FORM 2
THE PATENT ACT, 1970
(39 OF 1970)
AND
THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
(See section 10; rule 13)
1. TITLE OF THE INVENTION: "PIPERAZINE DERIVATIVES"
2. APPLICANT(S)

(a) Name: UNICHEM LABORATORIES LIMITED
(b) Nationality: An Indian Company
(c) Address: Unichem Bhavan, Prabhat Estate, Off. S.V. Road, Jogeshwari (W), Mumbai-400102, Maharashtra, India
3. PREAMBLE TO THE DESCRIPTION:
The following specification particularly describes the invention and the manner in which it is to be performed.

PIPERAZINE DERIVATIVES
FIELD OF THE INVENTION:
The present invention is related to novel process for the preparation of piperazine derivatives and novel intermediates useful for preparation thereof.
BACKGROUND OF THE INVENTION:
L-proline compounds derivatives show a dipeptidyl peptidase (DPP-IV) inhibitory activity. The derivatives having substituent introduced into the y-position of proline have a potent DPP-IV inhibitory activity. Derivatives of such L-proline compounds are useful for the treatment or prophylaxis of diabetes, obesity, HIV infection, cancer metastasis and like are disclosed in U.S. Patent No. 7,074,794. The side chain moiety introduced at y-position is substituted piperazine derivatives. U. S. Patent No. 7,807,671 disclosed some compounds useful for the treatment of HIV and AIDS which have this side chain piperazine derivative moiety.
Such side chain piperazine derivative moiety was prepared by two methods which were disclosed in U. S. Patent No. 7,807,671 wherein method 1 teaches addition of piperazine to the solution of XpY-Z in THF, dioxane or DMF at RT or 115°C for 17 hours.
In method 2 the solution of piperazine in dry THF was added to n-BuLi at RT. After that Xi-Y-Z was added to the solution and stirred for I to 10 hours at RT to 115°C wherein A is H or Li.

U. S. patent application No. 2013/0310396 disclosed the reaction of XrY-Z with piperazine in DMF, while stirring K2CO3 and Pd(OAc)2 were added and heated to 110°C for 12 hours and solid was filtered.
PCT application No. 2014/041560 disclosed specific example to produce such piperazine derivative. That example is generically represented as below in which compound of formula NH2-Y-Z with bis (2-chloroethyl) N-protected derivative compound to obtain piperazine derivative.
Where in Xi is halogen atom and Y and Z are as described in the U. S. Patent No.
7,807,671.
Above said processes disclosed use of hazardous chemicals such as n-BuLi and
Pd/ (OAc)2 which are difficult to handle at plant level. There is potential for the
formation of dimer impurity and resulting into lower yield.
Therefore industry needs a better process for the preparation novel intermediates
to prepare certain DPP-IV inhibitors and compounds useful for the treatment of
HIV and AIDS.
OBJECT OF THE INVENTION:
The main object of the present invention is to provide novel compounds of
formula (1), (la) and (2).
Another object of the invention is to provide the process to produce compounds of
the formula (1) and (la).
Yet another object of the invention is to provide the process to produce compound
of formula (2) which is useful for the preparation of compound of formula (1) and
(la).
Another object of the present invention is to provide the novel process for the
preparation of compound of formula (3) or (3a) or salts thereof which is useful to
prepare certain DPP-IV inhibitors and to treat HIV and AIDS;

wherein X and "A" group is defined in detailed description of the invention, and "m" is 1 to 2.
SUMMARY OF THE INVENTION:
Accordingly is provided the compounds of formula (1), (la) and (2);
wherein and X, m and A are as defined hereafter
Accordingly is provided the process for producing compound of formula (1) comprising steps of;
(a) reacting compound of formula (4) with reducing agent in presence of suitable solvent form reaction mixture;

(b) reacting compound of formula (5) or compound of formula (2) with the reaction mixture obtained in step (a) to obtain compound of formula (I); wherein and X, Xi, m and "A" are as defined hereafter.
Accordingly is provided the process for producing compound of formula (1)
comprises;
reacting compound of formula (2) with compound of formula (6) in presence of
suitable base and suitable to obtain compound of formula (1); wherein X, m and
"A" are as defined hereafter.
Accordingly is provided the process for producing compound of formula (la)
comprises;
reacting compound of formula (2) with compound of formula (6a) in presence of suitable solvent and suitable base to obtain compound of formula (la); wherein X, m and "A" are as defined hereafter.
Accordingly is provided the process for producing compound of formula (2) comprising steps of;
(a) is same as Step (a) of scheme I;
(b) reacting compound of formula (5) with the reaction mixture obtained in step (a) to obtain compound of formula (2); wherein Xi, X, m and "A" are as defined hereafter.

Accordingly is provided process for producing compound of formula (3) comparing steps of;
(a) reacting of compound of formula (1) with compound of (4) in presence of suitable base and suitable solvent to obtain compound of formula (5);
(b) optionally isolating compound of formula (5);
(c) deprotecting compound of formula (5) to obtain compound of formula (3); wherein "P" is protecting group, X, m and "A" are as defined hereafter.
Accordingly is provided process for producing compound of formula (3) comprises, reacting compound of formula (1) with ammonia; wherein X, m and "A" are as defined hereafter.
Accordingly is provided process for producing compound of formula (3a) comprises, reacting compound of formula (la) with ammonia; wherein X, m and "A" are as defined hereafter.
DETAILED DESCRIPTION OF THE INVENTION:
The present invention provides the compounds of formula (1), (la) and (2);

X is halogen, -S(=0)2R1, -Si (R2)3, aryl or substituted aryl, "m" is 1 to 2, R1 and R2 defined as below A is selected form the group consisting of below wherein ^^ sign indicate site of attachment to N atom;

The compounds and the intermediates of the present invention can be produced by the following methods.
Scheme 1 shows the process for producing compound of formula (1) comprising steps of;
(a) reacting compound of formula (4) with reducing agent in presence of suitable solvent at the temperature range from 0°C to 100°C to form reaction mixture;
(b) reacting compound of formula (5) or compound of formula (2) with the reaction mixture obtained in step (a) followed by raising the temperature to reflux temperature; preferably at temperature 60° to 100°C to obtain compound of formula (1); wherein X1 is, -OR1, -COR1, -SO2R1, aryl or substituted aryl; X is halogen, -S(=0)2R1, -Si (R2X aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloaikylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, —OR5, — COR6, —C02R7, —CONR8R9 or — SO1R10 wherein R1,R2, R3R4, R5, Re, R7, Rs, R9 and Rio are the same or

different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and Rg and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents; Scheme 2 shows the process for producing compound of formula (1) comprises;
reacting compound of formula (2) with compound of formula (6) in presence of suitable base and suitable solvent at temperature at about 25°C to 40°C to obtain compound of formula (1); wherein X, m and "A" are as defined in scheme 1. Scheme 3 shows the process for producing compound of formula (la) comprises;
reacting compound of formula (2) with compound of formula (6a) in presence of suitable solvent and suitable base at temperature at about 25°C to 40°C to obtain compound of formula (la); wherein X, m and "A" are as defined in scheme 1. Scheme 4 shows the process for producing compound of formula (2) comprising steps of;

(a) is same as Step (a) of scheme 1;
(b) reacting compound of formula (5) with the reaction mixture obtained in step
(a) to obtain compound of formula (2). The reaction conditions are same as described in Step (b) of scheme 1. X\, X, m and "A" are as defined in scheme 1.
Scheme 5: shows the process for producing compound of formula (3) comparing
steps of;
(a) reacting of compound of formula (1) with compound of (4) in presence of suitable base and suitable solvent to obtain compound of formula (5);"'1 ' ' " '
(b) optionally isolating compound of formula (5);
(c) deprotecting compound of formula (5) to obtain compound of formula (3); wherein "P" is protecting group, X, m and "A" are as defined in scheme 1.
The above mentioned step (a) is carried out at temperature range 70°C to 100°C. The reaction is successfully carried out with or without isolation of compound represented by general formula (5).
Deprotection of compound of formula (5) is carried out in presence of suitable reagents, depending on the type of protective group and the reagents may be selected from the group consisting of acids like hydrochloric acid, trifluoroacetic acid, hydrobromic acid, sulphuric acid, hydrobromic acid, p-toluene sulfonic acid, boron tribromide, formic acid; reduction using palladium/carbon, palladium'

acetate or palladium hydroxide, base such as piperidine, ammonia, methylamine and cyclohexyl amine at temperature range 60°C-100°C to obtain compound of formula (3).
The deprotection reaction may be carried out in presence or absence of the
solvent. The solvent may be selected from water, alcohols such as methanol,
ethanol, 1-propanol, 2- propanol, tertiary-butanol; ketones such as acetone, methyl
ethyl ketone; nitriles such as acetonitrile, propionitrile; amides such as formamide,
N,N-dimethylformarnide, N,N- dimethylacetamide, l,3-dimethyl-2-
imidazolidinone; ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, 1 ,4-dioxane, tetrahydrofuran, tetrahydropyran; esters such as ethyl formate, ethyl acetate, propyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, methylene dichloride; hydrocarbons such as n-hexane, cyclohexane, benzene, toluene and methyl cyclohexane; sulfoxides such as dimethyl sulfoxide; polar solvents such as sulfolane, hexamethylphosphorylamide; or mixture(s) thereof.
After the completion of reaction, the obtained product is quenched into the ice water followed by extraction with any known method in the art. Layers are separated and pH of aqueous layer is adjusted to 10-12 by base. The example of base includes but not limited to K2C03, Na2C03, Li2C03, NaHC03, LiHC03, KHC03, NaOAc, KOAc, KOH, NaOH, LiOH, NH4OH, TEA, trimethylamine, or aqueous solution thereof or mixture(s) thereof.
Scheme 6 shows the process for producing compound of formula (3) comprises, reacting compound of formula (1) with ammonia;
wherein X, m and "A" are as defined in scheme 1.

Scheme 7 shows the process for producing compound of formula (3a) comprises, reacting compound of formula (la) with ammonia;
wherein X, m and "A" are as defined in scheme 1.
In the present invention, ammonia source is in the form of ammonia gas, methanolic ammonia or aqueous ammonia in the presence of suitable solvent. This reaction is carried out under pressure in autoclave at temperature 20°C to 50°C. Compound of formula (3) or (3a) may be converted into salt such as acetate salt by conventional method known in the art. Other acid addition salts may also be prepared using appropriate acid. Isolation/Extraction of compound of formula (1), (la) ,(2), (3), (3a) and (5) can be carried out by any method known in the art such as cooling, filtration, centrifugation, washing, drying and using suitable solvent combination thereof.
The example of suitable solvent may be selected from, but is not limited to halogenated hydrocarbons such as water, methylene chloride, ethylene chloride, chloroform and carbon tetrachloride; alcohols such as methanol, ethanol, 1 -propyl alcohol, 2-propanol, tert-butanol; esters such as ethyl formate, ethyl acetate, isopropyl acetate and butyl acetate; amides such as formamide, N,N-dimethylformamide, N,N-dimethylacetamide; sulfoxides such as dimethyl sulfoxide; nitrile such as acetonitrile, propionitrile; ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, 1 ,4-dioxane, tetrahydrofuran, tetrahydropyran; hydrocarbons such as benzene, toluene, cyclohexane, n-hexane and methyl cyclohexane; ketones such as acetone, methyl ethyl ketone; polar aprotic solvents such as l,3-dimethyl-2-imidazolidinone, sulfolane, Hexamethylphosphoramide or mixture(s) thereof.
The example of suitable base may include but not limited to K2CO3, Na2C03, Li2C03, NaHC03, LiHC03, KHCO3, NaOAc, KOAc, KOH, NaOH, LiOH,

NH4OH, Potassium tert-butoxide, sodium ethoxide, sodium methoxide, n-BuLi,
sec-BuLi, t-BuLi, methyllithium, sodium amide ,lithium diisopropylamide,
sodium hydride or potassium hydride, LiHMDS, NaHMDS, KHMDS and LiTMP
TEA, trimethylamine, DIPEA, pyridine, dimethyl amino pyridine and piperidine
or aqueous solution thereof or mixture(s) thereof.
The example of reducing agent includes but not limited to NaBH4, NaBH3CN and
Sodium triacetoxyborohydride (STAB), preferably NaBELt
The example of protecting group includes but not limited to aralkyl such as
benzyl, p-nitrobenzyl, benzhydryl, trityl; acyl such as formyl, acetyl, propionyl,
methoxyacetyl, methoxypropionyl, benzoyl, thienylacetyl, thiazolylacetyf,
tetrazolylacetyl, thiazolylglyoxyloyl, thienylglyoxyloyl; lower alkoxy-carbonyl
such as methoxycarbonyl, ethoxycarbony], tert-butoxycarbonyl; aralkyloxy-
carbonyl such as benzyloxycarbonyl, p-nitrobenzyloxycarbonyl, 9-
fluorenylmethyloxycarbonyl; lower alkane sulfonyl such as methane sulfonyl,
ethane sulfonyl; aryl sulfonyl such as toluene sulfonyl; tri- (lower alkyl) silyl such
as trimethylsilyl; and triphosgene and other carboxybenzyl (Cbz), 2,2,2,-
trichloroethyl carbamate (Troc), ethyl carbamate, ally carbamate (Alloc), ethyl
caramate, acyl, trifluroacetamide, allyamine, triphenylmethyl, and
trichloromethoxy.
Alkyl is preferably linear or branched alkyl having 1 to 8 carbon atoms, such as
methyl, ethyl, propyl, isopropyl, butyl, isobutyi, tert-butyl, pentyl, hexyl, octyl and
the like.
Cyctoalkyl preferably has 3 to 7 carbon atoms, and is exemplified by cyclopropyl,
cyclopentyl, cyclohexyl, cycloheptyl and the like.
Cycloalkylalkyl has a cycloalkyl moiety, which is equivalent to that mentioned
above, and an alkyl moiety which is preferably linear or branched and has 1 to 3
carbon atoms. Examples thereof include cyclopropylmethyl, 2-cyclobutylethyl, 3-
cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, cycloheptylmethyi and
the like.
Aryl is preferably phenyl, naphthy] or ortho fused bicyclic group having 8 to 10
ring atoms wherein at least one ring is an aromatic ring (e.g., indenyl) and the like.

Arylalkyl has an aryl moiety, which is equivalent to that mentioned above, and an alkyl moiety which is preferably linear or branched and has 1 to 3 carbon atoms. Examples thereof include benzyl, benzhydryl, phenethyl, 3-phenylpropyl, 1-naphthylmethyl, 2-(t-naphthyl)ethyl, 2-(2-naphthyl)ethyl, 3-(2-naphthyl)propyl and the like.
Heteroaryl is preferably a 5 or 6-membered ring group having carbon and 1-4
hetero atoms (oxygen, sulfur or nitrogen), an ortho fused bicyclic heteroaryl
having 8 to 10 ring atoms, which is derived therefrom, particularly a benz
derivative, those derived from fusing a propenylene, trimethylene or
tetramethylene group therewith, stable N-oxide thereof and the like. Examples
thereof include pyrrolyl, furyl, thienyl, oxazolyl, isoxazolyl, imidazolyl, thiazolyl,
isothiazolyl, pyrazolyl, triazolyl, tetrazolyl, 1,3,5-oxadiazolyl, 1,2,4-oxadiazplyl,
1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl,
1,2,4-triazinyl, 1,2,3-triazinyl, 1,3,5-triazinyl, benzoxazolyl,benzisoxazolyl,
benzothiazolyl, benzisothiazolyl, benzimidazolyl, oxazolopyridyl,
imidazopyridazinyl, thianaphthenyl, isothianaphthenyl, benzofuranyl, isobenzofuranyl, benzothienyl, chromenyl, isoindolyl, indolyl, indolinyl, indazolyl, isoquinolyl, quinolyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, 2,1,3-benzoxadiazolyl, benzoxazinyl and the like. Heteroarylalkyl has a heteroaryl moiety, which is equivalent to that mentioned above, and an alkyl moiety which is preferably has 1 to 3 carbon atoms and linear or branched. Examples thereof include 2-pyrrolylmethyl, 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 2-thienylmethyl, 2-(2-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 2-(4-pyridyl)ethyl, 3-(2-pyrrolyl)propyl, 4-imidazolylmethyl and the like.
Halogen is exemplified by chlorine, bromine, fluorine and iodine. Of the above-mentioned substituents, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl and heterocycle are optionally substituted by the following 1 or more substituents.
The substituents may be, for example, halogen, hydroxyl group, nitro, cyano, trifluoromethyl, alkyl, alkoxy, alkylthio, formyl, acyloxy, oxo, phenyl, 2-pyridyl,

3-pyridyl, 4-pyridyl, 4-piperidinyl, 2-morpholinoethyl, 3-picolyl, arylalkyl, — COORa; — CH2COORa, —OCH2COORa, —CONRbRc, —CH2CQNRb Rc (Q is =0 or =S), —OCH2CONRbRc, — COO(CH2)2NReRf, —S02T,, —CONRdS02T,, —NReRf, —NRgCHO, —NRgCOT2, —NRgCOOT2, —NRgCONR;R„ — NRkS02T3, —S02NRiRm, —S02NRnCOT4, methylenedioxy, ethyleneoxy and the like.
These substituents may have substituents, and phenyl, 2-pyridyl and 4-piperidinyl having substituents are exemplified by 4-cyanophenyl, 4-chlorophenyl, 4-methoxyphenyl, 5-cyano-2-pyridyl, l-ethoxycarbonyl-4-piperidinyl and the like. Ra-Rn show hydrogen, alkyl (as defined above) or arylalkyl (as defined above). Rb and Rc, Re and Rf, R{ and Rj3 and R, and Rm of —NRbRc, —NReRf, —NRjRj and — NR]Rm may be respectively bonded to each other to form heterocycles each optionally having 1 or 2 nitrogen atoms or oxygen atoms, and the heterocycle may be condensed with an aromatic ring optionally having substituents (as defined above, and optionally substituted by the aforementioned substituents). Moreover, —NReRf may show a heteroaryl having =0 (e.g., 2-pyrroMdinon-J-yl, succinimido, oxazolidin~2-on-3-yl, 2-benzoxazolinon-3-yl, phthalimido, cis-hexahydrophthalimido and the like). T1-T4 show hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, which may be substituted by the aforementioned substituents In the above-mentioned substituents of the substituents, halogen, alkyl and arylalkyl are exemplified by those mentioned above.
Haloalkyl is exemplified by trifluoromethyl, 2,2,2-trifluoroethyl, penta fluoroethyl and the like.
Heterocycle is a saturated or unsaturated monocyclic 4 to 7-membered ring group or 10 or 11-membered ring group, which is a spiro ring, having carbon and at least one nitrogen, and optionally other hetero atom (oxygen or sulfur). Examples thereof include azetidinyl, pyrrolidinyl, piperidino, piperazinyl, morpholino, 1,4-diazepanyl, 1,2,5,6-tetrahydropyridyl, thiomorpholino, oxothio morpholine, dioxothiomorpholino, 3-azaspiro[5,5]undecyl, 1,3,8-triazaspiro [4,5]decyl and the like.

Moreover, the above-mentioned heterocycle may be condensed with an aromatic ring (e.g., benzene ring, pyridine ring and the like) optionally having substituents. Examples thereof include indolinyl, isoindolinyl, 1,2,3,4-tetra hydroquinolyl, 1,2,3,4-tetrahydroisoquinolyl, phthalimido, indolyl and the like. The invention is further defined by reference to the following examples describing in details the preparation of compounds of the invention. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the purpose and interest of this -invention. The following examples are set to assist in understanding the invention and should not be construed as specifically limiting the invention described and claimed herein. Such variations of the invention, including the substitution of all equivalents now known or later developed, which would be within the purview of those skilled in the art. A change in experimental design, is to be considered to fall within the scope of the invention incorporated herein. Examples: Example No. 1: N,N-bis(2-chloroethyl)-3-methyl-l-phenyl-lH-pyrazol-5-amine
Sodium borohydride (35.0 gm, 0.989 moles) was added portion wise to stirred solution of chloroacetic acid (170.0 gm, 1.8 moles) in mixture of Toluene (350.0 ml) and THF (270.0 ml) at 0°C-100°C. The reaction mixture was stirred for 45 min (till no further evolution of hydrogen gas was observed) and 5-amino-3-methyl-1 -phenyl-lH-pyrazole (20.0 gm, 0.1149 moles) was added. Reaction temperature was slowly raised to reflux temperature (80-85° C). Reaction process was monitored by TLC (solvent system- 30:70 Ethyl acetate:Hexane). After completion, stopped heating and cooled to room temperature. Added 10% solution of sodium bicarbonate and extracted with (2 x 200ml) Ethyl acetate. The combined organic layer was washed with water (2 x 200ml) and separated the

layers. Solvent was removed from the organic layer to obtained crude product.
Yield: 33 gm.
Example No. 2: l-(3-methyl-l-phenyl-lH-pyrazol-5-yl)-4-tosylpiperazine
The title compound of example no. 1 (16.0 gm, 0.053 moles) and p-toluenesulfonamide (23.0gm, 0.134 moles) was added in N,N-dimethyl formamide (35ml) at 25°C. Added potassium carbonate (43.8gm, 0.318) and heated reaction mass to 90°C-95°C. Reaction was monitored by TLC (50:50% Ethyl acetate: hexane). After completion, reaction mixture was cooled to room temperature. Added Ethyl acetate (150 ml) and water (160ml), stirred for 15 min. Organic layers were separated. Aqueous layer was washed with Ethyl acetate (100ml) and separated the layers. Combined organic layer and washed with water (2 x 150ml) and 100ml brine solution and separated the layers. Solvent was removed under reduced pressure below 40deg. to give the titled compound (crude). Yield 19 gm. Example No. 3: l-(3-methyl-l-phenyl-lH-pyrazol-5-yl)piperazine
The title compound of example no. 2 (5.0gm, 0.013 moles) was added in Cone. H2SO4 (15 ml) at 25-30°C and stirred for 10 min. The reaction mixture was allowed to heat up to 90°-95°C for 3-5 hr. Reaction monitored by TLC (1:7:4, Methanol: MDC: Hexane). After completion'of reaction, stopped the heating and cooled to room temperature and quenched in crushed ice water (100ml). The reaction mixture was extracted with (2x 50ml) ethyl acetate and separated the layers. Aqueous layer was basified by using 2N NaOH solution up to pH 10-12

and extracted with ethyl acetate (2x 50ml). Separated and combined the layers. Solvents were removed to obtain title compound. Yield 2.2 gm. Example 4: N-(2-chloroethyl)-3-methyl-l -phenyl- lH-pyrazol-5-amine
Sodium borohydride (17.0 gm, 0.45 moles) was added portion wise to stirred solution of chloroacetic acid (85.0 gm, 0.9 moles) in mixture of Toluene (350.0 ml) and THF (270.0 ml) at 0°C-100°C. The reaction mixture was stirred for 45 min (till no further evolution of hydrogen gas was observed) and 5-amino-3-methyl-1 -phenyl-lH-pyrazole (20.0 gm, 0.1149 moles) was added. Reaction temperature was slowly raised to reflux temperature (80-85° C). Reaction process was monitored by TLC (solvent system- 30:70 Ethyl acetate:Hexane). After completion, stopped heating and cooled to room temperature. Added 10% solution of sodium bicarbonate and extracted with (2 x 200ml) Ethyl acetate. The combined organic layer was washed with water (2 x 200ml) and separated the layers. Solvent was removed from the organic layer to obtained crude product. Yield: 13 gm. Example 5: N,N-bis(2-chloroethyl)-3-methyl-l-phenyl-lH-pyrazol-5-amine
Sodium borohydride (17.0 gm, 0.45 moles) was added portion wise to stirred solution of chloroacetic acid (85.0 gm, 0.9 rrioles) in mixture of Toluene (350.0 ml) and THF (270.0 ml) at 0°C-100°C. The reaction mixture was stirred for 45 min (till no further evolution of hydrogen gas was observed) and N-(2-chloroethyl)-3-methyl-l -phenyl-lH-pyrazol-5-amine (20.0 gm, 0.1149 moles) was added. Reaction temperature was slowly raised to reflux temperature (80-85° C).

Reaction process was monitored by TLC (solvent system- 30:70 Ethyl acetate :Hexane). After completion, stopped heating and cooled to room temperature. Added 10% solution of sodium bicarbonate and extracted with (2 x 200ml) Ethyl acetate. The combined organic layer was washed with water (2 x 200ml) and separated the layers. Solvent was removed from the organic layer tq obtain crude product. Yield: 20 gm. Example 6: N,N-bis(2-chloroethyl)-3-methyf-l-phenyl-lH-pyrazol-5-amine
To a N-(2-chloroethyl)-3-methyl-l -phenyl-lH-pyrazol-5-amine (10 gm) in acetonitrile 100 ml, charged potassium carbonate and cooled to 15-20°C. Charged monochlorobromoethane at 15-20°C. Raised temperature to 40-45°C. After completion of reaction distilled out solvent under reduced pressure and charged 100ml water to residue. Extracted the product in MDC and washed with water, Organic layer dried over sodium sulphate and distilled out solvent under reduced pressure to give crude product. Yield 6.8 gm.
Among the compound represented by general formula (1) or (la); preferable compounds include a compound selected from list given below and can be produced using appropriate starting substances in same manner as Example 1, 5 and 6.
N-benzhydryl-2-chloro-N-(2-chloroethyl)ethanamine;5-(bis(2-chIoroethyl)amino)
iso phthalonitrile; N-(2-chloroethyl)-N-(3-chloropropyl)-4-nitrobenzenamine;
N,N-bis(2-chloroethyl)-2-(trifluoromethyl)benzenamine; N,N-bis(2-
chloroethyl)biphenyl-3-amine;ethyl2-(bis(2-chloroethyl)amino) benzoate;N,N-
bis(2-chloroethyl)pyridin-2-amine;2-(bis(2-chloroethyl) amino)nicotinonitrile; 2-
(bis(2-chloroethyl)amino)isonicotinonitrile; 6-(bis(2-
chloroethyl)amino)nicotinonitrile;6-(bis(2-chloroethyl)amino)-5-fluoro nicotinonitrile;N,N-bis(2-chloroethyl)-5-(trifluoromethyl)pyridin-2-amine;N,N-bis(2-chloroethyl)-3-(trifluoromethyl)pyridin-2-amine;N,N-bis(2-chloroethyl)-3-

fluoro-5-(trifluoromethyl) pyridin-2-amine; N,N-bis(2-chloroethyl)-5-
nitropyridin-2-amine; N,N-bis(2-chIoroethyI)-5-fIuoropyridin-2 -amine; N,N-
bis(2-chloroethyl)-3-fluoropyridin-2-amine; N,N-bis(2-chloroethyl)-3,5-
dichloropyridin-2-amine; 6-(bis(2-chloroethyl)amino)nicotinamide; 6-(bis(2-
chloroethyl)amino)-5-fluoronicotinamide;ethyl2-(bis(2-chloroethyl)amino)
nicotinate; ethyl 6-(bis(2-chloroethyl)amino)nicotinate; ethyl 6-(bis(2-
chloroethyl)amino)-5-chloronicotinate;N,N-bis(2-chloroethyl)-3-methylpyridin -
2-amine;3-(benzo[d]thiazol-2-yl)-N,N-bis(2-chloroethyl)pyridin-2-amine; 3,5-
dichloro-N,N-bis(2-chIoroethyl)pyridin-4-amine; N,N-bis(2-chloroethyl)-3-
methoxypyrazin-2-amine; 2-(4~(bis(2-chloroethyl)amino)-6-methylpyrimidin-2-
yl)phenol; N,N~bis(2-chloroethyl)-lH-benzo[d]imidazol-2-amine; N,N-bis(2-
chloroethyl)-7-(trifluoromethyl)-lH-benzo[d]imidazol-2-amine;N>N-bis(2-
chloroethyl)-6-fluoro-lH-benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)-6-
nitro-lH-benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)-l-methyl-lH-
benzo[d]imidazol-2-amine;N,N-bis(2-chloroethyl)-l-methyl-5-(trifluoro-methyl) -
lH-benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)-5-fluoro-l-methyl-1H-
benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)-l-phenyls 1H-
benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)benzo[d]oxazol-2-amine; 2-
(bis(2-chJoroethyl)amino)benzo[d]oxazole-5-carbonitrile;N,N-bis(2-chloro ethyl)-
5-methoxybenzo[d]oxazol-2-amine;N,N-bis(2-chloroethyl)oxazolo[4;5-b]pyridin-
2-amine;N,N-bis(2-chloroethyl)-6-methoxybenzo[d]thiazol-2-amine; N,N-bis(2-
chloroethyl)benzo[d]thiazol-2-amine;2-(bis(2-chloroethyl)amino)
benzo[d]thiazole-5-carbonitriIe; 2-(bis(2-chIoroethyI)amino)benzo[d]thiazole-6-
carbonitrile;N,N-bis(2-chloroethyl)-6-(trifluoromethyl) benzo[d]thiazol-2-amine;
5-chloro-N,N-bis(2-chloroethyl)benzo[d]thiazol-2-amine; 6-chloro-N,N-bis(2-
chloroethyl)benzo[d]thiazol-2-amine; N,N-bis(2-chloroethyl)-5-
nitrobenzo[d]thiazol-2-amine; N,N-bis(2-chloroethyl)-6-nitrobenzo[d]thiazol-2-
amine; N,N-bis(2-chloroethyl)-3.Tfluoronaphthalen-l-amine;N,,Nrbis(27
chloroethyl)-4-nitro naphthalen-1 -amine; N.N-bis(2-chloroethyl)quinolin-4-
amine; N;N-bis(2-chloroethyl)-7-(trifluoromethyl)quinoIin-4-amine; N,N-bis(2-
chloroethyl)-2-(trifluoromethyl)quinolin-4-amine; N,N-bis(2-chloroethyl)-8-

methyl-2-(trifluoromethyl)quinolin-4-amine; N,N-bis(2-chloroethyl)-2,6-
bis(trifluoromethyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-2,8-bis (trifluoro
methyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-6-methoxy-2-(trifluoro
methyl)quinolin-4-amine;N,N-bis(2-chloroethyI)-7-methoxy-2-(trifluoro
methyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-8-methoxy-2-(trifluoro methyl)
quinolin-4-amine;N,N-bis(2-chIoroethyl)-8-fluoro-2-(trifluoro methyl) quinolin-4-
amine;N,N-bis(2-chIoroethyl)-6-fluoro-2-(trifluoromethyl) quinolin-4-amine;
methyl 4-(bis(2-chloroethyl)amino)quinoline-2-carboxylate; methyl 4-(bis(2-
chloroethyl)amino)quinoline-3-carboxylate;4-(bis(2-chloroethyl)
amino)quinoline-2-carbonitrile;4-(bis(2-chloroethyl)amino)quinoline-2-
carboxamide;N4,N4-bis(2-chloroethyl)quinoline-2,4-diamine;N,N-bis(2-chloro
ethyl)-2-phenylquinolin-4-amine;N;N-bis(2-chloroethyl)-2-methylquinolin-4-
amine;N,N-bis(2-chloroethyl)isoquinolin-l-amine; l-(bis(2-chloroethyl) amino)
isoquinoline-4-carbonitrile;N,N-bis(2-chloroethyl)-4-fluoroisoquinolin-l-amine;
N,N-bis(2-chloroethyl)-2-(trifluoro methyl)quinazolin-4-amine; N,N-bis(2-
chloroethyl)-2-phenylquinazolin-4-amine;N,N-bis(2-chloroethyl) quinolin-2-
amine; N,N-bis(2-chloroethyl)quinoline-8-sulfonamide; N,N-bis(2-
chloroethyl)chroman-5-amine; N,N-bis(2.-chloroethyl)-4-phenylpyrj,midin-5:
amine;N,N-bis(2-chloroethyl)-3-phenylpyrazin-2-amine;N,N-bis(2-chloroethyl) -
3-(piperidin-l-yl) pyrazin-2-amine; N,N-bis(2-chloroethyl)-3-(piperazin-l-
yl)pyrazin-2-amine;N,N-bis(2-chloroethyl)-l -phenyl- 1,4,5,6-tetrahydro
pyrimidin-2-amine;N,N-bis(2-chloroethyl)-3-phenyl pyridin-2-amine;N,N-bis(2-
chloroethyl)-4-phenylpyrimidin-2-amine;2-(2-(bis(2-chloroethyl) amino)-6-
methylpyrimidin-4-yl)phenol;N5,N5-bis(2-chloroethyl)-N3,N3-dimethyl-6-phenyl
pyridazine-3,5-diamine; N,N-bis(2-ch!oroethyl)-3-phenylpyridazin-4-amine;5-
(bis(2-chloroethyl)amino)-6-phenylpyridazin-3-ol;3-(bis(2-chloro ethyl)amino)-2-
phenyl-lH-inden-l-one;(2-(bis(2-chloroethyl)amino)pyridin-3-yl)(pyridin-2-
yl)methanone;(2-(bis(2-chloroethyl)amino)pyridin-3-yl) (morpholino)
methanone;3-(2-(2-(bis(2-chloroethyl) ,^ amino) pyridin-3-yl)-2-
oxoethyl)benzonitrile; N-benzyl-2-(bis(2-chloroethyl)amino)nicotinamide; 2-(bis(2-chloroethyl)amino)-N-cyclohexylnicotinamide;2-(bis(2-ch!oro

ethyl)amino)-N-phenylnicotinamide; (2-(bis(2-chloroethyl)amino)pyridin-3-
y])(thiazol-2-yl)methanone; 2-(bis(2-chloroethyl)amino)-N-(5-methy]isoxazol-3-
yl)nicotinamide; N,N-bis(2-chloroethyl)-4-(pyrrolidin-l-yl)-l,2,5-thiadiazol-3-
amine; N,N-bis(2-chloroethyl)-4-fluoro-l,2,5-thiadiazol-3-amine; 3-[bis(2-
chloroethyI)amino]-4-phenyl-l,2,5-thiadiazoIe-l,l-dione;N,N-bis(2-chloro ethyl)-
1 -phenyl-lH-tetrazol-5-amine;N,N-bis(2-chloroethyl)-l-(3-methoxy phenyl)-1H-
tetrazo 1-5-amine; N,N-bis(2-chloroethyl)-l-(4-methoxyphenyl)-lH-tetrazol-5-
amine;3-(5-(bis(2-chloroethyl)amino)-lH-tetrazol-l-yl) benzonitrile;4-(5-(bis(2-
chloroethy!)amino)-1 H-tetrazol-1 -yl)benzonitrile; N,N-bis(2-chloroethy 1)-1 -
(pyridin-2-yl)-lH-tetrazol-5-amine;N,N-bis(2-chloroethyl) -1-cyclohexyl-lH-
tetrazo 1-5 -amine; N,N-bis(2-chloroethyl)-l-(thiazol-2-yl)-lH-tetrazol-5-amine;
N,N-bis(2-chloroethyl)-l-(oxazol-2-yl)-lH-tetrazol-5-amine; N,N-bis(2-
chloroethyl)-4-phenyl-4H-l,2,4-triazol-3-amJne; N,N-bis(2-chloroethyl)-5-
phenyl-3H-l>2,3-triazol-4-amine;N,N-bis(2-chloroethyl)-4-phenyl-1,2,5-
oxadiazol-3-amine; N,N-bis(2-chloroethyl)-2-phenyl-2H-l,2,4-triazol-3-amine;
N,N-bis(2-chIoroethyI)-5-(methyIthio)-2-phenyl-2H-1,2,4-triazoI-3-amine; N,N-
bis(2-chloroethyl)-5-methoxy-2-phenyl-2H-l,2,4-triazol-3-amine; N,N-bis(2-
chloroethyl)-5-(methylsulfonyl)-2-pheny!-2H-l,2,4-triazol-3-amine; N3,N3-bis(2-
chloroethyl)-N5,N5-dimethyl-l-phenyl-lH-l,2,4-triazole-3,5-diamine; N,N-bis(2-
chloroethyl)-5-methyl-4-phenyl-4H-l,2,4-triazoI-3-amine; 5-(bis(2-
chloroethyl)amino)-4-phenyl-4H-l,2,4-triazol-3-ol; N,N-bis(2-chloroethyl)-2-
methyl-5-phenyl-2H-l,2,3-triazol-4-amine; N,N-bis(2-chloroethyl)-5-(pyridin-2-
yl)-lH-l,2,3-triazol-4-amine;N,N-bis(2-chloroethyl)-5-(thiazol-2-yl)-]H-l,2,3-
triazol-4-amine; N,N-bis(2-chloroethyl)-4-phenyl-l,2,5-thiadiazol-3-amine; N,N-
bis(2-chloroethyl)-3-(pyridin-2-yl)-3H-l,2;3-triazol-4-amine; N,N-bis(2-
chloroethyl)-3-phenyl-3H-l,2,3-triazol-4-amine; N,N-bis(2~chloroethyl)-3-
phenyl-1,2,4-thiadiazoI-5-amine; N,N-bts(2-chIoroethyi)-1 -methyl-5-phenyl-1H-pyrazol-4-amine; N,N-bis(2-chloroethyl)-l-(2-morphoiinoethyl)-3-phenyl-lH-pyrazol-4-amine; methyl 2-(4-(bis(2-chloroethyl)amino)-3-phenyl-lH-pyrazol-l-yl)acetate;2-(4-(bis(2-chloro ethyl) amino)-3-phenyl-lH-pyrazol-l-yl)acetonitrile; N,N-bis(2-chloroethyl)-1 -(2-(dimethylamino)ethy l)-3-phenyl-1 H-pyrazol-4-

amine; N,N-bis(2-chloroethyl)-3-phenyl-l-(pyridin-2-ylmethyl)-lH-pyrazol-4-
amine; N,N-bis(2-chloroethyl)-1 -phenyl-1 H-pyrazol-5-amine; N,N-bis(2-
chloroethyl)-3-methyl-l-phenyl-lH-pyrazol-5-amine; N,N-bis(2-chloroethyl)-l-
(pyridin-2-yI)~lH-pyrazol-5-amine; N,N-bis(2-chIoroethyl)-5-phenyl-lH-pyrazol-
4-amine; N,N-bis(2-chloroethyl)-5-(pyridin-2-yl)-lH-pyrazol-4-amine; N,N-bis(2-
chloroethyl)-1 -phenyl-1 H-imidazol-2-amine; N,N-bis(2-chloroethyl)-5-methyl-1 -
phenyl- lH-imidazol-2-amine; N,N-bis(2-chloroethyl)-l-phenyl-4,5-dihydro-lH-
imidazol-2-amine; N,N-bis(2-chloroethyl)-l,3-dimethyl-lH-pyrazol-5-amine;4-
(2-(bis(2-chloro ethyl)amino)thiazol-4-yl)benzonitrile;methyl2-(6-(bis(2-
chloroethyl) amino) imidazo[ 1,2-b]pyridazin-2-yl)-2-methylpropanoate;N ,N-bis(2-chloroethyl) benzo[c][l;2,5]oxadiazol-5-amine;l,l-bis(2-chloroethyl)-3-(2,6-dimethyl phenyl)urea; 1 -(bis(2-chloroethyl)amino)-4-phenylazetidin-2-one; N,N-bis(2-chloroethyl)-2-phenylazetidin-l-amine;N;N-bis(2-chloroethyl)-2-phenyl pyrrolidin-l -amine; methyl 4-(bis(2-chloroethyl)amino)piperidine-l-carboxylate;N,N-bis(2-chloroethyl)-3-(3,5-dimethyl-lH-pyrazol-l-yl) qui noxalin-2-amine.
Among the compound represented by general formula (2); preferable compounds include a compound selected from list given below and can be produced using appropriate starting substances in same manner as Example 4;
N-benzhydryl-2-chloroethanamine; 5-(2-chloroethylamino)isophthalonitrile; N-(3-
chloropropyl)-4-nitrobenzenamine; N-(2-chIoroethyl)-2-(trifluoro
methyl)benzenamine; N-(2-chloroethyl)biphenyi-3-amine; ethyl 2-(2-chloro
ethylamino)benzoate; N-(2-chloroethyl)pyridin-2-amine; 2-(2-chloro
ethylamino)nicotinonitrile; 2-(2-chloroethylamino)isonicotinonitrile; 6-(2-
chloroethylamino)nicotinonitrile; 6-(2-chloroethylarnino)-5-fluoro nicotinonitrile; N-(2-chloroethyl)-5-(trifluoromethyl)pyridin-2-amine;N-(2-chloroethyl)-3-(trifluoromethyl)pyridin-2-amine;N-(2-chloroethyl)-3-fluoro-5-

(trifiuoromethyl)pyridin-2-amine;N-(2-chloroethyl)-5-nitropyridin-2-amine; N-(2-
chloroethyI)-5- fluoropyridin-2-amine; N-(2-chloroethyl)-3- fluoropyridin-2-
amine; N-(2-chloroethyl)-3,5- dichloropyridin-2-amine; 6-(2-chloroethylamino)
nicotinamide; 6-(2-chloroethylamino)-5-fluoronicotinamide; ethyl 2-(2-chloro
ethyl am ino)nicotinate; ethyl 6-(2-chloroethylamino)nicotinate; ethyl 5-chloro-6-
(2-chloroethylamino)nicotinate; N-(2-chloroethyl)~3-methy!pyridin-2-amine; 3-
(benzo[d]thiazol-2-yl)-N-(2-chloroethyl)pyridin-2-amine; 3,5-dichloro-N-(2-
chloroethyl)pyridin-4-amine; N-(2-chloroethyl)-3-methoxypyrazin-2-amine; 2-(4-
(2-chloroethylamino)-6-methylpyrimidin-2-yl)phenol; N-(2-chloroethyl)-lH-
benzo[d]imidazol-2-amine;N-(2-chloroethyl)-7-(trifluoromethyl)-lH-
benzo[d]imidazol-2-amine; N-(2-chloroethyl)-6-fluoro-lH-benzo[d]imidazol-2-
amine; N-(2-chloroethyl)-6-nitro-lH-benzo[d]imidazol-2-amine; N-(2-
chloroethyl)-1 -methyl-1 H-benzo[d]imidazol-2-am ine; N-(2-chloroethy 1)-1 -
methyl-5-(trifluoromethyl)-lH-benzo[d]imidazol-2-amine; N-(2-chloroethyl)-5-
fluoro-1 -methyl-1 H-benzo[d] im idazol-2-amine; N-(2-chloroethy 1)-1 -phenyl-1H-
benzo[d]imidazol-2-amine; N-(2-chloroethyl)benzo[d]oxazol-2-amine; 2-(2-
chloroethyiamino)benzo[d]oxazoie-5-carbonitrile; N-(2-chIoroethyl)-5-
methoxybenzo[d]oxazol-2-amine; N-(2-chloroethyl)oxazolo[4,5~b]pyridin-2-
amine; N-(2-chloroethyl)-6-methoxybenzo[d]thiazol-2-amine; N-(2-chloro
ethyl)benzo[d]thiazol-2-amine; 2-(2-chloroethylamino)benzo[d]thiazole-5-
carbonitrile; 2-(2-chloroethylamino)benzo[d]thiazole-6-carbonitrile; N-(2-
chloroethyl)-6-(trifluoromethyl)benzo[d]thiazol-2-amine; 5-chloro-N-(2-
chloroethyl)benzo[d]thiazol-2-amine; 6-chloro-N-(2-chloroethyl) benzo
[d]thiazol-2-amine; N-(2-chloroethy l)-5-nitrobenzo[d]thiazol-2-am ine; N-(2-
chloroethyl)-6-nitrobenzo[d]thiazol-2-amine; N-(2-chloroethyl)-3-fluoro
naphthalen-1-amine; N-(2-chloroethyl)-4-nitronaphthalen-l-amine; N-(2-chloro
ethyl)quinolin-4-amine; N-(2-chloroethyl)-7-(trifluoromethyl)quinolin-4-amine;
N-(2-chloroethyl)-2-(trifluoromethyl)quinolin-4-amine;N-(2-chloro ethyl)-8-
methyl-2-(trifluoromethyl) quinolin-4-amine; N-(2-chloroethyl)-2,6-
bis(trifluoromethyl)quinolin-4-amine; N-(2-chloroethyl)-2,8-bis(trifluoro
methyl)quinolin-4-amine; N-(2-chloroethyl)-6-methoxy-2-(trifluoromethyl)

quinolin-4-amine; N-(2-chloroethyl)-7-methoxy-2-(trifluoromethyl)quinolin-4-
amine; N-(2-chloroethyl)-8-methoxy-2-(trifluoromethyl)quinolin-4-amine; N-(2-
chloroethyl)-8-fluoro -2-(trifluoromethyl) quinolin-4-amine; N-(2-chloro ethyl) -
6-fluoro -2-(trifluoromethyl)quinolin-4-amine; methyl 4-(2-chloro
ethylamino)quinoline-2-carboxylate; methyl 4-(2-chloroethylamino)quinoline-3-
carboxylate; 4-(2-chloroethylamino)quinoline-2-carbonitrile; 4-(2-chloro ethyl)
amino)quinoline-2-carboxamide; N4-(2-chloroethyl)quinoline-2,4-diamine; N-(2-
chloroethyl)-2-phenylquinolin-4-amine; N-(2~chloroethyl)-2-methylquinolin-4-
amine; N-(2-chloroethyl)isoquinolin-l-amine; l-(2-chloro
ethylamino)isoquinoline-4-carbonitrile; N-(2-chloroethyl)-4-fluoroisoquinolin-1 -
amine; N-(2-chloroethyl)-2-(trifluoromethyl)quinazolin-4-amine; N-(2-chloro
ethyl)-2-phenylquinazolin-4-amine; N-(2-chloroethyl)quinolin-2-amine; N-(2-
chloroethyl)quinoline-8-sulfonamide; N-(2-chloroethyl)chroman-5-amine; N-(2-
chloroethyl)-4-phenylpyrimidin-5-amine; N-(2-chloroethyl)-3-phenyl pyrazin-2-
amine; N-(2-chloroethyl)-3-(piperidin-l -yl)pyrazin-2-amine; N-(2-chloroethyI)-3-
(piperazin-1 -yl)pyrazin-2-am ine; N-(2-chloroethyl)-1 -phenyl-1,4,5,6-
tetrahydropyrimidin-2-amine; N-(2-chloroethyl)-3-phenylpyridin-2-amine; N-(2-
chloroethyl)-4-phenylpyrimidin-2-amine; 2-(2-(2-chloro ethylamino)-6-
methylpyrimidin-4-yl)phenol; N5-(2-chloroethyl)-N3,N3-dimethyl-6-
phenylpyridazine-3,5-diamine; N-(2-chloroethyl)-3-phenyl pyridazin-4-amine; 5-
(2-chloroethylamino)-6-phenylpyridazin-3-ol; 3-(2-chloroethylamino)-2-phenyl-
IH-inden-l-one; (2-(2-chloroethylamino)pyridin-3-yl)(pyridin-2-yl)methanone;
(2-(2-chloroethylamino)pyridin-3-yl) (morpholino) methanone; 3-(2-(2-(2-
chloroethylamino)pyridin-3-yl)-2-oxoethyl) benzonitrile; N-benzyl-2-(2-
chloroethylamino)nicotinamide; 2~(2-chloroethylamino)-N-
cyclohexylnicotinamide; 2-(2-chloroethylamino)-N-phenylnicotinamide;(2-(2-chloroethylamino)pyridin-3-yl)(thiazol-2-yl) methanone; 2-(2-chloroethylamino)-"N-(5-methylisoxazol-3-yl)nicotinamide; N-(2-chloroethyl)-4-(pyrrolidin-l-yl)-l,2,5-thiadiazol-3-amine; N-(2-chloro ethyl)-4-fluoro-l,2,5-thiadiazol-3-amine; 3-(2-chloroethy l)amino-4-phenyl-1,2,5-thiadiazole-1,1 -dione; N-(2-chloroethyl)-1 -phenyl-lH-tetrazol-5-amine; N-(2-chloroethyl)-l-(3-methoxyphenyl)-lH-tetrazol-

5-amine; N-(2-chloro ethyl)-l-(4-methoxyphenyl)-lH-tetrazol-5-amine; 3-(5-(2-
chloroethyIamino)-lH-tetrazol-l-yl)benzonitrile; 4-(5-(2-chloroethylamino)-lH-
tetrazol-1 -yl) benzonitri ie; N-(2-chloroethyI)~ 1 -(pyridin-2-yl)-1 H-tetrazol-5-
amine; N-(2-chloroethyl)-l-cyclohexyl-lH-tetrazol-5-amine; N-(2-chloroethyl)-l -
(thiazol-2-yl)-1 H-tetrazoI-5-amine; N-(2-chloroethy 1)-1 -(oxazol-2-y I)-1H-
tetrazol-5-amine; N-(2-chloroethyl)-4-phenyl-4H-1,2,4-triazol-3-amine; N-(2-
chloro ethyl)-5-phenyl-3H-l,2,3-triazol-4-amine; N-(2-chloroethyl)-4-phenyl-
l,2,5-oxadiazol-3-amine; N-(2-chloroethyl)-2-phenyl-2H-l,2,4-triazol-3-amine;
N-(2-chloroethyl)-5-(methylthio)-2-phenyl-2H-l,2,4-triazol-3-amine; N -(2-chloro
ethyl)-5-methoxy-2-phenyl-2H-l,2,44riazol-3-amine; N-(2-chloroethyl)-5-
(methylsulfonyl)-2-phenyl-2H-l,2,4-triazol-3-amine; N3-(2-chloroethyl)-N5,N5-
dimethyl-1 -phenyl-] H-1,2,4-triazole-3,5-diamine; N-(2-chloroethyl)-5-methyl-4-
phenyl-4H-1,2,4-triazol-3-amine; 5-(2-chloroethylamino)-4-phenyl-4H-1,2,4-
triazol-3-ol; N-(2-chloroethyl)-2-methyl-5-phenyl-2H-l,2,3-triazol-4-amine; N-(2T
chloroethyl)-5-(pyridin-2-yl)-lH-l,2,3-triazol-4-amine; N-(2-chloroethyl)-5-
(thiazol-2-yl)-lH-l,2,3-triazol-4-amine; N-(2-chloroethyl)-4-phenyl-l,2,5-
thiadiazol-3-amine; N-(2-chloroethyl)-3-(pyridin-2-yl)-3H-1,2,3-triazol-4-
amine;N-(2-chloroethyl)-3-phenyl-3H-l>2,3-triazol-4-amine; N-(2-chloroethyl)-3-
phenyl-l,2,4-thiadiazol-5-amine; N-(2-chloroethyl)-l-methyl-5-phenyl-lH-
pyrazol-4-amine; N-(2-chloroethyl)-l-(2-morpholinoethyl)-3-phenyl-lH-pyrazol-
4-amine; methyl 2-(4-(2-chloroethylamino)-3-phenyl-lH-pyrazol-l-yl)acetate; 2-
(4-(2-chloroethylamino)-3-phenyl-1 H-pyrazol-1 -yl)acetonitrile; N-(2-
chloroethyl)-1 -(2-(dimethylamino)ethyl)-3-pheny 1- lH-pyrazol-4-amine; N-(2-
chloroethyI)-3-phenyl-l-(pyridin-2-ylmethyl)-lH-pyrazoI-4-amine; N-(2-
chloroethyl)-1-phenyl-1 H-pyrazol-5-amine; J>J-(2-chloroethyl)-3-methyl-l-phenyl-lH-pyrazoI-5-amine; N-(2-chloroethyl)-l-(pyridin-2-yl)-lH-pyrazol-5-amine; N-(2-chloroethyl)-5-phenyl-lH-pyrazol-4-amine; N-(2-chloroethyl)-5-(pyridin-2-yl)-1 H-pyrazol-4-amine; N-(2-chloroethyl)-1 -phenyl-1 H-imidazol-2-amine; N-(2-chloroethyl)-5-methyl-l-phenyl-lH-im idazol-2-amine;N-(2-chloroethyl)-l-phenyl-4,5-dihydro-lH-imidazol-2-amine; N-(2-chloroethyl)-l,3-dimethyl-lH-pyrazol-5-ainine; 4-(2-(2-chloroethylamino)thiazol-4-yl)benzonitrile; methyl 2-(6-

(2-chloro ethyl amino)imidazo[l,2-b]pyridazin-2-yl)-2-methylpropanoate; N-(2-
chloroethyl) benzo[c][l,2,5]oxadiazol-5-amine; l-(2-chloroethyl)-3-(2,6-dimethyl
phenyl) urea; l-(2-chloroethylamino)-4-phenylazetidin-2-one; N-(2-chloroethyl)-
2-phenylazetidin-l-amine; N-(2-chloroethyl)-2-phenylpyrrolidin-l-amine; methyl
4-(2-chloroethylamino)piperidine-l-carboxylate; N-(2-chloroethyl)-3-(3,5-
dimethyl-1 H-pyrazol-1 -y l)quinoxalin-2-amine.

WE CLAIM:
1. A compound of formula (1), (la) and (2);
wherein X is halogen, -S (=0)2R1, -Si (R2)3, aryl or substituted aryl, wherein R1 and R2 are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, substituted aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, "m" is 1 to 2, "A" is selected from the group consisting of;

wherein

sign indicate site of attachment to N atom.

2. A process to prepare compound of formula (1) comprising steps of;
(a) reacting compound of formula (4) with reducing agent in presence of suitable solvent to form reaction mixture;

(b) reacting compound of formula (5) or compound of formula (2) with the reaction mixture obtained in step (a) to obtain compound of formula (1); wherein X1is, -OR1; -COR1, -SO2R1, aryl or substituted aryl; X is halogen, -S(=0)2R1, -Si (R2H aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, —OR5, —COR6, —CO2R7, —CONR8R9 or —S02Rio wherein R1,R2, R3R4, R5, R6, R7, R8, R9 and Rm are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and R8 and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents.
3. A process to prepare compound of formula (1) comprises,
reacting compound of formula (2) with compound of formula (6) in presence 0f suitable base and suitable solvent; wherein X is halogen . S(=0)2R1, .Si (R2)3, aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, _ OR5, _CoR6, —CO2R7, —CONR8R9 or —SO2R10 wherein R1,R2, R3R45 R5, R6, R7, R8, R9 and R1O are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and R8 and R9 may be bonded to each other to form heterocycles each optionally

containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloaikylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents.
4. A process to prepare compound of formula (la) comprises,
reacting compound of formula (2) with compound of formula (6a) in presence of suitable solvent and suitable base; wherein X is halogen, -S(=0)2R1, -Si (R2)3, aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloaikylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, — OR5, —COR6, —CO2R7, —CONR8R9 or —SO2R10 wherein R,,R2, R3R4, R5, R6, R7, Rs, R9 and Rio are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloaikylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and Rs and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloaikylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents.
5. A process to prepare compound of formula (3) comprising steps of;

(a) reacting compound of formula (1) with compound of (4) in presence of suitable base and suitable solvent to obtain compound of formula (5);
(b) optionally isolating compound of formula (5);
(c) deprotecting compound of formula (5) to obtain compound of formula (3); wherein X is halogen, -S(=0)2R1; -Si (R2X aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, —OR5, —CORe, — CO2R7, —CONR8R9 or—SO2R10 wherein R,,R2, R3R4, R5, Re, R7, Rs, R9 and Rio are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and R8 and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed wmVan aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents and p is protecting group.
6. A process to prepare compound of formula (3) comprises;
reacting compound of formula (1) with ammonia; wherein X is halogen, -S(=0)2R1, -Si (R2)3, aryl or substituted aryl, "A" is alkyl, cycloalkyl,

cycloalkylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, — OR5, —COR6, —CO2R7, —CONR8R9 or —S02R10 wherein Rl5R2, R3R4, R5, R6, R7, R8, R9 and R10 are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and R8 and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents.
7. A process to prepare compound of formula (3a) comprises;
reacting compound of formula (la) with ammonia; wherein X is halogen, -S(=0)2R1, -Si (R2H aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, —OR5, —COR6, — CO2R7, —CONR8R9 or — SO2Ri0 wherein Ri,R2, R3R4, R5, Re, R7, Rs, R9 and Rio are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and R8 and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an
*
aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents.

8. A process to prepare compound of formula (2) comprising steps of;
(a) reacting compound of formula (4) with reducing agent in presence of suitable solvent to form reaction mixture;
(b) reacting compound of formula (5) with the reaction mixture obtained in step (a) to obtain compound of formula (2); wherein X1 is, -OR1, -COR1, -S02Ri, aryl or substituted aryl; X is halogen, -S(=0)2R1, -Si (R2H aryl or substituted aryl, "A" is alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,heteroaryl, heteroarylalkyl, —NR3R4, —OR5, —COR6, —CO2R7, —CONR8R9 or — S02Rio wherein R1,R2, R3R4, R5, R6, R7, R8, R9 and R10 are the same or different and each is independently a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or haloalkyl, or R3 and R4, and R8 and R9 may be bonded to each other to form heterocycles each optionally containing 1 or 2 nitrogen atoms or oxygen atoms, said heterocycle optionally being condensed with an aromatic ring optionally having substituents, m is 1 or 2, and of the above-mentioned groups, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl and heterocycle each optionally have substituents.
9. The process according to claim 2,3,4,5 and 8; wherein suitable solvent is selected form the group consisting of water, methylene chloride, ethylene chloride, chloroform and carbon tetrachloride; alcohols such as methanol, ethanol, 1 -propyl alcohol, 2-propanol, tert-butanol; esters such as ethyl formate, ethyl acetate, isopropyl acetate and butyl acetate; amides such as formamide, N,N-dirnethylformarnide, N.N-dimethylacetamide; sulfoxides such as dimethyl sulfoxide; nitrile such as acetonitrile, propionitrile; ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, 1 ,4-dioxane,

tetrahydrofuran, tetrahydropyran; hydrocarbons such as benzene, toluene, cyciohexane, n-hexane and methyl cyclohexane; ketones such as acetone, methyl ethyl ketone; polar aprotic solvents such as l,3-dimethyl-2-imidazolidinone, sulfolane, Hexamethylphosphoramide or mixture(s) thereof.
10. The process according to claim 2 and 8; wherein reducing agent is selected form the group consisting of NaBH4, NaBH3CN and Sodium triacetoxyborohydride (STAB).
11. The process according to claim 3, 4 and 5; wherein suitable base is selected form the group consisting of K2CO3, Na2CO3, LiCO3, NaHCO3, LiHCOs, KHCO3, NaOAc, KOAc, KOH, NaOH, LiOH, NH4OH, Potassium tert-butoxide, sodium ethoxide, sodium methoxide, n-BuLi, sec-BuLi, t-BuLi, methyllithium, sodium amide ,lithium diisopropylamide, sodium hydride or potassium hydride, LiHMDS, NaHMDS, KHMDS and LiTMP TEA, trimethylamine, DIPEA, pyridine, dimethyl amino pyridine and piperidine or aqueous solution thereof or mixture(s) thereof.
12. The process according to claim 5; wherein protecting group is selected form the group consisting of benzyl, p-nitrobenzyl, benzhydryl, trityl,formyl, acetyl, propionyl, methoxyacetyl, methoxypropionyl, benzoyl, thienylacetyl, thiazolylacetyl, tetrazolylacetyl, thiazolylglyoxyloyl, thienylglyoxyloyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, benzyloxycarbonyJ, p-nitrobenzyloxycarbonyl, 9-fluorenylmethyloxycarbonyl, methane sulfonyl, ethane sulfonyl, toluene sulfonyl, trimethylsilyl; and triphosgene and other carboxybenzyl (Cbz), 2,2,2,-trichloroethyl carbamate (Troc), ethyl carbamate, ally carbamate (Alloc), ethyl caramate, acyl, trifluroacetamide, allyamine, triphenylmethyl, and trichloromethoxy.

13. The process according to claim 6 and 7; wherein ammonia source is in the form of ammonia gas, methanoiic ammonia or aqueous ammonia.
14. The compound (1) or (la) according to claim 1 is selected form the group consisting of;N-benzhydryl-2-chloro-N-(2-chloroethyl) ethanamine;5-(bis(2-chloroethyl)amino) iso phthalonitrile; N-(2-chloroethyl)-N-(3-chloropropyl)-4-nitrobenzenamine;N,N-bis(2-chloro ethyl)-2-(trifluoromethyl)benzenamine;N,N-bis(2-chloroethyl)biphenyl-3-amine; ethyl 2-(bis(2-chloroethyl)amino)benzoate; N,N-bis(2-chIoroethyl)pyridin-2-amine;2-(bis(2-chloroethyl)amino)nicotinonitrile; 2-(bis(2-chloroethyl)amino)isonicotinonitrile;6-(bis(2-chloroethyl) amino)nicotinonitrile;6-(bis(2-chloroethyl)amino)-5-fluoronicotino nitrile; N,N-bis(2-chloroethyl)-5-(trifluoromethyl)pyridin-2-amine;N,N-bis(2-chloroethyl)-3-(trifluoromethyl)pyridin-2-amine;N,N-bis(2-chloroethyl)-3-fluoro-5-(trifluoromethyl) pyridin-2-amine; N,N-bis(2-chloroethyl)-5-nitropyridin-2-amine; N,N-bis(2-chloroethyl)-5-fiuoropyridin-2-amine; N,N-bis(2-chloroethyl)-3-fluoropyridin-2-amine; N,N-bis(2-chloroethyl)-3,5-dichloropyridin-2-amine; 6-(bis(2-chloroethyl)amino)nicotinamide; 6-(bis(2-chloroethyl)amino)-5-fluoronicotinamide; ethyl 2-(bis(2-chloroethyl)amino)nicotinate; ethyl 6-(bis(2-chloroethyl)amino)nicotinate;ethyl6-(bis(2-chloroethyl)amino)-5-chloronicotinate; N,N-bis(2-chloroethyl)-3-methylpyridin-2-amine; 3-(benzo[d]thiazoI-2-yl)-N,N-bis(2-chloroethyl)pyridin-2-amine; 3,5-dichloro-N,N-bis(2-chloroethyl)pyridin-4-amine;N,N-bis(2-chloroethyl) -3-methoxypyrazin-2-amine;2-(4-(bis(2-chloroethyl)amino)-6-methyl pyrimidin-2-yl)phenol; N,N-bis(2-chloroethyl)-1 H-benzo[d] imidazol-2~ amine;N,N-bis(2-chIoroethyl)-7-(trifluoromethyl)-lH-benzo[d]imidazoi -2-amine;N,N-bis(2-chloroethyl)-6-fluoro-lH-benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)-6-nitro-lH-benzo[d]imidazol-2-amine; N,N-bis(2-chloroethyl)-! -methyl-1 H-benzo[d]imidazol-2-amine; N,M-bis(2-chloroethyl)-l-methyl-5-(trifluoromethyl)-lH-benzo[d]imidazol-2-

amine;N,N-bis(2-chloroethyl)-5-fluoro-l-methyl-lH-benzo[d] imidazol-2-
amine;N,N-bis(2-chloroethyl)-l-phenyl-lH-benzo[d] imidazol-2-amine;
N,N-bis(2-chloroethyl)benzo[d]oxazol-2-amine; 2-(bis(2-
chloroethyl)amino)benzo[d]oxazole-5-carbonitrile;N,N-bis(2-chloroethyl)-
5-methoxybenzo[d]oxazol-2-amine;N,N-bis(2-chloroethyl)oxazolo[4,5-
b]pyridin-2-amine; N,N-bis(2-chloroethyl)-6-methoxybenzo[d]thiazol-2-
amine;N,N-bis(2-chloroethyl) benzo[d] thiazol-2-amine;2-(bis(2-
chloroethyl)amino)benzo[d]thiazole-5-carbonitrile;2-(bis(2-
chloroethyl)amino)benzo[d]thiazole-6-carbonitrile;N,N-bis(2-chloroethyl)-
6-(trifluoromethyl) benzo[d]thiazol-2-amine; 5-chloro-N,N-bis(2-
chloroethyl)benzo[d]thiazol-2-amine; 6-chioro-N,N-bis(2-
chloroethyl)benzo[d]thiazol-2-amine; N,N-bis(2-chloroethyl)-5-
nitrobenzo[d]thiazol-2-amine; N,N-bis(2-chloroethyl)-6-
nitrobenzo[d]thiazoI-2-amine;N,N-bis(2-chloroethyl)-3-fIuoro naphthalen-
1 -amine;N,N-bis(2-chloroethyl)-4-nitro naphthalen-1 -amine;N,N-bis(2-
chloroethyl)quinolin-4-amine; N,N-bis(2-chloroethyl)-7-
(trifluoromethyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-2-
(trifluoromethyl)quinolin-4-amine; N,N-bis(2-chIoroethyI)-8-methyl-2-
(trifluoromethyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-2,6-
bis(trifluoromethyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-2,8-bis
(trifluoromethyl)quinolin-4-amine;N,N-bis(2-chloroethyl)-6-methoxy-2-
(trifluoromethyl) quinolin-4-amine; N,N-bis(2-chloroethyl)-7-methoxy-2-
(trifluoromethyl)quinolin-4-amine; N,N-bis(2-chloroethyl)-8-methoxy-2-
(trifluoromethyl)quinolin-4-amine;N,N-bis(2-chloro ethyl)-8-fluoro2-
(trifluoromethyl)quinolin-4-amine; N,N-bis(2-chloroethyl)-6-fluoro -2-
(trifluoromethyl)quinolin-4-amine; methyl 4-(bis(2-
chloroethyl)amino)quinoline-2-carboxylate; methyl 4-(bis(2-
chIoroethyl)amino)quinoline-3-carboxylate;4-(bis(2-chloroethyl)
amino)quinoline-2-carbonitrile;4-(bis(2-chIoroethyl)amino)quinoline-2-
carboxamide; N4,N4-bis(2-chloroethyl)quinoline-2,4-diamine; N,N-bis(2-
chloroethyl)-2-phenylquinolin-4-amine; N,N-bis(2-chloroethyl)-2-

methylquinolin-4-amine; N,N-bis(2-chloroethyl)isoquinolin-l-amine; 1-
(bis(2-chJoroethyl)amino)isoquino]ine-4-carbonitrile; N,N-bis(2-
chIoroethyl)-4-fluoroisoquinolin-I-amine;N,N-bis(2-chloroethyl)-2-
(trifluoro methyl)quinazolin-4-amine; N,N-bis(2-chloroethyl)-2-
phenyIquinazoJin-4-amine; N,N-bis(2-chIoroethyI)quinoiin-2-amine; N,N-
bis(2-chloroethyl)quinoline-8-sulfonamide;N,N-bis(2-chloroethyl)
chroman-5-amine; N,N-bis(2-chloroethyl)-4-phenylpyrimidin-5-amine;
N,N-bis(2-chloroethyl)-3-phenylpyrazin-2-amine;NsN-bis(2-chloroethyl) -
3-(piperidin-l-yl) pyrazin-2-amine; N,N-bis(2-chloroethyl)-3-(piperazin-l-
yl)pyrazin-2-amine;N,N-bis(2-chloroethyl)-l-phenyl-l,4,5,6-
tetrahydropyrimidin-2-amine;N,N-bis(2-chloroethyl)-3-phenyl pyridin-2-
amine;N,N-bis(2-chloroethyl)-4-phenylpyrimidin-2-amine;2-(2-(bis(2-
chloroethyl)amino)-6-methyipyrimidin-4-yl)phenol;N5,N5-bis(2-
chloroethyl)-N3,N3-dimethyl-6-phenyI pyridazine-3,5-diamine; N,N-
bis(2-chloroethyl)-3-phenylpyridazin-4-amine; 5-(bis(2-
chIoroethyI)amino)-6-phenyIpyridazin-3-oi; 3-(bis(2-chloroethyi)amino)-
2-phenyl-lH-inden-l-one;(2-(bis(2-chloroethyl) amino)pyridin-3-
yl)(pyridin-2-yl)methanone;(2-(bis(2-chloroethyl) amino)pyridin-3-
yl)(morpholino)methanone;3-(2-(2-(bis(2-chloroethyl) amino) pyridin-3-
yl)-2-oxoethyl)benzonitrile; N-benzyl-2-(bis(2-
chloroethyl)amino)nicotinamide;2-(bis(2-chloroethyl)amino)-N-
cyclohexylnicotinamide;2-(bis(2-chloroethyl)amino)-N-phenyl
nicotinamide;(2-(bis(2-chloroethyl)amino)pyridin-3-yl)(thiazol-2-
yl)methanone;2-(bis(2-chloroethyl)amino)-N-(5-methylisoxazo]-3-
yl)nicotinamide;N,N-bis(2-chloroethyl)-4-(pyrrolidin-l-yl)-lJ255-
thiadiazol-3-amine; N,N-bis(2-chloroethyl)-4-fluoro-l,2,5-thiadiazol-3-
amine; 3-[bis(2-chloroethyI)amino]-4-phenyi-l,2,5-thiadiazoIe-I,J-dione;
N,N-bis(2-chloroethyl)-1 -phenyl- lH-tetrazo 1-5-amine; N,N-bis(2-
chloroethyl)-l-(3-methoxyphenyl)-lH-tetrazol-5-amine; N,N-bis(2-
chloroethyl)-l-(4-methoxyphenyI)-lH-tetrazol-5-amine; 3-(5-(bis(2-
chloroethyl)amino)-1 H-tetrazol-1 -yl)benzonitrile; 4-(5-(bis(2-

chloroethyl)amino)-lH-tetrazol-l-yl)benzonitrile;N,N-bis(2-chloro ethyl)-
l-(pyridin-2-yl)-lH-tetrazol-5-amine; N,N-bis(2-chloroethyl)-l-
cyclohexyl-lH-tetrazol-5-amine; N,N-bis(2-chloroethyl)-1 -(thiazol-2-yl)-
lH-tetrazol-5-amine; N,N-bis(2-chloroethyl)~l-(oxazoI-2-yI)-lH-tetrazol-
5-amine; N,N-bis(2-chloroethyl)-4-phenyl-4H-l,2,4-triazol-3-amine; N,N-
bis(2-chloroethyl)-5-phenyl-3H-l52,3-triazol-4-amine; N,N-bis(2-
chloroethyl)-4-pheny 1-1,2,5-oxadiazol-3-amine; N5N-bis(2-chloroethyl)-2-
phenyl-2H-l,2,4-triazol-3-amine;N,N-bis(2-chloroethyl)-5-(methylthio)-2-
phenyl-2H-l,2,4-triazol-3-amine;N,N-bis(2-chloro ethyl)-5-methoxy-2-
phenyl-2H-l,2,4-triazol-3-amine; N,N-bis(2-chloroethyl)-5-
(methylsulfonyl)-2~phenyl-2H-l,2,4-triazol-3-amine; N3,N3-bis(2-
chloroethyl)-N5,N5-dimethyl-1 -phenyl-1H-1,2,4-triazole-3,5-diamine;
N,N-bis(2-chloroethyl)-5-methyl-4-phenyl-4H-1,2,4-triazol-3-amine; 5-
(bis(2-chIoroethyl)amino)-4-phenyl-4H-l,2,4-triazol-3-ol; N,N-bis(2-
chloroethyl)-2-methyl-5-phenyl-2H-1,2,3-triazol-4-amine; N,N-bis(2-
chloroethyl)-5-(pyridin-2-yl)-lH-l,2,3-triazol-4-amine; N,N-bis(2-
chloroethyl)-5-(thiazol-2-yl)-lH-l,2,3-triazol-4-amine; N,N-bis(2-
chloroethyl)-4-phenyl-l,2,5-thiadiazoI-3~amine; N,N-bis(2-chloroethyl)-3-
(pyridin-2-yl)-3H-l,2,3-triazol-4-amine; N,N-bis(2-chloroethyl)-3-phenyl-
3H-l,2,3-triazol-4-amine;N,N-bis(2-chloroethyl)-3-phenyl-l;2,4-
thiadiazol-5-amine;N,N-bis(2-chloroethyl)-l-methyl-5-phenyl-lH-
pyrazol-4-amine; N,N-bis(2-chloroethyl)-l-(2-morpholinoethyl)-3-phenyl-
lH-pyrazol-4-amine; methyl 2-(4-(bis(2-chloroethyl)amino)-3-phenyl-l H-
pyrazol-l-yl)acetate;2-(4-(bis(2-chloroethyl)amino)-3-phenyl-lH-pyrazol-
l-yl)acetonitrile; N,N-bis(2-chloroethyl)-l-(2-(dimethylamino)ethyl)-3-
phenyl-lH-pyrazol-4-amine; N,N-bis(2-chloroethyl)-3-phenyl-l-(pyridin-
2-y lmethyl)-1 H-pyrazol-4-am ine; N,N-bts(2-chloroethyl)-1 -phenyl-1H-
pyrazol-5-amine; N,N-bis(2-chloroethyl)-3-methyl-1 -phenyl-1 H-pyrazol-
5-amine; N,N-bis(2-chloroethyl)-1 -(pyridin-2-yl)-1 H-pyrazol-5-
amine;N,N-bis(2-chloroethyl)-5-phenyl-lH-pyrazol-4-amine; N,N-bis(2-
chloroethyl)-5-(pyridin-2-yl)-lH-pyrazol-4-amine; N,N-bis(2-

chloroethyl)-1 -phenyl-1 H-imidazol-2-amine; N,N-bis(2-chloroethy I)-5-
methyl-1-phenyl-lH-imidazol-2-amine; N,N-bis(2-chloroethyl)-l-phenyl-
4,5-dihydro-lH»imidazol-2-amine; N,N-bis(2-chloroethyl)-l,3-dimethyl-
1 H-pyrazol-5-amine; 4-(2-(bis(2-chloroethyl)amino)thiazol-4-
yl)benzonitrile; methyl 2-(6-(bis(2-chloroethyl)amino)imidazo[l,2-
b]pyridazin-2-yl)-2-methyIpropanoate; N,N-bis(2-
chloroethyl)benzo[c][l,2,5]oxadiazol-5-amine; l,l-bis(2-chloroethyl)-3-
(2,6-dimethylphenyl)urea; 1 -(bis(2-chloroethyl)amino)-4-phenylazetidin-
2-one; N,N-bis(2-chloroethyl)-2-phenylazetidin-1 -amine; N,N-bis(2-
chloroethyl)-2-phenylpyrrolidin-l-amine; methyl 4-(bis(2-
chloroethyl)amino)piperidine-l-carboxylate; N,N-bis(2-chIoroethyl)-3-(3,5-dimethyl-lH-pyrazol-l-yl)quinoxalin-2-amine.
15. The compound (2) according to claim 1 is selected form the group
consisting of; N-benzhydryl-2-chloroethanamine; 5-(2-
chIoroethylamino)isophthalonitrile; N-(3-chloropropyI)-4-
nitrobenzenamine; N-(2-chloroethyi)-2-(trifluoromethyl)benzenamine; N-
(2-chloroethyl)biphenyl-3-amine; ethyl 2-(2-chloroethylamino) benzoate;
N-(2-chloroethyl)pyridin-2-amine; 2-(2-chloro ethylamino) nicotinonitrile;
2-(2-chloroethylamino)isonicotinonitrile; 6-(2-chloro
ethylamino)nicotinonitrile; 6-(2-chloroethylamino)-5-fluoro nicotine
nitrile; N-(2-chloroethyl)-5-(trifluoromethyl)pyridin-2-amine;N-(2-
chloroethyl)-3-(trifluoromethyl)pyridin-2-amine;N-(2-chloroethyl)-3-
fluoro-5-(trifluoromethyl)pyridin-2-amine;N-(2-chloroethyl)-5-nitro
pyridin-2-amine; N-(2-chloroethyl)-5- fluoropyridin-2-amine; N-(2-
chloroethyl)-3- fluoropyridin-2-amine; N-(2-chloroethyl)-3,5- dichloro
pyridin-2-amine; 6-(2-chloroethylamino)nicotinamide; 6-(2-chloro
ethylamino)-5-fluoronicotinamide; ■•< > ethyl 2-(2-chloroethylarnino)
nicotinate; ethyl 6-(2-chloroethylamino)nicotinate; ethyl 5-chloro-6-(2-chloroethylamino)nicotinate; N-(2-chloroethyl)-3-methylpyridin-2-amine; 3-(benzo[d]thiazol-2-yl)-N-(2-chloroethyl)pyridin-2-amine; 3,5-dichloro-

N-(2-chIoroethyI)pyridin-4-atnine; N-(2-chIoroethyI)-3-methoxypyrazin-2-
amine; 2-(4-(2-chloroethylamino)-6-rnethyl pyrimidin-2-yl)phenol; N-(2-
chloroethyl)-lH-benzo[d]imidazoJ-2-amine;N-(2-chJoroethyl)-7-
(trifluoromethyl)-lH-benzo[d]imidazol-2-amine; N-(2-chloroethyl)-6-
fluoro-lH-benzo[d]imidazol-2-amine; N-(2-chloroethyl)-6-nitro-lH-
benzo[d]imidazol-2-amine; N-(2-chloroethyl)-l-methyl-1H-
benzo[d]imidazol-2-amine; N-(2-chloroethyl)-l-methyl-5-
(trifluoromethyl)-lH-benzo[d]imidazol-2-amine; N-(2-chloroethyl)-5-
fluoro-1 -methyl- lH-benzo[d] imidazol-2-amine; N-(2-chloroethyl)-1 -
phenyl-1H-benzo[d]imidazol-2-amine; N-(2-chloroethyl) benzo [djoxazol
-2-amine; 2-(2-chloroethylamino)benzo[d]oxazole-5-carbonitrile; N-(2-
chloroethyl)-5-methoxybenzo[d]oxazol-2-amine; N-(2-
chloroethyl)oxazolo[4,5-b]pyridin-2-amine; N-(2-chloroethyl)-6-
methoxybenzo[d]thiazol-2-amine; N-(2-chloroethyl)benzo[d]thiazol-2-
amine; 2-(2-chloroethylamino)benzo[d]thiazole-5-carbonitrile; 2-(2-
chloroethylamino)benzo[d]thiazole-6-carbonitrile; N-(2-chloroethyl)-6-
(trifluoromethyl)benzo[d]thiazol-2-amine; 5-chloro-N-(2-chloroethyl)
benzo[d]thiazol-2-amine; 6-chloro-N-(2-chloroethyl)benzo[d]thiazol-2-
amine; N-(2-chIoroethyl)~5-nitrobenzo[d]thiazoI-2-amine; N-(2-chIoro
ethyl) -6-nitrobenzo[d]thiazol-2-amine; N-(2-chloroethyl)-3-fluoro
naphthalen-1 -amine; N-(2-chJoroethyl)-4-nitronaphthalen-1 -amine; N-(2-
chloroethyl)quinolin-4-amine; N-(2-chloroethyl)-7-(trifluoromethyl)
quinolin-4-amine; N-(2-chloroethyl)-2-(trifluoromethyl)quinolin-4-
amine;N-(2-chIoroethyl)-8-methyl-2-(trifluoromethyl) quinolin-4-amine;
N-(2-chloroethyl)-2,6-bis(trifluoromethyl)quinoIin-4-amine; N-(2-
chloroethyl)-2,8-bis(trifluoromethyl)quinolin-4-amine; N-(2-chloroethyI) -
6-methoxy-2-(trifluoromethyl)quinolin-4-amine; N-(2-chloroethyl) -7-
methoxy-2-(trifluoromethyI)quinoIin-4-amine; N-(2~chloroethyl) -8-
methoxy-2-(trifluoromethyl)quinolin-4-amine; N-(2-chloroethyl) -8-fluoro
-2-(trif!uoromethyI) quinolin-4-amine; N-(2-chloroethyl) -6-fluoro -2-
(trifluoromethyl)quinolin-4-amine; methyl 4-(2-

chloroethylamino)quinoline-2-carboxylate; methyl 4-(2-chloro
ethy!amino)quinoIine-3-carboxylate; 4-(2-chloroethyiamino)quinoiine-2-
carbonitrile; 4-(2-chloroethyl)amino)quinoline-2-carboxamide; N4-(2-
chloroethyl)quinoline-2,4-diamine; N-(2-chloroethyl)-2-phenyl quinolin-4-
amine; N-(2-chloroethyl)-2-methylquinolin-4-amine; N-(2-
chloroethyl)isoquinolin-l-amine; i-(2-chloroethylamino)isoquinoline-4-
carbonitrile; N-(2-chloroethyl)-4-fluoroisoquinolin-l-amine; N-(2-
chloroethyl)-2-(trifluoromethyl)quinazolin-4-amine; N-(2-chloroethyl)-2-
phenylquinazolin-4-amine; N-(2-chloroethyl)quinolin-2-amine; N-(2-
chloroethyl)quinoline-8-sulfonamide; N-(2-chloroethyl)chroman-5-amine;
N-(2-chloroethyl)-4-phenylpyrimidin-5-amine; N-(2-chloroethyl)-3-
phenylpyrazin-2-amine; N-(2-chloroethyl)-3-(piperidin-1 -yl)pyrazin-2-
amine; N-(2-chloroethyl)-3- (piperazin-l-yl)pyrazin-2-amine; N-(2-
chloroethyl)-l-phenyl-l;4,5,6-tetrahydropyrimidin-2-amine; N-(2-
chloroethyl)-3-phenylpyridin-2-amine; N-(2-chloroethyl)-4-
phenylpyrimidin-2-amine; 2-(2-(2-chloroethylamino)-6-methylpyrimidin-
4-y])phenol; N5-(2-chioroethyl)-N3,N3-dimethyl-6-pheny]pyridazine-3,5-
diamine; N-(2-chloroethyl)-3-phenylpyridazin-4-amine; 5-(2-
chloroethylamino)-6-phenylpyridazin-3-ol; 3-(2-chloroethylamino)-2-
phenyl-lH-inden-1-one; (2-(2-chloro ethylamino) pyridin-3-yl)(pyridin-2-
yl)methanone; (2-(2-chloroethylamino)pyridin-3-
yl)(morpholino)methanone; 3-(2-(2-(2-chloroethylamino)pyridin-3-yl)-2-
oxoethyl)benzonitri!e; N-benzyl-2-(2-ohioroethyiamino) nicotinamide;^
(2-chloroethylamino)-N-cyclohexylnicotinamide; 2-(2-chloroethylamino)-
N-phenylnicotinamide;(2-(2-chloroethylamino) pyridin-3-yl)(thiazol-2-
yl)methanone; 2-(2-chloroethylamino)-N-(5-methylisoxazol-3-
yl)nicotinamide; N-(2-chloroethyl)-4-(pyrrolidin-l-yl)-l,2,5-thiadiazol-3-
amine; N-(2-chloroethyl)-4-fluoro-l,2;5-thiadiazol-3-amine; 3-(2-
chloroethyl)amino-4-phenyl-l,2,5-thiadiazole-l,l-dione; N-(2-
chloroethyl)-1 -phenyl-1 H-tetrazol-5-amine; N-(2-chloroethy 1)-1 -(3-
methoxyphenyl)-lH-tetrazol-5-amine; N-(2-chloroethyl)-l-(4-

methoxyphenyl)-lH-tetrazol-5-amine; 3-(5-(2-chloroethylamino)-lH-
tetrazol-l-yl)benzonitrile; 4-(5-(2-chloroethyl amino)-lH-tetrazol-l-
yl)benzonitrile; N-(2-chloroethyJ)-l-(pyridin-2-yl)-lH-tetrazol-5-amine;
N-(2-chloroethyl)-l-cyclohexyl-lH4etrazol-5-amine; N-(2-chloroethyl)-l -
(thiazoI-2-yi)-1 H-tetrazoi-5-amine; N-(2-chloroethyI)-1-(oxazol-2-yI)-1H-
tetrazol-5-amine; N-(2-chloroethyl)-4-phenyl-4H-1,2,4-triazol-3-amine; N-
(2-chloroethyl)-5-phenyl-3H-1,2,3-triazol-4-amine; N-(2-chloroethy l)-4-
phenyl-l,2,5-oxadiazol-3-amine; N-(2-chloroethyl)-2-phenyl-2H-l,2,4-
triazol-3-amine; N-(2-chloro ethyl)-5-(methylthio)-2-phenyl-2H-1,2,4-
triazol-3-amine; N-(2-chloroethyl)-5-methoxy-2-phenyl-2H-l,2,44riazol-
3-amine; N-(2-chloroethyl)-5-(methylsulfonyl)-2-phenyl-2H-l,2,4-triazoi-
3-amine; N3-(2-chloroethyl)-N5,N5-dimethyl-1 -phenyl-1H-1,2,4-triazole-
3,5-diamine; N-(2-chloroethyl)-5-methy l-4-phenyl-4H-1,2,4-triazol-3-
amine; 5-(2-chloroethylamino)-4-phenyl-4H-l,2,4-triazol-3-ol; N-(2-
chloroethy!)-2-methyl-5-phenyl-2H-l,2,3-triazol-4-amine; N-(2-
chloroethyl)-5-(pyridin-2-yl)-lH-l,2,3-triazol-4-amine; N-(2-chloroethyl)-
5-(thiazol-2-yl)-IH-l,2,3-triazol-4-amine; N-(2-chloroethyl)-4-phenyl-
l,2,5-thiadiazol-3-amine; N-(2-chloroethyl)-3-(pyridin-2-yl)-3H-l,2,3-
triazol-4-amine;N-(2-chloroethyl)-3-phenyl-3H-l,2,3-triazol-4-amine; N-
(2-chloroethyl)-3-phenyl-l,2,4-thiadiazol-5~amine; N-(2-chloroethyl)-l-
methyI-5-phenyI-lH-pyrazoI-4-amine; N-(2-chIoroethyl)-l-(2-
morpholinoethyl)-3-phenyl~lH-pyrazol-4-amine; methyl 2-(4-(2-
chloroethylamino)-3-phenyl-1H-pyrazol-l-yl)acetate; 2-(4-(2-
chloroethylamino)-3-phenyl-1H-pyrazol-l-yl)acetonitrile; N-(2-
chloroethyl)-l-(2-(dimethylamino)ethyl)-3-phenyl-lH-pyrazol-4-amine; N-(2-chloroethyl)-3-phenyl-l-(pyridin-2-yl,methy])-lH-pyrazo]-4-amine; N-(2-chloroethyl)-l -phenyl- lH-pyrazol-5-amine; N-(2-chloroethyl)-3-methyI-1 -phenyl-1 H-pyrazoi-5-amine; N-(2-chloroethyl) -1 -(pyridin-2-y I)-lH-pyrazol-5-amine; N-(2-chloroethyl)-5-phenyl-lH-pyrazol-4-amine; N-(2-chloroethyl)-5-(pyridin-2-yl)-lH-pyrazol-4-amine; N-(2-chloroethyl)-l-phenyl-lH-imidazol-2-amine; N-(2-chloroethyl) -5-methyl-l-phenyl-IH-

imidazoI-2-amine;N-(2-ch!oro ethyl) -l-phenyI-4,5-dihydro-lH-imidazol-
2-amine; N-(2-chloroethyl)-l,3-dimethyl-lH-pyrazol-5-amine; 4-(2-(2-
chloroethylamino)thiazol-4-yl)benzonitrile; methy] 2-(6-(2-
chloroethylamino)imidazo[l,2-b]pyridazin-2-yl)-2-methylpropanoate; N-
(2-chloroethyl) benzo [c] [l,2,5]oxadiazol-5-amine; l-(2-chloroethyl)-3-
(2,6-di methyl phenyl)urea; l-(2-chloroethylamino)-4-phenylazetidin-2-
one; N-(2-chloroethyl)-2-phenylazetidin-l-amine; N-(2-chloroethyl)-2-
phenylpyrrolidin-1-amine; methyl 4-(2-chloroethylamino)piperidine-l-
carboxylate; N-(2-chloroethyl)-3-(3,5-dimethyl-1 H-pyrazol-1 -
yI)quinoxalin-2-amine.