Field of the Invention
Provided herein are substituted aromatic sulphonamides, which are tRNA synthetase inhibitors, and hence can be used as antimicrobial agents. Compounds disclosed herein can be used for the treatment or prevention of a condition caused by or contributed to by gram-positive, gram-negative, anaerobic bacteria or fungal organisms, more particularly against bacterium, for example, Staphylococci, Enterococci, Streptococci, Haemophilus, Moraxalla, Escherichia, CMamydia, Rickettsiae, Mycoplasm, Legionella, Mycobacterium, Helicobacter, Clostridium, Bacleroides, Corynebacterium, Bacillus or Enterobactericeae, and fungal organisms, for example, Aspergillus, Blastomyces, Candida, Coccidiodes, Cryptococcus, Epidermophyton, Hendersonula, Histoplasma, Microsporum, Paecilomyces, Paracoccidiodes, Pneumocystis, Trichophyton, or Trichosporium. Processes for the preparation of these compounds, pharmaceutical compositions thereof, and method of treating microbial infections are also provided.
Background of the Invention
Antibiotics are of immense value for combating infectious diseases. In recent decades, the effectiveness of antibiotics has been threatened by an inexorable rise in the prevalence of microbial drug resistance. Some important pathogens have serious resistance problems Staphylococcus aureus is perhaps the most significant of these pathogens. It causes community and hospital acquired infections and is associated with high morbidity and mortality rates. Vancomycin has been used as the antibiotic of last resort to treat methicillin-resistance Staphylococcus aureus infections (MRSA) with multiple resistance. Strains with some level of resistance to vancomycin (Vancomycin intermediates resistant Staphylococcus aureus, VISA) have been known since 1996, but the newly identified highly resistant strain (VRSA) heralds a new stage in the battle with this pathogen. Other serious treatment problems include multidrug resistance in tuberculosis, vancomycin resistant enterococci (VRE), resistance owing to extended spectrum p-lactamases (ESBLs) in Enterobacteriaceae and Pseudomonas aeruginosa, and penicillin resistance in Streptococcus pneumonias.
These circumstances have prompted efforts to develop new antibiotics that overcome the emerging antibiotic resistance bacteria. The amino acyl tRNA synthetases are essential enzymes found in all living organisms. These enzymes have emerged as an attractive target for the development of new antibiotics. Amino acyl tRNA synthetases charge tRNA molecules with their corresponding amino acid, an essential step in protein synthesis. There are 20 tRNA synthetases, most of which correspond to attractive broad-spectrum antibacterial targets. This is a validated target class in that pseudomonic acid A, also known as mupirocin, a natural product

from Pseudominas fluorescent, inhibits isoleucyl tRNA synthtase and is marketed as a topics' antibiotic Bactropan. Other known natural products directed against amino acyl tRr-V synthetases include borrelidin, furanomycin, granaticin, indolmycin, ochartoxin A, a id cispentacin, none of them has been developed as antibiotic compounds.
U.S. Patent Application Nos. 20040224981 and 20030013724 disclose tRNA synthetase inhibitors. WO 00/18772 discloses condensed imidazolidinone as tRNA synthetase inhibitors. U.S. Patent Nos. 5,191,093 and 4,916,155 disclose crystalline pseudomonate, process for its production and its use in human and veterinary medicines. U.S. Patent No. 4,916,155 discloses crystalline calcium pseudomonate or the hydrate thereof, and their use in human and veterinary medicine.
Novel synthetic compounds, which target tRNA synthetases, offer clear advantages as useful therapeutic agents to curb the threat of drug resistance.
Summary of the Invention
Accordingly, this invention provides substituted aromatic sulphonamides which are tRNA synthetase inhibitors, and hence can be used for the treatment of microbial infections, and processes for the synthesis of these compounds. Pharmaceutically acceptable salt5;, pharmaceutically acceptable solvates, stereoisomers, prodrugs, metabolites, polymorphs and N-oxides of these compounds having same type of activity are also provided. Pharmaceutical compositions containing the disclosed compounds (Formula 1) together with pharmaceutically acceptable carriers, excipients or diluents, which can be used for the treatment of microbial infections. Other aspects will be set forth in the accompanying description which follows and in part will be apparent from the description or may be learnt by the practice of the invention.
In one aspect, there are provided compounds having the structure of Formula 1,

pharmaceutically acceptable salts, pharmaceutically acceptable solvates, stereoisomers, prodrugs, metabolites and N-oxide thereof, wherein:
Cy can be cycloalkyl or heterocyclyl;

X and Z can be alkylene;
Y can be NRi (wherein RI can be hydrogen or alkyl);
R can be alkyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroarylalkyl, heterocycloalkyl.
In a second aspect, there is provided a method for treating or preventing a subject suffering from a condition caused by or contributed to by Gram-positive, Gram-negative, anaerobic bacteria or fungal organisms, comprising administering to said subject, a therapeutically effective amount of a compound or a pharmaceutical composition disclosed herein.
Bacterium, for example, Staphylococci, Enterococci, Streptococci, Haemophilus, Moraxalla, Escherichia, Chlamydia, Rickettsiae, Mycoplasm, Legionella, Mycobacteriutn, Helicobacter, Clostridium, Bacteroides, Corynebacterium, Bacillus or Enterobactericeae may cause the bacterial infections.
Organisms, for example, Aspergillus, Blastomyces, Candida, Coccidiodes, Cryptococcus, Epidermophyton, Hendersonula, Histoplasma, Microsporum, Paecilomyces, Paracoccidiodes, Pneumocystis, Trichophyton, or Trichosporium, Enterobactericeae may cause the fungal infections.
The conditions may be, for example, community acquired pneumonia, upper and lower respiratory tract infections, skin and soft tissue infections, hospital acquired lung infections or bone and joint infections, and other bacterial infections, for example, mastitis, catheter infection, foreign body, prosthesis infections or peptic ulcer disease.
In a third aspect, there are provided processes for the preparation of compounds as disclosed herein.
In yet another aspect, provided herein are methods for treating or preventing a condition caused by or contributed to by gram-positive, gram-negative, anaerobic bacteria or fungal organisms, comprising administering to the subject in need thereof therapeutically effective amounts of one or more compounds or pharmaceutical composition described herein .in combination with one or more aminoacyl tRNA synthetase (i.e., mupirocin) inhibitors, antibacterial agents or mixture thereof.
The following definitions apply to terms as used herein:
The term "alkyl," unless otherwise specified, refers to a monoradical branched or unbranched saturated hydrocarbon chain having from 1 to 20 carbon atoms. This term can be exemplified by groups such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-decyl, tetradecyl, and the like. Alkyl groups may be substituted further with one or more substituents selected from alkenyl, alkynyl, alkoxy.

cycloalkyl, cycloalkenyl, acyl, acylamino, acyloxy, alkoxycarbonylamino, azido, cyano, halogen, hydroxy, oxo, thiocarbonyl, carboxy, carboxyalkyl, aryl, heterocyclyl, heteroaryl, arylthio, thioi. alkylthio, aryloxy, nitro, aminosulfonyl, aminocarbonylamino, -NHC(=O)Rf, -NRfRq, -C(=O)NRtRq, -NHC(=O)NRfRq,, -C(=O)heteroaryl, C(=O)heterocyclyl, -O-C(=O)NRfRq {wherein Rf and Rq are independently selected from hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, heterocyclyl, heteroaryl, heterocyclylalkyl, heteroarylalkyl}, nitro, or -S02R6 (wherein R6 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aryl, heterocyclyl, heteroaryl, heteroarylalkyl or heterocyclylalkyl). Unless otherwise constrained by the definition, alkyl substituents may be further substituted by 1-3 substituents selected from alkyl, carboxy, -NRfRq: -C(=O)NRtRq, -OC(=O)NRfRq , -NHC(=O)NRfRq (wherein Rf and Rq are the same as defined earlier), hydroxy, alkoxy, halogen, CF3, cyano, and -SO2R6, (wherein R6 are the same as defined earlier); or an alkyl group also may be interrupted by 1-5 atoms of groups independently selected from oxygen, sulfur or -NRa- {wherein Ra is selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, acyl, aralkyl, -C(=O)ORf (wherein Rf is the same as defined earlier), SO2R6 (where Rg is as defined earlier), or -C(=O)NRfRq (wherein Rf and Rq are as defined earlier)}. Unless otherwise constrained by the definition, all substituents may be substituted further by 1-3 substituents selected from alkyl, carboxy, -NRfRq, -C (=O)NRfRq, -0-C(=0)NRf£q (wherein Rf and Rq are the same as defined earlier) hydroxy, alkoxy, halogen, CFs, cyano, and -SOaRe (where R6 is same as defined earlier); or an alkyl group as defined above that has both substituents as defined above and is also interrupted by 1-5 atoms or groups as defined above.
The term "alkylene" herein refers to -(CH)m- wherein m can be an integer ranging from '0 to 4 and one or more hydrogen can optionally be substituted with alkyl, hydroxy, halogen or oximes.
The term "cycloalkyl," unless otherwise specified, refers to cyclic alkyl groups of from 3 to 20 carbon atoms having a single cyclic ring or multiple condensed rings, which may optionally contain one or more olefmic bonds, unless otherwise constrained by the definition. Such cycloalkyl groups can include, for example, single ring structures, including cyclopropyl. cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl cyclooctyl, and the like, or multiple ring structures, including adamantanyl, and bicyclo [2.2.1] heptane, or cyclic alkyl groups to which i,« fused an aryl group, for example, indane, and the like. Spiro and fused ring structures can also be included. Cycloalkyl groups may be substituted further with one or more substituents selected from alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkenyl, acyl, acylamino, acyloxy, alkoxycarbonylamino, azido, cyano, halogen, hydroxy, oxo, thiocarbonyl, carboxy, carboxyalkyl, arylthio, thiol, alkylthio, aryl, aralkyl, aryloxy, aminosulfonyl, aminocarbonylamino, -NRfRq, -NHC(=O)NRtRq, -NHC(=O)Rf, -C(=O) NRfRq, -O-C(=O)NRfRq (wherein Rf and Rq are the same
5

as defined earlier), nitro, heterocyclyl, heteroaryl, heterocyclylalkyl, heteroarylalkyl, or -S02Ro (wherein R6 is same as defined earlier). Unless otherwise constrained by the definition, cycloalkyl substituents optionally may be further substituted by 1-3 substituents selected from alkyl, carboxy, hydroxy, alkoxy, halogen, CF3, -NRfRq, -C(=O)NRrRq, -NHC(=O)NRtRq ,'-OC(=O)NRfRq (wherein Rt- and Rq are the same as defined earlier), cyano or -SO2R6 (where R6 is same as defined earlier). "Cycloalkylalkyl" refers to alkyl-cycloalkyl group linked through alkyl portion, wherein the alkyl and cycloalkyl are the same as defined earlier.
The term "aryl," unless otherwise specified, refers to carbocyclic aromatic groups, for example, phenyl, biphenyl or napthyl ring and the like, optionally substituted with 1 to 3 substituents selected from halogen (e.g., F, Cl, Br, I), hydroxy, alkyl, alkenyl, alkynyl, cycloalkyl, arylthio, thiol, alkylthio, alkoxy, acyl, aryloxy, CFs, cyano, nitro, COORe (wherein Reis hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, heterocyclylalkyl, heteroarylalkyl), NHC(=O)Rf, NHC(=S)Rf, -NRtRq, -C(=O)NRt-Rq, -NHC(=O)NRfRq, -O-C(=O)NRfRq (wherein R,- and Rq are the same as defined earlier), -SOaRe (wherein Re is same as defined earlier), -SC>2(NH)R6, -NHSOiRe (wherein Re is same as defined earlier), carboxy, heterocyclyl, heteroaryl, heterocyclylalkyl. heteroarylalkyl or amino carbonyl amino. The aryl group optionally may be fused with a cycloalkyl group, wherein the cycloalkyl group may optionally contain heteroatoms selected from O.NorS.
The term "heteroaryl," unless otherwise specified, refers to an aromatic ring structure containing 5 or 6 ring atoms, or a bicyclic aromatic group having from 8 to 10 ring atoms, with one or more heteroatom(s) independently selected from N, O or S optionally substituted with 1 to 4 substituent(s) selected from halogen (e.g., F, Cl, Br, I), hydroxy, alkyl, alkenyl, alkynyl. cycloalkyl, arylthio, thiol, alkylthio, acyl, carboxy, aryl, alkoxy, aralkyl, cyano, nitro. heterocyclyl, heteroaryl, -NRfRq, CH=NOH, -(CH2)wC(=O)Rg (wherein w is an integer from 0-4 and Rg is hydrogen, hydroxy, ORf, NRtRq, -NHORZ or -NHOH}, -C(=O)NR,Rq and'-NHC(=0)NRfRq, -SO2R6, -O-C(=O)NR,-Rq, -O-C(=O)Rf, -O-C(=O)ORf (wherein R6, Rf and Rq are as defined earlier, and Rz is alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, heteroarylalkyl or heterocyclylalkyl). Unless otherwise constrained by the definition, the substituents are attached to a ring atom, i.e., carbon or heteroatom in the ring. Examples of heteroaryl groups include oxazolyl, imidazolyl, pyrrolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, thiazolyl, oxadiazolyl. benzoimidazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, isoxazolyl, triazinyl, furanyl, benzofuranyl, indolyl, benzothiazolyl, benzoxazolyl, isoquinolinyl, quinolinyl, 2-oxo-2,3-dihydro-lH-benzimidazol-5-yl, 2,4-dioxo-l,4-dihydro-2H-3,l-benzoxazin-6-yl, 3-methyl-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl, 1,3-benzodioxol-5-yl, 2-oxo-2,3-dihydro-1,3-benoxazol-6-yl, l-methyl-2-oxoindolin-5-yl, 3-oxo-2,3-dihydro-l,2-benzisoxazol-5-yl, 2-oxo-
6

l,2,3,4-tetrahydroquinazolin-6-yl, l-methyl-2,3-dioxoindolin-5-yl, 3,3-difluoro-2-oxoindolin-5-
yl, thieno[3,2-c]pyridin-2-yl, 2-oxochroman-6-yl, l-benzothiophen-2-yl, 5.7
dimethyl[l,2,4]triazolo[l,5-a]pyrimidin-2-yl, 2,4-dioxo-3,4-dihydro-2H-l,3-benzoxazin-6-yl, 2-methyl-4-oxo-4H-chromen-7-yl, 2-methyl-l,3-benzothiazol-5-yl, l,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-6-yl, 3-(2-amino-2-oxoethyl)-2-oxo-2,3-dihydro-l,3-benzoxazol-6-yl, 2-(methylthio)-l,3-benzothiazol-6-yl, l,3-benzothiazol-6-yl, 1-methyl-lH-imidazol-4-yl, 2-(2-amino-2-oxoethyl)-4-methyl-l,3-thiazol-5-yl, l-benzofuran-5-yl, 4-methoxy-7-niethylthieno[3,2-d]pyrimidin-6-yl, l,4-dioxo-l,2,3,4-tetrahydrophthalazin-5-yl and the like.
The term 'heterocyclyl," unless otherwise specified, refers to a non-aromatic monocyclic or bicyclic cycloalkyl group having 5 to 10 atoms wherein 1 to 4 carbon atoms in a ring are replaced by heteroatoms selected from 0, S or N, and optionally are benzofused or fused heteroaryl having 5-6 ring members and/or optionally are substituted, wherein the substituents are selected from halogen (e.g., F, Cl, Br, I), hydroxy, alkyl, alkenyl, alkynyl, cycloalkyl, acyl, aryl, alkoxy, alkaryl, cyano, nitro, oxo, carboxy, heterocyclyl, heteroaryl, -O-C(=O)Rf, -O-C(=O)ORf -C(=O)NRfRq, SO2R6, -O-C(=O)NRfRq, -NHC(=O)NRfRq, -NRtRq (wherein R6. Rf and Rq are as defined earlier) or guanidine. Heterocyclyl can optionally include rings having one or more double bonds. Unless otherwise constrained by the definition, the substituents are attached to the ring atom, i.e., carbon or heteroatom in the ring. Also, unless otherwise constrained by the definition, the heterocyclyl ring optionally may contain one or more olefinic bond(s). Examples of heterocyclyl groups include oxazolidinyl, tetrahydrofuranyl, dihydrofuranyl, dihydropyridinyl, dihydroisoxazolyl, dihydrobenzofuryl, azabicyclohexyl, dihydroindolyl, pyridinyl, isoindole 1,3-dione, piperidinyl, piperazinyl, l-benzothiophen-6-yl 1,1-dioxide, 2-methyl-4-oxo-4H-chromeii-' 7-yl, 1,3-dioxoisoindolin-4-yl, 4-methyl-1,4-diazepan-1 -yl, thiomorpholin-4-yl and the like.
The groups "aryl, heteroaryl and heterocyclyl" can optionally be substituted with
substituent(s) selected from alkyl, haloalkyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, aralkyl,
heteroarylalkyl, heterocycloalkyl, halogen, hydroxy, alkoxy, cyano, nitro, nitroso aryloxy,
haloalkoxy, CORb, CSRb, COORh, S(O)aRb, OCOORh, NHSO2Rb, NHCORb, NHCSRb, (CH)0.
2C(=O)NRcRd or NRcRj (wherein Rb, Rc and Rd are independently selected from hydrogen, alkyl,
aryl, heteroaryl, heterocyclyl and a is an integer ranging from 0-2. Unless otherwise constrained,
all substituents may optionally be further substituted by substituent(s) defined earlier. * -
The term "antibacterial agents" as used herein refers to agent, which destroys bacteria or inhibits their growth, for example, pencillins, cephalosporins, aminoglycosides, tetracyclines, macrolides, lincosamides, streptogramins, fluoroquinolones, polypeptides, rifampicin, cycloserine, aminocyclitols, glycopeptides or oxazolidinones. Aminoacyl tRNA synthetase inhibitors and the antibacterial agents may be widely chosen from among those known in the prioT
art or subsequently discovered and/or hereafter discovered and/or hereafter developed.
7 -

The term "pharmaceutically acceptable s61vates" refers to solvates with either water (e.g.,
hydrates, hemihydrate or sesquihydrate), or pharmaceutically acceptable solvents, for example
solvates with common organic solvents as ethanol and the like. Such solvates are also
encompassed within the scope of the disclosure. ,
The present invention also includes within its scope prodrugs of these agents. In general, such prodrugs will be functional derivatives of these compounds, which are readily convertible in vivo into the required compound. Conventional procedure for the selection and preparation of suitable prodrug derivatives are described, for example, in "Design of Prodrugs", ed. H Bundgaard and, Elsevier, 1985. As used herein the term "prodrugs" refers to the compounds that are rapidly transformed in vivo to yield the parent compound of Formula I, for example by hydrolysis in blood.
The disclosed compounds may get metabolized in vivo and these metabolites are also encompassed within the scope of this invention.
The term "polymorphs" includes all crystalline form as well as amorphous forms for
compounds described herein and as such are included in the present invention. ,
The phrase "pharmaceutically acceptable carriers" is intended to include non-toxic, inert solid, semi-solid or liquid filler, diluent, encapsulating material or formulation auxiliary of any type.
The term "pharmaceutically acceptable salts" refer to a salt prepared from pharmaceutically acceptable monovalent, divalent or trivalent non-toxic metal or organic base: Examples of such metal salts include, but are not limited to, lithium, sodium, potassium, calcium, magnesium, zinc, aluminum and the like. Examples of such organic bases include, but are not limited to, amino acid, ammonia, mono-alkyl ammonium, dialkyl ammonium, trialkyl ammonium and N-methyl glucamine and the like. The free acid forms of compounds of the present invention may be prepared from the salt forms, if desired, by contacting the salt with dilute aqueous solution of an acid, such as hydrochloric acid. The base addition salts may differ from the free acid forms of the compounds of this invention in such physical characteristics as solubility and melting point.
The term "pharmaceutically acceptable salts" can further refer to salts prepared from pharmaceutically acceptable non-toxic inorganic or organic acids. Examples of such inorganic acids include, but are not limited to, hydrochloric, hydrobromic, hydroiodic, nitrous, nitric, carbonic, sulfuric, phosphoric acid, and the like. Appropriate organic acids include, but are not limited to aliphatic, cycloaliphatic, aromatic, heterocyclic, carboxylic and sulfonic classes of organic acids, for example, formic, acetic, propionic, succinic, glycolic, gluconic, lactic, malic, tartaric, citric, ascorbic, glucuronic, maleic, fumaric, pyruvic, aspartic, glutamic, benzoic,
8

anthranilic, mesylic, salicylic, p-hydroxybenzoic, phenylacetic, mandelic, embonic. methanesulfonic, ethanesulfonic, benzenesulfonic, panthenic, toluenesulfonic, ?-hydroxyethanesulfonic acid and the like.
The compounds of present invention include stereoisomers. The term "stereoisomer" refers to compounds, which have identical chemical composition, but differ with regard to arrangement of the atoms and the groups in space. These include enantiomers, diastereomerg, geometrical isomers, atropisomer and conformational isomers as defined by the IUPAC 1974 Recommendations for Section E. All these stereoisomers are included within the scope of this invention.
The term "subject" as used herein refers to human or lower mammal.
The term "treatment", as used herein, unless otherwise indicated, includes the treatment or prevention of a bacterial or fungal infection as provided in the method of the present invention
The term "pharmaceutically acceptable" means approved by regulatory agency of the federal or a state government or listed in the U.S. Pharmacopoeia or other generally recognized pharmacopoeia for use in animals, and more particularly in humans.
Detailed Description of the Invention
The compounds disclosed herein may be prepared by techniques well known in the art and familiar to the average synthetic organic chemist. In addition, the compounds of the present invention may be prepared by the following reaction sequences as depicted in Schemes I, II, III, IV, V, VI, VII,VIII, IX, X, XI and XII.

The sulfonamide of Formula 5 can be prepared according to Scheme I. Thus, reacting a compound of Formula 2 with a compound of Formula 3 gives a compound of Formula 4, which on oxidation gives sulfonamide of Formula 5 (wherein R is same as defined earlier).
The reaction of a compound of -Formula 2 with a compound of Formula 3 to giveva compound of Formula 4 can be carried out in one or more organic bases, for example, pyridine. triethylamine, trimethylamine, tributylamine, N-ethyldiisopropylamine, 4-N,N-dimethylaminopyridine, N-methylmorpholine or 2,6-lutidine. The oxidation of a compound of Formula 4 to give a compound of Formula 5 can be carried out in the presence of one or more
9

oxidizing agents, for example, Dess-Martin periodinane, 2-iodoxybenzoic acid, N-chlorosuccinimide, pyridinium chlorochromate, Swern Oxidation reagent (oxalyl chloride arid dimethylsulfoxide), Pfitzner-Moffatt Oxidation reagent (dicyclohexylcarbodiimide and dimethylsulfoxide), Jones Oxidation reagent (chromic acid, aqueous sulfuric acid and acetone), pyridinium dichromate, l-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride or in mixtures thereof, in one or more solvents, for example, chlorinated solvents (chlorofonfi, dichloromethane, carbon tetrachloride or dichloroethane), polar aprotic solvents (dimethylsulfoxide, dimethylformamide, acetone, tetrahydrofuran, acetonitrile) or in mixture thereof. N-Chlorosuccinimide can be used in combination with dimethyl sulphide and 1-ethyl-3(3-dimethylaminopropyl) carbodiimide hydrochloride can be used in combination with dimethylsulfoxide.
Scheme-ll


The compound of Formula 8 can be prepared according to Scheme II. Thus, reacting a compound of Formula 6 (when R is 4-nitrophenyl) with a reducing agent gives the corresponding amine, which on reaction with 2,5-dimethoxytetrahydrofuran gives a compound of Formula 7. which is finally oxidized to give a compound of Formula 8 (wherein RI is 5-membered nitrogen containing heteroaryl).
The reduction of a compound of Formula 6 (wherein R is 4-nitrophenyl) to give
corresponding amine compound can be carried out in the presence of one or more reducing
agents, for example, Raney Nickel in hydrazine hydrate or ammonium formate, zinc, tin or iron in
the presence of hydrochloric acid, lithium aluminium hydride, or hydrogenation over palladium-
charcoal in presence of ammonium formate. The amine compound thus formed can be converted
to a compound of Formula 7 by reaction with 2,5-dimethoxytetrahydrofuran in one or more polar
protic solvents, for example, water, methanol, ethanol or acetic acid. The oxidation of a
compound of Formula 7 to give a compound of Formula 8 can be carried out using the procedures
described in Scheme I.

The compound of Formula 14 can be prepared according to Scheme III. Thus, reacting a compound of Formula 9 with a compound of Formula 10 gives a compound of Formula 11, which on treatment with tosyl chloride gives a compound of Formula 12, which on reaction with a compound of Formula Cy-Ha (wherein Ha is halogen) gives a compound of Formula 13, which is finally deprotected to give a compound of Formula 14 (wherein Cy is the same as defined earlier).
The reaction of a compound of Formula 9 with a compound of Formula 10 to give a compound of Formula 11 can be carried out in one or more solvents, for example, chlorinated solvent (chloroform, dichloromethane, carbon tetrachloride or dichloroethane), polar aprotic solvent (dimethylsulfoxide, dimethylformamide or dioxane) or in mixtures thereof. The reaction of a compound of Formula 11 with tosyl chloride to give a compound of Formula 12 can be carried out in one or more solvents, for example, ethers (diethyl ether, dioxane, or tetrahydrofuran), chlorinated solvent (dichloromethane, dichloroethane or chloroform) or in mixtures thereof. The reaction of a compound of Formula 11 with tosyl chloride can be carried out in alkali or alkaline metal hydroxide, for example, potassium hydroxide, sodium hydroxide, calcium hydroxide or in mixtures thereof. The reaction of a compound of Formula 12 with a compound of Formula Cy-Ha to give a compound of Formula 13 can be carried out in the presence of magnesium turnings in one or more solvents, for example, ethers (diethyl ether, dioxane or tetrahydrofuran), chlorinated solvent (dichloromethane or chloroform) or mixtures thereof. The deprotection of a compound of Formula 13 to give a compound of Formula 14 can be carried out in the presence of one or more mineral acids, for example, hydrochloric, hydrobromic, hydroiodic acid or in the presence of one or more organic acids, for example trifluoroacetic acid, p-toluenesulphonic acid or camphor sulphonic acid in one or more solvents, for example, polar protic solvent (water, methanol, ethanol, propanol, isopropanol or tert-butanol), polar aprotic solvent (diethyl ether, acetonitrile or dioxane), or chlorinated solvent (dichloromethane, chloroform or carbon tetrachloride).
11

The compound of Formula 16 can be prepared according to Scheme IV. Thus, a compound of Formula 15 is reduced to give a compound of Formula 16.
The reduction of a compound of Formula 15 to give a compound of Formula 16 can be carried out in one or more reducing agents, for example, hydrogenation over platinum oxide in the presence of one or more organic acids, for example, acetic or trifluoroacetic acid, or ruthenium oxide alone.

The compound of Formula 18 can be prepared according to Scheme V. Thus, reacting a compound of Formula 5 with a compound of Formula 17 gives a compound of Formula 18 (wherein Cy, X and R are the same as defined earlier).
The reaction of a compound of Formula 5 with a compound of Formula 17 to give a compound of Formula 18 can be carried out in the presence of one or more reducing agents, for example, sodium cyanoborohydride, sodium borohydride or sodium triacetoxyborohydride in one or more polar protic solvents, for example, methanol, ethanol, propanol, isopropanol or water, polar aprotic solvent (acetonitrile), or chlorinated solvent (dichloromethane, chloroform or carbon tetrachloride) in the presence of molecular sieves (4A)

The compound of Formula 22 can be prepared according to Scheme VI.Thus, reacting a compound of Formula 17 with a compound of Formula 19 gives a compound of Formula 20, which is further N-protected to give a compound of Formula 21. The compound of Formula 21 is finally reduced to give a compound of Formula 22.
The reductive amination of a compound of Formula 19 to give a compound of Formula 20 can be carried out under similar conditions as that of conversion of a compound of Formula 17 to give a compound of Formula 18. The protection of a compound of Formula 20 to give a compound of Formula 21 can be carried out with di-tert-butyl dicarbonate, in the presence of one or more organic bases, for example, triethylamine, trimethylamine, N-ethyldiisopropylamine, 2,6-lutidine, pyridine or tert-butylamine in one or more chlorinated solvents (dichloromethane, dichloroethane, chloroform or tetrachloromethane), or dioxane. The reduction of a compound of Formula 21 to give a compound of Formula 22 can be carried out in the presence of a reducing agent, for example, Raney Nickel in hydrazine hydrate or ammonium formate, zinc, tin or iron in the presence of hydrochloric acid, lithium aluminium hydride or hydrogenation over palladium-charcoal in presence of ammonium formate.

The compound of Formula 18 can also be prepared in an alternative pathway, according to scheme VII. Thus, reacting a compound of Formula 22 with a compound of Formula 3 gives a compound of Formula 23, which upon deprotection gives a compound of Formula 18.
The reaction of a compound of Formula 22 with a compound of Formula 3 to give a compound of Formula 23 can be carried out under similar condition as that of conversion of compound of Formula 2 to give a compound of Formula 4. The deprotection of compound of Formula 23 to give compound of Formula 18, can be carried out under similar conditions as thai of conversion of compound of Formula 13 to give a compound of Formula 14.
The compound of Formula 27 can be prepared according to Scheme VIII. Thus, reduction of a compound of Formula 24 gives a compound of Formula 25 which on reaction with a

compound of Formula 3 forms a compound of Formula 26, which on deprotection gives a compound of Formula 27.
The reduction of a compound of Formula 24 to give a compound of Formula 25 can be carried out under similar conditions as that of conversion of a compound of Formula 21 to give a compound of Formula 22. The reaction of a compound of Formula 25 with a compound of Formula 3 can be carried out similarly as that of conversion of a compound of Formula 2 to give a compound of Formula 4. The deprotection of a compound of Formula 26 to form a compound of Formula 27 can be carried out under similar condition as that of deprotection of a compound of Formula 13 to give a compound of Formula 14.

The compound of Formula 32 can be prepared according to Scheme IX. Thus, reacting a compound of Formula 22 with a compound of Formula 28 (wherein Ha is same as defined earlier) gives a compound of Formula 29 which is then converted to a compound of Formula 31 (wherein R3 can be heteroaryl, for example, imidazolyl, 1,2,4-triazol-l-yl, 3,5-dimethyl-lH-pyrazol-l-yl or benzimidazolyl), which on deprotection gives a compound of Formula 32.
The reaction of a compound of Formula 22 with a compound of Formula 28 to give a compound of Formula 29 can be carried out similarly as conversion of a compound of Formula 2 to form a compound of Formula 4. The reaction of a compound of Formula 29 with a compound of Formula 30 (wherein R} is same as defined as earlier) to give a compound of Formula 31 can be carried out with potassium fluoride/basic alumina , cerium(III) chloride heptahydrate/sodium iodide supported on neutral alumina in the presence polar aprotic solvents (dimethylsulphoxide. dimethylformamide, N-methyl pyrrolidone or acetonitrile). The deprotection of a compound of Formula 31 to form a compound of Formula 32 can be carried out under similar condition as that
of deprotection of a compound of Formula 13 to give a compound of Formula 14.
15

Formula 38
Scheme-X

The compound of Formula 38 can be prepared according to Scheme X. Thus, reacting a compound of Formula 22 with a compound of Formula 33 gives a compound of Formula 34 which is then converted to a compound of Formula 35. The compound of Formula 35 is then converted to a compound of Formula 37 (wherein R4 can be heterocyclyl group, for example. piperazin-1-yl, thiomorpholin-4-yl, 4-methyl-l,4-diazepan-4-yl), which on deprotection gives a compound of Formula 38.
The reaction of compound of Formula 22 with a compound of Formula 33 to give a compound of Formula 34 can be carried out similarly as conversion of a compound of Formula 2 to form a compound of Formula 4. The conversion of a compound of Formula 34 to form a compound of Formula 35 can be carried out in the presence of one or more reagents, for example, potassium iodide, lithium iodide, sodium iodide or tetra butyl ammonium iodide, in solvent for example, acetone, dimethylformamide, dimethylsulphoxide or acetonitrile. The compound of Formula 35 can be reacted with a compound of Formula 36 to form a compound of Formula 37 in the presence of one or more organic bases, for example, triethylamine, trimethylamine, pyridine, N-ethyldiisopropylamine, 2,6-lutidine or tert-butylamine, in polar aprotic solvents for example, dimethylsulphoxide, dimethylformamide or acetonitrile. The deprotection of compound of Formula 37 to form a compound of Formula 38 can be carried out under similar condition as that of deprotection of a compound of Formula 13 to give a compound of Formula 14.
16

The compounds of Formulae 41, 43 and 45 can be prepared following Scheme XI. Thus, a compound of Formula 39 (wherein Rj can be heteroaryl group, for example, l-benzofuran-5-yl or thiophene-3-yl, and E is an acid protecting group, for example, methyl, ethyl, or isopropylj is reduced to give a compound of Formula 40 (Path A) which on deprotection gives a compound of Formula 41. The compound of Formula 39 is hydrolysed to give a compound of Formula 42 (Path B), which on deprotection gives a compound of Formula 43. The compound of Formula 42 is converted to a compound of Formula 44, which on deprotection gives a compound of Formula 45.
The reduction of a compound of Formula 39 to form a compound of Formula 40 (Path A) is carried in a solvent for example methanol, ethanol, isopropanol, water or mixture (s) thereof with suitable reducing agent, for example, sodium borohydride, lithium aluminium hydride or diisobutylaluminum hydride. The deprotection of compound of Formula 40 to form a compound of Formula 41 can be carried out under similar condition as that of deprotection of a compound of Formula 13 to give a compound of Formula 14.
The hydrolysis of a compound of Formula 39 to form a compound of Formula 42 can be carried out in a solvent selected from, for example methanol, ethanol, tetrahydrofuran, dioxane. water or mixture(s) thereof in the presence of a base for example lithium hydroxide, potassium hydroxide or sodium hydroxide. The deprotection of a compound of Formula 42 to form a
17

compound of Formula 43 can be carried out under similar condition as that of deprotection of e compound of Formula 13 to give a compound of Formula 14.
Amidation of a compound of Formula 42 to form a compound of Formula 44 can i: _ carried out with ammonia solution in a solvent for example dimethyl formamide, tetrahydrofun i, dioxane or diethyl ether and a base for example triethylamine, N,N-dimethylaminopyridine, 2,6-lutidine, 1-methylpiperidine, N,N-diisopropylethylamine or N-methylmorpholine, in the presence of a additives for example hydroxybenzotriazole, 3-hydroxy-3,4-dihydro-4-oxo- 1,2,3-benzotriazine, 2-hydroxypyridine, N-hydroxysuccinimide or l-hydroxy-7-azabenzotriazole, with a suitable condensing agent for example, dicyclohexyl carbodimide, l-(3-dimethylaminopropyl>-3-ethylcarbodimide hydrochloride, chlortripyrrolidinophosphonium hexafluorophosphate or (benzotriazol-l-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate. The deprotection of compound of Formula 44 to form a compound of Formula 45 can be carried out under similar condition as that of deprotection of a compound of Formula 13 to give a compound of Formula 14.
The compounds of Formula 47 can be prepared following Scheme XII. Thus, compound of Formula 46 (wherein Ry can be aryl, heteroaryl, for example, benzene, benzothiophene or indane and n is selected from an integer ranging from 1-2) is demethylated to give a compound of
Formula 47.
The demethylation of a compound of Formula 46 to form a compound of Formula 48 can be carried out with boron tribromide in presence of chlorinated solvent for example dichloromethane, chloroform or tetrachloromethane, or sodium methane thiolate in presence of bases, for example, sodium methoxide, potassium tert-butoxide or sodium ethoxide in a solvent selected from, for example, dimethylformamide or dimethoxyethane.
In the above schemes, where the specific bases, oxidizing agents, reducing agents. coupling agents, solvents, etc., are mentioned, it is to be understood that other bases, oxidizing agents, reducing agents, coupling agents, solvents, etc., known to those skilled in the art may be used. Similarly, the reaction temperature and duration may be adjusted according to the desired needs.

The compounds disclosed herein possess antimicrobial activity against gram-positive' gram-negative, anaerobic bacteria and fungal infections. They are useful as antimicrobial agei.i; for the treatment of infectious diseases in human and animal.
Compounds of the present invention useful for such purpose are listed below:
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -2-oxo-2,3-dihydro-1H-
benzimidazole-5-sulfonamide (Compound No. 1);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-lH-
benzimidazole-5-sulfonamide (Compound No. 2);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl )phenyl] -2,4-dioxo-1,4-dihydro-2H-3,1 -
benzoxazine-6-sulfonamide (Compound No. 3);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-2-oxo-2,3-dihydro-
1,3-benzothiazole-6-sulfonamide (Compound No. 4);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -3-methyl-2-oxo-2,3-dihydro-
l,3-benzothiazole-6-sulfonamide (CompoundNo. 5);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -1,3-benzodioxole-5-
sulfonamide (Compound No. 6);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-l,3-benzodioxole-5-
sulfonamide (Compound No. 7);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide hydrochloride (Compound No. 8);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-5-[2-(methylthio)pyrimidin-4-
yl]thiophene-2-sulfonamide (Compound No. 9);
Methyl 3-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyn
thiophene-2-carboxylate (Compound No. 10);
3 -({[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] amino} sulfonyl)thiophene-2-
carboxylic acid (Compound No. 11);
3-({[2-( {[(1 S)-2-cyclohexyl-1-methylethyl] amino} methyl)phenyl] amino} sulfonyl)thiophene-2-
carboxamide(Compound No. 12);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] thieno[3,2-c]pyridine-2-
sulfonamide(Compound No. 13);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-4- methylbenzenesulfonamide
(Compound No. 14);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4-methylbenzenesulfonamide
(Compound No. 15);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-l-nitrosoindoline-6-
sulfonamide (Compound No. 16);
N-[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methy l)phenyl] -1 -nitrosoindoline-6-sulfonamide
(Compound No. 17);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methy l)phenyl] -N'-pyrimidin-2-ylbenzene-1,4-
disulfonamide (Compound No. 18);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-l-benzothiophene-6-
sulfonamide 1,1-dioxide (Compound No. 19);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -1 -benzothiophene-6-
sulfonamide 1,1-dioxide (Compound No. 20);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]isoquinoline-5-sulfonamide
(Compound No. 21);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino} methyl)phenyl]isoquinoline-5-sulfonamide
(Compound No. 22);
3-({[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino} methyl)phenyl]amino}sulfonyl)
thiophene-2-carboxylic acid (Compound No. 23);

N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-l-methyl-2-oxoindoline-5-
sulfonamide (Compound No. 24); ,
N-[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -1 -methyl-2-oxoindoline-5 -sulfonamide (Compound No. 25); N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2-oxochromane-6-sulfonamide
(Compound No. 26);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-3-oxo-2,3-dihydro-l,2-
benzisoxazole-5-sulfonamide (Compound No. 27);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-lH-benzimidazole-5-
sulfonamide (Compound No. 28);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-l,3-benzoxazole-6-
sulfonamide (Compound No. 29);
N-[2-( {[(1S)-1 -cyclohexylethyl] amino} methyl)phenyl] -4-( 1 H-pyrrol-1 -yl)benzenesulfonamide
(Compound No. 30);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-4-(lH-pyrrol-l-yl)benzenesulfonamide
(Compound No. 31);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-l-benzothiophene-2-sulfonamide (Compound
No. 32);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-5,7-dimethyl[l,2,4]triazolo[l,5-
a]pyrimidine-2-sulfonamide (Compound No. 33);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-5,7-
dimethyl[l,2,4]triazolo[l,5-a]pyrimidine-2-sulfonamide (CompoundNo. 34);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -3-methyl-2-oxo-2,3-dihydro-
l,3-benzoxazole-6-sulfonamide (CompoundNo. 35);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-2-oxo-2,3-dihydro-
l,3-benzoxazole-6-sulfonamide (CompoundNo. 36);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-3-ethyl-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide(Compound No. 37);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-ethyl-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide (Compound No. 38);
2-Acetyl-N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl) phenyl]-7-methoxy-l-
benzofuran-4-sulfonamide (Compound No. 39);
2-Acetyl-N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl) phenyl]-7-methoxy-l-
benzofuran-4-sulfonamide (Compound No. 40);
N-[2-( {[(1 S)-1-cyclohexylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-1,3-benzoxazole-6-
sulfonamide (Compound No. 41);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -2,4-dioxo-3,4-dihydro-2H-1,3 -
benzoxazine-6-sulfonamide (Compound No. 42);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -5-methoxy-1 -benzothiophene-2-
sulfonamide (Compound No. 43);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-6-hydroxy-l-benzothiophene-
2-sulfonamide (Compound No. 44);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-5-hydroxy-l-benzothiophene-2-
sulfonamide (Compound No. 45);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4,7-dimethoxy-l-
benzothiophene-2-sulfonamide (Compound No. 46);
N-[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -4,7-dimethoxy-1 -
benzothiophene-2-sulfonamide (Compound No. 47);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -7-methoxy-2-oxo-2H-
chromene-6-sulfonamide (Compound No. 48);
N-[2-({[(lS)-2-cyclohexyl-l -methylethyl] amino }methyl)phenyl]-2-oxo-2H-chromene-6-
sulfonamide (Compound No. 49);
20

N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -2-oxo-2H-chromene-6-
sulfonamide (Compound No. 50);
(4E)-N-[2-({[(lS)-2-cyclohexyl-l-methylethyl] amino}methyl) phenyl]-4-
(hydroxyimino)chromane-6-sulfonamide (Compound No. 51);
(4E)-N-[2-({[(lS)-2-cyclopentyl-l-methylethyl] amino}methyl) phenyl]-4-
(hydroxyimino)chromane-6-sulfonamide (Compound No. 52);
N-[4-({[2-({[(1S)-1 -cyclohexylethyljamino}methyl)phenyl]amino} sulfonyl)phenyl]-1 -methyl-
lH-imidazole-4-sulfonamide (Compound No. 53);
4-Amino-N-[2-({[(lS)-l-cyclohexylethyl]amino}methyl)phenyl] benzenesulfonamide
(Compound No. 54);
N- [2-( {[(1 S)-1 -cyclohexylethyl] amino} methyl)phenyl] -4-(methylsulfonyl)benzenesulfonamide
(Compound No. 55);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -1,3-dioxoisoindoline-4-
sulfonamide (Compound No. 56);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -1,3 -dioxoisoindoline-4-
sulfonamide (Compound No. 57);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -2-(trifluoromethyl)-1H-
benzimidazole-5-sulfonamide (Compound No. 58);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)pheny 1] -2-methyl-4-oxo-4H-chromene-
7-sulfonamide (Compound No. 59);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-methyl-l,3-benzothiazole-5-
sulfonamide (Compound No. 60);
N-[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -2-methyl-4-oxo-4H-chromene-
7-sulfonamide (Compound No. 61);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2-methyl-l,3-benzothiazole-5-
sulfonamide (Compound No. 62);
2-[({4-[(lZ)-buta-l,3-dien-l-ylamino]phenyl}sulfonyl)amino]benzyl benzylcarbamate
(Compound No. 63);
N-[4-( {[2-( {[(1 S)-1 - cyclohexylethyl]amino}methyl)phenyl]amino} sulfonyl) phenyl]thiophene-2-
sulfonamide (Compound No. 64);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -5,6-dihydroxy-1 -
benzothiophene-2-sulfonamide (Compound No. 65);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -6-hydroxy-1 -benzothiophene-2-
sulfonamide (Compound No. 66);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl]-5,6-dihydroxy-1 -
benzothiophene-2-sulfonamide (Compound No. 67);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-6-methoxy-l-benzothiophene-
2-sulfonamide(Compound No. 68);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-5,6-dimethoxy-l-
benzothiophene-2-sulfonamide (Compound No. 69);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino } methyl)phenyl] -6-methoxy-1 -benzothiophene-2-
sulfonamide (Compound No. 70);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl]amino} methyl)phenyl]-5,6-dimethoxy-1 -
benzothiophene-2-sulfonamide (Compound No. 71);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino} methyl)phenyl]-l,4-dimethyl-2,3-dioxo-
l,2,3,4-tetrahydroquinoxaline-6-sulfonamide (CompoundNo. 72);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-l,4-dimethyl-2,3-dioxo-l, 2,3,4-
tetrahydroquinoxaline-6-sulfonamide (Compound No. 73);
2-[6-({[2-({[(1 S)-2-cyclopentyl-1 -methylethyl]amino}methyl) phenyl]amino}sulfonyl)-2-oxo-
l,3-benzoxazol-3(2H)-yl]acetamide (CompoundNo. 74);
N-[2-({[(lS,2R)-2-cyclohexyl-2-hydroxy-l-methylethyl]amino} methyl)phenyl]-2-oxo-2,3-
dihydro-l,3-benzoxazole-6-sulfonamide (Compound No. 75);
21

N-[2-({[(lS,2R)-2-cyclohexyl-2-hydroxy-l-methylethyl]amino} methyl)phenyl]-4-nitrobenzenesulfonamide (Compound No. 76);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino]methyl)phenyl]-5-[2-(methylsulfonyl)pyrimidin-4-yl]thiophene-2-sulfonamide (Compound No. 77); N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-(methylthio)-1.3-benzothiazole-6-sulfonamide (Compound No. 78);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino]methyl)phenyl]-2-(methylthio)-1.3-benzothiazole-6-sulfonamide (Compound No. 79); N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino| methyl )phenyl]-l,3-benzothiazole-6-
sulfonamide (Compound No. 80);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2-(methylthio)-1.3-
benzoxazole-6-sulfonamide (Compound No. 81);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino]methyl)phenyl]-2-(methylthio)-1.3-
benzoxazole-6-sulfonamide (Compound No. 82);
N-[4-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]aminojmethyl)- phenyl]amino}sullbnvl)phen\ |-
1-methyl- lH-imidazole-4-sulfonamide(Compound No.83);
N-[4-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]aminoJ methyl)
phenyl]amino}sulfonyl)phenyl]thiophene-2-sulfonamide (Compound No. 84);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino] methyl )phenyl]-4-
[(methylsulfonyl)amino]benzenesulfonamide (Compound No. 85);
N-[5-({[4-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino} methyl)
phenyl]amino}sulfonyl)phenyl]amino}sulfonyl)-4-methyl-1.3-thiazol-2-yl]acetamide (CompouiH
No. 86);
Methyl 5-({[2-({[(15)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]amino j sullbin )-1 -
benzofuran-2-carboxylate(Compound No. 87);
Methyl 5-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino) methyl)phenyl]amino j sulibm 1)-1
benzofuran-2-carboxylate(Compound No. 88);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-(hydroxymeth\-l)-l-
benzofuran-5-sulfonamide (Compound No. 89);
N-[2-({[(15)-2-cyclohexyl-l-methylethyl]amino}mcthyl)phenyl]-2-(hydroxymethyl)-l-
benzofuran-5-sulfonamide (Compound No. 90);
5-({[2-({[(15)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)-l -ben/orurun-
2-carboxylic acid (Compound No. 91);
2-[6-({[2-({[(15)-2-cyclohexyl-l-methylethyl]amino' methyl)phenyl]aminoj sulibm l)-2-o\o-1.3-
benzoxazol-3(2//)-yl]acetamide (Compound No. 92);
3-(Cyanomethyl)-A^-[2-({[(liS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl|-2-iv\o-2.;-
dihydro-1,3-benzoxazole-6-sulfonamide (Compound No. 93);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}mcthyl)phenyl]-l,3-benzothiazole-2-
sulfonamide (Compound No. 94);
N-[2-({[(liS)-2-cyclopentyl-l-methylethyl]amino} methyl )phenyl]-l,3-benzothiax.ole-2-
sulfonamide (Compound No. 95);
N-[2-({[(15r)-2-cyclohexyl-l-methylethyl]amino)methyl)phenyl]-3,4-
dimethoxybenzenesulfonamide (Compound No. 96);
N-[2-({[(15)-2-cyclohexyl-l-methylethyl]amino}meth>-l)phenyl]-3,4-
dihydroxybenzenesulfonamide (Compound No. 97);
N-[2-({[(15)-2-cyclopentyl-l-methylethyl]amino]methyl)phenyl]-3.4-
dihydroxybenzenesulfonamide (Compound No. 98);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]aminojmethyl)phenyl]quinoline-6-sullbn amide
(Compound No. 99);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino)methyl)phenyl]quinoline-6-sultbnamii.lc
(Compound No. 100);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino] methyl)phenyl]-2-(trifluorometh\ 1)-1.3-
benzothiazole-6-sulfonamide (Compound No. 101);

N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-(trifluoromethyl)-l,3-
benzothiazole-6-sulfonamide (Compound No. 102);
N-[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)pheny 1] -1 H-benzotriazole-5-
sulfonamide (Compound No. 103);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-lH-benzotriazole-5-
sulfonamide(Compound No. 104);
N-(2- {[(2-cyc lohexylethyl)amino] methyl} phenyl)-2-hydroxy-1,3 -benzothiazole-6-sulfonamide
(Compound No. 105);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-2-oxo-2H-chromene-6-sulfonamide
(Compound No. 106);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-2-methyl-l,3-benzothiazole-5-sulfonamide
(Compound No. 107);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-5-fluoro-l-benzothiophene-2-sulfonamide
(Compound No. 108);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-l,3-benzothiazole-6-sulfonamide (Compound
No. 109);
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-2,4-dioxo-l,2,3,4-tetrahydroquinazoline-6-
sulfonamide (Compound No. 110);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4,7-dimethyl-l-
benzothiophene-2-sulfonamide (CompoundNo. Ill);
N-[2-( {[(1 S)-2-cyclohexyl-1-methylethyl] amino } methyl)phenyl]-4,7-dimethyl-1-benzothiophene-
2-sulfonamide (Compound No. 112);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-l-benzothiophene-2-
sulfonamide (Compound No. 113);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -4,6-dimethyl-1 -
benzothiophene-2-sulfonamide (Compound No. 114);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-4,6-dimethyl-l-benzothiophene-
2-sulfonamide (Compound No. 115);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -5 -methyl-1 -benzothiophene-3-
sulfonamide (Compound No. 116);
N-[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -5 -methyl-1 -benzothiophene-2-
sulfonamide (Compound No. 117);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4-methoxy-7-methylthieno[3,2-
d]pyrimidine-6-sulfonamide (Compound No. 118);
N-[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl]amino}methyl)phenyl]-5-methyl-1 -benzothiophene-2-
sulfonamide (Compound No. 119);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -3 -methyl-1 -benzothiophene-2-
sulfonamide (Compound No. 120);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-5-methyl-l-benzothiophene-3-
sulfonamide (Compound No. 121);
N-[2-({[(l S)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-l,2,3,4-
tetrahydroquinazoline-6-sulfonamide (Compound No. 122);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methy l)phenyl] -2-oxo-1,2,3,4-
tetrahydroquinazoline-6-sulfonamide (Compound No. 123);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl]amino} methyl)phenyl] -1 -methyl-2,3-dioxoindoline-5 -
sulfonamide (Compound No. 124);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-l-methyl-2,3-dioxoindoline-5-
sulfonamide (Compound No. 125),
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-3,3-difluoro-2-oxoindoline-5-
sulfonamide (Compound No. 126);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -3,3-difluoro-1 -methyl-2-
oxoindoline-5-sulfonamide (Compound No. 127);
23

N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3,3-difluoro-l-methyl-2-oxoindoline-5-sulfonamide (Compound No. 128); N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3,3-difluoro-2-oxoindoline-5
sulfonamide (Compound No. 129); N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-(isobutylamino)-l,3-
benzoxazole-6-sulfonamide (Compound No. 130);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -2-(isobutylamino)-1,3-benzoxazole-6-sulfonamide (Compound No. 131);
2-Amino-N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-lH-benzimidazole-5-sulfonamide (Compound No. 132);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]quinoline-8-sulfonamide (Compound No. 133);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]quinoline-8-sulfonamide (Compound No. 134);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2,5-dimethyl-l,3-benzothiazole-6-sulfonamide (Compound No. 135);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2,5-dimethyl-l,3-benzothiazole-6-sulfonamide (Compound No. 136);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-7-methyl-l-benzothiophene-2-sulfonamide (Compound No. 137);
5 -Chloro-N-[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -1,3 -benzothiazole-2-sulfonamide (Compound No. 138);
2-Amino-5-({[2-({[(lS)-2-cyclohexyl-l- methylethyl]amino}methyl)phenyl]amino}sulfonyl) phenyl trifluoroacetate (Compound No. 139);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-sulfonamide (Compound No. 140);
N- [5 -({[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] amino} sulfonyl)-2,3 -dihydro-lH-inden-2-yl]acetamide (Compound No. 141);
N-[5-( {[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] amino } sulfonyl)-2,3 -dihydro-lH-inden-2-yl]acetamide (Compound No. 142);
N-[2-( {[(1 S)-2-cyclohexyl-1-methylethyl]amino} methyl)phenyl] -1-formylindoline-5-sulfonamide (Compound No. 143);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-l-formylindoline-5-sulfonamide (Compound No. 144);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -6-methoxyindane-5-sulfonamide (Compound No. 145);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-6-methoxyindane-5-sulfonamide (Compound No. 146);
N- [4-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -2,4-dioxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide (Compound No. 147);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-6-hydroxyindane-5-sulfonamide (Compound No. 148);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -6-hydroxyindane-5-sulfonamide (Compound No. 149);
N-[5-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)-2,3-dihydro-lH-inden-l-yl]acetamide (Compound No. 150);
N- [5-( {[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl]amino } sulfonyl)-2,3-dihydro-lH-inden-l-yl]acetamide (Compound No. 151);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-(4-methylpiperazin-l-yl)propane-l-sulfonamide (Compound No. 152);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-[(3R,5S)-3,5-dimethylpiperazin-l-yl]propane-l-sulfonamide (Compound No. 153);
24

N-[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl]amino} methyl)phenyl]-3-piperidin-1 -ylpropane-1 -sulfonamide (Compound No. 154);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-morpholin-4-ylpropane-l-sulfonamide (Compound No. 155); N-(2-{[(2-cyclopentylethyl)amino]methyl}phenyl)-2-oxo-2H-chromene-6-sulfonamide
(Compound No. 156); N-(2-{[(2-cyclopentylethyl)amino]methyl}phenyl)-2-methyl-l,3-benzothiazole-5-sulfonamide
(Compound No. 157);
N-(2-{[(2-cyclopentylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-l,3-benzothiazole-6-
sulfonamide (Compound No. 158);
4-Chloro-N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2H-chromene-
6-sulfonamide (Compound No. 159);
4-Chloro-N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2H-chromene-
6-sulfonamide (Compound No. 160);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-4-fluoro-2-oxo-2H-chromene-6-
sulfonamide (Compound No. 161);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4-fluoro-2-oxo-2H-chromene-
6-sulfonamide(Compound No. 162);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -2-oxo-4-(trifluoromethyl)-2H-
chromene-6-sulfonamide (Compound No. 163);
4-Amino-N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -2-oxo-2H-chromene-
6-sulfonamide (Compound No. 164);
4-Amino-N-(2-{[(2-cyclopentylethyl)amino]methyl}phenyl)benzenesulfonamide (Compound No.
165);
N-(4-{[(2-{[(2-cyclopentylethyl)amino]methyl}phenyl)amino]sulfonyl}phenyl)thiophene-2-
sulfonamide (Compound No. 166);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2-(lH-imidazol-l-
yl)ethanesulfonamide (Compound No. 167);
N-[2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino } methyl)phenyl] -2-( 1H-1,2,4-triazol-1 -
yl)ethanesulfonamide (Compound No. 168);
N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl] -2-(3,5-dimethyl-1 H-pyrazol-1-
yl)ethanesulfonamide(CompoundNo. 169);
2-( 1 H-benzimidazol-1 -yl)-N- [2-( {[(1 S)-2-cyclohexyl-1 -methylethyl]amino} methyl)phenyl]
ethanesulfonamide (Compound No. 170);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-2-(lH-tetrazol-l-
yl)ethanesulfonamide (Compound No. 171);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -3 -(4-methyl-1,4-diazepan-1 -
yl)propane-l-sulfonamide (Compound No. 172);
N-[2-( {[(1 S)-2-cyclopentyl-1 -methylethyl]amino} methyl)phenyl]-3-piperazin-1 -ylpropane-1 -
sulfonamide (Compound No. 173);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -3-thiomorpholin-4-ylpropane-
1-sulfonamide (Compound No. 174);
N- [2-( {[(1 S)-2-cyclopentyl-1 -methylethyl] amino} methyl)phenyl] -3-( 1 H-tetrazol-1 -yl)propane-1 -
sulfonamide (Compound No. 175);
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3-(3,4-dihydroisoquinolin-
2(lH)-yl)propane-l-sulfonamide (Compound No. 176);
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl] amino }methyl)phenyl]-2-oxo-4-(trifluoromethyl)-2H-
chromene-6-sulfonamide (Compound No. 177);
N-(2-{[(2-morpholin-4-ylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-l,3-benzoxazole-6-
sulfonamide (Compound No. 178).
Because of their antimicrobial activity, the compounds described herein may be administered to an animal for treatment orally, topically, rectally, internasally, or by a parenteral
25

route. The pharmaceutical compositions of the present invention comprise a pharmaceutically effective amount of compounds described herein formulated together with one or mere pharmaceutically acceptable carriers.
Solid form preparations for oral administration include capsules, tablets, pills, powders granules, cachets and suppositories. For solid form preparations, the active compound can be mixed with at least one inert, pharmaceutically acceptable excipients or carrier, for example, sodium citrate, dicalcium phosphate and/or a filler or extenders, for example, starches, lactose, sucrose, glucose, mannitol and silicic acid; binders, for example, carboxymethylcellulose, alginates, gelatins, polyvinylpyrrolidinone, sucrose, or acacia; disintegrating agents, for example, agar-agar, calcium carbonate, potato starch, alginic acid, certain silicates and sodium carbonate; absorption acceletors, for example, quaternary ammonium compounds; wetting agents, for example, cetyl alcohol, or glycerol mono stearate; adsorbants, for example, Kaolin; lubricants , for example, talc, calcium stearate, magnesium stearate, solid polyethyleneglycol, sodium luaryl sulphate and mixture thereof. In the case of capsules, tablets, or pills, the dosage form may also comprise buffering agents.
The solid preparation of tablets, capsules, pills and granules can be prepared with coating and shells, for example, enteric coating and other coatings well known in the pharmaceutical formulating art.
Liquid form preparations for oral administration can include pharmaceutically acceptable emulsions, solutions, suspensions, syrups and elixirs. For liquid form preparations, the active compound can be mixed with water or other solvent, solubilizing agents and emulsifiers, for example, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethylformamide, oils, for example, cottonseed, groundnut, corn, germ, olive, castor and sesame oil), glycerol, and fatty acid esters of sorbitan and mixture thereof. Besides inert diluents, the oral composition can also include adjuvants, for example, wetting agents, emulsifying agents, suspending agents, sweetening agents, flavouring agents and perfuming agents.
Injectible preparations, for example, sterile injections, aqueous suspensions may be formulated according to the art using suitable dispersing or wetting and suspending agent. Among the acceptable vehicles and solvents that may be employed are water, Ringer's solution and isotonic sodium chloride.
Dosage forms for tropical or transdermal administration of compounds provided herein include ointments, pastes, creams, lotions, gels, powders, solutions, sprays, inhalants or patches. The active compound can be admixed under sterile condition with a pharmaceutically acceptable
26

carrier and any needed preservatives or buffers as may be required. Ophthalmic formulations eardrops, eye ointments, powder and solution are also contemplated as being within the scope of this invention.
The pharmaceutical preparation can be provided in a unit dosage form. In such forms, the preparation is subdivided into unit doses containing appropriate quantities of the active component. The unit dosage form can be packaged preparation, the package containing discrete capsules, powders, in vials or ampoules, and ointments capsule, sachet, tablet, gel, cream itself or it can be the appropriate number of any of these packaged forms.
Examples set forth below demonstrate general synthetic procedures for the preparation of representative compounds. The examples are provided to illustrate particular aspect of the disclosure and do not constrain the scope of the present invention as defined by the claims.
Experimental
Synthesis of compound of Formula 3 Method A:
Heterocycle/heteroaryl (1 equiv.) was added slowly to chlorosulphonic acid (15 equiv.) cooled a* 0 C. After complete addition, reaction mixture was allowed to come at room temperature ar'J stirred overnight. The reaction mixture was then poured onto crushed ice, solid if precipitated, was filtered out or extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford corresponding sulphonyl chloride.
Method B
Heterocycle/heteroaryl (1 equiv.) was added slowly to chlorosulphonic acid (15 equiv.) at 0 °C. After complete addition, reaction mixture was stirred for Ih (0°C-room temperature), then heated at 70 C for 4h. Work up was done as usual in method A.
Method C
Heterocycle/heteroaryl (1 equiv.) was added slowly to chlorosulphonic acid (15 equiv.) at -15 °C. After complete addition, reaction mixture was further cooled to -20°C and stirred at this temperature for 4h .Work up was done as usual in method A.
Method D
Aromatic hydrocarbon (33.7 mmol) dissolved in acetonitrile (30 mL) was added slowly to chlorosulphonic acid (505.5 mmol) cooled at 0°C. After complete addition, reaction mixture was heated to 55-60°C for 3h .Work up was done as usual in method A.

Method E
Heterocycle/heteroaryl (30.67 mmol) was added slowly to chlorosulphonic acid (61.34 mmolj 'S. 0°C. To the resulting mixture, thionyl chloride (92.01 mmol) was then added dropwise at the same temperature. After complete addition, reaction mixture was heated at 150°C for 2h .Work up was done as usual in method A.
Method F
Tert-butyl lithium (12 mmol) was added to heterocycle/heteroaryl (10 mmol) dissolved in dry tetrahydrofuran (50 mL) at -78°C. Sulphur dioxide was passed through the above reaction mixture for Ih at the same temperature. The reaction mixture was then allowed to come to ambient temperature. Dichloromethane (50 mL) was added to the above mixture followed by addition of N-bromosuccinimide (11 mmol) and resulting mixture was stirred for overnight. The reaction mixture was evaporated in vacua and the resulting residue was taken in dichloromethane. The organic layer was washed with water, brine and dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to afford the corresponding sulphonyl chloride.
Method G
Mercapto-heterocycle/heteroaryl (0.44 mmol) was dissolved in dichloromethane (2 mL). Water (1 mL) was added to above solution followed by addition of concentrated hydrochloric acid (3.6 mmol,0.3 mL) at 0°C. Sodium hypochlorite (3.5 mmol, 5 mL) was added dropwise to resulting mixture at the same temperature and reaction mixture was then allowed to come at an ambient temperature (2 h). Organic layer was separated, washed with sodium sulphite, water, brine and dried over anhydrous sodium sulphate. Solvent was removed under reduced pressure to afford the corresponding sulphonyl chloride.
Method H
Chlorine gas was passed to aqueous acetic acid (50 %, 60 mL) which was cooled prior at
-5°C to 0°C for 20 min. A suspension of mercapto-heterocycle/heteroaryl (59.8 mmol) in aqueous acetic acid (50 %, 60 mL) was added to the above reaction mixture with continuous stirring and continuous supply of chlorine gas maintaining the reaction temperature below 3 °C for 2h. After complete addition, the yellow suspension was stirred for 15-20 min at 0°C with continuous bubbling of chlorine gas. The reaction mixture was then quickly filtered through Buchner funnel. The precipitate obtained was washed with ice-water and then dissolved in cold dichloromethane (100 mL) and the solution was filtered through sintered funnel quickly. The filterate was washed using cold aqueous saturated sodium bicarbonate solution followed by cold brine. The organic layer was separated and dried over anhydrous sodium sulphate solution at -10°C for Ih. It was
28

filtered through celite and the filterate was concentrated under vaccum till thick slurry was obtained, at this point dry diethyl ether was added and the contents of the flask were cooled in dry ice-acetone bath for 10 min. Corresponding sulphonyl chloride thus obtained was filtered and washed using cold diethyl ether and dried under vacuum,
Method I
Acetic acid (14.5 mmol) and concentrated hydrochloric acid (14.5 mmol) was taken in a three neck round bottom flask and sulphur dioxide was passed through it for about 35 min (Solution A). Meanwhile, amino-heterocycle/heteroaryl (14.5 mmol) was taken in single neck round bottom flask and a mixture of hydrochloric acid (14.5 mmol) and water (8 mL) were added and the reaction mixture was stirred for 10 min. The reaction was then cooled to -15°C to -10°C. Sodium nitrite (15.68 mmol) dissolved in water (1.6 mL), was added to the reaction mixture dropwise maintaining temperature below -10°C. After complete addition the resulting mixture was allowed to stir for 10 min at same temperature (Solution B). Copper (I) Chloride (3.77 mmol) was added to the above three neck round bottom flask (Solution A) and stirred for 10 min and then cooled to -20°C. Diazotized solution (Solution B) was added slowly to the above mixture. After complete addition, reaction mixture was allowed to stir at room temperature for 30 min. Work up was done as usual in method A.
Method J
Sulphuryl chloride (58 mmol) was added to dimethylformamide (58 mmol) cooled to 0°C. The resulting solution was stirred for 15 min. Aromatic hydrocarbon (58 mmol) was then added slowly maintaining the temperature below 10°C. The reaction mixture was then heated for 2 h at 100°C and then poured on to ice and extracted with dichloromethane. Organic phase was separated and dried over anhydrous sodium sulphate and concentrated to afford a crude residue. The residue was purified by column chromatography over silica gel (100-200 mesh) using dichloromethane as eluant to afford the corresponding sulphonyl chloride
Following sulphonyl chlorides were prepared by the method described above:
2-Oxo-2,3-dihydro-lH-benzimidazole-5-sulfonyl chloride 2,4-Dioxo-1,4-dihydro-2H-3, l-benzoxazine-6-sulfonyl chloride 3-Methyl-2-oxo-2,3-dihydro-l,3-benzothiazole-6-sulfonyl chloride J, 3-Benzodioxole-5-sulfonyl chloride Thieno[3,2-c]pyridine-2-sulfonyl chloride 1 -Nitrosoindoline-6-sulfonyl chloride 4-[(Pyrimidin-2-ylamino)sulfonyl]benzenesulfonyl chloride 1-Benzothiophene-6-sulfonyl chloride 1,1-dioxide
29

'.,•////,v-'/'//i'-O-.W///O/M'/ chloride
1 •', i!n .••-.'-o\oiinloHne'-5-sulfonyl chloride
MM, li,'iiiiui//('-fi-M/lfonvl chloride
'M. '' i ,/!//](//•/>-1.2-henzisoxazole-5-sulfony/chloride
I'//'/,;//r///, 2.4jlrhizolol 1.5-ti]pyrimidine-2-siilfonyl chloride i'\ ///i/ ! o.\/i-2.3-dihydro-l. 3-benzoxazole-6-snlfonyl chloride
>'.•/!/ .' M\o 2.1-dihydro-1,3-benzoxazole-6-sulfonyl chloride l, v/i / iuciho\y-l-henzofuran-4-sulfonyl chloride
/'.'MM ,v i-iHhydr<>-2H-1,3-benzoxazine-6-sulfonyl chloride \ -•'. •//;, - \ r / -li(.'iizoihiophene-2-sulJonyl chloride
i','/'/. ///('\ i•-1-hcnzolhiophene-2-sulfonyl chloride '<•', /// ' •. r '-i>\o-2lt-chroinene-6-sulfonvl chloride
\M \-7 chroniciie-6-sulfomi chloride ~ i >!,'M'i\i>/iii/t>/i/ic--/-Mi/fonvl chloride
/ / •'//;.'/1 iniclhyh-111-h(.>nzintiduzole-5-sitlfonyl chloride \\'in\i I i>\o-Hl-chronicnc-7-siilfonyl chloride I.V//M ,'- /..>-/'(•n:othiu:ole-5-sulfonyl chloride \ \ //;M,I I-hcnzoihiophcue-2-sulfonyI chloride ' / '////i ilh>\-\--1-henzoiliiophene-2-suIjonyl chloride
I }i' HI 111 \ I- 2.3-c lioxo-1,2,3,4-telrnhydrociiiinoxaline-6-siilfonyl chloride
' liinihi- "~()\<>cihyi)-2-oxo-2,3-dihydro-l,3-beiizoxazole-6-sulfonyl chloride
-it !-!\ ii/i/ni-1,3-henzolhia:ole-6-sulfonyl chloride
./,///i iihini-1.3-/h'iizoxcizole-6-siil/onyl chloride ;;/i .•' " i(ihli>r,)\ulj(uiyl)-l-henzofurcin-2-curboxykite
/M .<.' . nhiu:.olc-2-Milfonyl chloride ,!/,>/!/!:• fi-M/l/i>/i\-/ chloride : i ;/;/,M/•t>nn'ih\'h-l,3-hcnzothiuzole-6-siilfonyl chloride
/'c•••/ M//V,i:: I •lh'ii:oihi(>phene'-2-siilfom'l chloride
' •'"//, ///i /- I-bcnzoihiophene-2-sulfonyl chloride
:,'i/i\i I lh'iizoihiophene-2-siilfonyl chloride
/'////, ili\'l-1-hcn:t>lhiophene-2-si/[fonyl chloride
••'.•///1 / / -l\'irolhiophene-3-sulfonyl chloride
:\ ///i" r •iiicihyhhieiiol3.2-d]p\rimidine-6-sulfonyl chloride

2-Oxo-l,2,3,4-tetrahydroquinazoline-6-sulfonyl chloride 1-Methyl-2,3-dioxoindoline-5-sulfonyl chloride 3,3-Difluoro-2-oxoindoline-5-sulfonyl chloride 2-(lsobutylamino)-l,3-benzoxazole-6-sulfonyl chloride 2,5-Dimethyl-l,3-benzothiazole-6-sulfonyl chloride 7-Methyl-1 -benzothiophene-2-sulfonyl chloride 5-Chloro-l,3-benzothiazole-2-sulfonyl chloride 2,4-Dioxo-l,2,3,4-tetrahydrophthalazine-5-sulfonyl chloride 2-Acetamidoindane-5-sulfonyl chloride 1 -Formylindoline-5-sulfonyl chloride 6-Methoxyindane-5-sulfonyl chloride 1 -Acetamidoindane-5-sulfonyl chloride 2-Oxo-2H-chromene-6-sulfonyl chloride 2-Oxo-2,3-dihydro-l,3-benzothiazole-6-sulfonyl chloride 4-Chloro-2-oxo-2H-chromene-6-sulfonyl chloride 4-Fluoro-2-oxo-2H-chromene-6-sulfonyl chloride 2-Oxo-4-(trifliioromethyl)-2H-chromene-6-snlfonyl chloride l-Bemothiophene-2-sulfonyl chloride
Example 1: Preparation of Compound of Formula 4
To a solution of a compound of Formula 2 (40.6 mmol) in pyridine (20 mL), a compound of Formula 3 (44.7 mmol) was added portion wise at about 0-5°C. The reaction mixture was allowed to come at an ambient temperature and stirred overnight. The solvent was evaporated under reduced pressure. Water was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified bv column chromatography to yield the required product.
Example 2: Preparation of Compound of Formula 5
To a solution of compound of Formula 4 (25.9 mmol) in dichloromethane (125 mL) was added Dess-Martin Periodinane (38.9 mmol). The reaction mixture was stirred overnight at an ambient temperature, filtered, and the mother liquor was washed with aqueous sodium bicarbonate solution. The organic layer was dried and evaporated under reduced pressure. The residue was purified by column chromatography to give the desired product.
Example 3: Preparation of Compound of Formula 6
31

The compound of Formula 6 was prepared using the procedure described for compound of Formula 4.
Example 4: Preparation of Compound of Formula 7
To a solution of compound of Formula 6 (48.8 mmol) taken in methanol (100 mL) and cooled to 0°C, was added Raney Ni (1.5 g, w/w), followed by dropwise addition of hydrazine hydrate (146.4 mmol) and it was stirred for 2 h, filtered through celite pad and the filterate was evaporated to dryness. The residue was taken in dichloromethane and washed with water, the dichloromethane layer was evaporated to afford the corresponding amine. The amine (35.97 mmol, obtained above) and 2,5dimethoxytetrahydrofuran (71.9 mmol) were dissolved in acetic acid (50 mL).The reaction mixture was stirred at 90°C for 2h and then concentrated. The residue was extracted with ethyl acetate. Organic layer was washed with water, brine and dried over anhydrous sodium sulphate. Solvent was removed and the residue was purified over silica gel column.
Example 5: Preparation of Compound of Formula 8
The compound of Formula 8 was prepared using the procedure described for compound of Formulas.
Example 6: Preparation of Compound of Formula 11
To a solution of L-alaniol (108 mmol) in dichloromethane (100 mL) was added di-terl-Butyl dicarbonate (113 mmol) slowly at about 0-5°C. The reaction mixture was stirred for about 3 h at an ambient temperature. The reaction mixture was diluted with dichloromethane and washed with water, brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography to give the desired product.
Example 7: Preparation of Compound of Formula 12
To a solution of compound of Formula 11 (668 mmol) in ether (500 mL) was added tosyl chloride (802 mmol). The reaction mixture was stirred for about 15 min and cooled to 0°C. Potassium hydroxide (5344 mmol, powdered) was added portionwise. The reaction mixture was refluxed at about 40-50 C for about 3 h. The reaction mixture was diluted with water and the compound was extracted with ethyl acetate. The organic layer was dried and evaporated under reduced pressure. The product was purified by column chromatography over silica gel to give the desired compound.
Example 8: Preparation of Compound of Formula 13 V
In a two-necked round bottom flask Mg (478 mmol) was suspended in diethyl ether (100-125 mL), cooled to 0°C, added slowly a compound of Formula Cy-Ha (478 mmol), and diluted
32

with tetrahydrofuran (100-110 mL). A crystal of iodine was added to titurate the reaction. The reaction mixture was stirred for about 2 h. The reaction mixture was cooled to about -40 C and added CuBr-Me2S complex (9.5 mmol) to it. Compound of Formula 12 (95.5 mmol) dissolved m tetrahydrofuran (100 mL) was added slowly to the reaction mixture. The reaction mixture was stirred for about 2 h and quenched by adding saturated ammonium chloride solution. The reaction mixture was stirred overnight and was extracted with ethyl acetate. The organic layer was dried and evaporated under reduced pressure. The product was purified by column chromatography.
Example 9: Preparation of Compound of Formula 14
The deprotection of a compound of Formula 13 to give a compound of Formula 14 was carried out following the methods well known in the art.
Example 10: Preparation of Compound of Formula 16
(l/?,25')-2-amino-l-phenylpropan-l-ol (132.3 mmol) was dissolved in acetic acid (100 mL). Platinum oxide (13.23 mmol) was added to it and the suspension was stirred at about 50 psi (Hz) for 24 h .The reaction mixture was filtered through celite pad. The mother liquor was evaporated to get the final component as the acetate salt. This was used as such for next step without furti.~r purification.
Example 11: Preparation of Compound of Formula 18 (via scheme-V)
To a solution of compound of Formula 5 (0.94 mmol) in methanol (5 mL) was added compound of Formula 17 (1.42 mmol.). After stirring for about 1 h, sodium cyanoborohydride (2.83 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight and then evaporated the solvent under reduced pressure. The residue was dissolved in dichloromethane, washed with water, brine and dried over anhydrous sodium sulfate. The product was purified by column chromatography.
Example 12: Preparation of Compound of Formula 20 ,
To a solution of compound of Formula 17 (118 mmol) in dichloroethane (150 mL) was added compound of Formula 19 (118 mmol). After stirring for about 3 h at room temperature, sodium triacetoxyborohydride (354 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight, filtered and the filterate was basified with sodium bicarbonate solution. The filterate was extracted with dichloromethane, washed with water, brine and dried over anhydrous sodium sulfate. The organic layer was evaporated to afford the desired compound.
Example 13: Preparation of Compound of Formula 21
33

The compound of Formula 20 (103 mmol.) was taken in dichloromethane (300mL) and i.-it triethylamine (155 mmol) was added at an ambient temperature. It was cooled to 0 C and Ji-tert-butyl dicarbonate (113 mmol) was added drop wise and the contents were stirred at an ambient temperature overnight, quenched with water and extracted in dichloromethane. Solvent was evaporated and the crude product was purified over silica gel column.
Example 14: Preparation of Compound of Formula 22
The compound of Formula 21 (55.25 mmol) was taken in methanol (300 mL) and cooled to 0 °C. To this Raney Nickel (4g, w/w) was added, followed by drop wise addition of hydrazine hydrate (155 mmol). The reaction mixture was stirred at an ambient temperature for about 2 h and filtered through celite pad. The filterate was evaporated to dryness and the residue was taken in dichloromethane and washed with water. The dichloromethane layer was evaporated to afford the desired product.
Example 15: Preparation of Compound of Formula 23
The compound of Formula 23 was prepared using the procedure described for compound of Formula 4.
Example 16: Preparation of Compound of Formula 18 (via scheme-VII)
The deprotection of a compound of Formula 23 to give a compound of Formula 18 was carried out following the methods well known in the art.
Example 17: Preparation of Compound of Formula 25
The compound of Formula 25 was prepared using the procedure described for compound of Formula 22.
Example 18: Preparation of Compound of Formula 26
The compound of Formula 26 was prepared using the procedure described for compound of Formula 4.
Example 19: Preparation of Compound of Formula 27
The deprotection of a compound of Formula 26 to give a compound of Formula 27 was carried out following the methods well known in the art.
Example 20: Preparation of Compound of Formula 29
The compound of Formula 22 (4.3 mmol.) was taken in dichloromethane (25 mL) and triethylamine (12.9 mmol) followed by compound of Formula 28 (5.4 mmol) were added at 0 C. The reaction mixture was stirred at room temperature for 2h. The reaction mixture was diluted
with dichloromethane and washed with water and brine. The organic layer was dried over
34

anhydrous sodium sulphate, filtered and evaporated under reduced pressure to afford the desnp<. product.
Example 21: Preparation of Compound of Formula 31
To a solution of compound of Formula 29 (0.46 mmol) in acetonitrile (2 mL), a compound of Formula 30 (0.69 mmol), and potassium fluoride/basic-alumina (10 mol %, O.OlSg) were added in one portion. The resulting mixture was stirred for 18 h. The catalyst was separated by filtration, with dichloromethane as solvent and the filtrate was washed with water and brine. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated to give crude product which was then purified by chromatography to afford the desired compound.
Example 22: Preparation of Compound of Formula 32
The deprotection of a compound of Formula 31 to give a compound of Formula 32 was carried out following the methods well known in the art.
Example 23: Preparation of Compound of Formula 34
The compound of Formula 34 was prepared using the procedure described for compound of Formula 29.
Example 24: Preparation of Compound of Formula 35
To a solution of compound of Formula 34 (6.3 mmol) in acetone (25 mL) was added sodiufn iodide (31.7 mmol). The reaction mixture was refluxed for 15 h. The reaction mixture was cooled, diluted with ethyl acetate and washed with water and brine solution. The organic layer was dried over anhydrous sodium sulphate, decanted and evaporated to yield crude product, which was purified by column chromatography.
Example 25: Preparation of Compound of Formula 37
To a solution of compound of Formula 35 (0.44 mmol) in dimethylformamide (5 mL) were added sequentially diisopropylethylamine (1 mL) and a compound of Formula 36 (2.2 mmol). The resulting mixture was stirred at room temperature for 4h. The reaction mixture was then poured into water (500 mL) and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and evaporated to yield crude product, which was purified by column chromatography.
Example 26: Preparation of Compound of Formula 38 • •
The deprotection of a compound of Formula 37 to give a compound of Formula 38 was carried out following the methods well known in the art.
Example 27: Preparation of Compound of Formula 41
35

The compound of Formula 39 (0.69 mmol) was taken in methanol (20 mL) and sodiiir, borohydride (2.7 mmol) was added at 0°C .The reaction mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was extracted with ethylacetate. The organic layer was dried over anhydrous sodium sulphate, filtered, and evaporated to afford the desired compound.
Example 28: Preparation of Compound of Formula 41
The deprotection of a compound of Formula 40 to give a compound of Formula 41 was carried out following the methods well known in the art.
Example 29: Preparation of Compound of Formula 42
The compound of Formula 39 (0.9 mmol) was dissolved in methanol (5 mL), concentrated potassium hydroxide solution (10 mL) was added to the above solution and the reaction was refluxed at 90-100°C for 3-4h. Reaction mixture was evaporated in vacua to obtain a residue which was neutralized with 50% hydrochloric acid solution. The aqueous mixture was then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrorfs sodium sulphate, filtered and evaporated to afford the desired compound.
Example 30: Preparation of Compound of Formula 43
The deprotection of a compound of Formula 42 to give a compound of Formula 43 was carried out following the methods well known in the art.
Example 31: Preparation of Compound of Formula 44
The compound of Formula 42 (0.4 mmol), l-(3-dimethylaminopropyl)-3-ethylcarbodimidc hydrochloride (1.2 mmol) and 1-hydroxybenzotriazole (0.8 mmol) were taken in dry dimethylformamide and cooled to 0°C. N-methylmorpholine (1.2 mmol) was added to the above mixture dropwise and stirred for 30 min, then 40% ammonia solution (in excess) was added and reaction mixture was stirred overnight. The reaction mixture was quenched with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over anhydrous sodium sulphate, filtered and evaporated in vacua to afford the desired compound.
Example 32: Preparation of Compound of Formula 45
The deprotection of a compound of Formula 44 to give a compound of Formula 45 was carried out following the methods well known in the art.
Example 33: Preparation of Compound of Formula 47
The compound of Formula 46 (0.69 mmol) was taken in dichloromethane (20 mL) and cooled to -78°C. Boron tribromide (14.19 mmol) was added and the reaction mixture was stirred overnight.
36

The reaction was cooled and quenched with sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate and washed with sodium bicarbonate solution and water. The organic layer was dried over anhydrous sodium sulphate solution, filtered and evaporated in vacua to afford the desired compound.
The following compounds were prepared analogously, following the above general procedures:
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-lH-
benzimidazole-5-sulfonamide (Compound No. 1);
EIMS (m/z): 443 (M+l); M.Pt.: 116-118 °C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-lH-
benzimidazole-5-sulfonamide (Compound No. 2);
EIMS (m/z): 429 (M+l); M.Pt.: 112-116°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2,4-dioxo-l,4-dihydro-2H-3,l-
benzoxazine-6-sulfonamide (Compound No. 3);
EIMS (m/z): 471 (M+l); M.Pt.: 50-54°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-2-oxo-2,3-dihydro-r,3~
benzothiazole-6-sulfonamide (Compound No. 4);
EIMS (m/z): 460(M+1); M.Pt.: 83-85 °C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-2-oxo-2,3-dihydro-l,3-
benzothiazole-6-sulfonamide (Compound No. 5);
EIMS (m/z): 474(M+1); M.Pt.: 92-95°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-l,3-benzodioxole-5-sulfonamid^
(Compound No. 6);
EIMS (m/z): 417(M+1); sticky '•
N-[2-({[(lS)-2-cyclohexyl-1 -methylethyljam ino} methyl)phenylj-l, 3-benzodioxole-5-sulfonam ide
(Compound No. 7);
EIMS (m/z): 431(M+1); sticky
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide hydrochloride (Compound No. 8);
EIMS (m/z): 430(M+1); M.Pt.: 158-1601^(decomposition)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-5-[2-(methylthio)pyrimidin-4-
yl]thiophene-2-sulfonamide (CompoundNo. 9);
EIMS (m/z): 503.15(M+1); M.Pt.: 158-159°C
Methyl 3-({[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)
thiophene-2-carboxylate (Compound No. 10);
EIMS (m/z): 451(M+1); M.Pt.: 72-74°C
37

3-(([2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)thiophene-2-
carboxylic acid (Compound No. 11);
EIMS (m/z): 43 7(M+1); M.Pt.: 151-153°C
3-({[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]amino}sitlfonyl)thiophene-2-
carboxamide (Compound No. 12);
EIMS (m/z): 436(M+1); M.Pt.: 91-93°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino)methyl)phenyl]thieno[3,2-c]pyridine-2-
sulfonamide(Compound No. 13);
EIMS (m/z): 430(M+1)
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-4- methylbenzenesulfonamide
(Compound No. 14);
EIMS (m/z): 401(M+1)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-4-methylbenzenesulfonamide
(Compound No. 15);
EIMS (m/z): 387(M+1)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-l-nitrosoindoline-6-sulfonamide
(Compound No. 16);
EIMS (m/z): 443(M+1)
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-l-nitrosoindoline-6-sulfonamide
(Compound No. 17);
EIMS (m/z): 457.30(M+1)
N-[2-({[(lS)-2-cydohexyl-l-methykthyl]amino}methyl)phenyl]-N'-pyrimidin-2-ylbenzene-l,4-
disitlfon amide (Compound No. 18);
EIMS (m/z): 544(M+1); M.Pt.: 186-188°C
N-[2-(([(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-l-benzothiophene-6-sulfonamide
1,1-dioxide (Compound No. 19);
EIMS (m/z): 475(M+1); M.Pt.: 144-146°C
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-l-benzothiophene-6-sulfonamide
1,1-dioxide (Compound No. 20);
EIMS (m/z): 461 (M+l); M.Pt.: 136-138°C
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]isoquinoline-5-sulfonamide
(Compound No. 21);
EIMS (m/z): 424(M+1); M.Pt.: 110-112°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino} methyl)phenyl]isoquinoline-5-sulfonamide
(Compound No. 22);
EIMS (m/z): 437(M+1); M.Pt.: 80-82°C
38

3-({[2-({[(lS)-2-cydopentyl-l-methylethyl]amino) melhyl)phenyl]anuno!sulfonyh thiophene-2-carhoxylic add (Compound No. 23); EIMS (m/z): 423(M+l); M.Pt.: 224-226°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-l-methyl-2-oxoithl<>ri!h'~^ -sulfonamide (Compound No. 24); EIMS (m/z): 456(M+1); M.Pt.: 128-131°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}melhyl)phenyl]-l-methyl-2-t)xtiiihli>linL'-^-sulfonamide (Compound No. 25); EIMS (m/z): 442(M+1); sticky N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2-oxochr(>mtini'-h^itltt>ihiinnk'
(Compound No. 26);
EIMS (m/z): 457(M+1); M.Pt.: 114-116°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)pheuyI]-3-oxo-2.3-dihydro-1. J-
benzisoxazole-5-sulfonamide (CompoundNo. 27);
EIMS (m/z): 444(M+1); M.Pt.: 148-150°C
N-(2-{[(2-cydohexylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-lH-henziniiikiioU -:•
sulfonamide (Compound No. 28);
EIMS (m/z): 429.18(M+1); M.Pt.: 124-UtfC
N-(2-([(2-cydohexylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-1.3-hL>nzoxir:.«li'-()-
sulfonamide (Compound No. 29);
EIMS (m/z): 430.30(M+1); M.Pt.: 194-196°C
N-[2-({ [(I S)-l-cydohexylethyl]amino}methyl)phenyl]-4-(lH-pyrrol-l-yl)hcii:c>h'\nitiiiitininlc
(Compound No. 30);
EIMS (m/z): 438.23(M+1); M.Pt.: 120-122°C
N-(2-{[(2-cydohexylethyl)amino]methyl}phenyl)-4-(lH-pyrrol-l-yl)ben:eiiesull<>ihiniuk'
(Compound No. 31);
EIMS (m/z): 438.30(M+1); M.Pt.: 138-140°C
N-(2-{[(2-cydohexylethyl)amino]methyl}phenyl)-l-benzothiophene-2-sulf<)]ninihk' i( 'o/n/niinid
No. 32);
EIMS (m/z): 429.31 (M+l); M.Pt.: 128-130°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-5. 7-di/nc'/hy//1.^ -//iriii~(>ln/ /..^
a]pyrimidine-2-sulfonamide (Compound No. 33);
EIMS (m/z): 457(M+1); M.Pt.: 114-116°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-5. 7-dii
a]pyrimidine-2-sulfonamide (Compound No. 34);
EIMS (m/z): 443(M+1); M.Pt.: 156-158°C

N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-2-oxo-2,3-dihydro-l,'t
benzoxazole-6-sulfonamide (Compound No. 35);
EIMS (m/z): 458(M+1); M.Pt.: 48-49°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide (Compound No. 36);
EIMS (m/z): 444(M+1); M.Pt.: 55-56° C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-3-ethyl-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide(CompoundNo. 37);
EIMS (m/z): 472.06 (M+l); M.Pt.: 47-50°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-3-ethyl-2-oxo-2,3-dihydro-l,3-
benzoxazole-6-sulfonamide (Compound No. 38);
EIMS (m/z): 458(M+1); sticky
2-acetyl-N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl) phenyl]-7-methoxy-l-
bemofur an-4-sulfonamide (Compound No. 39);
EIMS (m/z.): 499(M+1); M.Pt.: 56-58°C
2-acetyl-N-[2-(([(lS)-2-cydopentyl-l-methylethyl]amino}methyl) phenyl]-7-methoxy-l-
benzofuran-4-sulfonamide (Compound No. 40);
EIMS (m/z): 485(M+1); M.Pt.: 50-52°C
N-[2-({[(IS)-l-cydohexylethyl]amino}methyl)phenyl]-2-oxo-2,3-dihydro-l,3-benzoxazole-6-
sulfonamide (Compound No. 41);
EIMS (m/z): 430(M+1); M.Pt.: 135-13 fC
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2,4-dioxo-3,4-dihydro-2H-l,3-
benzoxazine-6-sulfonamide (Compound No. 42);
EIMS (m/z): 458(M+1); M.Pt.: 117-118°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-5-methoxy-l-benzothiophene-2-
sulfonamide (Compound No. 43);
EIMS (m/z): 472.66(M+1); M.Pt.: 58-60°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-6-hydroxy-l-benzothiophene-2-
sulfonamide (Compound No. 44);
EIMS (m/z): 444.61(M+1); M.Pt.: 170-172°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-5-hydroxy-l-benzothiophene-2-
sulfonamide (Compound No. 45);
EIMS (m/z): 458.63(M+1); M.Pt.: 89-91°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl) phenylJ-4,7-dimethoxy-l-
benzothiophene-2-sulfonamide (CompoundNo. 46);
EIMS (m/z): 488.66(M+1); M.Pt.: 67-69°C
40

N-[2- ({[(1 S)-2-cyclohexyl-1 -methylethyl] am ino} methyl)phenyl]-4,7-dimethoxy-1 -benzothiophene -2-sulfonamide (CompoundNo. 47); EIMS (m/z): 502.69(M+1); M.Pt.: 148-15(fC N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-7-methoxy-2-oxo-2H-chromene-
6-sulfonamide (Compound No. 48);
EIMS (m/z): 471(M+1); M.Pt.: 95.7°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-2-oxo-2H-chromene-6-
sulfonamide (Compound No. 49);
EIMS (m/z): 455(M+1); M.Pt.: 83.4°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2H-chromene-6-
sulfonamide (Compound No. 50);
EIMS (ni/z): 441(M+1); M.Pt.: 101. fC
(4E)-N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl) phenyl]-4-
(hydroxyimino)chromane-6-sulfonamide (Compound No. 51);
EIMS (ni/z): 472(M+1); M.Pt.: 128.4°C
(4E) -N-[2- ({[(IS) -2-cydopentyl-1 -methylethyl] am ino} me thy I) phenyl]-4-
(hydroxyimino)chromane-6-sulfonamide (Compound No. 52);
EIMS (ni/z): 457(M+1); M.Pt.: 139.8°C
N-[4-({[2-({[(lS)-l-cydohexylethyljamino}methyl)phenyl]amino} sulfonyl)phenyl]-l-methyl-1H-
imidazole-4-sulfonamide (Compound No. 53);
EIMS (ni/z): 533(M+1); M.Pt.: 178-180°C
4-amino-N-[2-({[(lS)-l-cydohexylethyl]amino}methyl)phenyl] benzenesulfonamide (Compound
No. 54);
EIMS (m/z): 388(M+1); Oily liquid
N-[2-({[(lS)-l-cydohexylethyl]amino}methyl)phenyl]-4-(methylsulfonyl)benzenesulfonamide
(Compound No. 55);
EIMS (m/z): 467(M+1); M.Pt.: 65-6fC
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-l,3-dioxoisoindoline-4-
sulfonamide (Compound No. 56);
EIMS (m/z): 442(M+1); M.Pt.: 206-208°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-l,3-dioxoisoindoline-4-
sulfonamide (CompoundNo. 57);
EIMS (m/z): 456(M+1); M.Pt.: 206-208°C
N-[2-({[(I S)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-2-(trifluoromethyl)-lH-
benzimidazole-5-sulfonamide (Compound No. 58);
EIMS (m/z): 495(M+1)
41

N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2-methyl-4-oxo-4H-chromene-7-
sulfonamide (Compound No. 59);
EIMS (nt/z): 455(M+1); M.Pt.: 149-151°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2-methyl-l,3-benzothiazole-5-
sulfonamide (Compound No. 60);
EIMS (m/z): 444(M+1)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2-methyl-4-oxo-4H-chromene'-7-
sulfonamide (Compound No. 61); EIMS (m/z): 455(M+1); M.Pt.: 149-151°C
N-[2-({[(lS)-2-cydohexyl-l-methykthyl]amino}methyl)phenyl]-2-methyl-l,3-benzothiazole-5-
sulfonamide (Compound No. 62);
EIMS (m/z): 458(M+1)
2-[({4-[(lZ)-buta-l,3-dien-l-ylamino]phenyl}sulfonyl)amino]benzyl benzylcarbamate
(Compound No. 63);
EIMS (m/z): 581(M+1); M.Pt.: 85-8 fC
N-[4-({[2-({[(!S)-l- cydohexylethyl]amino}methyl)phenyl]amino}sulfonyl) phenyl]thiophene~2-
sulfonamide (Compound No. 64);
EIMS (m/z): 534(M+1); M.Pt.: 113-115°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-5,6-dihydroxy-l-benzothiophem-
2-sulfonamide (Compound No. 65);
EIMS (m/z): 475.16(M+I); M.Pt.: 153-15 fC
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-6-hydroxy-l-benzothiophene-2-
sulfonamide (Compound No. 66);
EIMS (m/z): 459.3 7(M+1)
N-[2- ({[(lS)-2-cydopentyl-1 -methylethyl]amino}methyl)phenyl]-5,6-dihydroxy-1 -
benzothiophene-2-sulfonamide (CompoundNo. 67);
EIMS (m/z): 461.18(M+1); M.Pt.: H4-U6°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-6-methoxy-l-benzothiophene-2-
sulfonamide(CompoundNo. 68);
EIMS (m/z): 459.3(M+1); M.Pt.: 67-69°C
N-[2-(([(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-5,6-dimethoxy-l-
benzothiophene-2-sulfonamide (Compound No. 69);
EIMS (m/z): 489.2(M+1); M.Pt.: 53-55°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-6-methoxy-l-benzoMophene-2-
sulfonamide (Compound No. 70);
EIMS (m/z): 473.34(M+1); M.Pt.: 68-70°C
42

N-[2-({[(l S)-2-cyclohexyl-1 -methylethyl] amino} methyl)phenyl]-5,6-dimethoxy-1 -benzothiophene-
2-sulfonamide (Compound No. 71);
EIMS (m/z): 503.25(M+1); M.Pt.: 60-62°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino} methyl)phenyl]-l,4-dimethyl-2,3-dioxo-l,2,3,^•
tetrahydroquinoxaline-6-sulfonamide (Compound No. 72);
EIMS (m/z): 485.37(M+1); M.Pt.: 177-178°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-l,4-dimethyl-2,3-dioxo-l,2,3,4-
tetrahydroquinoxaline-6-sulfonamide (Compound No. 73);
EIMS (m/z): 499.42(M+1); M.Pt.: 182-183°C
2-[6-({ [2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl) phenyl]amino}sulfonyl)-2-oxo-l,3-
benzoxazol-3(2H)-yl]acetamide (CompoundNo. 74);
EIMS (m/z): 487.19(M+1); M.Pt.: 92-94°C
N-[2-({[(lS, 2R)-2-cydohexyl-2-hydroxy-l-methylethyl]amino} methyl)phenyl]-2-oxo-2,3-
dihydro-l,3-benzoxazole-6-sulfonamide (CompoundNo. 75);
EIMS (m/z): 460.17(M+1); M.Pt.: 128-130°C
N-[2-({[(lS,2R)-2-cydohexyl-2-hydroxy-l-methylethyl] amino} methyl)phenyl]-4-
nilrobenzenesulfonamide (Compound No. 76);
EIMS (m/z): 448.15(M+1); M.Pt.: 165-167°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-5-[2-(methylsulfonyl)pyrimidin~
4-yl]thiophene-2-sulfonamide (Compound No. 77);
EIMS (m/z): 535(M+1); M.Pt.: 97-99°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-2-(methylthio)-1,3-
benzothiazole-6-sulfonamide (Compound No. 78);
EIMS (m/z): 476.17(M+1)
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-2-(methylthio)-l,3-benzothiazole-
6-sulfonamide (Compound No. 79;
EIMS (m/z): 490.21(M+1); M.Pt.: 43-45°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-l,3-benzothiazole-6-sulfonamide
(Compound No. 80);
EIMS (m/z): 444.18(M+1); M.Pt.: 55-56°C
N-[2- ({[(1S) -2-cydohexyl-l -methylethyl] amino} methyl)phenyl]-2- (methylthio)-l,3-benzoxazole-
6-sulfonamide (Compound No. 81);
EIMS (m/z): 474.22(M+1); M.Pt.: 44-46°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-2-(methylthio)-l,3-benzoxazole-
6-sulfonamide (Compound No. 82);
EIMS (m/z): 460.17(M+1)
43

N-[4-({[2-({[(lS)-2-cydohexyl-l-methylethyl]amino)methyl)-phenyl]amino}sulfonyl)phenyl]-l-
methyl- lH-imidazole-4-sulfonamide(Compound No.83);
EIMS (m/z): 546(M+1); M.Pt.: 164.5-165°C
N-[4- ({[2- ({[(lS)-2-cydohexyl-1 -methylethyl] am ino} methyl)
phenyl]amino}sulfonyl)phenyl]thiophene-2-sulfonamide (Compound No. 84);
EIMS (m/z): 548(M+1); M.Pt.: 166.9-172°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-4-
[(methylsulfonyl)amino]benzenesulfonamide (Compound No. 85);
EIMS (m/z): 480(M+1); M.Pt.: 139.8-142°C
N-[5-({[4-({[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)
phenyl]amino}sulfonyl)phenyl]amino}sulfonyl)-4-methyl-l,3-thiazol-2-yl]acetamide (Compound
No. 86);
EIMS (m/z): 620(M+1); M.Pt.: 176.8-178°C
Methyl 5-({[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)-!-
benzofuran-2-carboxylate(CompoundNo. 87);
EIMS (m/z): 47L35(M+1)
Methyl 5- ({[2 -({[(1S) -2-cydohexyl-1 - methylethyl] amino} methyl)phenyl]amino}sulfonyl)-l-
benzofuran-2-carboxylate(Compound No. 88);
EIMS (m/z): 485.35(M+1)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-2-(hydroxymethyl)-l-
benzofuran-5-sulfonamide (Compound No. 89);
EIMS (m/z): 443.29(M+1)
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-2-(hydroxymethyl)-l-benzofuran-
5-sulfonamide (Compound No. 90);
EIMS (m/z): 457.31(M+1)
5-({[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]amino}sulfonyl)-l-benzofuran-2-
carboxylic acid (Compound No. 91);
EIMS (m/z): 471.26(M+1)
2-[6- ({[2-({[(l S)-2-cydohexyl-1 -methylethyl] amino}methyl)phenyl] amino} sulfonyl)-2-oxo-l, 3-
benzoxazol-3(2H)-yl]acetamide (Compound No. 92);
EIMS (m/z): 501.33(M+1); M.Pt.: 95-97°C
3-(Cyanomethyl)-N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-2-oxo-2,3-
dihydro-l,3-benzoxazole-6-sulfonamide (Compound No. 93);
EIMS (m/z): 483.34(M+1); M.Pt.: 108-110°C
N-[2- ({[(IS) -2-cydohexyl-1 -methylethyl] am ino} methyl)phe nyl]-1,3-benzothiazole-2-sulfonamide
(Compound No. 94);
44

EIMS (m/z): 444.32(M+1); M.Pt.: 97-99°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-l,3-benzothiazole-2-sulfonamidc
(Compound No. 95);
EIMS (m/z): 430.34(M+1); M.Pt.:94-96°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-3,4-
dimethoxybenzenesulfonamide (Compound No. 96);
EIMS (m/z): 447(M+l); sticky
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-3,4-
dihydroxybenzenesulfonamide (CompoundNo. 97);
EIMS (m/z): 419(M+1); M.Pt.: 101-103°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-3,4-
dihydroxybenzenesulfonamide (Compound No. 98);
EIMS (m/z): 405(M+1); M.Pt.: 109-110°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]quinoline-6-sulfonamide
(Compound No. 99);
EIMS (m/z): 424.31(M+1); M.Pt.: 138-140°C
N-[2-({[(lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]quinoline-6-sulfonamide
(Compound No. 100);
EIMS (m/z): 438.40(M+1)
N-[2-({[(l S)-2-cydohexyl-1 -methylethyl] amino} methyl)phenyl]-2-(trifluoromethyl) -1,3-
benzothiazole-6-sulfonamide (Compound No. 101);
EIMS (m/z): 512.31(M+1)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-2-(trifluoromethyl)-1,3-
benzothiazole-6-sulfonamide (Compound No. 102);
EIMS (m/z): 498.38(M+1)
N-[2-({[(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-lH-benzotriazole-5-sulfonamide
(Compound No. 103);
EIMS (m/z): 414.38(M+1); M.Pt.: 204-206°C
N-[2-({[(l S) -2-cydohexyl-l -methylethyl] amino} methyl)phenyl]-l H-benzotriazole-5-
sulfonamide(Compound No. 104);
EIMS (m/z): 428.34(M+1); M.Pt.: 188-190°C
N-(2-{[(2-cydohexylethyl)amino]methyl}phenyl)-2-hydroxy-l,3-benzothiazole-6-sulfonamide
(Compound No. 105);
EIMS (m/z): 446.29(M+1); M.Pt.: 118-120°C
N-(2-{[(2-cydohexylethyl)amino]methyl}phenyl)-2-oxo-2H-chromene-6-sulfonamide (Compound
No. 106);
45

EIMS (m/z): 441.35(M+1); M.Pt.: 110-112°C
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-2-methyl-l,3-benzothiazole-5-sulfonamide (Compound No. 107);
EIMS (rn/z): 444.29(M+1); M.Pt.: 142-143.8°C
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-5-fluoro-l-benzothiophene-2-sulfonamide (Compound No. 108); EIMS (m/z): 447.3(M+1); M.Pt.: 134-13^ C
N-(2-{[(2-cyclohexylethyl)amino]methyl}phenyl)-l,3-benzothiazole-6-sulfonamide (Compound No. 109);
EIMS (m/z): 430.27(M+1); M.Pt.: 132-134°C
N-(2-{[(2-cyclohexylethyl)amino]inethyl}phenyl)-2,4-dioxo-l,2,3,4-letrahydroquinazoline-6-sulfonamide (Compound No. 110); EIMS (m/z): 457.31(M+1); M.Pt.: 238-240° C
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4,7-dimethyl-1-benzothiophene-2-sulfonamide (CompoundNo. Ill); EIMS (m/z): 457.31(M+1)
N-[2- ({[(I S) -2-cyclohexyl-1 -methylethyljam ino} methyl)phenyl]-4,7-dimethyl-1-benzothiophene-2-siilfonamide (Compound No. 112); EIMS (m/z): 471.33(M+1); M.Pt.: 130-131°C
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-l-benzothiophene-2-sulfonamide (Compound No. 113); EIMS (m/z): 457.28(M+1); M.Pt.: 130-132°C
N-[2-({[(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-4,6-dimelhyl-1-benzothiophene-2-sulfonamide (Compound No. 114); EIMS (m/z): 457.28(M+1); M.Pt.: 46-49°C
N-[2-({[(lS)-2-cyclohexyl-l-methylethyl]amino}methyl)phenyl]-4,6-dimethyl-1-benzothiophene-2-sulfonamide (Compound No. 115); EIMS (nt/z): 471.33(M+1); M.Pt.: 55-5 fC
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-5-methyl-l-benzothiophene-3-sulfonamide (Compound No. 116); EIMS (m/z): 443.29(M+1); sticky
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-5-methyl-l-benzothiophene-2-sulfonamide (Compound No. 117); EIMS (m/z): 443.61(M+1); sticky
N-[2-({[(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-4-methoxy-7-methylthieno[3,2-d]pyrimidine-6-sulfonamide (Compound No. 118);
46

I-IIMS (m/z): 475.26(M+1)
A'-/- - (II (lS)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-5-methyl-l-benzothiophene-2-Mil/oniimide (Compound No. 119); I IMS (m/z): 457.28(M+1); M.Pt.: 63-6 fC
\-l2-C, I (lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-3-methyl-l-benzothiophene-2-Mil/oihimide (CompoundNo. 120); I-IMS (m/z): 443.31(M+1); M.Pt.: 103-105''C
\~l 2-( H (lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-5-methyl-l-benzothiophene-3-\////oininiic/e (CompoundNo. 121); I-1 MS (m/z): 457.28(M+1); M.Pt.: 58-60°C
,\ -/2-(l/(lS)-2-cyclopentyl-l-methylethylJamino}methyl)phenylJ-2-oxo-l,2,3,4-icirahyilroquinazoline-6-sulfonamide (CompoundNo. 122); I-IMS (m/z):443.36 (M+l); M.Pt.: 119-122°C
\-/2-(t'/(l S)-2-cydohexyl-l-methylethyl] amino}methyl)phenyl]-2-oxo-l, 2,3,4-iciruhvdro(/uinazolirie-6-siilfonamide (Compound No. 123); I-1 MS (m/z):457.31 (M+l); M.Pt.: 120-123°C
\'-/ J1 - (If (I S) - 2-cyclohexyl-1 -methylethyl] am ino} methyl)phenyl] -1 -methyl-2,3-dioxoindoline-5-M/l/oininiidc (Compound No. 124); 1.1 MS (m/z): 470(M+1); M.Pt.: 68-7J°C
A'-/ J - ill (I S) -2 -cyclopentyl-1 -methylethyl] amino} methyl)phenyl]-l-methyl-2,3-dioxoindoline-5-M/l/oiumiide (CompoundNo. 125); 1 IMS (m/z): 456(M+1); M.Pt.: 68-69°C
A -/ 2- (// (I S)-2-cyclohexyl-l-methylethyl] amino} methyl)phenyl]-3,3-difluoro-2-oxoindoline-5-Milloiuimide (CompoundNo. 126); IIIMS (m/z): 478.34(M+1); M.Pt.: 93-95°C
\-/2-(t/(lS)-2-cyc/ohexyl-l-methylethyl]amino}methyl)phenyl]-3,3-difluoro-l-methyl-2-<>.\<>indo/i>K'-5-sulfonamide (CompoundNo. 127); 1.1MS (m/z): 492.41 (M+l); M.Pt.: 63-66°C
\-/2-(,'/(lS) -2-cyclopentyl-1 -methylethyl] am ino}methyl)phenyl]-3,3-difluoro-l -m ethyl-2-i>.\uiinloHne-5-siilfonamide (CompoundNo. 128); I.I MS (m/z): 478.38(M+l);M.Pt.: 53-55°C
\-j „-( 11 (lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-3,3-difluoro-2-oxoindoline-5-Mil/oiHimidc' (Compound No. 129); I IMS (m/z): 464.32(M+1); M.Pt.: 88-90°C
\-l2-(il(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2-(isobutylamino)-l,3-hcnio\aiole-6-sulfonamide (Compound No. 130);
47

I-IMS (m/z): 485.47(M+1);M.Pt.: 58-60aC
\-/2-(l/( lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2-(isobutylamino)-l,3-
hcn-()\iizok-6-sulfonamJde (CompoundNo. 131);
1.1 MS (m/z): 499.46(M+1); M.Pt.: 138-14(fC
2-. \niino-N-[2-(t[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-lH-benzimidazole-5-
\tilfoiuiiiiide (CompoundNo. 132);
I'IMS (m/z.): 442(M+1); M.Pt.: 142-145°C
A'-/ -1- (If (lS)-2-cydohexyl-l -methylethyl]amino}methyl)phenyl]quinoline-8-sulfonamide
i( 'anipoundNo. 133);
I.I MS (m/z): 438.35(M+1); M.Pt.: 180-182°C
\-j 2-( If (lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]quinoline-8-sulfonamide
i( '(impoundNo. 134);
1.1 MS (IH/Z): 424.33(M+1); M.Pt.: 175-17 fC
\-/--(,'[(I S)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2,5-dimethyl-1,3-bemothiazole
fi-M/lfoiu/iuic/e (CompoundNo. 135);
1.1 MS (m/z): 472.41(M+1); M.Pt.: 129-131''C
\-j 2~( ll(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-2,5-dimethyl-l,3-benzothiazoh-
(>-M//Jo/u/i>iicle (CompoundNo. 136);
/.7W.V (m/z): 458.36(M+1); M.Pt.: 132-13 fC
\-/2-(l/(IS)-2-cyclohexyl-l-methylethyl]amwo}methyl)phenyl]-7-methyl-l-benzothiophene-2-
^iiljonumide (CompoundNo. 137);
I.I MS (m/z): 457.39(M+1); M.Pt.: 136-138°C
^( 'hl()ro-N-[2-([[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-l,3-benzothiazole-2-
\iiljonamide (CompoundNo. 138);
I-IMS (m/z): 478.32(M+1);M.Pt.: 95-9fC
_-. \iiii)io-5-(t[2-({[(lS)-2-cydohexyl-l- methylethyl]amino}methyl)phenyl]amino}sulfonyl)
I'lh'nyl irijhioroacetate (CompoundNo. 139);
1.1 MS (m/z): 514.39(M+l);M.Pt.: 122-124°C
\-/2-fl'/(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenylJ-l,4-dioxo-l,2,3,4-
icirtiliyilrophthalazine-5-sulfonamide (CompoundNo. 140);
I IMS (m/z): 457.38(M+1); M.Pt.: 186-188°C
\ -I'5-(If'2-(l[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)-2,3-dihydro-
III iiuh>n-2-yl]acetamide (CompoundNo. 141);
1 IMS (m/z): 484(M+I); M.Pt.: 63-66°C
A 15-( 112-([[( lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)-2,3-
i lihydro-1 H-inden-2-yl]acefamide (Compound No. 142);
48

S (m/z): 47()(M+1); M.Pt.: 58-60°C
\-/2-( i'[(IS)-2-cycIohexyl-l-methylethyl]amino}methyl)phenyl]-l-formylindoline-5-sulfonciiuic!(j
K '(impound No. 143);
I.IMS (m/z): 456(M+1)
\-j2-(ll(lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-l-formylindoline-5-sulfonamic ?.
(('(impound No. 144); 1 IMS (m/z): 442(M+1)
\-/2-(/'I(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl]-6-methoxyindane-5-sidfonami('ij (( 'ompoundNo. 145); I-IMS (m/z): 443(M+l)
\~j 2-( tl (lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-6-methoxyindane-5-sulfonamitle i( 'ampound No. 146); I.I MS (m/z): 457(M+1); M.Pt.: 80-81°C
\-/4-(lf(lS)-2-cychperityl-l-methylethyl]arnirio}methyl)phenyl]-2,4-dioxo-l,2,3,4-id/ ti/iy(/roc/i//nazoline-6-sulfonamide (CompoundNo. 147); ill MS (m/z): 457(M+1); M.Pt.: 155-158°C
\ -I2~( !j nS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-6-hydroxyindane-5-sitlfonamid(.< i( '(impound No. 148); i:iMS (m/z): 443(M+1); M.Pt.: 90-91°C
A'-/ 2- (,'/ (I S)-2-cydopentyl-1 -methylethyl] am ino}methyl)phenyl]-6-hydroxyindane-5-sulfonamid<> i( 'ompoundNo. 149); HI MS (in/?,): 429(M+1); M.Pt.: 80-81°C
\ -I^-(Jl2-(l[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]amino}sulfonyl)-2,3-dihydro 11l-indeii- I-y/Jacetamide (Compound No. 150); /•IMS (m/z): 484(M+1);M.Pt.: 54-55°C
\-j 5-<; 12-( I [(lS)-2-cydopentyl-l-methylethyl] amino}methyl)phenyl] amino}sulfonyl)-2,3-t/i/ivi/ro-lfl-inden-l-yljacetamide (CompoundNo. 151); I-1.MS (m/z): 47()(M+1)
\ -12-i,'/'(IS)-2-cydopentyl-1-methylethyl]amino}methyl)phenyl]-3-(4-methylpiperazin-l-y/ipro/Hiiie-l-siilfonamide (CompoundNo. 152); I-IMS (m/z): 437.44(M+1); Oily
\-!2-(ll(l S)-2-cydopentyl-1 -methylethyl] am ino}methyl)phenyl]-3-[(3R, 5S)-3,5-ilimci!iylpiperazin-l-yl]propane-l-sulfonaniide (CompoundNo. 153); I-IMS (m/z): 451.54(M+1); Oily
\»!2-( H (lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-3-piperidin-l-ylpropane-l-\nljoiniinide (CompoundNo. 154);
49

I-IMS (m/z.): 422.48(M+1); Oily \-l2-(l[(IS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-3-morpholin-4-ylpropane-l-
.Mil/o/ifiiiiidc' (Compound No. 155); I-IMS (in/7,): 424.41(M+1); Oily \-<2-ll(2-c}'dopentylethyl)amino]methyl}phenyl)-2-oxo-2H-chromene-6-sulfonamide (Compound
\o. 156):
I'IMS (m/7.): 427(M+1); M.Pt.: 74.1-75.2° C
\-(2-![(2-cydopentykthyl)anrino]methyl}phenyl)-2-methyl-l,3-benzothiazole-5-sulfonamide
i( 'om/)onnd No. 157);
I/IMS (m/z): 430(M+1); M.Pt.: 68.9- 74.2° C
\-i J-/ / (2-cydopentylethyl)amino]methyl}phenyl)-2-oxo-2,3-dihydro-l,3-benzothiazole-6-
Miltoiuniu'de (Compound No. 158);
I.1MS (m/7.): 432(M+1); M.Pt.: 122.4-128°C
/-( '/i/(>ro-N-/2-(([(lS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2H-chromene-
f)-Mi//oii(imide (Compound No. 159);
l-IMS (m/z): 476(M+1); M.Pt.: 8l-82°C
-/--( 'hloro-N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2H-chromene-6-
Milloiuinucli' (Compound No. 160);
I-IMS (m/7.): 490(M+1); M.Pt.: 87.8-89°C
\ '-/ 2- ( ,'/( I S)-2-cydohexyl-l -me thy I ethyl] ami no} methyl)phenyl]-4-fluoro-2-oxo-2H-chromerie-6-
^nllonnnude (Compound No. 161);
I-IMS (m/7.): 473(M+1); M.Pt.: 98.2-99°C
\-j2-( H( lS)-2-cydopentyl-l-methylethyl]amino}methyl)phenyl]-4-fluoro-2-oxo-2H-chromene-6-
\ /i/ li >iiciniic/L'f Compound No. 162);
111 MS (m/z): 459(M+1); M.Pt.: 89° C
\-/2~( !/(IS)-2-cyclopentyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-4-(trifluoromethyl)-2H-
c/n <>inci)L'-6-siilfonaiiiide (Compound No. 163);
i:iMS (m/z): 509(M+l);M.Pt.: 156°C
-{-. \inino-N-[2-({[(lS)-2-cydohexyl-l-methylethyl]amino}methyl)phenyl]-2-oxo-2H-chromenc-6-
\nlloiuimide (Compound No. 164);
I.I MS (m/7.): 470(M+1); M.Pt.: 185' 'C
-/-. \niino-N-(2-{[(2-cydopentylethyl)amino]methyl}phenyl)benzenesulfonamide (Compound No.
I/IMS (m/7.): 374.41(M+1); M.Pt.: 134-

tin ,:): 520.JKM + 1); M.I't.: 68-70"C
' 111 > / S)-2-c\\'/ohc.\\'l~ I -niL'ih\'/clh\'/ /iiiiiiiiOi'nicl/n'/ )/>lh'ii\'l /~2~i 11l-unuLi"i>l-!
I /I AY //;; :j; 405.j8(M+l); Oily
' / } i ,' / * ISi -2-c\'i'/i>/ic.\v/-l -iiic//iy/L'lhvl/(ii)iin<>!iiiclln'l)/>lii.'ini /-2-i ///-/. _\ / //'/ll^lnli(lc (( 'onijitniinl \o. I6H): / / sAY //// ;J: -fO(>.JV(.\[ + l ); Oily
. ' /;/( /.S'j .''-c\'L'/olh'.\vl-I-iii(.'lhyli'l/i\i/iiniin<)llnh'l/n'/lf)lh'iiyl /-2-i.\^-J/i/:cili\ I -1 1 1 / : , -. /ii,ii/c\/i//<>iiiiniii/<.'(( 'oiii/Hitiiid \o. 169): .' / i/.Y //// :j; •!.^:!.45>:
I n/.Y r/// J: 4^5.4(M+I): Oily
• . ' ,• ;/'• !S>-2-i-]'c/t>/ic.\Y/-/-iiie/hylc//n'//(iiiiin<>!iiici/>y/)/>/i<.'/iy//-2-( / 1 /-ic//\/-/H'ii/y/- l-iiicl/n'/ci/iyl/iiininafniclhy/ i/>/h'ii\1/-3-i I //-/(//•./:.«'/ /
,•' i •'/,;/'//, /(' l( /UllftDIIIU/ \ '(>. 1~5);
i i/,S ///; ;j: 4I)~.4(M+1); Oily
. . ' i , / ' l.^i-2 -c\\'/o/h'/ilv/- l-nn.'lh\'k'lhyl l
HAY /m J; 4~<).43(M+1); Oily
i i i i iSi-2--cycl<>/i<.'.\y/-/-iiiL'l/iy/i'l/i\'//iiiiiiii<>!i>n'lhyl)ji/ii.'>iy//-2-<>.\'t>--l--iiri!//ii' •'''.''., <•/( ii-\////n/iti/i/i(/c i( 'oiiipinnul \o. 1"~): /'>AY ,/;/ ,-j; 5:J(M\-I); M.l>f.: 89" C

i IMS (in :.): 433(
\\ 1'ilc ihe present invention has been described in terms of its specific embodiments, cerian MI. '.hi icaiions and equivalents will be apparent to those skilled in the art and are intended in .'•-included \\iihin the scope of the present invention.
Microbiological activity
Microbroih minimum inhibitory concentration (MIC) was performed using \'('( Iv inc'lioj iii Cation adjusted Mueller llinton broth for facultative cultures (S.uurcus. l-jucrm-in•< /••> iii'1 ('aiion adjusted Mueller llinton broth +2.5% lysed horse blood for S./^ici/niouiuc. \1U .r'.nnsi //.i/i/Iucirae strains was performed by NCCLS broth dilution method using HTM broil 1 i\ rniL'hi groun cultures were adjusted to 0.5 Mcfarland using normal saline and dilutci 1' IIIIK- - I mg in concentration of stock solution of drug in DMSO/distilled \\atersol\cnl gi\eu , \< ( i N manual \\ere prepared. NCCLS double dilutions were done to get the ivqunv o •liivniraiion range of the drugs in the 96 well microtiter plates using the respecti\e media. ' >' iii )| ruliuiv broth was added in wells already containing 100 |ul of broth containing antibiotic .•
•\t appro\imatel\ 3-7x10- CFU/ml. The plates were incubated at 37°C for about 1 X-24 h. ['r.
i. MH. cnii'aiion of drug at which there was complete disappearance of growth \\as considcicd :
\ I j,
( ninpoiinds of this invention have shown good activity againsts microbial strains. Some ' !!K' ri'inpoimds described herein have shown very good activity against microbial strains. ! -\:!iiip c. Sirc/nococci/s piK'iimoniae, HuemophUhis influen~ac\ Streptococcus ji\'o^cih^
''/.//''/I ii>i:iH\-it.\ iiureits.

6. The method according to claim 4 wherein bacterium is selected from Staphylococd,
Enterococci, Streptococci, Haemophilus, Propionibacterium, Moraxalla, Escherichia
Chlamydia, Rickettsiae, Mycoplasm, Legionella, Mycobacterium, Helicobact^'
Clostridium, Bacteroides, Corynebacterium, Bacillus or Enter obactericeae, and the fungal
organism is selected from Aspergillus, Blastomyces, Candida, Coccidiodes, Cryptococcus
Epidermophyton, Hendersonula, Histoplasma, Microsporum, Paecilomyces.
Paracoccidiodes, Pneumocystis, Thchophyton, or Trichosporium.
7. The method according to claim 4 wherein the condition is selected from community
acquired pneumonia, upper and lower respiratory tract infections, skin and soft tissue

infections, hospital acquired lung infections or bone and joint infections, mastitis, catheler infection, foreign body, acne vulgaris, prosthesis infections and peptic ulcer disease.