1 -(2-methylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-( {5-[ 1 -(4-methylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5-[ 1 -(4-methylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-l-methyl-lH-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -methyl-1 H-pyrazole-5-thiol;
1 -ethyl -4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -ethyl-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
l-benzyl-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -benzyl-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2-chlorophenyl)-4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3-chlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-chlorophenyl)-4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(2,5-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(2,6-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-bromophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1-(3-bromophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-fluorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(2-fluorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,4-dimethylphenyl)-4-[ 1 (4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-l-(4-methylphenyl)-lH-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
l-methyl-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-methyl-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-ethyl-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -ethyl-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-l-(2-methylpropyl)-lH-pyrazole-5-thiol;
4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
l-benzyl-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-benzyl-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol;
4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5 -thiol;
1 -(2-chlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[l -(3-methyibenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1-(4-chlorophenyl)-4-[ 1-(3-methylbenzyl)-2H-tetrazol-5-yl] -1 H-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2,4-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3,4-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3,4-dichlorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3,5-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3,5-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol;
l-(2-bromophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2-bromophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-bromophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5 -thiol;
1 -(3-bromophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-bromophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(4-bromophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(4-fluorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-fluorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2-fluorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2-fluorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2,3-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2,3-dimethylphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,4-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,4-dimethylphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,5-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,5-dimethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,6-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,6-dimethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3,4-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3,4-dimethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3,5-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3,5-dimethylphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2-ethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-ethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-ethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(4-ethylphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(4-methoxyphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(4-methoxyphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-l-(2-methylphenyl)-lH-pyrazole-5-thiol;
4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -(3-methylphenyl)-1 H-pyrazole-5-thiol;
4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-l-(3-methylphenyl)-lH-pyrazole-5-thiol;
1 -methyl-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -methyl-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -ethyl-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -ethyl-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yI]-1 H-pyrazole-5-thioI;
1 -(2-methylpropyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-methylpropyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -benzyl-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -benzyl-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol;
4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-l -phenyl- lH-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2-chlorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3-chlorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(4-chlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,4-dichlorophenyi)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,6-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3,4-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3,4-dichlorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3,5-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3,5-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2-bromophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2-bromophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3-bromophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-bromophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-bromophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(4-bromophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-fluorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-fluorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2-fluorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,4-dimethylphenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,4-dimethylpheny])-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; i -(2-ethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-methoxyphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-methylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-methylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-methylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-methylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 5-[5-(benzylsulfanyl)-l-methyl-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-ethyl-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-ethyl-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[l-benzyl-5-(benzylsulfanyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1-(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3-bromophenyl)-l-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl] -1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1-(2-ethylphenyl)-1 H-pyrazol-4-yl]-1-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-methyl-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-phenyl-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3 -chlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1-(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1-(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1-(4-ethylphenyl)-1 H-pyrazol-4-yl]-1-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[l-benzyl-5-(benzylsulfanyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3 -chlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methyl ethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl] -2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l -(2,5-dichlorophenyl)-l H-pyrazol-4-yl]-l -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-l -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3 -bromophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methyl ethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl] -1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1-(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-2-( 1-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1-(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1-(1-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methyl ethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
2-benzyl-5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5-[5-(benzylsulfanyl)-l-ethyl-lH-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-(5-benzylsulfanyl-1 -isobutyl-1 H-pyrazol-4-yl)-2H-tetrazole;
1 -Benzyl-5-(5-benzylsulfanyl-1 -isobutyl-1 H-pyrazol-4-yl)-2H-tetrazole;
2-Benzyl-5-(l -benzyl-5-benzylsulfanyl-1 H-pyrazol-4-yl)-2H-tetrazole;
l-Benzyl-5-(l-benzyl-5-benzylsulfanyl-lH-pyrazol-4-yl)-2H-tetrazole;
2-Benzyl-5-(5-benzylsulfanyl-1 -phenyl-1 H-pyrazol-4-yl)-2H-tetrazole; 1 -Benzyl-5-(5-benzylsulfanyl-1 -phenyl-1 H-pyrazol-4-yl)-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2-chloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-chloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-l-(3-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(3-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(4-chloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-chloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-l-(2,5-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,5-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2,6-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,6-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(3,4-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(3,4-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1-(3,5-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(3,5-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(3-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(3-bromo-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(4-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(4-bromo-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(4-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,3-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,5-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-l -(2,5-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2,6-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,6-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-l-(3,4-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; l-Benzyl-5-[5-benzylsulfanyl-l-(3,4-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-l-(3,5-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(3,5-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(2-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1-(4-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-[5-benzylsulfanyl-1 -(4-methoxy-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-methoxy-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole; 2-Benzyl-5-(5-benzylsulfanyl-1 -o-tolyl-1 H-pyrazol-4-yl)-2H-tetrazole; 1 -Benzyl-5-(5-benzylsulfanyl-1 -o-tolyl-1 H-pyrazol-4-yl)-2H-tetrazole; 2-Benzyl-5-(5-benzylsulfanyl-l-p-tolyl-lH-pyrazol-4-yl)-2H-tetrazole; I -Benzyl-5-(5-benzylsulfanyl-1 -p-tolyl-1 H-pyrazol-4-yl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-methyl-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[l-benzyl-5-(benzylthio)-lH-pyrazol-4-yl]-l-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1-(2-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl] -1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(p-tolyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
4-({5-[5-(benzylsulfanyl)-l-methyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-( {5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl jmethyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-[[5-(l-benzyl-5-(benzylthio)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl]methyl) benzonitrile;
4-[[5-( 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl]methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-l -(2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-l H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-l -(2-bromophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)- l-(3-bromophenyl)-lH-pyrazol-4-yl]-l H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)benzonitrile;
4-( {5-[5-(benzylthio)-l -(4-fluorophenyl)-l H-pyrazol-4-yl]-l H-tetrazol-1 -yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1-(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl (methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-l -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( (5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl jmethyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile; 4.({5.[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-l -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(o-tolyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(p-tolyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(p-tolyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl) benzonitrile;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-ethyl-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-l -(4-methoxybenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-phenyl-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-l -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(o-tolyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-lmethyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)- lmethyl-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-ethyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-isobutyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[ 1-benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-phenyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-phenyl-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-l -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3 -methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-l -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1-(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1-(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(o-tolyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(o-tolyl)-l H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl] -1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzyIthio)-1 -(3 -bromophenyl)-1 H-pyrazol-4-yl] -1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl] -1 -(4-nitrobenzyl)-2H-tetrazole;
1,2-bis( 1 -methyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -ethyl-4-(2-methyl-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -isobutyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -benzyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-methyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,6-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane,
1,2-bis( 1 -(2-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,3-dimethylphenyl)-4-(2-methyI-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disuIfane;
1,2-bis( 1 -(2,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,6-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane,
1,2-bis( 1 -(3,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(4-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(4-methoxyphenyl)-4-(2-methy]-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-methyl-2H-tetrazol-5-yl)-1-(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-methyl-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l -methyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-ethyl-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -isobutyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -benzyl-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2,6-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,6-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-C3,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-(2-ethylphenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazoI-5-yI)disulfane;
l,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-(4-methoxyphenyl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-(o-tolyl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-(p-tolyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-ethyl-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -isobutyl-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -benzyl-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-chlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1-(4-chlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,6-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-bromophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3-bromophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-bromophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-fluorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-fluorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2,6-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(3,4-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3,5-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-ethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-ethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-l-(o-tolyl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-l-(p-tolyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-isobutyl-lH-pyrazol-5-yl)disulfane; 1,2-bis( 1 -benzyl-4-(2-benzyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3-chlorophenyl)-lH-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,3-dichlorophenyl)-lH-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l -(2,5-dichlorophenyl)-l H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3-bromophenyl)-lH-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-bromophenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,5-dimethylphenyl)-lH-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazol-5-yl)disulfane; l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(o-tolyl)-lH-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazoI-5-yl)-l -ethyl-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -isobutyl-1 H-pyrazol-5-yl)disulfane; 1,2-bis( 1-benzyl-4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane; 1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(3-chlorophenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1-(2,3-dichlorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l -(2,4-dichlorophenyl)-l H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1-(2,5-dichlorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(3,4-dichlorophenyl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(3-bromophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(4-bromophenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1-(2,3-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(2,6-dimethylphenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(3,4-dimethyIphenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(3,5-dimethylphenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-methyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5,-disulfanediylbis(l-ethyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-
diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-isobutyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-
diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-benzyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-
diyl))bis(methylene))dibenzonitrile;
4,4*-((5,5'-(5,5'-disulfanediylbis(l-phenyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-
diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2-chlorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-
5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3-chlorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-
5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5,-(5,5,-disulfanediylbis(l-(4-chlorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-
5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2,3-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5,-(5,5'-disulfanediylbis(l-(2,4-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2,5-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5'-(5,5'-disulfanediylbis(l-(2,6-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3,4-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5'-(5,5'-disulfanediylbis(l-(3,5-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2-bromophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-
5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3-bromophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-
5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(4-bromophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5,-disulfanediylbis(l-(4-fluorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5'-(5,5'-disulfanediylbis(l-(2-fluorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2,3-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2,4-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2,5-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5,-(5,5'-disulfanediylbis(l -(2,6-dimethylphenyl)-1 H-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5,-(5,5*-disulfanediylbis(l-(3,4-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5,-disulfanediylbis(l-(3,5-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2-ethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(4-ethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(4-methoxyphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4*-((5,5,-(5,5'-disulfanediylbis(l-(p-tolyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(o-tolyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-l-methyl-lH-pyrazol-5-yl) disulfane;
1,2-bis( 1 -ethyl-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -isobutyl-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-benzyl-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1-phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(3-chlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(4-chlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2,3-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2,4-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1-(2,5-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2,6-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(3,4-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(3,5-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(l-(2-bromophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(3 -bromophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(l -(4-bromophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(4-fluorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2-fluorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-l)disulfane;
1,2-bis( 1-(2,5-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,6-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(3,4-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(3,5-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-ethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-ethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-methoxyphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -methyl-4-(2-(3 -methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-ethyl-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-isobutyl-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-benzyl-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3-chlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(4-chlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,3-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,4-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2,6-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(3,5-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-bromophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-bromophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-fluorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-fluorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,3-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yI)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,4-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,6-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(3,4-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-ethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-ethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-methoxyphenyl)-4-(2-(3 -methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1-(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1-(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -methyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-ethyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-isobutyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -benzyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-nitrobenzyl)-2H-tetrazoI-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-chlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3-chlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-chlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,6-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3,4-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-bromophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3 -bromophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(4-bromophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-fluorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-fluorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,4-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2,5-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,6-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3,5-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-ethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-ethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-methoxyphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane; or
1,2-bis(4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane.
The present disclosure further provides a process for preparing a substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I, comprising:
treating a compound of formula III
Formula HI with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent to obtain the compound of formula I, and its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein:
Ri is selected from -SH, -SCH2Ph, -SR or -S-SRi'; where R is a CM alkyl and R|' is a group of formula II where * denotes the point of attachment
Formula II R2 is selected from a straight chain or a branched C1.7 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, F, I, NO2, CN, CM alkyl, phenyl, or a C1-C4 alkoxy; R3 is selected from a straight chain or a branched chain C1.7 alkyl, or a C6-C14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, CM alkyl, phenyl or a C1-C4 alkoxy; and R4 is selected from CI, Br or I.
An embodiment of the present disclosure provides a process for preparing substituted pyrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof of formula I, comprising:
treating a compound of formula III
with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent to obtain the compound of formula I, and its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein:
Ri is selected from -SH, -SCH2Ph, -SR or -S-SR,'; where R is a CM alkyl and Ri' is a group of formula II where * denotes the point of attachment
R2is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; and R3 is selected from a straight chain or a branched chain Q.4 alkyl, or a phenyl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, Q.2 alkyl, phenyl or a C1-C4 alkoxy; and
R4 is selected from CI, Br or I.
The thiol used in the present disclosure is suitably selected from a CM alkyl thiol or benzyl thiol; and the alkali metal hydrosulfide is selected from sodium hydrosulfide or potassium hydrosulfide.
In accordance with the present disclosure, the polar solvent is selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water.
Another embodiment of the present disclosure provides a process for preparing substituted pyrazole compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating a compound of formula HI with a benzyl thiol in the presence of sodium hydride and N,N-dimethylformamide to obtain a compound of formula I, and its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein: Ri is -SCH2Ph; R2 is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, N02, CN, C1.2 alkyl, or a CrC2 alkoxy; R3 is selected from a straight chain or a branched chain CM alkyl or a C6 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from phenyl;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or a C1-C4 alkoxy; and R4 is selected from CI, Br or I, wherein the formula of the compounds have the same meaning as described in the foregoing paragraphs.
Yet another embodiment of the present disclosure provides a process for preparing a substituted pyrazole compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating a compound of formula III with sodium hydrosulfide, in the presence of N,N-dimethylformamide to obtain a compound of formula I, and its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein:
R1 is -SH, or -S-SRi'; where R is a CM alkyl and Ri' is a group of formula II where * denotes the point of attachment
Formula II R.2 is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, N02, CN, C1-2 alkyl, or a C,-C2 alkoxy; R3 is selected from a straight chain or a branched chain CM alkyl or a C6 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, Q.2 alkyl, phenyl or a C1-C4 alkoxy; and R4 is selected from CI, Br or I.
Still another embodiment of the present disclosure provides a process for preparing a substituted pyrazole compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating malononitrile with a compound of formula VIII wherein R5 is independently selected from a straight or a branched CM alkyl, in presence of acetic anhydride to obtain a compound of formula VII;
wherein R5 is selected from a straight or a branched CM alkyl;
treating the compound of formula VII with an optionally substituted N-alkyl hydrazine sulfate, or an optionally substituted N-aryl hydrazine sulfate, and an organic base in the presence of an alcohol to obtain a compound of formula VI;
wherein R3 is selected from a straight chain or a branched chain C1-4 alkyl or a C6 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, Q-2 alkyl, phenyl or a C1-C4 alkoxy;
treating the compound of formula VI with sodium nitrite, cuprous halide and a mineral acid to obtain a compound of formula V;
wherein R3 is as defined above; and R4 is selected from CI, Br or I;
treating the compound of formula V with an optionally substituted sodium azide in the presence of a ammonium halide and a polar solvent to obtain a compound of formula IV;
where in R3 and R4 are as defined above;
alkylating the compound of formula IV with a dialkyl sulfate and a inorganic base in the presence of a polar solvent to obtain a compound of formula III or its regio-isomers,
wherein R2 is selected from a CM alkyl; and said alkyl is optionally substituted with a phenyl group; the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, N02, CN, C1-2 alkyl, or a Ci-C2 alkoxy; and
treating the compound of formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent to obtain a compound of formula I its derivatives, salts, stereo-isomers, or regio-isomers thereof.
The organic or the inorganic base used in the process of the present disclosure is suitably any base selected from alkali metal hydroxide, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; alkali metal carbonate, such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline.
In accordance with the present disclosure, the alcohol used in the process is selected from methanol, ethanol or propanol; and the mineral acid is selected from hydrochloric acid, hydrobromic acid, sulfuric acid or nitric acid.
The polar solvent used in the reactions of the present disclosure is selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water.
In accordance with the present disclosure, the cuprous halide is selected from cuprous chloride, cuprous bromide or cuprous iodide.
In an aspect of the present disclosure, the ammonium halide is selected from ammonium chloride, ammonium bromide or ammonium iodide. Tri-n-butyl tin halide is suitably selected from tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide and can also be used in place of ammonium halide.
The thiol used in the present disclosure is suitably selected from a C\ alkyl thiol or benzyl thiol; and the alkali metal hydrosulfide is selected from sodium hydrosulfide or potassium hydrosulfide.
An embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivative, salt, stereo-isomer, regio-isomer thereof, comprising:
treating malononitrile with a triethyl orthoformate in the presence of acetic anhydride to obtain 2-(ethoxymethylene)malononitrile;
treating the 2-(ethoxymethylene)malononitrile with N-methyl hydrazine sulfate and triethyl amine in the presence of methanol to obtain 5-amino-l-methyl-l//-pyrazole-4-carbonitrile;
chlorinating the 5-amino-l-methyl-l//-pyrazole-4-carbonitrile with sodium nitrite, cuprous chloride and hydrochloric acid to obtain 5-chloro-l-methyl-l//-pyrazole-4-carbonitrile;
treating the 5-chloro-l-methyl-l//-pyrazole-4-carbonitrile with sodium azide in the presence of either ammonium chloride and N,N-dimethylformamide, or tributyl tin chloride and toulene to obtain 5-(5-chloro-l -methyl- l//-pyrazol-4-yl)-2//-tetrazole;
methylating the 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2//-tetrazole) with a dimethyl sulfate and a potassium carbonate in the presence of acetone to obtain 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-1 -methyl-2//-tetrazole) or 5-(5-chloro-1 -methyl- l//-pyrazol-4-yl)-2-methyl-2//-tetrazole) or mixtures thereof; and
treating the 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-l-methyl-2//-tetrazole) or 5-(5-chloro-1-methyl-l//-pyrazoI-4-yl)-2-methyl-2i/-tetrazole), or mixtures thereof with benzyl thiol in the presence of N,N-dimethylformamide and sodium hydride to obtain 5-(5-(benzylsulfanyl)-1 -methyl-l#-pyrazol-4-yl)-1 -methyl-2//-tetrazole, or 5-(5-(benzylsulfanyl)-1 -methyl- l//-pyrazol-4-yl)-2-methyl-2Z/-tetrazole, or mixture thereof, of formula I.
Another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivative, salt, stereo-isomer, regio-isomer thereof, comprising:
treating malononitrile with a triethyl orthoformate in the presence of acetic anhydride to obtain 2-(ethoxymethylene)malononitrile;
treating the 2-(ethoxymethylene)malononitrile with N-methyl hydrazine sulfate and triethyl amine in the presence of methanol to obtain 5-amino-l-methyl-l//-pyrazole-4-carbonitrile;
chlorinating the 5-amino-l-methyl-l//-pyrazole-4-carbonitrile with sodium nitrite, cuprous chloride and hydrochloric acid to obtain 5-chloro-l-methyl-l//-pyrazole-4-carbonitrile;
treating the 5-chloro-l -methyl-l//-pyrazole-4-carbonitrile with sodium azide in the presence of either ammonium chloride and N,N-dimethylformamide, or tributyl tin chloride and toulene to obtain 5-(5-chloro-l-methyl-li/-pyrazol-4-yl)-2//-tetrazole;
methylating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole) with a dimethyl sulfate and potassium carbonate in the presence of acetone to obtain 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-l-methyl-2//-tetrazole), or 5-(5-chloro-1 -methyl-\H-pyrazol-4-yl)-2-methyl-2//-tetrazole), or mixtures thereof; and
treating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-l-methyl-2//-tetrazole), or 5-(5-chloro-1-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole), or mixtures thereof, with sodium hydrosulfide in the presence of N,N-dimethylformamide to obtain (l-methyl-4-(l-methyl-2#-tetrazol-5-yl)-l//-pyrazole-5-thiol), or (1 -methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or (1,2-bis-( 1 -methyl-4-(2-methyl-2//-tetrazol-5-yl)-1 //-pyrazol-5-yl)disulfane), or mixtures thereof, of formula I.
Still another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating a compound of formula XIV with phosphoryl chloride in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, dichloromethane, 1,2-dichloroethane, or tetrahydrofuran, to obtain a compound of formula XIII;
wherein:
R.3 is selected from a straight or a branched chain C1.7 alkyl; or a C6-C14 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1-5 alkyl, phenyl, or a C1-C4 alkoxy; treating the compound of formula XIII with hydroxylamine hydrochloride in the presence of an alcohol selected from methanol, ethanol or propanol, to obtain a compound of formula XII; and
treating the compound of formula XII with sodium azide in the presence of ammonium chloride and a polar solvent selected from N,N- dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone,tetrahydrofuran or water, to obtain the compound of formula XL
reacting a compound of formula XI with an alkylating agent such as alkyl halide, or dialkyl sulfate in the presence of a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic bases such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline, to obtain a compound of formula X;
wherein:
R3 is selected from a straight or a branched chain C1-7 alkyl; or a C6-Q4 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, 1, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C|.5 alkyl, phenyl, or a C1-C4 alkoxy; and halogenating the compound of formula X with a halogenating agent selected from N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, to obtain the compound of formula III or its regio-isomers.
treating the compound of formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water to obtain a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof.
Yet another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating a compound of formula XIV with iodine and a strong oxidizing agent such as hydrogen peroxide in aqueous medium to obtain a compound of formula XVI;
R.3 is selected from a straight or a branched chain C1.7 alkyl; or a C6-C14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl, or a C1-C4 alkoxy; treating the compound of formula XVI with either potassium ferrocyanide and palladium (II) acetate in the presence of a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, n-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water; or
sodium cyanide or copper cyanide in the presence of cuprous halides such as cuprous iodide and N,N-dimethyl ethylene diamine with a non polar solvent such toluene, xylene, or benzene, to obtain a compound of formula XV; and
Formula XV
treating the compound of formula XV with sodium azide and either tri-n-butyl tin chloride in the presence of a non polar solvent selected from toluene, xylene or benzene; or ammonium chloride and N,N-dimethylformamide, to obtain the compound of formula XI.
reacting a compound of formula XI with an alkylating agent such as alkyl halide, or dialkyl sulfate in the presence of a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic bases such as
triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline, to obtain a compound of formula X;
wherein:
R3 is selected from a straight or a branched chain C1.7 alkyl; or a C6-Q4 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl, or a C1-C4 alkoxy; and
halogenating the compound of formula X with a halogenating agent selected from N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of polar solvent selected from N,N-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, to obtain the compound of formula III or its regio-isomers.
treating the compound of formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water to obtain a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof.
An embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating a 1 -methyl- l//-pyrazole with phosphoryl chloride in the presence of N,N-dimethylformamide, to obtain a 1-methyl-l//-pyrazole-4-carbaldehyde;
treating the 1-methyl-l//-pyrazole-4-carbaldehyde with hydroxylamine hydrochloride in the presence of ethanol, to obtain a 1- methyl -l//-pyrazole-4-carbaldehyde oxime;
treating the 1-methyl-l//-pyrazole-4-carbaldehyde oxime with sodium azide in the presence of ammonium chloride and N,N-dimethylformamide, to form the 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole;
reacting 5-(l -methyl- li/-pyrazole-4-yl)-2//-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl- l//-pyrazol-4-yl)-2//-tetrazole; and
chlorinating the 2-methyl-5-(l -methyl-li/-pyrazole-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole or 5-(5-chloro-1 -methyl- l//-pyrazole-4-yl)-1 -methyl-2//-tetrazole) or mixtures thereof;
treating the 5-(5-chloro-l-methyl-li/-pyrazole-4-yl)-2-methyl-2//-tetrazole or 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-l-methyl-2//-tetrazole) or mixtures thereof with benzyl thiol in the presence of a N,N-dimethylformamide and sodium hydride to obtain compound 5-(5-(benzylsulfanyl)-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole or 5-(5-(benzylsulfanyl)-1 -methyl- l#-pyrazol-4-yl)-1 -methyl-2//-tetrazole, or mixture thereof of formula I, wherein R1 is -SCH2PI1;
Another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating 1-methyl-l//-pyrazole with phosphoryl chloride in the presence of N,N-dimethylformamide, to obtain 1-methyl-l//-pyrazole-4-carbaldehyde;
treating the 1-methyl-li/-pyrazole-4-carbaldehyde with hydroxylamine hydrochloride in the presence of ethanol, to obtain 1-methyl-l//-pyrazole-4-carbaldehyde oxime;
treating the 1 -methyl- l//-pyrazole-4-carbaldehyde oxime with sodium azide in the presence of ammonium chloride and N,N-dimethylformamide, to form the 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole;
reacting the 5-(l-methyl-l//-pyrazole-4-yl)-2//-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l-methyl-lZ/-pyrazol-4-yl)-2//-tetrazole;
chlorinating the 2-methyl-5-(l-methyl-l//-pyrazole-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole;
treating the 5-(5-chloro-1 -methyl-1 //-pyrazole-4-yl)-2-methyl-2//-tetrazole with sodium hydrosulfide in the presence of a N,N-dimethylformamide to obtain the compounds (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or (1-methyl-4-(l-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or its disulfide (1,2-bis-(l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazol-5-yl) disulfane), or mixture thereof, of the formula
Yet another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating 1-methyl-l//-pyrazole with iodine and hydrogen peroxide in aqueous medium to obtain 4-iodo-l-methyl-l//-pyrazole;
treating the 4-iodo-l-methyl-l//-pyrazole with potassium ferrocyanide and palladium (II) acetate in the presence of sodium carbonate, and N,N-dimethylacetamide, to obtain 1-methyl-l//-pyrazole-4-carbonitrile;
treating the 1 -methyl-1 H-pyrazole-4-carbonitrile with sodium azide and either with tri-n-butyl tin chloride in the presence of toluene, or ammonium chloride in the presence of N,N-dimethylformamide to obtain 5-(l -methyl- li/-pyrazol-4-yl)-2//-tetrazole;
reacting the 5-(l-methyl-l//-pyrazol-4-yl)-2Z/-tetrazole with methyl iodide or dimethyl sulphate, in the presence of potassium hydroxide or potassium carbonate to obtain 2-methyl-5-(l -methyl-l//-pyrazol-4-yl)-2//-tetrazole;
chlorinating the 2-methyl-5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2#-tetrazole;
treating the 5-(5-chloro-l -methyl- l//-pyrazole-4-yl)-2-methyl-2i/-tetrazole with benzyl thiol in the presence of N,N-dimethylformamide and sodium hydride to obtain compound 5-(5-(benzylthio)-1 -methyl- l//-pyrazol-4-yl)-2-methyl-2i/-tetrazole or 5-(5-(benzylthio)-l-methyl-l//-pyrazol-4-yl)-l-methyl-2//-tetrazole or mixture thereof, of formula I, wherein Rj is -SCH2PI1;
Still another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, comprising:
treating 1-methyl-l//-pyrazole with iodine and hydrogen peroxide in aqueous medium to obtain 4-iodo-l -methyl-li7-pyrazole;
treating the 4-iodo-l -methyl-l//-pyrazole with potassium ferrocyanide and palladium (II) acetate in the presence of sodium carbonate, and N,N-dimethylacetamide, to obtain 1 -methyl- l//-pyrazole-4-carbonitrile;
treating the 1-methyl-lH-pyrazole-4-carbonitrile with sodium azide and either with tri-n-butyl tin chloride in the presence of toluene, or ammonium chloride in the presence of N,N-dimethylformamide to obtain 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole;
reacting the 5-(l -methyl- l//-pyrazol-4-yl)-2//-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl- l//-pyrazol-4-yl)-2//-tetrazole;
chlorinating the 2-methyl-5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l -methyl- \H-pyrazol-4-yl)-2-methyl-2//-tetrazole;
treating the 5-(5-chIoro-1 -methyl- l//-pyrazole-4-yl)-2-methyl-2//-tetrazole with sodium hydrosulfide in the presence of a N,N-dimethylformamide to obtain the compounds (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or (1-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or its disulfide (1,2-bis-(1-methyl-4-(2-methyl-21/-tetrazol-5-yl)-l//-pyrazol-5-yl) disulfane), or mixture thereof, of the formula
The substituted pyrazole compounds of formula I its derivatives, salts, stereo-isomers, or regio-isomers thereof, may be prepared as outlined in the Schemes. Scheme 1: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers, or regio-isomers thereof.
The compound of formula I as above, is prepared by the reaction of a compound of formula III with a thiol in the presence of a suitable polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water.
In the compound of formula I above, R1 is selected from -SCH2PI1; R2 is selected from a straight chain or a branched C1-7 alkyl; wherein said alkyl is optionally substituted with phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, F, I, C1-5 alkyl, phenyl, or a C1-C4 alkoxy; R3 is selected from a straight chain or a branched chain C1.7 alkyl, or a C6-Q4 aryl group; and wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl or a C1-C4 alkoxy; R4 is selected from CI, Br or I.
Scheme 2: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers, or regio-isomers thereof.
Compounds of formula I, as above, is prepared by the reaction of a compound of formula III with an alkali metal hydrosulfide and sodium hydride in the presence of a suitable polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water.
In the compounds of formula I above, Ri is selected from -SH, -SCFbPh, -SR or -S-SRi'; where R is a CM alkyl and Rj' is a group of formula II where * denotes the point of attachment
Formula II R.2 is selected from a straight chain or a branched C1-7 alkyl; wherein said alkyl is optionally substituted with phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl,phenyl, or a C1-C4 alkoxy;
R3 is selected from a straight chain or a branched chain C1.7 alkyl, or a C6-C14 aryl group; and
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl or a C1-C4 alkoxy; R4 is selected from CI, Br or I.
Scheme 3: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers, or regio-isomers thereof.
Malononitrile (IX) is reacted with a compound of formula VIII, wherein all symbols are as defined earlier, to yield a 2-(alkylrnethylene)malononitrile of formula VII. The reaction is carried out using acetic anhydride at a temperature in the range of 95-110 °C.
The compound of formula VII, is cyclized to obtain a compound of formula VI by a cyclization reaction. The reaction is carried out with a suitable hydrazine such as an N-alkyl hydrazine sulfate, N-alkyl hydrazine, or N-aryl hydrazine, in the presence of a base selected from alkali metal hydroxide is selected from sodium hydroxide, potassium hydroxide or lithium hydroxide; alkali metal carbonate is selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and organic base is selected from triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline and an alcohol selected from methanol, ethanol or propanol for about 1-2 hours at reflux temperature.
The compound of formula VI is converted to a compound of formula V by treatment with a halogenating agent such as cuprous halide selected from cuprous chloride, cuprous bromide or cuprous iodide, and sodium nitrite in the presence of a mineral acid selected from hydrochloric acid, hydrobromic acid, sulfuric acid or nitric acid at room temperature.
The compound of IV is prepared from reaction of the compound of formula V with an ammonium halide selected from ammonium chloride, ammonium bromide or ammonium iodide and an optionally substituted sodium azide. The reaction is carried out in a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water. The reaction temperature range from 110 °C to 120 °C. Alkylating a compound of formula IV with a dialkyl sulfate and a base selected from alkali metal hydroxide such as sodium hydroxide, potassium hydroxide or lithium hydroxide; alkali metal carbonate such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water yields a compound of formula III, its regio-isomers thereof.
The compound of formula III or its regio-isomer is reacted with a thiol in the presence of a polar solvent selected from N,N-dimethylforrnamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water (Scheme 1) or by the reaction of the compound of formula III with an alkali metal hydrosulfide and sodium hydride in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water (Scheme 2) to obtain the compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof
wherein R1 is selected from -SH, -SCH2Ph, -SR or -S-SR1'; where R is a CM alkyl and R(' is a group of formula II where * denotes the point of attachment R2 is selected from a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, F, I, NO2, CN, C1.5 alkyl, phenyl, or a CM alkoxy; R3 is selected from a straight chain or a branched chain C1.7 alkyl, or a C6-14 aryl group; and wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1-5 alkyl, phenyl or a C1-C4 alkoxy; R4 is selected from CI, Br or I.
Scheme 4: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers. or reeio-isomers thereof.
The compound of formula XIV is reacted with phosphoryl chloride in the presence of N,N-dimethylformamide to yield the compound of formula XIII, treating of compound of formula XIII with hydroxyl amine hydrochloride in presence of ethanol or ethyl acetate to obtain compound of formula XII.
The compound of formula XII is subjected to a cyclization reaction in the presence of sodium azide and N,N-dimethylformamide by heating at 50-120°C, preferably 90-100°C to obtain a compound of formula XI.
Compound of formula XI is further converted to a compound of formula X by treating with a methylating reagents such as dimethyl sulfate, methyl iodide or methyl bromide and potassium carbonate, in the presence of acetone.
Halogenating the compound of formula X with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in presence of acetonitrile, yields the compound of formula III or its region-isomer.
The compound of formula III or its regio-isomer is reacted with a thiol in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water (Scheme 1) or by the reaction of the compound of formula III with an alkali metal hydrosulfide and sodium hydride in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water to obtain the compound of formula I its derivatives, salts, stereo-isomers, or regio-isomers thereof.
wherein R\ is selected from -SH, -SCH2Ph, -SR or -S-SRi'; where R is a CI-4 alkyl
and Ri' is a group of formula II where * denotes the point of attachment
R2 is selected from a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, F, 1, NO2, CN, C1.5 alkyl, phenyl, or a C1-C4 alkoxy; R3 is selected from a straight chain or a branched
chain C1.7 alkyl, or a C6-Q4 aryl group; and wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl or a C1-C4 alkoxy; R4 is selected from CI, Br or I.
Scheme 5: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers, or regio-isomers thereof.
A compound of formula XIV is reacted with iodine in the presence of oxidizing agent in aqueous media to obtain a compound of formula XVI,
Treating the compound of formula XVI with sodium ferrocyanide in presence of palladium(II) acetate, sodium carbonate and N,N-dimethylacetamide to obtain a compound of formula XV.
The compound of formula XV is converted to a compound of formula XI by treatment with sodium azide with either tri-n-butyl tin chloride in the presence of toluene or ammonium chloride in presence of dimethylformamide by heating at 100-110°C about 10-12 hours. Compound of formula XI is further converted to a compound of formula X by treating with a methylating reagents such as dimethyl sulfate, methyl iodide or methyl bromide and potassium carbonate, in the presence of acetone.
Halogenating the compound of formula X with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in presence of acetonitrile, yields the compound of formula III or its regio-isomer.
The compound of formula III or its regio-isomer is reacted with a thiol in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water (Scheme 1) or by the reaction of the compound of formula III with an alkali metal hydrosulfide and sodium hydride in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water to obtain the compound of formula I its derivatives, salts, stereo-isomers, or regio-isomers thereof.
wherein R, is selected from -SH, -SCH2Ph, -SR or -S-SR,'; where R is a CI-4 alkyl and Rj' is a group of formula II where * denotes the point of attachment
R2 is selected from a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, F, I, NO2, CN, C1.5 alkyl, phenyl, or a C1-C4 alkoxy; R3 is selected from a straight chain or a branched chain C1-7 alkyl, or a C6-C14 aryl group; and wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1-5 alkyl, phenyl or a C1-C4 alkoxy; R4 is selected from CI, Br or I. In the compound of formula VI, X is selected from CI, Br, or I.
Abbreviations
The following abbreviations are employed in the description:: DMF: N,N-dimethylformamide, DCE:
Dichloroethane, THF: Tetrahydrofuran,
AICI3: Aluminium Chloride,
AlBr3: Aluminium Bromide,
AII3: Aluminium Iodide,
H2O2: Hydrogen peroxide,
AC2O: Acetic anhydride,
DCM: Dichloromethane,
HC1: Hydrochloric acid,
DI water: De-ionized water,
DM water: Demineralized water,
M/C: Moisture content,
MR: Molar ratio,
T: Times,
MP: Melting point,
BP: Boiling point,
w/w: weight/weight
Examples
The disclosure will now be illustrated with working examples, which is intended to illustrate the working of disclosure and not intended to take restrictively to imply any limitations on the scope of the present disclosure.
All stereo-isomers or regio-isomers of the compounds of the instant disclosure are contemplated, either in admixture or in pure or substantially pure form. Preparation of Example 1: 5-(5-(benzylsulfanyl)-l-methyl-l.H-pyrazol-4-yl)-2-methyl-2//-tetrazole Step 1: 2-(ethoxymethylene)malononitrile
A mixture of triethyl orthoformate (67.3 gm, 0.454 moles) and malononitrile (20.0gm, 0.302 moles) in acetic anhydride (77.2 gm, 0.75 moles) was refluxed for 4-5 hours at 110-140°C. The reaction was monitored by GC. Reaction mixture was cooled to room temperature. Concentrated the reaction mixture at 70°C at reduced pressure to yield crude solid product, 2-(ethoxymethylene)malononitrile. The crude product was further purified either by vacuum distillation to yield pure product, 2-(ethoxymethylene)malononitrile.
Dry wt : 36.0 gm
Yield : 1.80 w/w (98%)
HPLC purity : 99%
MP : 65-67 °C
Step 2: 5-amino-l-methyl-l//-pyrazole-4-carbonitrile
A solution of 2-(ethoxymethylene)malononitrile (20.0 gm, 0.163 moles) in methanol (80.0 ml) was slowly added to a mixture of N-methyl hydrazine sulfate (23.5 gm, 0.163 moles), triethyl amine (33.0 gm, 0.326 moles) and methanol (30.0 gm). The reaction mixture was refluxed for 1-2 hour. The progress of the reaction was monitored by HPLC. Excess methanol was distilled out at reduced pressure. To the above residue distilled water (40.0 ml) was added and the reaction mass was cooled to 0-15°C. 15% (w/v) aqueous sodium hydroxide solution (18.0 ml) was added to the above reaction mixture and the reaction mixture thereto was stirred for 30-45 min at 0-5°C, filtered, washed with cold water (400 ml) and air dried to yield 5-amino-l-methyl-l//-pyrazole-4-carbonitrile at 50-75°C.
Drywt : 15.4 gm
Yield : 0.77 w/w (77%)
HPLC purity : 98.67%
MP : 216-221 °C
Step 3: (i) 5-chloro-l-methyl-l//-pyrazole-4-carbonitrile
A mixture of 5-amino-l-methyl-l//-pyrazole-4-carbonitrile (12.1 gm, 0.099 moles),
hydrochloric acid (72.6 ml, strength: 35-37%) in DM water (60.0 ml) was stirred at room
temperature. Reaction mixture was cooled to 0 to 5°C and sodium nitrite solution (by
dissolving sodium nitrite (8.2 gm, 0.119 moles) in DI water (240 ml)) was slowly added. The
reaction mixture was stirred for 1-1.5 hours at 0 to 5°C. Urea solution [prepared by dissolving
urea (1.2 gm) in DI water (6.0 ml)] is added slowly to the reaction mixture. Solid cuprous
chloride (12.8 gm, 0.129 moles) was added to the above reaction mixture, stirred the reaction
mixture for 3-4 hours at 0 to 5°C. Then the reaction temperature was raised to room
temperature and stirred for 12-18 hours. Progress of the reaction was monitored by HPLC. To
the above reaction mixture was added DI water (120 ml) and 25% (w/v) aqueous sodium
hydroxide solution (80.0 ml) to adjust the pH to 3-3.5. 1,2-dichloroethane was poured to the
reaction mixture and stirred for 10-15 min at 45-50°C. The inorganic salt was filtered off
through hyflo bed. The organic layer was separated and aqueous layer was extracted with 1,2-
dichloroethane. The entire organic layer was transferred to the reaction vessel and washed
with 10% brine solution (50.0 ml). The organic layer was evaporated to obtain the 5-chloro-
1 -methyl-1 Z/-pyrazole-4-carbonitrile.
Drywt : 11.8gm
Yield : 0.97 w/w (84%)
HPLC purity : 93.34%
MP : 55-60°C
(ii) 5-bromo-1 -methyl-1 //-pyrazole-4-carbonitrile
A mixture of 5-amino-l-methyl-l//-pyrazole-4-carbonitrile (20 gm, 1.63 moles),
hydrobromic acid (280 ml, strength: 48%) in DM water (605 ml) was stirred at room at 0 to
5°C and sodium nitrite solution (by dissolving sodium nitrite (16.94 gm, 0.245 moles) in DI
water (242 ml)) was slowly added. Solid cuprous bromide (37.22 gm, 0.260 moles) was
added to the above reaction mixture, stirred the reaction mixture for 3-4 hours at 5 to 5°C.
Then the reaction temperature was raised to room temperature and stirred for 15-18 hour. To
the above reaction mixture cold DI water (1000 ml) was added at 0-5 °C and stirred the
resulting suspension for 1-2 hour. Progress of the reaction was monitored by HPLC. The
solid product was filtered, washed with cold DI water (200 ml) and dried at 60-65°Cto afford
the product, 5-bromo-1-methyl-l//-pyrazole-4-carbonitrile,.
Drywt :21.2gm
Yield : 1.06 (69%)
HPLC purity : 99.58%
MP : 90-93 °C
Step 4: (i) 5-(5-chloro-l -methyl- l//-pyrazole-4-yl)-2i/-tetrazole
5-chloro-1-methyl-l/f-pyrazole-4-carbonitrile (13.0 gm, 0.092 moles), was dissolved in DMF (40 ml), followed by addition of ammonium chloride (9.9 gm, 0.184 moles) and sodium azide (12.0 gm, 0.184 moles) and stirred at 100-140°C for 10-16 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled at 0-5°C and quenched with aqueous HC1 (78.0 ml) and stirred for 30-60 min at 0-5°C. The solid material obtained was filtered, washed with cold DM water (40 ml) and dried at 60-65°C to yield the product, 5-(5-chloro-l -methyl-l//-pyrazole-4-yl)-2//-tetrazole
Drywt : 16.2 gm
Yield : 1.25w/w(96%)
HPLC purity : 99.26%
MP : 215-219°C
(ii) 5-(5-bromo-1 -methyl- 17/-pyrazole-4-yl)-2//-tetrazole
5-bromo-1-methyl-l//-pyrazole-4-carbonitrile (14.85 gm, 0.0798 moles), was dissolved in toluene (148 ml), and tri-n-butyl tin chloride (64.83 gm, 0.199 moles) and sodium azide (12.93 gm, 0.199 moles) were added to it. The reaction mixture was stirred at 100-145°C for 7-8 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled at 10-15°C and 10% ethanolic HC1 solution (100 ml) was added and stirred for 1-1.5 hours at 10-15°C. The inorganic salt was filtered off, washed with ethanol (30 ml). Mother liquor and washings are collected and excess toluene and ethanol was recovered at 50-55°C under reduced pressure. Poured di-isopropyl ether (100 ml) to the above residue and stirred the resulting solid for 1-2 hours at 20-25°C. The solid product was filtered, washed with di-isopropyl ether (30 ml) and dried at 60-65°C to obtain the product, 5-
(5-bromo-1 -methyl- li/-pyrazol-4-yl)-2//-tetrazole
Dry wt : 17 gm
Yield : 1.14w/w(93%)
HPLC purity : 99.72%
MP : 202-207°C
Step 5: (i) 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole)
5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole (10.0 gm, 0.0541 moles), was dissolved in acetone (50.0 ml). Potassium carbonate (6.0 gm, 0.0433 moles) was added and stirred for about 1 hour at 20-30°C. To this mixture, slowly added a solution of DMS (9.5 gm, 0.0757 moles) in acetone (10.0 ml) maintaining the temperature below 30°C. The reaction mixture was stirred at room temperature for about 1 hour and monitored the progress of the reaction by HPLC. The inorganic solids were filtered off. Acetone was distilled off from the filtrate to obtain the crude product containing 5-(5-chloro-l -methyl-li7-pyrazole-4-yl)-2-methyl-2//-tetrazole), its regio-isomer, 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-l-methyl-2Z/-tetrazole), or mixture thereof. Both the regio-isomers were separated by column chromatography.
The following data is of 5-(5-chloro-l -methyl-l//-pyrazole-4-yl)-2-methyl-2#-tetrazole)
Dry wt : 7.81 gm
Yield : 0.78w/w(73%)
HPLC purity : 99.12%
MP : 125-127°C
(ii) 5-(5-bromo-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole)
Dissolve 5-(5-bromo-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole (Ic) (9.5 gm, 0.0414 moles) in acetonitrile (100 ml). Potassium hydroxide (5.71 gm, 0.10 moles) and methyl iodide (24.5 gm, 0.171 moles) were added and stirred at 20-30°C for 20-25 hours. The progress of the reaction was monitored by HPLC. The acetonitrile was recovered at 55-60°C at reduced pressure. To the above residue dichloromethane (100 ml) and DI water (100 ml) was added and stirred the above reaction mixture for 10-15 min at 20-25°C. The reaction mixture was allowed to settle. The organic layer was separated and aqueous layer was
extracted with DCM. The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (50 ml). Stirred for 10-15 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the crude product. Both the regio-isomers were separated by column chromatography by eluting ethyl acetate/ hexane (50:50).
The following data is of 5-(5- bromo-1 -methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole)
Dry wt : 5 gm
Yield : 0.52 w/w (50%)
HPLC purity : 99.95%
Step 6: (i) 5-(5-(benzylsulfanyl)-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole.
To 5-(5-chloro-l-methyl-l#-pyrazol-4-yl)-2-methyl-2#-tetrazole (10 gm, 0.0505
moles) obtained from step 5(i), DMF (30 ml), sodium hydride (60% in oil, 1.33 gm, 0.055
moles) and benzyl thiol (6.57gm, 0.053 moles) were added. The reaction mixture was stirred
at 20-25°C under nitrogen for 2 hour. Progress of the reaction was monitored by TLC. The
reaction mixture was cooled to 0-10°C, added slowly DI water (200 ml). The solid product
was filtered, washed with water (50 ml). Poured hexane (100 ml) to the above crude product
and stirred the suspension for 1 hour at 20-25°C. The solid product obtained was filtered,
washed with hexane (50 ml) and dried to yield the product, 5-(5-(benzylsulfanyl)-l-methyl-
l//-pyrazol-4-yl)-2-methyl-2#-tetrazole at 40-45 °C.
Drywt : 13 gm
Yield : 1.3 w/w (65%)
HPLC purity : 99.26%
(ii) 5-(5-(benzylsulfanyl)-1 -methyl-lZ/-pyrazol-4-yl)-2-methyl-2//-tetrazole.
A mixture of 5-(5-bromo-l -methyl-l//-pyrazol-4-yl)-2-methyl-2i7-tetrazole (17.7 gm, 0.072 moles), sodium hydride (2.59 gm, 0.108 moles), benzyl thiol (9.89 gm, 0.079 moles) and DMF (80 ml) was stirred at 60-80°C for 1 hour. The progress of the reaction was monitored by HPLC and TLC. The reaction mixture was cooled at 0-10°C and slowly added DI water (200 ml). The solid product was filtered, washed with water (50 ml) and hexane (100 ml) to afford the product, 5-(5-(benzylsulfanyl)-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole
Drywt : 16 gm
Yield : 0.91 w/w (78 %)
HPLC purity : 99.43%
Compounds 2-270 were prepared by following the experimental procedure of Example 1 using appropriate intermediates.
Example 271: Preparation of l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol).
Step 1: 2-(ethoxymethylene)malononitrile
The preparation of 2-(ethoxymethylene)malononitrile was carried out in a manner similar to that described in Step 1 of Example 1. Step 2: 5-amino-1 -methyl-1 //-pyrazole-4-carbonitrile
The 5-amino-1-methyl-l//-pyrazole-4-carbonitrile was synthesized according to the above method described in Step 2 of Example 1.
Step 3: 5-chloro-l-methyl-l//-pyrazole-4-carbonitrile or 5-bromo-l-methyl-l//-pyrazole-4-carbonitrile
The preparation of 5-chloro-l -methyl-l//-pyrazole-4-carbonitrile or 5-bromo-l-methyl-l//-pyrazole-4-carbonitrile was carried out in a manner similar to that described in Step 3 of Example 1.
Step 4: 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole or 5-(5-bromo-l-methyl-\H-pyrazole-4-yl)-2//-tetrazole
The preparation of 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2/7-tetrazole or 5-(5-bromo-1 -methyl- l//-pyrazole-4-yl)-2//-tetrazole was carried out in a manner similar to that described in Step 4 of Example 1.
Step 5: 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole) or 5-(5-bromo-l-methyl-17/-pyrazole-4-yl)-2-methyl-2//-tetrazole)
The preparation of 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole) or 5-(5-bromo-l -methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole) was carried out in a manner similar to that described in Step 5 of Example 1. Step6:(l-methyl-4-(2-methyl-2i/-tetrazol-5-yl)-l/f-pyrazole-5-thiol)
To the above 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole), obtained from Step 5 (6 gm), added DMF (30 ml), sodium hydrosulfide (8 gm). The reaction mixture was heated at 100-120°C under nitrogen. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-10°C and slowly added dil. HCL (IN) to make acidic pH. Ethyl acetate layer was partitioned and washed with brine (10%, 30 ml). Thereafter, ethyl acetate was distilled off at 50°C at reduced pressure to obtain (1-methyl-4-(2-methyl-2#-tetrazol-5-yl)-1 //-pyrazole-5-thiol). Dry weight: 5.5gm Yield: 0.96w/w (98%) Purity: 95%
Compounds 272- 541 were prepared by following experimental procedure of Example 271 using the appropriate intermediates.
Example 542: Preparation of (l,2-bis-(l-methyl-4-(2-methyl-2/y-tetrazol-5-yl)-l#-pyrazol-5-yl)disulfane)
Step 1: 2-(ethoxymethylene)malononitrile
The preparation 2-(ethoxymethylene)malononitrile was carried out in a manner similar to that described in Step 1 of Example 1. Step 2: 5-amino-l-methyl- l//-pyrazole-4-carbonitrile
The 5-amino-l-methyl-l//-pyrazole-4-carbonitrile was synthesized according to the above method described in Step 2 of Example 1.
Step 3: 5-chloro-l-methyl-l//-pyrazole-4-carbonitrile or 5-bromo-l-methyl-l//-pyrazole-4-carbonitrile
The preparation of 5-chloro-l-methyl-li/-pyrazole-4-carbonitrile or 5-bromo-l-methyl-l//-pyrazole-4-carbonitrile was carried out in a manner similar to that described in Step 3 of Example 1.
Step 4: 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole or 5-(5-bromo-l-methyl-lif-pyrazole-4-yl)-2//-tetrazole
The preparation of 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole or 5-(5-bromo-1 -methyl- l#-pyrazole-4-yl)-2//-tetrazole was carried out in a manner similar to that described in Step 4 of Example 1.
Step 5: 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2i/-tetrazole) or 5-(5-bromo-l-methyl-li/-pyrazole-4-yl)-2-methyl-2//-tetrazole)
The preparation of 5-(5-chloro-l-methyl-17/-pyrazole-4-yl)-2-methyl-2//-tetrazole) or 5-(5-bromo-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole) was carried out in a manner similar to that described in Step 5 of Example 1. Step6:(l,2-bis-(l-methyl-4-(2-methyl-2^-tetrazol-5-yl)-l//-pyrazol-5-yl)disulfane)
To the above 5-(5-chloro-l-methyl-lH-pyrazole-4-yl)-2-methyl-2H-tetrazole), obtained from Step 5 (6 gm), added DMF (30 ml), sodium hydrosulfide (8 gm). The reaction mixture was heated at 100-120°C under nitrogen for 10-14 hour. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-10°C and slowly added dil. HC1 (IN) to make acidic pH. Ethyl acetate layer was partitioned and washed with brine (10%, 30 ml). Thereafter, ethyl acetate was distilled off at 50°C at reduced pressure to obtain (1,2-bis(l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane).
Dry weight: 5.5gm
Yield: 0.96w/w (98%)
Purity: 85%
Compounds 543-811 were prepared by following experimental procedure of Example 542 using the appropriate intermediates.
Example 1(a): 5-(5-(benzylsulfanyl)-l-methyl-l/7-pyrazol-4-yl)-2-methyl-2//-tetrazole. Step 1: 1-methyl-l//-pyrazole-4-carbaldehyde
A mixture of phosphoryl chloride (467 gm, 3.045 moles) and DMF were stirred for 1 hour at 0-5°C. The reaction is exothermic so temperature should be below 5°C. To this slowly added 1-methyl-l//-pyrazole (50 gm, 0.6090 moles) and stirred for 30 min at 0-5°C. Then slowly raised the temperature from 20-30°C to 60-70°C and stirred for 10-15 hours. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5°C, to this added ethyl acetate (250 ml), DM water (1 L) and aqueous ammonia solution (350 ml, pH-6 to 7). The reaction mixture was stirred for 1 hour at 20-30°C. The inorganic salt obtained was filtered off, washed with ethyl acetate (250 ml). The filtrate was transferred in to a separating funnel. The reaction mixture was allowed to settle. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel, stirred for 10-15 min and separated the final aqueous layer and organic layer. The combined organic layer having 1 -methyl- l//-pyrazole-4-carbaldehyde and ethyl acetate was used as such for Step 2 without any purification or isolation at this step. Step 2: 1- methyl -l//-pyrazole-4-carbaldehyde oxime
A mixture of the combined organic layer having 1-methyl-l//-pyrazole-4-carbaldehyde and ethyl acetate obtained from step 1, hydroxylamine hydrochloride (63.48 gm, 0.9135 moles) were refluxed at 70-80°C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5°C, to this added DM water (100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5°C. The reaction mixture was stirred for 10 min at 20-30°C. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 1 -methyl- l//-pyrazole-4-carbaldehyde oxime.
Dry wt : 60 gm
Yield : 1.2w/w(79%)
HPLC purity : 99.78%
Step 3: 5-(l-methyl-l#-pyrazol-4-yl)-2//-tetrazole
1-methyl-l//-pyrazole-4-carbaldehyde oxime (84 gm, 0.6713 moles) obtained in step 2,
ammonium chloride (89.77 gm, 1.6783 moles), sodium azide (109.11 gm, 1.6783 moles)
were taken in DMF (420 ml). The reaction mixture was stirred for 10-12 hours at 110-120°C.
The progress of the reaction was monitored by HPLC. To the above reaction mixture at 0-
10°C, added DM water (500 ml). Acidify reaction mixture using dil. HC1 (5N). The reaction
mixture was stirred for 2 hours at 0-10°C, filtered the product, washed with cold DM water
(200 ml) and dried the product, 5-(l-methyl-l#-pyrazol-4-yl)-2//-tetrazole at 60-70°C.
Dry wt : 75 gm
Yield : 0.89w/w(74%)
HPLC purity : 99.98%
Step 4: 2-methyl-5-(l-methyl-lH-pyrazol-4-yl)-2H-tetrazole
A mixture of 5-(1-methyl-l#-pyrazol-4-yl)-2//-tetrazole (100 gm, 0.6660 moles), potassium
hydroxide (74.74 gm, 1.332 moles) and acetonitrile (500 ml) were stirred for 10 min at 20-
25°C. To the above mixture added methyl iodide (378.12 gm, 2.664 moles), stirred for 10-15
hours at 20-25°C and progress of the reaction was monitored by HPLC. Excess acetonitrile
was recovered at 60-70°C at reduced pressure. DCM (500 ml) and DM water (500 ml) was
added to the reaction mixture, stirred for 30 min and the reaction mixture was kept
undisturbed for 15 min. The organic layer was separated and aqueous layer was extracted
with DCM (500 ml), stirred for 10 min and separated the final aqueous layer and organic
layer. The organic layer was evaporated to obtain 2-methyl-5-(l-methyl-lH-pyrazol-4-yl)-
2H-tetrazole, or l-methyl-5-(l-methyl-lH-pyrazol-4-yl)-2H-tetrazole, or mixture thereof.
The desired regio-isomer, 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole, was isolated
by column chromatography using ethyl acetate and hexane as eluent.
Dry wt : 46 gm
Yield : 0.46w/w(42%)
HPLC purity : 99.97
Step 5: 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2/f-tetrazole
To a solution of 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole (10 gm, 0.609 moles)
in acetonitrile (50 ml) was added N-chlorosuccinimide (8.22 gm, 0.0615 moles). The reaction
mixture was stirred for 30 min at 60°C. Progress of the reaction was monitored by HPLC.
Excess acetonitrile was recovered at 40-50°C under reduced pressure. DI water (100 ml) was
poured to the crude product at 20-25°C. The reaction mixture was stirred for 1 hours at 20-
25°C, filtered the product, washed with cold DM water (50 ml) and dried the product, 5-(5-
chloro-1 -methyl-li/-pyrazol-4-yI)-2-methyl-2/f-tetrazole at 60-70°C.
Dry wt : 12 gm
Yield : 1.2w/w(92%)
HPLC purity : 99.51%
MP : 124-127°C
Step 6: 5-(5-(benzylsulfanyl)-1 -methyl-l//-pyrazol-4-yl)-2-methyl-2#-tetrazole.
5-(5-(benzylsulfanyl)-1 -methyl-1 //-pyrazol-4-yl)-2-methyl-2/7-tetrazole was synthesized
according to the method described in Step 6(i) of Example 1.
Similarly, Compounds 2-270 can also be prepared by the experimental procedure described in this example 1(a). Example 271(a): (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-17/-pyrazole-5-thiol)
To the above 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole),
obtained from Step 5 of Example 1(a) (6 gm), added DMF (30 ml), sodium hydrosulfide (8
gm). The reaction mixture was heated at 100-120°C under nitrogen for 10-14 hour. Progress
of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-10°C and
slowly added dil. HC1 (IN) to make acidic pH. Ethyl acetate layer was partitioned and
washed with brine (10%, 30 ml). Thereafter, ethyl acetate was distilled off at 50°C at reduced
pressure to obtain (l-methyl-4-(2-methyl-2i/-tetrazol-5-yl)-l/f-pyrazole-5-thiol).
Dry weight : 5.5gm
Yield : 0.96w/w (98%)
Purity : 95%
Similarly, Compounds 272 -541 can also be prepared by the experimental procedure described in this example 271(a).
Example 542(a): (1,2-bis-(l -methyl-4-(2-methyl-2i/-tetrazol-5-yl)- l#-pyrazol-5-
yl)disulfane)
To the above 5-(5-chloro-l-methyl-lH-pyrazole-4-yl)-2-methyl-2H-tetrazole), obtained from Step 5 (6 gm), added DMF (30 ml), sodium hydrosulfide (8 gm)- The reaction mixture was heated at 100-120°C under nitrogen for 10-14 hour. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-10°C and slowly added dil. HC1 (IN) to make acidic pH. Ethyl acetate layer was partitioned and washed with brine (10%, 30 ml). Thereafter, ethyl acetate was distilled off at 50°C at reduced pressure to obtain (1,2- bis(l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane).
Dry weight : 5.5gm
Yield : 0.96w/w (98%)
Purity : 85%
Similarly, Compounds 543 -8111 can also be prepared by the experimental procedure described in this example 542(a).
Example 1(b): 5-(5-(benzylsulfanyl)-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole. Step 1: 4-iodo-l-methyl-l//-pyrazole
A mixture of 1-methyl-l//-pyrazole (7) (37 gm, 0.6090 moles), iodine (57.1 gm, 0.225
moles), hydrogen peroxide (9.2 gm, 0.27 moles) and DI water (110 ml) were stirred for 24
hour at 20-30°C. Progress of the reaction was monitored by HPLC and TLC. The reaction
mixture was cooled to 5-10°C. The reaction mixture was quenched with 20% aqueous sodium
bisulfite (100 ml) and stirred for 1 hour at 5-10°C. The solid product obtained was filtered
off, washed with cold DI water (100 ml) and dried at 40-45°C to yield the product, 4-iodo-l-
methyl-1 //-pyrazole.
Dry wt : 56 gm
Yield : 1.51 w/w(60%)
Step 2: 1-methyl-lH-pyrazole-4-carbonitrile
To a solution of 4-iodo-l-methyl-l//-pyrazole (55 gm, 0.264 moles) in N,N-dimethylacetamide (100 ml) was added potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles) and sodium carbonate (27.98 gm, 0.264 moles). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90-110°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30°C, to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 °C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70°C. The mixture was degassed for 2 hour at reduced pressure at 60-70°C, cooled the mixture to 20-30°C. Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-3 0°C. The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-50 °C to yield the product, 1-methyl-lH-pyrazole-4-carbonitrile,.
Dry wt : 17.94 gm
Yield : 0.32 w/w (63%);
Step 3: 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole
1-methyl-lH-pyrazole-4-carbonitrile (18 gm, 0.168 moles) obtained in step 2, tri-n-butyl tin
chloride (65 gm, 0.218 moles), sodium azide (14 gm, 0.201moles) were taken in toluene (180
ml). The reaction mixture was stirred for 24 hours at 110-120°C. The progress of the reaction
was monitored by HPLC. The above reaction mixture was cooled to 10-15°C, to this added
10% ethanolic HC1 solution (100 ml, pH= 1-2). The reaction mixture was stirred for 1-1.5
hours at 10-15°C, filtered off the inorganic salts, washed with ethanol (30 ml). The mother
liquor and washings were collected and toluene and ethanol was recovered at 50-55°C at
reduced pressure. To the above residue at 20-25°C, added di-isopropyl ether (100 ml), stirred
for 1-2 hours at 20-25°C, filtered the solid, washed with di-isopropyl ether (30 ml) and dried
at 60-65°C to yield the product, 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole.
Dry wt : 25 gm
Yield : 1.4 w/w (99%)
Step 4: 2-methyl-5-(l-methyl-lH-pyrazol-4-yl)-2H-tetrazole
The preparation of 2-methyl-5-(l -methyl-1 H-pyrazol-4-yl)-2H-tetrazole was carried out in a
manner similar to that described in Step 4 of Example 1(a).
Step 5: 5-(5-chloro-l-methyl-li/-pyrazol-4-yl)-2-rnethyl-277-tetrazole
The 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole was synthesized
according to the method described in Step 5 of Example 1(a).
Step 6: 5-(5-(benzylsulfanyl)-1 -methyl- l//-pyrazol-4-yl)-2-methyl-2//-tetrazole.
5-(5-(benzylsulfanyl)-l-methyl-li/-pyrazol-4-yl)-2-methyl-2//-tetrazole was synthesized
according to the method described in Step 6(i) of Example 1.
Similarly, the compounds 2- 270 can also be prepared by the experimental procedure described in example 1(b) using appropriate intermediates. Example 271(b): (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol) Step 1: 4-iodo-l-methyl-l//-pyrazole
The preparation of 4-iodo-l-methyl-l//-pyrazole was carried out in a similar manner to that described in Step 1 of Example 1(b). Step 2: 1-Methyl-lH-pyrazole-4-carbonitrile
The preparation of 1-Methyl-1 H-pyrazole-4-carbonitrile was carried out in a similar manner
to that described in Step 2 of Example 1(b).
Step 3: 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole
The preparation of 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole was carried out in a similar
manner to that described in Step 3 of Example 1(b).
Step 4: 2-methyl-5-(l-methyl-1 H-pyrazol-4-yl)-2H-tetrazole
The preparation of 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole was carried out in a manner similar to that described in Step 4 of Example 1(a).
Step 5: 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2/f-tetrazole
The 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2-tetrazole was synthesized
according to the method described in Step 5 of Example 1(a).
Step 6: Synthesis of (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol)
Synthesis of (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol) was synthesized according to the method described in Example 271 (a).
Similarly, the compounds 272-541 can also be prepared by the experimental procedure described in example 271(b) using appropriate intermediates.
Example 542(b): (1,2-bis( 1 -methyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane).
Step 1: 4-iodo-l-methyl-l//-pyrazole
The preparation of 4-iodo-l-methyl-l//-pyrazole was carried out in a similar manner to that described in Step 1 of Example 1(b). Step 2: 1-Methyl-lH-pyrazole-4-carbonitrile
The preparation of 1-Methyl-lH-pyrazole-4-carbonitrile was carried out in a similar manner to that described in Step 2 of Example 1(b). Step 3: 5-(l-methyl-li/-pyrazol-4-yl)-2//-tetrazole
The preparation of 5-(l -methyl- l//-pyrazol-4-yl)-2//-tetrazole was carried out in a similar manner to that described in Step 3 of Example 1(b). Step 4: 2-methyl-5-(l-methyl-lH-pyrazol-4-yl)-2H-tetrazole
The preparation of 2-methyl-5-(l-methyl-lH-pyrazol-4-yl)-2H-tetrazole was carried out in a manner similar to that described in Step 4 of Example 1(a). Step 5: 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole The 5-(5-chloro-l -methyl- l#-pyrazol-4-yl)-2-methyl-2//-tetrazole was synthesized according to the method described in Step 5 of Example 1(a). Step6:(l,2-bis(l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane).
The (1,2-bis(l -methyl-4-(2-methyl-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane) was synthesized according to the method described in Example 542(a).
Similarly, Compounds 543 -811 can also be prepared by the experimental procedure described in this example 542(a).
Although the subject matter has been described in considerable detail with reference to certain preferred embodiments thereof, other embodiments are possible. As such, the spirit and scope of the present disclosure should not be limited to the description of the preferred embodiment contained therein.
We Claim:
1. A compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof,
wherein:
R, is selected from -SH, -SCH2Ph, -SR or -S-SRi'; where R is a CM alkyl and Ri' is a group of formula II, where * denotes the point of attachment
R2 is selected from a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, F, I, NO2, CN, C1-5 alkyl, phenyl, or C1-C4 alkoxy; and
R3 is selected from a straight chain or a branched chain C1.7 alkyl, or C6-Q4 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl or C1-C4 alkoxy.
2. The compound as claimed in claim 1, wherein:
R1 is selected from -SH, -SCH2Ph, -SR or -S-SRi'; where R is a CM alkyl and Ri' is a group of formula II where * denotes the point of attachment
R2 is selected from a Q.3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; said the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, NO2, CN, C1-2 alkyl, or a C1-C2 alkoxy; and
R3 is selected from a straight chain or a branched chain CM alkyl, or a phenyl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or aCj-C2 alkoxy.
3. The compound as claimed in claim 1, wherein:
R1 is -SH;
R2 is selected from a C1.3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, NO2, CN, Q.2 alkyl, or a C1-C2 alkoxy; and R3 is selected from a straight chain or a branched chain CM alkyl or a phenyl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from phenyl group; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or a C1-C4 alkoxy.
4. The compound as claimed in claim 1, wherein:
R1 is -SCH2Ph;
R.2 is selected from a C\.2 alkyl; wherein said alkyl is optionally substituted with a phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, NO2, CN, C1-2 alkyl, or a CrC2 alkoxy; and R3 is selected from a straight chain or a branched chain CM alkyl or C6 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from phenyl;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1.2 alkyl, phenyl or a C1-C4 alkoxy. 5. The compound as claimed in claim 1, wherein:
R1 is -S-SR1'; where R is a CI-4 alkyl and Rj' is a group of formula II where * denotes the point of attachment R2 is selected from a C1.3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; said phenyl group is optionally substituent with one or more substituent independently selected from CI, Br, N02, CN, C1-2 alkyl, or a C1-C2 alkoxy; and R3 is selected from a straight chain or a branched chain CM alkyl or C6 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from phenyl;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or a C1-C4 alkoxy. 6. The compound as claimed in claim 1 selected from:
1 -methyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
1 -methyl-4-( 1 -methyl-2H-tetrazol-5-yl)-l H-pyrazole-5-thiol;
1 -ethyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
l-ethyl-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
1 -(2-methylpropyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
l-(2-methylpropyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
l-benzyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
1 -benzyl-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
4-(2-methyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol; 4-( 1 -methyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol; l-(2-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(2-chlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-(l -methyl-2H-tetrazol-5-yl)-l H-pyrazole-5-thiol; 1 -(4-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1-(4-chlorophenyl)-4-( 1-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,3-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(2,3-dichlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dichlorophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(4-bromophenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-(l -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,4-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
1 -(2,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1-(2,6-dimethylphenyl)-4-( 1-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thioI; 1 -(2-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1-(4-methoxyphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-( 1 -methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-methylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5 -thiol; l-(2-methylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-methylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(4-methylphenyl)-4-(l-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazole-5-thiol; 1 -ethyl-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -ethyl-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol; 4-(l -ethyl-2H-tetrazol-5-yl)-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol; 1 -benzyl-4-(2-ethyl-2H-tetrazol-5-yl)-l H-pyrazole-5-thiol; 1 -benzyl-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol; 4-(l -ethyl-2H-tetrazol-5-yl)-l -phenyl-1 H-pyrazole-5-thiol; l-(2-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(2-chlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(4-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-chlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,3-dichlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,5-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,6-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,4-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -( 3,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-( 3,5-dichlorophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3-bromophenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol; 4-(l-ethyl-2H-tetrazol-5-yl)-l-(2-fluorophenyl)-lH-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(2,5-dimethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-( 1 -ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; 1 -(3,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
l-(2-ethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
1 -(2-ethylphenyl)-4-(l -ethyl-2H-tetrazol-5-yl)-l H-pyrazole-5-thiol;
l-(4-ethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
l-(4-ethylphenyl)-4-(l-ethyl-2H-tetrazol-5-yl)-lH-pyrazole-5-thiol;
4-(2-ethyl-2H-tetrazol-5-yl)-l-(4-methoxyphenyl)-lH-pyrazole-5-thiol;
4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-(2-ethyl-2H-tetrazol-5-yl)-l-(2-methylphenyl)-lH-pyrazole-5-thiol;
4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
4-( 1 -ethyl-2H-tetrazol-5-yl)-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
l-methyl-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -methyl-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-ethyl-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -ethyl-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
l-benzyl-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -benzyl-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3-chlorophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,5-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[2-(l -methylethyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol;
1 -(2,6-dichlorophenyl)-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3,4-dichlorophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(3,5-dichlorophenyl)-4-[2-( 1-methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-[ 1 -(1 -methyl ethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-bromophenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-fluorophenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,4-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 4-[2-(l-methylethyl)-2H-tetrazol-5-yl]-l-(2-methylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[2-( 1 -methylethyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
4-[l -(1 -methylethyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazole-5-thiol;
4-(l -benzyl-2H-tetrazol-5-yl)-l -methyl-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazole-5-thiol;
4-(l -benzyl-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(2-methylpropyl)-lH-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(2-methylpropyl)-lH-pyrazole-5-thiol;
1 -benzyl-4-(2-benzyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
1-benzyl-4-( 1-benzyl-2H-tetrazol-5-yl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3-chlorophenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(3-chlorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,3-dichlorophenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,3-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dichlorophenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,4-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,5-dichlorophenyl)-1 H-pyrazole-5-thiol;
4-(l -benzyl-2H-tetrazol-5-yl)-1 -(2,5-dichlorophenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,6-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,6-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3,4-dichlorophenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,4-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(3-bromophenyl)-lH-pyrazole-5-thiol;
4-(l -benzyl-2H-tetrazol-5-yl)-1 -(3-bromophenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-bromophenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(4-bromophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(4-fluorophenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,3-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,3-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,5-dimethylphenyl)-lH-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2,5-dimethylphenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1-(2,6-dimethylphenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(2,6-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1-(3,4-dimethylphenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,4-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,5-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(3,5-dimethylphenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazole-5-thiol;
4-( 1 -benzyl-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazole-5-thiol;
4-(l -benzyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(4-methoxyphenyl)-lH-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-(l -benzyl-2H-tetrazol-5-yl)-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
4-(l-benzyl-2H-tetrazol-5-yl)-l-(4-methylphenyl)-lH-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -methyl-1 H-pyrazole-5-thiol;
4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-methyl-lH-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -ethyl-1 H-pyrazole-5-thiol;
4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -ethyl-1 H-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
1 -benzyl-4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -benzyl-4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazoI-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol; 4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-chlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3-chlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3-chlorophenyl)-l H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-chlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,3-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,3-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,5-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,5-dichlorophenyl)-l H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,6-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,6-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,4-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,4-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3,5-dichlorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,5-dichlorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-bromophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3-bromophenyl)-lH-pyrazole-5-thiol; 4-[l-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(3-bromophenyl)-lH-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-bromophenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-bromophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-fluorophenyl)-lH-pyrazole-5-thiol; 4-[2-( 1 -bromobenzyl)-2H-tetrazol-5-yl]-l -(4-fluorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-fluorophenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-fluorophenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,3-dimethylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-l -(2,3-dimethylphenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,4-dimethylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-l -(2,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2,6-dimethylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2,6-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-ylj-1 -(3,4-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(3,5-dimethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-ethylphenyl)-1 H-pyrazole-5-thiol; 4-[l -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-ethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(4-ethylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-ethylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-l-(2-methylphenyl)-lH-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(4-bromobenzyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol; 4-{[5-(l-methyl-5-suIfanyl-1 H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile; 4-{[5-(l-methyl-5-sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yl] methyl} benzonitrile; 4- {[5-( 1 -ethyl-5-sulfanyl-1 H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile; 4- {[5-( 1 -ethyl-5-sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yljmethyl }benzonitrile; 4-( {5-[ 1 -(2-methylpropyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( (5-[ 1 -(2-methylpropyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-{[5-(l-benzyl-5-sulfanyl-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile; 4- {[5-( 1 -benzyl-5-sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yl]methyl} benzonitrile; 4- {[5-( 1 -phenyl-5-sulfanyl-1 H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl }benzonitrile; 4- {[5 -(1 -phenyl-5 -sulfanyl-1 H-pyrazol-4-yl)-1 H-tetrazol-1 -yljmethyl} benzonitrile; 4-({5-[l-(2-chlorophenyl)-5-sulfanyMH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl) benzonitrile;
4-( (5-[ 1 -(2-chlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl) benzonitrile;
4-({5-[l-(3-chlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3-chlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yI]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(4-chlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-chlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(2,3-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2,3-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[l-(2,4-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2,4-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[l-(2,5-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2,5-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[ 1 -(2,6-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)
benzonitrile;
4-( {5-[ 1 -(2,6-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(3,4-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3,4-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(3,5-dichlorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3,5-dichlorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)
benzonitrile;
4-({5-[l-(2-bromophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(4-bromophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-bromophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-l H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-fluorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-fluorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2-fluorophenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-({5-[l-(2-fluorophenyl)-5-sulfanyl-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyI)
benzonitrile;
4-({5-[l-(2,3-dimethylphenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2,3-dimethylphenyl)-5-sulfanyl-l H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl)
benzonitrile;
4-( {5-[ 1 -(2,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)
benzonitrile;
4-( {5-[ 1 -(2,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(2,5-dimethylphenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2,5-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(2,6-dimethylphenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2,6-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[ 1 -(3,4-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3,4-dimethylphenyl)-5-sulfanyl-l H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl)
benzonitrile;
4-( {5-[ 1 -(3,5-dimethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(3,5-dimethylphenyl)-5-sulfanyl-l H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-({5-[l-(2-ethylphenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2-ethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[ 1 -(4-ethylphenyl)-5-sulfanyl-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-ethylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-methoxyphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[ 1 -(4-methoxyphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl)
benzonitrile;
4-( {5-[ 1 -(2-methylphenyl)-5-sulfanyl-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(2-methylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[l-(4-methylphenyl)-5-sulfanyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[ 1 -(4-methylphenyl)-5-sulfanyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -methyl-1 H-pyrazoIe-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-l -methyl-1 H-pyrazole-5-thiol;
l-ethyl-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -ethyl-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
l-benzyl-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -benzyl-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3-chlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
l-(2,3-dichlorophenyl)-4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-
thiol;
1 -(2,4-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,4-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,5-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,5-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
l-(2,6-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-
thiol;
1 -(2,6-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
l-(3,4-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-
thiol;
1 -(3,4-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(3,5-dichlorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(3,5-dichlorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-bromophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3-bromophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3-bromophenyl)-4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(4-bromophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(4-bromophenyl)-4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(4-fluorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-fluorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-fluorophenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-fluorophenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2,3-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,3-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,4-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,4-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,5-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2,5-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
l-(2,6-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-
thiol;
1 -(2,6-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl] -1 H-pyrazole-5-
thiol;
l-(3,4-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-
thiol;
1 -(3,4-dimethylphenyl)-4-[ 1 (4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
l-(3,5-dimethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-
thiol;
1 -(3,5-dimethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-
thiol;
1 -(2-ethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-ethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-ethylphenyl)-4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5 -thiol;
1 -(4-ethylphenyl)-4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(4-methoxyphenyl)-1 H-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol;
4-[l-(4-methoxybenzyl)-2H-tetrazol-5-yl]-l-(2-methylphenyl)-lH-pyrazole-5-thiol;
4-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]-l-(4-methylphenyl)-lH-pyrazole-5-thiol;
4-[ 1 -(4-methoxybenzyl)-2H-tetrazol-5-yl]-1 -(4-methylphenyl)-1 H-pyrazole-5-thiol;
l-methyl-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -methyl-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-ethyl-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1-ethyl-4-[ 1-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -(2-methylpropyl)-1 H-pyrazole-5-thiol;
4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-l -(2-methylpropyl)-1 H-pyrazole-5-thiol;
l-benzyl-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -benzyl-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(2-chlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(3-chlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(3-chlorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(4-chlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,3-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,3-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,4-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
1 -(2,4-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
l-(2,5-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2,5-dichlorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol;
l-(2,6-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(3,4-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,5-dichlorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-bromophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(2-bromophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3-bromophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-bromophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(4-bromophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-fiuorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-fluorophenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(2-fluorophenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(2,3-dimethylphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,5-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[ 1 -(3 -methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[l-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,5-dimethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-ethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-ethylphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-ethylphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-methoxyphenyl)-4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-l -(2-methylphenyl)-1 H-pyrazole-5-thiol; 4-[2-(3-methylbenzyl)-2H-tetrazol-5-yl]-1-(3-methylphenyl)-1 H-pyrazole-5-thiol; 4-[ 1 -(3-methylbenzyl)-2H-tetrazol-5-yl]-1 -(3-methylphenyl)-1 H-pyrazole-5-thiol; l-methyl-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -methyl-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-ethyl-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -ethyl-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-methylpropyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-methylpropyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-benzyl-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-benzyl-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-l-phenyl-lH-pyrazole-5-thiol; 4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 -phenyl-1 H-pyrazole-5-thiol; l-(2-chlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-chlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3-chlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3-chlorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-chlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-chlorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,3-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,3-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,4-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,5-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl] -1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2,6-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(3,4-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,5-dichlorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,5-dichlorophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-bromophenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol;
1 -(3-bromophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(3-bromophenyl)-4-[ 1-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-bromophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-bromophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(4-fluorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(4-fluorophenyl)-4-[ 1-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1-(2-fluorophenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2-fluorophenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thioI; 1 -(2,3-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-ylj-1 H-pyrazole-5-thiol; 1 -(2,3-dimethylphenyl)-4-[l -(4-nitrobenzyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]~ 1 H-pyrazole-5-thiol; 1 -(2,4-dimethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,5-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,5-dimethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(2,6-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2,6-dimethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(3,4-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(3,4-dimethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-l H-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; l-(3,5-dimethylphenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(2-ethylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methoxyphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; l-(4-methoxyphenyl)-4-[l-(4-nitrobenzyl)-2H-tetrazol-5-yl]-lH-pyrazole-5-thiol; 1 -(2-methylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5 -thiol; 1 -(2-methylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methylphenyl)-4-[2-(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 1 -(4-methylphenyl)-4-[ 1 -(4-nitrobenzyl)-2H-tetrazol-5-yl]-1 H-pyrazole-5-thiol; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2-methylpropyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1-(4-chlorophenyl)-1 H-pyrazol-4-yl]-1-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-l -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3-bromophenyl)-1 -pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyI)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl] -1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1-(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-1 -methyl-2H-tetrazoIe; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[l-benzyl-5-(benzylsulfanyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,4-dichlorophenyl)-l H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl] -1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl] -2-ethyl-2H-tetrazole; 5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazoIe;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-1 -ethyl-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylpropyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylsulfanyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l -(3-chlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(3 -chlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methyl ethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-( 1 -methyl ethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -rnethylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-l -(1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-
2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yI]-1 -(1 -methylethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(l-methyl ethyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methyl ethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(2-methylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-
tetrazole;
5-[5-(benzylsulfanyl)-1 -(4-methylphenyl)-1 H-pyrazol-4-yl]-1 -(1 -methylethyl)-2H-
tetrazole;
2-benzyl-5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-(5-benzylsulfanyl-1 -isobutyl-1 H-pyrazol-4-yl)-2H-tetrazole;
l-Benzyl-5-(5-benzylsulfanyl-l-isobutyl-lH-pyrazol-4-yl)-2H-tetrazole;
2-Benzyl-5-( 1 -benzyl-5-benzylsulfanyl-1 H-pyrazol-4-yl)-2H-tetrazole;
1 -Benzyl-5-( 1 -benzyl-5-benzylsulfanyl-1 H-pyrazol-4-yl)-2H-tetrazole;
2-Benzyl-5-(5-benzylsulfanyl-1 -phenyl-1 H-pyrazol-4-yl)-2H-tetrazole;
1 -Benzyl-5-(5-benzylsulfanyl-1 -phenyl-1 H-pyrazol-4-yl)-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(2-chloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(2-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(3-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(3-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(4-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(4-chloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,4-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(2,5-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(2,5-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,6-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,6-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(3,4-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(3,4-dichloro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(3,5-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1-Benzyl-5-[5-benzylsulfanyl-1-(3,5-dichloro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(2-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(3-bromo-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(3-bromo-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(4-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-bromo-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(4-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2-fluoro-phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-fluoro-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(2,3-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-
tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(2,4-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-
tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,5-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-l -(2,5-dimethyl-phenyl)-l H-pyrazol-4-yl]-2H-
tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(2,6-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(2,6-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(3,4-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
l-Benzyl-5-[5-benzylsulfanyl-l-(3,4-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-l-(3,5-dimethyl-phenyl)-lH-pyrazol-4-yl]-2H-
tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(3,5-dimethyl-phenyl)-1 H-pyrazol-4-yl]-2H-
tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(2-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(2-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(4-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-1 -(4-ethyl-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-[5-benzylsulfanyl-1 -(4-methoxy-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
1 -Benzyl-5-[5-benzylsulfanyl-l -(4-methoxy-phenyl)-1 H-pyrazol-4-yl]-2H-tetrazole;
2-Benzyl-5-(5-benzylsulfanyl-1 -o-tolyl-1 H-pyrazol-4-yl)-2H-tetrazole;
l-Benzyl-5-(5-benzylsulfanyl-l-o-tolyl-lH-pyrazol-4-yl)-2H-tetrazole;
2-Benzyl-5-(5-benzylsulfanyl-1 -p-tolyl-1 H-pyrazol-4-yl)-2H-tetrazole;
1 -Benzyl-5-(5-benzylsulfanyl-1 -p-tolyl-1 H-pyrazol-4-yl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl] -1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-isobutyl-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-l -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl] -1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-l -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3 -bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(2-fluorophenyl)-1 H-pyrazol-4-yl]-1-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl] -1 -(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1-(4-bromobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(o-tolyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-2-(4-bromobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-1 -(4-bromobenzyl)-2H-tetrazole;
4-({5-[5-(benzylsulfanyl)-l-methyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( (5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( (5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-[[5-(l-benzyl-5-(benzylthio)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl]methyl)
benzonitrile;
4-[[5-( 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl]methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-phenyl-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( (5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl} methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl} methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl} methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( (5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl] -1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl jmethyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( (5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-
yl}methyl) benzonitrile;
4-({5-[5-(benzylthio)-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-l -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl}methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl} methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl }methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl jmethyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl} methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-
yl}methyl) benzonitrile;
4-( {5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -
yl} methyl) benzonitrile;
4-( (5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 H-tetrazol-1 -yl}methyl)
benzonitrile;
4-( {5-[5-(benzylthio)-1-(p-tolyl)-1 H-pyrazol-4-yl]-2H-tetrazol-2-yl }methyl)
benzonitrile;
4-({5-[5-(benzylthio)-l-(p-tolyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)
benzonitrile;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-ethyl-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-isobutyl-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-phenyl-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl] -1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-bromophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl] -1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl] -1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(o-tolyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(o-tolyl)-1 H-pyrazol-4-yl]-1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(p-tolyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1-(p-tolyl)-1 H-pyrazol-4-yl]-1-(4-methoxybenzyl)-2H-tetrazole;
5-[5-(benzylthio)-lmethyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-lmethyl-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -ethyl-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-isobutyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-2-(3 -methylbenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-phenyl-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(3 -methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl] -2-(3 -methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1-(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5 - [5-(benzylthio)-1-(3,4-dimethylphenyl)-1 H-pyrazol-4-yl] -1-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-methoxyphenyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(o-tolyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1-(o-tolyl)-1 H-pyrazol-4-yl]-1-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-1 -(3-methylbenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-l-methyl-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -methyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylsulfanyl)-1 -ethyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -isobutyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[l-benzyl-5-(benzylthio)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[ 1 -benzyl-5-(benzylthio)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -phenyl-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3 -chlorophenyl)-1 H-pyrazol-4-yl] -1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-chlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1-(2,6-dichlorophenyl)-1 H-pyrazol-4-yl]-1-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,4-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-
tetrazole;
5-[5-(benzylthio)-1 -(3-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-bromophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-fluorophenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1-(2,5-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(2-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(4-ethylphenyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(o-tolyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1-(o-tolyl)-1 H-pyrazol-4-yl]-1-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-l-(p-tolyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-[5-(benzylthio)-1 -(p-tolyl)-1 H-pyrazol-4-yl]-1 -(4-nitrobenzyl)-2H-tetrazole;
1,2-bis( 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -ethyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -isobutyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-benzyl-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-methyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-chlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(2,3-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2,6-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(3,5-dichlorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane,
1,2-bis( 1 -(2-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(3-bromophenyl)-4-(2-methyI-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(4-bromophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(2,3-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(l-(2,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,6-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(3,4-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane,
1,2-bis(l -(3,5-dimethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-ethylphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(4-methoxyphenyl)-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-methyl-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-methyl-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-methyl-lH-pyrazol-5-yl)disulfane;
1,2-bis(l-ethyl-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -isobutyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -benzyl-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(3-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l-(4-chlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,3-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(2,6-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
1,2-bis(l-(3,4-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-bromophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1-(4-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,3-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,6-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dimethylphenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-(2-ethylphenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazoI-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-ethyl-2H-tetrazol-5-yl)-l-(p-tolyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -ethyl-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-isobutyl-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -benzyl-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l-(3-chlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l-(4-chlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1, 2-bis(l-(2,3-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l-(2,4-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,6-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3,4-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-bromophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-bromophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-fluorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(2-fluorophenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,3 -dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2,4-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2,5-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2,6-dimethyIphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(l -(3,4-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1-(3,5-dimethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2-ethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-ethylphenyl)-4-(2-isopropyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-l-(4-methoxyphenyl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-isopropyl-2H-tetrazol-5-yl)-l-(p-tolyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -isobutyl-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-benzyl-4-(2-benzyl-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3-chlorophenyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(2,3-dichlorophenyl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,6-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1-(3,4-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3,5-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(3-bromophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-bromophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,3-dimethylphenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,4-dimethylphenyl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-l-(3,5-dimethylphenyl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-benzyl-2H-tetrazol-5-yl)-1-(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -methyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -ethyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -isobutyl-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-benzyl-4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-chlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1-(3-chlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-chlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,3-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,4-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,5-dichlorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l -(2,6-dichlorophenyl)-l H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(3,4-dichlorophenyl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-l-(3,5-dichlorophenyl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-bromophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(3-bromophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-bromophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-fluorophenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-fluorophenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,3 -dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,4-dimethylphenyl)-1 H-pyrazol-
5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,5-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2,6-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(3,4-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(3,5-dimethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(2-ethylphenyl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-ethylphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(4-methoxyphenyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-bromobenzyl)-2H-tetrazol-5-yl)-1-(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-methyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediyIbis(l-ethyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l -isobutyl-1 H-pyrazole-5,4-diyl))bis(2H-tetrazole-
5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-benzyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-
diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5,-disulfanediylbis(l-phenyl-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-
diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2-chlorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5'-(5,5'-disulfanediylbis(l-(3-chlorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis( 1 -(4-chlorophenyl)-1 H-pyrazole-5,4-diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l -(2,3-dichlorophenyl)-1 H-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2,4-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis( 1 -(2,5-dichlorophenyl)-1 H-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5"-(5,5'-disulfanediylbis(l-(2,6-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methyIene))dibenzonitrile;
4,4'-((5,5,-(5,5'-disulfanediylbis(l-(3,4-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-
tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3,5-dichlorophenyl)-lH-pyrazole-5,4diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2-bromophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3-bromophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5'-(5,5*-disulfanediylbis(l-(4-bromophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5'-(5,5'-disulfanediylbis(l-(4-fluorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4,-((5,5*-(5,5'-disulfanediylbis(l-(2-fluorophenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5,-(5,5'-disulfanediylbis(l-(2,3-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5,-disulfanediylbis(l-(2,4-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5,-(5,5'-disulfanediylbis(l-(2,5-dimethylphenyl)-lH-pyrazole-5,4-diy]))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5,-(5,5*-disulfanediylbis(l-(2,6-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3,4-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(3,5-dimethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(2-ethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5,-disulfanediylbis(l-(4-ethylphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
454'.((555'.(555'.disulfanediylbis(l-(4-methoxyphenyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis( 1 -(p-tolyl)-1 H-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
4,4'-((5,5'-(5,5'-disulfanediylbis(l-(o-tolyl)-lH-pyrazole-5,4-diyl))bis(2H-tetrazole-5,2-diyl))bis(methylene))dibenzonitrile;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-l -methyl-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-ethyl-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -isobutyl-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -benzyl-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l, 2-bis(l-(3-chlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-chlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1, 2-bis(l -(2,3-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-
5-yl)disulfane;
1,2-bis( 1 -(2,4-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol- 5-yl)disulfane;
l,2-bis(l-(2,6-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(3,4-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-
5-yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2-bromophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(4-bromophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(4-fluorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-fluorophenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2,3-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1H-
pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,4-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1H-
pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1H-
pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,6-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1H-
pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-
pyrazol-5-yl)disulfane;
l,2-bis(l-(3,5-dimethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-
pyrazol-5-yl)disulfane;
l,2-bis(l-(2-ethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(l -(4-ethylphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(4-methoxyphenyl)-4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-
5-yl)disulfane;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -methyl-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-ethyl-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-isobutyl-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)
disulfane;
1,2-bis( 1 -benzyl-4-(2-(3 -methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l-phenyl-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2-chlorophenyl)-4-(2-(3 -methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(3-chlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-chlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2,3-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,4-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(2,5-dichIorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazoI-5-yl)disulfane;
1,2-bis( 1 -(2,6-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(3,4-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-
5-yl)disulfane;
1,2-bis( 1 -(3,5-dichlorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-
5-yl)disulfane;
l,2-bis(l-(2-bromophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(4-bromophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(l -(4-fluorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-fluorophenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,3-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1-(2,4-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -(2,5-dimethylphenyl)-4-(2-(3 -methylbenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-
5-yl)disulfane;
l,2-bis(l-(2,6-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-
5-yl)disulfane;
l,2-bis(l-(3,4-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(3,5-dimethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-ethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(l -(4-ethylphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l H-pyrazol-5-yl)disulfane;
l,2-bis(l-(4-methoxyphenyl)-4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-l-(o-tolyl)-lH-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(3-methylbenzyl)-2H-tetrazol-5-yl)-1 -(p-tolyl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-methyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
1,2-bis( 1 -ethyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -isobutyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis( 1 -benzyl-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-yl)disulfane;
1,2-bis(4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 -phenyl-1 H-pyrazol-5-yl)disulfane;
l,2-bis(l-(2-chlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-yl)disulfane;
l,2-bis(l-(3-chlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(4-chlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2,3-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1-(2,4-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2,5-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
L2-bis( 1 -(2,6-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(l -(3,4-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(3,5-dichlorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2-bromophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(l-(3-bromophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(l-(4-bromophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(l -(4-fluorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2-fluorophenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis(l -(2,3-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(2,4-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1-(2,5-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis(l -(2,6-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(3,4-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(l-(3,5-dimethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(2-ethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
1,2-bis( 1 -(4-ethylphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 H-pyrazol-5-
yl)disulfane;
l,2-bis(l-(4-methoxyphenyl)-4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-lH-pyrazol-5-
yl)disulfane;
l,2-bis(4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-l-(o-tolyl)-lH-pyrazol-5-yl)disulfane;
or
1,2-bis(4-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1 -(o-tolyl)-1 H-pyrazol-5-yl)disulfane. 7. A process for preparing a compound of formula I, its derivatives, salts, stereo¬isomers, or regio-isomers thereof, comprising:
treating a compound of formula III
Formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent to obtain the compound of formula I, and its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein:
R1 is selected from -SH, -SCH2Ph, -SR or -S-SR1'; where R is a CM alkyl and R1'is a group of formula II where * denotes the point of attachment
R2 is selected from a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, F, I, CM alkyl, phenyl,or a C1-C4 alkoxy; and
R3 is selected from a straight chain or a branched chain Cj.7 alkyl, or a C6-Ci4 aryl
group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, Ci_5 alkyl, phenyl or a Q-C4 alkoxy; and R4 is selected from CI, Br or I
8. The process as claimed in claim 7, said process comprising: treating a compound of formula III
Formula HI with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent to obtain the compound of formula I, and its derivative, salt, stereo-isomer, regio-isomer thereof, wherein:
Ri is selected from -SH, -SCH2Ph, -SR or -S-SR1'; where R is a CM alkyl and Ri' is a group of formula II where * denotes the point of attachment
Formula II R2 is selected from a C1-3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and R3 is selected from a straight chain or a branched chain CM alkyl, or a phenyl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C1-2 alkyl, phenyl or a C1-C4 alkoxy; and R4 is selected from CI, Br or I.
9. The process as claimed in claim 7 or 8, wherein said thiol is selected from a CM alkyl thiol or benzyl thiol; and the alkali metal hydrosulfide is selected from sodium hydrosulfide or potassium hydrosulfide.
10. The process as claimed in claim 7, or 8 wherein the polar solvent is selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water.
11. The process as claimed in claim 7, comprising treating a compound of formula III
Formula III with a benzyl thiol in the presence of a sodium hydride and N,N-dimethylformamide to obtain a compound of formula I, and its derivative, salt, stereo-isomer, regio-isomer thereof, wherein: R1 is -SCH2Ph;
R2 is selected from a C1.3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, NO2, CN, C1-2 alkyl, or a C1-C2 alkoxy; and
R3 is selected from a straight chain or a branched chain C1-4 alkyl or a phenyl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C\.2 alkyl, phenyl or a CrC4 alkoxy; and R4 is selected from CI, Br or I 12. The process as claimed in claim 7, comprising treating a compound of formula III
Formula III with sodium hydrosulfide, in the presence of N,N-dimethylformamide to obtain a compound of formula I, and its derivatives, salts, stereo-isomers, regio-isomers thereof, wherein:
Ri is -SH, or -S-SRi', where R is a CM alkyl and Ri', is a group of formula II where * denotes the point of attachment
Formula II
R2 is selected from a C1.3 alkyl;
wherein said alkyl is optionally substituted with a phenyl group; the substituent when present in the phenyl group is one or more substituent independently selected from CI, Br, N02, CN, C1-2 alkyl, or C1-C2 alkoxy;
R3 is selected from a straight chain or a branched chain CM alkyl or a C6 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, C\.2 alkyl, phenyl or a C1-C4 alkoxy; and
R4 is selected from CI, Br or I 13. A process for preparing a compound of formula I, comprising:
treating malononitrile with a compound of formula VIII, wherein R5 is
independently selected from a straight or a branched CM alkyl, in the presence of
acetic anhydride to obtain a compound of formula VII, wherein R5 is selected from a
straight or a branched CM alkyl;
treating the compound of formula VII with an N-alkyl hydrazine sulfate and a
base in the presence of an alcohol to obtain a compound of formula VI;
Formula VII Formula VIII
treating the compound of formula VI with sodium nitrite, cuprous halide and a mineral acid to obtain a compound of formula V;
treating the compound of formula V with an optionally substituted sodium azide in the presence of a ammonium halide and a polar solvent to obtain a compound of formula IV;
Formula VI Formula V
alkylating the compound of formula IV with a dialkyl sulfate and a base in the presence of a polar solvent to obtain a compound of formula III; and
R3
treating the compound of formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent to obtain a compound of formula I
Formula III
14. The process as claimed in claim 13, wherein the base is selected from alkali metal hydroxides, alkali metal carbonates or organic bases.
15. The process as claimed in claim 14, wherein the alkali metal hydroxide is selected from sodium hydroxide, potassium hydroxide or lithium hydroxide; alkali metal carbonate is selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and organic base is selected from triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline.
16. The process as claimed in claim 13, wherein the alcohol is selected from methanol, ethanol or propanol; the mineral acid is selected from hydrochloric acid, hydrobromic acid, sulfuric acid or nitric acid; and the polar solvent is selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water.
17. The process as claimed in claim 13, wherein the ammonium halide is selected from ammonium chloride, ammonium bromide or ammonium iodide; and the cuprous halide is selected from cuprous chloride, cuprous bromide or cuprous iodide.
18. The process as claimed in claim 13, wherein the thiol is selected from Ci_4 alkyl thiol or benzyl thiol; and the alkali metal hydrosulfide is selected from sodium hydrosulfide or potassium hydrosulfide.
19. The process as claimed in claim 13, comprising:
treating malononitrile with a triethyl orthoformate in the presence of acetic anhydride to obtain 2-(ethylmethylene)malononitrile;
treating the 2-(ethylmethylene)malononitrile with N-methyl hydrazine sulfate and triethyl amine in the presence of methanol to obtain 5-amino-l -methyl- \H-pyrazole-4-carbonitrile;
chlorinating the 5-amino-l-methyl-l//-pyrazole-4-carbonitrile with sodium nitrite, cuprous chloride and hydrochloric acid to obtain 5-chloro-1 -methyl- \H-pyrazole-4-carbonitrile;
treating the 5-chloro-1-methyl-l//-pyrazole-4-carbonitrile with sodium azide in the presence of ammonium chloride and N,N-dimethylformamide to obtain 5-(5-chloro-1 -methyl-1 //-pyrazole-4-yl)-2//-tetrazole;
methylating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole) with a dimethyl sulfate and a potassium carbonate in the presence of acetone to obtain 5-(5-chloro-1 -methyl-1 //-pyrazole-4-yl)-1 -methyl-2//-tetrazole) or 5-(5-chloro-1 -methyl-lZ/-pyrazole-4-yl)-2-methyl-2//-tetrazole) or mixtures thereof; and
treating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-l-methyl-2//-tetrazole) or 5-(5-chloro-l -methyl-li/-pyrazole-4-yl)-2-methyl-2//-tetrazole), or mixtures thereof with benzyl thiol in the presence of N,N-dimethylformamide and sodium hydride to obtain 5-(5-(benzylsulfanyl)-l -methyl-l#-pyrazol-4-yl)-l-methyl-2//-tetrazole, or 5-(5-(benzylsulfanyl)-1 -methyl- l//-pyrazol-4-yl)-2-methyl-2//-tetrazole, or mixture thereof, of formula I. 20. The process as claimed in claim 13, comprising:
treating malononitrile with a triethyl orthoformate in the presence of acetic anhydride to obtain 2-(ethylmethylene)malononitrile;
treating the 2-(ethylmethylene)malononitrile with N-methyl hydrazine sulfate and triethyl amine in the presence of methanol to obtain 5-amino-l -methyl-\H-pyrazole-4-carbonitrile;
chlorinating the 5-amino-l-methyl-l//-pyrazole-4-carbonitrile with sodium nitrite, cuprous chloride and hydrochloric acid to obtain 5-chloro-1 -methyl-\H-pyrazole-4-carbonitrile;
treating the 5-chloro-1-methyl-l//-pyrazole-4-carbonitrile with sodium azide in the presence of ammonium chloride and N,N-dimethylformamide to obtain 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole;
methylating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2//-tetrazole) with a dimethyl sulfate and potassium carbonate in the presence of acetone to obtain 5-(5-
chloro-1 -methyl-1 //-pyrazole-4-yl)-1 -methyl-2//-tetrazole), or 5-(5-chloro-1 -methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole), or mixtures thereof; and
treating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-l-methyl-2//-tetrazole), or 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole), or mixtures thereof, with sodium hydrosulfide in the presence of N,N-dimethylformamide to obtain (1-methyl-4-( 1 -methyl-2//-tetrazol-5-yl)-1 //-pyrazole-5-thiol), (1 -methyl-4-(2-methyl-2//-tetrazol-5-yl)-1 //-pyrazole-5-thiol), or (1,2-bis-( 1 -methyl-4-(2-methyl-2#-tetrazol-5-yl)-l//-pyrazol-5-yl)disulfane), or mixtures thereof, of formula I. 21. A process for preparing a compound of formula I, comprising:
treating a compound of formula XIV with phosphoryl chloride in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, dichloromethane, 1,2-dichloroethane, or tetrahydrofuran, to obtain a compound of formula XIII;
Formula XIV Formula XIII
wherein:
R.3 is selected from a straight or a branched chain CI-7 alkyl; or a C6-C14 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, Ci_s alkyl, phenyl, or a C1-C4 alkoxy; treating the compound of formula XIII with hydroxylamine hydrochloride in the presence of an alcohol selected from methanol, ethanol or propanol, to obtain a compound of formula XII; and
treating the compound of formula XII with sodium azide in the presence of ammonium chloride and a polar solvent selected from N,N- dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone,tetrahydrofuran or water, to obtain the compound of formula XI.
reacting a compound of formula XI with an alkylating agent such as alkyl halide, or dialkyl sulfate in the presence of a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic bases such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline, to obtain a compound of formula X;
wherein:
R.3 is selected from a straight or a branched chain Ci_7 alkyl; or a C6-C14 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, CM alkyl, phenyl, or a C1-C4 alkoxy; and
halogenating the compound of formula X with a halogenating agent selected from N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of polar solvent selected from N,N-dimethylformarnide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, to obtain the compound of formula III.
treating the compound of formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water to obtain a compound of formula 1 22. A process for preparing a compound of formula I, comprising:
treating a compound of formula XIV with iodine and a strong oxidizing agent such as hydrogen peroxide in aqueous medium to obtain a compound of formula XVI;
wherein:
R.3 is selected from a straight or a branched chain C1-7 alkyl; or a C6-C14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl;
said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, CM alkyl, phenyl, or a Q-C4 alkoxy; treating the compound of formula XVI with either potassium ferrocyanide and palladium (II) acetate in the presence of a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, n-methyl-2- pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water; or
sodium cyanide or copper cyanide in the presence of cuprous halides such as cuprous iodide and N,N-dimethyl ethylene diamine with a non polar solvent such toluene, xylene, or benzene,
to obtain a compound of formula XV; and Formula XV
treating the compound of formula XV with sodium azide and either tri-n-butyl tin chloride in the presence of a non polar solvent selected from toluene, xylene or benzene; or ammonium chloride and N,N-dimethylformamide, to obtain the compound of formula XI.
reacting a compound of formula XI with an alkylating agent such as alkyl halide, or dialkyl sulfate in the presence of a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic bases such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline, to obtain a compound of formula X;
R.3 is selected from a straight or a branched chain Ci_7 alkyl; or a C6-C14 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituent independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, Ct.5 alkyl, phenyl, or a C1-C4alkoxy; and
halogenating the compound of formula X with a halogenating agent selected from N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, to obtain the compound of formula III.
treating the compound of formula III with a thiol or an alkali metal hydrosulfide in the presence of a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water to obtain a compound of formula I 23. The process as claimed in claim 21, for preparing a compound of formula I, its derivative, salt, stereoisomer or regioisomer thereof, comprising
treating a 1 -methyl-l//-pyrazole with phosphoryl chloride in the presence of N,N-dimethylformamide, to obtain a 1 -methyl- l#-pyrazole-4-carbaldehyde;
treating the 1-methyl-l//-pyrazole-4-carbaldehyde with hydroxylamine hydrochloride in the presence of ethanol, to obtain a 1- methyl -l//-pyrazole-4-carbaldehyde oxime;
treating the 1-methyl-l//-pyrazole-4-carbaldehyde oxime with sodium azide in the presence of ammonium chloride and N,N-dimethylformamide, to form the 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole;
reacting 5-(l -methyl- l//-pyrazole-4-yl)-2//-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl- li/-pyrazol-4-yl)-2//-tetrazole; and
chlorinating the 2-methyl-5-(l-methyl-l//-pyrazole-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-1 -methyl- \H-pyrazol-4-yl)-2-methyl-2//-tetrazole or 5-(5-chloro-1 -methyl-1 //-pyrazole-4-yl)-1 -methyl-2//-tetrazole) or mixtures thereof;
treating the 5-(5-chloro-l-methyI-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole or 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-l-methyl-2//-tetrazole) or mixtures thereof with benzyl thiol in the presence of a N,N-dimethylformamide and sodium hydride to obtain compound 5-(5-(benzylsulfanyl)-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole or 5-(5-(benzylsulfanyl)-1 -methyl-li/-pyrazol-4-yl)-1 -methyl-27/-tetrazole, or mixture thereof of formula I, wherein Ri is -SCtbPh; 24. A process for preparing a compound of formula I, comprising:
treating 1-methyl-l//-pyrazole with phosphoryl chloride in the presence of N,N-dimethylformamide, to obtain 1-methyl-l//-pyrazole-4-carbaldehyde;
treating the 1-methyl-l//-pyrazole-4-carbaldehyde with hydroxylamine hydrochloride in the presence of ethanol, to obtain 1-methyl-l//-pyrazole-4-carbaldehyde oxime;
treating the 1-methyl-l//-pyrazole-4-carbaldehyde oxime with sodium azide in the presence of ammonium chloride and N,N-dimethylformamide, to form the 5-(l-methyl-l//-pyrazol-4-yl)-2i/-tetrazole;
reacting the 5-(l-methyl-l//-pyrazole-4-yl)-2//-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole;
chlorinating the 2-methyl-5-(l-methyl-l/f-pyrazole-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l-methyl-\H-pyrazol-4-yl)-2-methyl-2//-tetrazole;
treating the 5-(5-chloro-1 -methyl- l//-pyrazole-4-yl)-2-methyl-2//-tetrazole with sodium hydrosulfide in the presence of a N,N-dimethylformamide to obtain the compounds (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-li/-pyrazole-5-thiol), or (1-methyl-4-(l-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or its disulfide (1,2-bis-(l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazol-5-yl) disulfane), or mixture thereof, of the formula
25. A process for preparing a compound of formula I, comprising:
treating 1-methyl-l//-pyrazole with iodine and hydrogen peroxide in aqueous medium to obtain 4-iodo-l-methyl-l//-pyrazole;
treating the 4-iodo-l-methyl-l//-pyrazole with potassium ferrocyanide and palladium (II) acetate in the presence of sodium carbonate, and N,N-dimethylacetamide, to obtain 1-methyl-l//-pyrazole-4-carbonitrile;
treating the 1-methyl-lH-pyrazole-4-carbonitrile with sodium azide and either with tri-n-butyl tin chloride in the presence of toluene, or ammonium chloride in the presence of N,N-dimethylformamide to obtain 5-(l-methyl-l//-pyrazol-4-yi)-2//-tetrazole;
reacting the 5-(l -methyl- l//-pyrazol-4-yl)-2//-tetrazole with methyl iodide or dimethyl sulphate, in the presence of potassium hydroxide or potassium carbonate to obtain 2-methyl-5-( 1 -methyl- l//-pyrazol-4-yl)-2//-tetrazole;
chlorinating the 2-methyl-5-(l-methyl-l//-pyrazol-4-yl)-27/-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l -methyl- \H-pyrazol-4-yl)-2-methyl-2//-tetrazole;
treating the 5-(5-chIoro-l-methyl-l//-pyrazole-4-yI)-2-methyl-2//-tetrazole with benzyl thiol in the presence of N,N-dimethylformamide and sodium hydride to obtain compound 5-(5-(benzylthio)-l-memyl-l//-pyrazol-4-yl)-2-methyl-2i/-tetrazole
or 5-(5-(benzylthio)-l -methyl- l//-pyrazol-4-yl)-l-methyl-2//-tetrazole or mixture thereof, of formula I, wherein Ri is -SCH2PI1;
26. A process for preparing a compound of formula I, comprising:
treating 1-methyl-l//-pyrazole with iodine and hydrogen peroxide in aqueous medium to obtain 4-iodo-l-methyl-l//-pyrazole;
treating the 4-iodo-l-methyl-17/-pyrazole with potassium ferrocyanide and palladium (II) acetate in the presence of sodium carbonate, and N,N-dimethylacetamide, to obtain 1-methyl-l//-pyrazole-4-carbonitrile;
treating the 1-methyl-lH-pyrazole-4-carbonitrile with sodium azide and either with tri-n-butyl tin chloride in the presence of toluene, or ammonium chloride in the presence of N,N-dimethylformamide to obtain 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole;
reacting the 5-(l-methyl-l//-pyrazol-4-yl)-2//-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l-methyl-l//-pyrazol-4-yl)-2#-tetrazole;
chlorinating the 2-methyl-5-(l -methyl-l//-pyrazol-4-yl)-2//-tetrazole with N-chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l-methyl-l//-pyrazol-4-yl)-2-methyl-2//-tetrazole;
treating the 5-(5-chloro-l-methyl-l//-pyrazole-4-yl)-2-methyl-2//-tetrazole with sodium hydrosulfide in the presence of a N,N-dimethylformamide to obtain the compounds (l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or (1-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazole-5-thiol), or its disulfide (1,2-bis-(l-methyl-4-(2-methyl-2//-tetrazol-5-yl)-l//-pyrazol-5-yl) disulfane), or mixture thereof, of the formula
| # | Name | Date |
|---|---|---|
| 1 | 2535-CHE-2012 FORM-5 26-06-2012.pdf | 2012-06-26 |
| 1 | 2535-CHE-2012-AbandonedLetter.pdf | 2018-04-10 |
| 2 | 2535-CHE-2012-DUPLICATE-FER-2017-10-12-10-31-19.pdf | 2017-10-12 |
| 2 | 2535-CHE-2012 FORM-3 26-06-2012.pdf | 2012-06-26 |
| 3 | 2535-CHE-2012-FER.pdf | 2017-09-19 |
| 3 | 2535-CHE-2012 FORM-2 26-06-2012.pdf | 2012-06-26 |
| 4 | abstract2535-CHE-2012.jpg | 2013-12-24 |
| 4 | 2535-CHE-2012 FORM-1 26-06-2012.pdf | 2012-06-26 |
| 5 | 2535-CHE-2012 DSECRIPTION (COMPLETE) 26-06-2012.pdf | 2012-06-26 |
| 5 | 2535-CHE-2012 FORM-3 05-09-2013.pdf | 2013-09-05 |
| 6 | 2535-CHE-2012 DSECRIPTION (COMPLETE) 1 26-06-2012.pdf | 2012-06-26 |
| 6 | 2535-CHE-2012 CORRESPONDENCE OTHERS 05-09-2013.pdf | 2013-09-05 |
| 7 | 2535-CHE-2012 CORRESPONDENCE OTHERS 26-06-2012.pdf | 2012-06-26 |
| 7 | 2535-CHE-2012 CORRESPONDENCE OTHERS 22-01-2013.pdf | 2013-01-22 |
| 8 | 2535-CHE-2012 CLAIMS 26-06-2012.pdf | 2012-06-26 |
| 8 | 2535-CHE-2012 FORM-1 22-01-2013.pdf | 2013-01-22 |
| 9 | 2535-CHE-2012 ABSTRACT 26-06-2012.pdf | 2012-06-26 |
| 9 | 2535-CHE-2012 OTHER PATENT DOCUMENT 22-01-2013.pdf | 2013-01-22 |
| 10 | 2535-CHE-2012 CORRESPONDENCE OTHERS 26-12-2012..pdf | 2012-12-26 |
| 10 | 2535-CHE-2012 POWER OF ATTORNEY 30-07-2012.pdf | 2012-07-30 |
| 11 | 2535-CHE-2012 CORRESPONDENCE OTHERS 30-07-2012.pdf | 2012-07-30 |
| 11 | 2535-CHE-2012 FORM-3 26-12-2012..pdf | 2012-12-26 |
| 12 | 2535-CHE-2012 CORRESPONDENCE OTHERS 30-07-2012.pdf | 2012-07-30 |
| 12 | 2535-CHE-2012 FORM-3 26-12-2012..pdf | 2012-12-26 |
| 13 | 2535-CHE-2012 CORRESPONDENCE OTHERS 26-12-2012..pdf | 2012-12-26 |
| 13 | 2535-CHE-2012 POWER OF ATTORNEY 30-07-2012.pdf | 2012-07-30 |
| 14 | 2535-CHE-2012 OTHER PATENT DOCUMENT 22-01-2013.pdf | 2013-01-22 |
| 14 | 2535-CHE-2012 ABSTRACT 26-06-2012.pdf | 2012-06-26 |
| 15 | 2535-CHE-2012 FORM-1 22-01-2013.pdf | 2013-01-22 |
| 15 | 2535-CHE-2012 CLAIMS 26-06-2012.pdf | 2012-06-26 |
| 16 | 2535-CHE-2012 CORRESPONDENCE OTHERS 22-01-2013.pdf | 2013-01-22 |
| 16 | 2535-CHE-2012 CORRESPONDENCE OTHERS 26-06-2012.pdf | 2012-06-26 |
| 17 | 2535-CHE-2012 CORRESPONDENCE OTHERS 05-09-2013.pdf | 2013-09-05 |
| 17 | 2535-CHE-2012 DSECRIPTION (COMPLETE) 1 26-06-2012.pdf | 2012-06-26 |
| 18 | 2535-CHE-2012 FORM-3 05-09-2013.pdf | 2013-09-05 |
| 18 | 2535-CHE-2012 DSECRIPTION (COMPLETE) 26-06-2012.pdf | 2012-06-26 |
| 19 | abstract2535-CHE-2012.jpg | 2013-12-24 |
| 19 | 2535-CHE-2012 FORM-1 26-06-2012.pdf | 2012-06-26 |
| 20 | 2535-CHE-2012-FER.pdf | 2017-09-19 |
| 20 | 2535-CHE-2012 FORM-2 26-06-2012.pdf | 2012-06-26 |
| 21 | 2535-CHE-2012-DUPLICATE-FER-2017-10-12-10-31-19.pdf | 2017-10-12 |
| 21 | 2535-CHE-2012 FORM-3 26-06-2012.pdf | 2012-06-26 |
| 22 | 2535-CHE-2012-AbandonedLetter.pdf | 2018-04-10 |
| 22 | 2535-CHE-2012 FORM-5 26-06-2012.pdf | 2012-06-26 |
| 1 | Search_strategy_2535_CHE_2012_31-08-2017.PDF |