Title of Invention

NOVEL ANTIBACTERIAL COMPOUNDS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM

Abstract Novel antibacterial compounds: process for their preparation and pharmaceutical compositions containing them. The present invention relates to novel triazole compounds of formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutical compositions containing them. where all symbols are as defined in the description.
Full Text Field of the Invention
The present invention relates to novel triazoie compounds of formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutical ly acceptable solvates and pharmaceutical compositions containing them. More particularly, the present invention relates to novel triazoles of the general fonnula {!).

then- derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutical compositions containing them.
The present invention also relates to a process for the preparation of the above said novel compoimds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutical compositions containing them.
The present invention also relates to novel intermediates, methods for their preparation and their use in the preparation of compounds of formula (I).
Baclcground of the Invention
Since the discovery of penicillin, pharmaceutical companies have produced more than one hundred antibacterial agents to combat a wide variety of bacterial infections. In the past several years, there has been rapid emergence of bacterial resistance to several of these antibiotics. The multidrug resistance among these bacterial pathogens may also be due to mutation leading to more virulent clinical isolation, the most disturbing milestone has been the acquisition of resistance to vancomycin, an antibiotic generally regarded as the agent of last resort for serious Gram-positive infections. This growing multidrug resistance has recently rekindled interest in the search for new structural class of antibiotic that inhibit or kill these bacteria possibly by novel mechanisms.
A problem of larger dimension is the increasing incidence of the more virulent, methicillin-resistant Staphylococcus aureas (MRSA) among clinical isolates found

worldwide. As with vancomycin resistant organisms, many MRSA strains are resistant to most 0^ the known antibiotics, but MRSA strains have remained sensitive to vancomycin. However, in view of the increasing reports of vancomycin resistant clinical isolates and growing problem of bacterial resistance, there is an urgent need for new molecular entities effective against the emerging and currently problematic Gram-positive organisms.
Recently, several oxazolidinones have been discovered, which inhibit protein synthesis by binding to the 50S-ribosomaI subunit which is close to the site to which chloramphenicol and Hncomycin bind but their mode of action is mechanistically distinct from these two antibiotics.
Various 1,2,3-triazoles, 1,2,4-triazoles and benzotriazoles have been reported to show various biological activities and have therefore found applications in medicinal chemistry. The literature survey shows the use of 1,2,3-triazoles, for the treatment of neuropathic pain and associated hyperalgesia, including trigeminal and herpectic neuralgia, diabetic neuropathic pain, migraine, causalgia and deafferentation syndromes such as brachial plexus avulsion, an anticoccidiostat, as antiproliferative agents, for antimetastatic activity in a model of ovarian cancer progression, for anti-inflammatory effect, controUing activity against noxious organisms, for the treatment of ischemia, anti-human inununodeficiency virus activity etc.
However, there are no reports of 1,2,3-triazole derivatives of the present invention being used for treating bacterial infections, specifically against multidrug resistant strains.
The new class of triazoles of the present invention is usefiil for the treatment of a number of resistant and sensitive gram-positive strains both in vitro and in vivo. (a) Chem. Pharm. Bull. 48(12), 1935-1946 (2000) discloses the triazoles of formula (ia) and (ib), which are reported as antifungal agents.


(b) US 6054471 discloses fluorinated triazoles of the formula (ii), which are reported for the treatment of neuropathic pain and associated hyperalgesia, including trigeminal and herpectic neuralgia, diabetic neuropathic pain, migraine, causalgia and deafferentation syndromes such as brachial plexus avulsion,

where Ph is an o-fluorinated phenyl group which may be additionally substituted by 1 or 2 halogen atoms selected from fluorine and chlorine; R1 is hydrogen, carbamoyl, N-(C2-C5) alkanoylcarbamoyl or N,N-di-(C1-C4)alkyIcarbamoyl; R^ is carbamoyl, N-(C2-C5) alkanoylcarbamoyl orN,N-di- (C1-C4) alylcarbamoyl.
An example of this class of compounds is shown in formula (iia),

(c) J. Med. Chem., 2843, 1991 discloses compound of formula (iii), which is an
anticoccidiostat and also been found to have antiproliferative activity in several disease
models and to posses antimetastatic activity in a model of ovarian cancer progression,

(d) J. Heterocycl. Chem., 609, 1989 discloses compound of formula (iv), which is
reported for anti-inflammatory effects.


(e) EPO publication no 0304221 A2 discloses compounds of formula (v),which are reported as antiproliferative reagents,

wherein p is 0 to 2; m is 0 to 4; and n is 0 to 5; X is O, S, SO, SO2, CO, CHCN, CHj or C=
NK6 where R^ is hydrogen, loweralkyl, hydroxy, loweralkoxy, amino loweralkylamino.
diloweralkylamino or cyano, and, R4 and R5 are independently halogen, cyano,
trifluoromethyl, loweralkanoyl, nitre, loweralkyl, loweralkoxy, carboxy, carbalkoxy,
trifluoromethoxy, acetamido, loweralkylthio, loweralkylsulfonyl, trichlorovinyl,
trifluoromethylthio. trifluoromethylsuifmyl, ortrifluoromethylsulfonyl;
R2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido. or
guanidino; and
R3 is carbamoyl, cyano. carbazoyi, amidino or N-hydroxycarbamoyl.
An example of this class of compounds is shown in formula (va).

Summary of the Invention
With an objective to develop novel compounds effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as MRSA, streptococci and enterococci as well as anaerobic organisms such as Bacteroides spp, Clostridia spp. species and acid-fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp., we focus our research to develop new :ompounds effective against the above mentioned organisms. Efforts in this direction have ed to the discovery of compounds having general formula (I) as defined above.

The present invention provides novel 1,2,3-triazoIe derivatives of the general formula (I) as defined above and their derivatives, their analogs, their tautomeric forms, their rotamers, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutical compositions containing them, or their mixtures having enhanced activities, without toxic effect or with reduced toxic effect.
A process for the preparation of novel 1,2,3-triazole derivatives of the formula (I) as defined above and their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts and their pharmaceutically acceptable solvates.
An aspect of the present invention is to provide pharmaceutical compositions containing compounds of the general formula (I), their analogs, their derivatives, their tautomers, their rotamers, their stereoisomers, their polymorphs, their salts, solvates or their mixtures in combination with suitable carriers, solvents, diluents and other media normally employed in preparing such compositions.
Detailed Description of the Invention
The present invention relates to compounds having the general formula (I),

wherein R1 represents halo, azido, thioalcohol, isothiocyanate, OR1*, NHR1" or N(R1")2, where
R1* represents hydrogen atom, or substituted or unsubstituted groups selected from (Cj-
C6)alkyl, acyl, thioacyl, (C1-C6)alkoxycarbonyI, (C3-C6)cycloalkoxythiocarbonyl, (C2-
C6)alkenyIoxycarbonyI, (C2-C6)alkenyIcarbonyl, heteroaryl, aryloxycarbonyl,
heteroarylcarbonyl, (CrC6)alkoxythiocarbonyl, (Cz-Cejalkenyloxythiocarbonyi,
aryloxythiocarbonyl, -C(=0)-C(=0)-(CrC6)alkyl, -C(=0)-C(=0)-aryl, -C(-0)-C(=0)-(C,-C6)alkoxy, -C(=0)-C(=0)-aryloxy, -(C=S)-S-(C,-C6)alkyl, -(C=S)-NH2, -(C=S)-NH-(C,-C6)alkyl, -C(=S)-N-((C1-C6)alkyi)2, -C(=S)-NH-(CrC6)alkenyl, (C=S)-(C=0)- (C-C6)aIkoxy, -{C=S)-{C=0)-aryIoxy, -C(=S)-0-(C=0)-(C1-C6)alkyl, C(=S)-C{-S)-(C|-a)alkyl, -C(=S)-C(-S)-aryl, -C(=S)-NH-C{=0)-aryi, -(C=NH)-NH2, -{C=NH)-(C,-

(:6)alkyl, -(C=NH)-aryI, S(0)2(C1-C6)alkyl, S(0)2aryl, thiomorpholinylthiocarbonyi,
pyrrolidinylthiocarbonyi or two R1* s together represent 5 or 6 member heterocycle ring
optionally having one or two hetero atoms; R^ and R^ may be same or different and
independently represent hydrogen, halogen atom, (C|-C6)alkyl group, halo(C,-C6)alkyl,
cyano, nitro, SR", NR\ OR1 where R1 represents substituted or unsubstituted (C1-C6}alkyl
group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or (Cp
C6)alkyl, S(0)n where n represents 0-2; Y", Y^ and Y^ may be same or different and
independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or
substituted or unsubstituted groups selected from (C|-C6)alkyl, hydroxy(C1-C6)alkyl, (d-
C6)alkoxy(C1-C6)alkyl, (C|-C6)alkoxycarbonyl, carboxy(C|-C6)aIkyl, (C|-C6)aIkylsulfonyl,
(C|-C6)alkylcarbonylamino(C|-C6)alkyl, arylcarbonyIamino(C1-C6)alky!, (C|-
C6)alkylcarbonyloxy(C]-C6)alkyl, amino(C1-C6)alkyl, mono{C|-C6)alkylamino, di{C1-Cejalkylamino, arylamino, (C!-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y , Y or Y represents =0 or =S group; or any two of Y", Y^ or Y""present on adjacent carbon atoms together may also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates.
Suitable groups represented by R"* may be selected from hydrogen atom, (C1-
C6)alkyl such as methyl, ethyl, propyl and the like, the (C1-C6)alkyl group may be
substituted; (C,-C7)acy] group such as -C(=0)H, -C(=0)CH3, -C(=0)CH2CH3, -
C(=0)(CH2)2CH3, -C(=0)(CH2)3CH3, -C{=0){CH2)4CH3, -C{=0)(CH2)5CH3, -C(=0)Ph and
the like, the acyl group may be substituted; thio(C1-C7)acyl group such as -C(=S)H, -
C(=S)CH3, -C(=S)CH2CH3, -C(^S)Ph and the like, the thioacyl group may be substituted;
(C1-C6)alkoxycarbonyl gnaup containing (C1-C6)alkyl group which may be linear or
branched such as methoxycarbonyl, ethoxycaibonyl, propoxycarbonyl, isopropoxycaibonyi
and the like, the {C1-C6)alkoxycarbonyl group may be substituted; (C3-
C6)cycloalkoxythiocarbonyl group such as cyclopropoxythiocarbonyl,
cyclobutoxytbiocarbonyl and die like, the (C3-C6)cycloalkoxythiocarbonyl may be substituted; (C2-C6)alkenylcarbonyl such as ethenylcarbonyl, propenylcarbonyl.

butenylparbonyl and the like, the (C2-C6)alkenylcarbonyl may be substituted; heteroaryl group such as pyridyl, furyl, thiophenyl, benzothiazoyl, puriny], benzimidazoyl, pyrimidinyl, tetrazolyl and the like, the heteroaryl group may be substituted; heteroarylcarbonyl such as pyridylcarbonyl, furylcarbonyl, thiophenyicarbony!, benzothiazoylcarbonyl, benzimidazoylcarbonyl, pyrimidinylcarbonyl, pyridazinecarbonyl, pyrimidinecarbonyl, pyrazinecarbonyl, tetrazolylcarbonyl and the like, the heteroarylcarbonyl group may be substituted , {C2-C6)alkenyloxycarbonyl group such as ethenyloxycarbonyl, propenyloxycarbonyl, butenyloxycarbonyl and the like, the (C2-C6)alkenyloxycarbonyl may be substituted; aryloxycarbonyl group such as phenoxycarbonyl, benzyloxycarbonyl group and the like, the aryloxycarbonyl group may be substituted; (C1-C6)alkoxythiocarbonyl group such as CH30-C(=S)-, C2H50-C(=S)- C3H7O-C(=S)- and the like, which may be substituted; (C2-C6)alkenyloxythiocarbonyl group such as ethenyloxythiocarbonyl, propenyloxythiocarbonyl, butenyloxythiocarbonyl and the like, the (C2-C6)alkenyloxythiocarbonyl group may be substituted; aryloxythiocarbonyl group such as (phenyl)0-C(=S)-, (ben2yl)0-C(=S)- and the like, which may be substituted; -C(=0)-C(=a)-(C1-C6)alkyl group such as -C(=0)-C(=0)methyl , -C(=0)-C(=0)ethyl, -C(=0)-C(=0)propyl and the like, which may be substituted; -C(=0)-C(=0)-aryl group such as -C(=0)-C(=0)phenyl, -C(=0)-C(=0)naphthyl and the like, which may be substituted; -C(=0)-C(-0)-(C1-C6)alkoxy group such as -C{=0)-C(=0)methoxy, -C{=0)-C(=0)ethoxy, -C(=0)-C(=0)propyioxy and the like, which may be substitlited; -C(=0)-C(=0)-aryloxy group such as -C(=0)-C(=0)phenyloxy, -C(=0)-C(=0)benzyloxy, which may be substituted; -(C=S)-S-CC1-C6)alkyl such as -(C=S)-S-methyl, -(C=S)-S-ethyl, -{C=S)-S-propyl and the like, which may be substituted; -(C=S)-NH2; -(C=S)-NH-(C1-C6)alkyl such as -(C=S)-NH-methyl, -(C=S)-NH-ethyI, -(C=S)-NH-propyl and the like, which may be substituted; -C(=S)-N-((C1-C6)alkyl)2 such as -C(=S)-N-(methyl)2, -C(=S)-N-(ethyl)2, -C(=S)-N-(propyl)2 and the like, which may be substituted; -C(=S)-NH-(C2-C6)alkenyl such as -C(=S)-NH-ethenyl, -CC=S)-NH-propenyI, -C(=S)-NH-butenyl and the like, which may be substituted; -{C=S)-(C=0)-(C,-C6)alkoxy such as -(C=S)-(C=0)-methoxy, -(C=S)-(C=0)-ethoxy, -(C=S)-(C=0>pTOpoxy and the like, which may be substituted; -(C=S)-(C=0)-aryloxy such as -(C=S)-(C=0)-phenyloxy, -(C=S)-(C=0)-naphthyloxy and the like, which may be substituted; -C(=S)-0-(C=0)-(C|-C6)alkyl such as -C(=S)-0-(C=O)-m«thyi, -

C(=S)-0-(C=0)-ethyi, -C(=S)-0-(C=0)-propyl and the like, which may be substituted; -C(=S)-C(=S)-(C,-C6)alkyl group such as -C(=S)-C(=S)methyI, -C(=S>C(=S)ethyl, -C(=S)-C(=S)propyl and the like, which may be substituted; -C(=S)-C(=S)aryl group such as -C(=S)-C(=S)phenyl, -C(=S)-C(=S)naphlhyl and the like, which may be substituted; -C(=S)-NH-C(=0)-aryl group such as -C(=S)-NH-C(=0)-phenyl, -C{=S)-NH-C(=0)-naphthyl and the like, -C(=S)-NH-C(=0)-aryl group may be substituted; -(C=NH)-NH2, -(C=NH)-(C,-C6)alkyl such as -(C=NH)-methyl, -(C=NH)-ethyl, -(C=NH)-propyl and the like, which may be substituted; -(C=NH)-aryl such as -{C=NH)-phenyl, -{C=NH)-naphthyl and the like, which may be substituted, thiomorpholinyhhiocarbonyl or pyrrolidinyhhiocarbonyl.
Two R1"s together form a 5 or 6 member heterocycle ring having one or two heteroatoms such as pyrrolidinyl, pyrrolyl, morpholinyl, thiomorpholinyl, benzothiazole, benzoimidazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and the like, the heterocycle formed may be substituted.
When the groups represented by R1" and heterocylces formed by two R1"s are substituted, the substituents may be selected from halogen atom such as chlorine, fluorine, bromine and iodine; hydroxy, amino, cyano, nitro, {C1-C6)alkyl, (C|-C6)alkoxy, =0, =S, aryl, hydroxyaryl, pyridyl, hydroxy(C[-C6)alkyl, mono(CrC6)alkyiamino such as methylamino, ethylamino, propylamino and the like; di(C1-C6)alkyiamino such as dimethylamino, diethylamino, dipropylamino and the like; (C1-C6)alkoxyaryl or carboxyl and its derivatives.
Suitable groups represented by R^ and R"" may be selected from hydrogen, halogen atom such as fluorine, chlorine or bromine; (C|-C6)alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, t-butyl, n-pentyl, iso-pentyl, n-hexyl and the like; halo(C1-C6)alkyl group such as halomethyl, haloethyl, halopropyl, trihalomethyl and the like, wherein the halo group is selected from fluorine, chlorine, bromine or iodine; cyano, nifro; SR1, NR^ OR1 where R1 represents substihited or unsubstituted (C|-C6)alkyl group such as methyl, ethyl, propyl, isopropyl and the like..
Suitable substitutents on R" are selected from hydroxy, halogen, nitro, amino, (C1-C6)alkoxy, carboxyl or cyano group.
Suitable groups represented by Z may be selected from S, O, -CH2, S=NR, S{=0)=NR wherein R represents hydrogen or (C1-C6)alkyl, S(Q)n where n represents 0-2.

Suitable groups represented by Y", Y^ and Y" are selected from hydrogen, halogen
such as fluorine, chlorine, bromine or iodine; cyano, nitro, fonnyl, hydroxy, amino,
substituted or unsubstituted (C1-C6)alkyl such as methyl, ethyl, n-propyi, isopropyl, n-butyl,
iso-butyl, t-buty! and the like; bydroxy(C|-C6)alkyI such as hydroxymethyl, hydroxyethyl,
hydroxypropyl and the like, which may be substimted; (C1-C6)alkoxy(C1-C6)alkyl group
such as methoxymethyl, methoxyethyl, ethoxyethyl, ethoxymethyl, methoxypropyl,
propoxymethyl, propoxyethyl and the like, which may be substituted; (C1-
C6)alkoxycarbonyI group such as methoxycarbonyl, ethoxycarbonyl and the like, which may
be substihJted; carboxy(C1-C6)alkyl such as CH3-COOH, CHj-CHrCOOH and the like,
which may be substimted; (C|-C6)alkylsuIfonyl group such as methylsulfonyl, ethylsulfonyl
and the like, which may be substituted; (C1-C6)alkylcarbonylairiino(C1-C6)alkyl groups such
as methylcarbonylaminomethyl, ethylcarbonylaminomethyl, methylcarbonylaminoethyl and
the like, which may be substituted; arylcarbonylamino(C1-C6)alkyl such as
phenylcarbonylaminomethyl, phenylcarbonylaminoethyl and the like, which may be
substituted; (C|-C6)alkylcarbonyloxy(C1-C6)alkyI group such as methylcarbonyloxymethyl,
ethylcarbonylxoymethyl, methylcarbonyloxyethyl, propylcarbonyloxymethyi,
propylcarbonyloxyethyl, propylcarbonyloxypropyl and the like, which may be substituted; amino(C1-C6)alkyl such as aminomethyl, aminoethyl, aminopropyl and the like, which may be substituted; mono(C|-C6)alkylamino such as methylamino, ethylamino, propylamino and the like, which may be substituted; di{C1-C6)alkylamino such as dimethylamino, diethylamino, dipropylamino and the like, which may be suljstituted; arylamino such as phenylamino, benzylamino and the like, which may be substituted; (C1-C6)alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy and the like, which may be substituted; aryl group such as phenyl, naphthyl and the like, which may be substituted; aiyloxy group such as phenoxy, naphthyloxy and the like, the aryloxy group may be substituted; aralkyl such as benzyl, phenethyl, C6H5CH2CH2CH2, naphthylmethyl and the like, the aralkyl group may be substituted; heteroaryl groups such as pyridyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, tetrazolyl, benzopyranyl, benzofuranyi and the like, which may be substituted; heteroaralkyl such as imidazolemethyl, imidazoleethyl, . pyridylmethyl, furyl methyl, oxazolemethyl, imidazolyl and the like, which may be substituted; heterocyclyl group such as pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl

and the like; heterocycloalkyl groups such as pyrrolidinemethyl, piperidinemelhyl, morpholinemethyl, piperazinemethy] and the like, which may be substituted. Any of Y", Y^ or Y^ may also represent =0 or =S group.
Suitable cyclic structure formed by Y", Y^ and Y" when present on adjacent carbon atoms which they are attached may be selected from substituted or unsubstituted benzene, pyridine, pyrrolidine, furan, thiophene, morpholine, piperazine, pyrrole and the like, the heterocycle formed may be substituted.
When the groups represented by Y", Y^ and Y^ are substituted, the substituents may be selected from hydroxy, nitro, cyano, amino, /ert-butyldimethylsilyloxy (TBSO), halogen atom, (C1-Cejalkyl, (C|-C6)alkoxy, (C3-C6)cycloaIkyl, aryl, benzyloxy, acyl or acyloxy group such as formyloxy, acetyloxy and the like. The remaining groups are as defined above.
Pharmaceutically acceptable salts forming part of this invention include salts derived
from inorganic bases such as Li, Na, K, Ca, Mg, Fe, Cu, Zn, Mn; salts of organic bases such
as N,N"-diacetyl ethyl enediamine, betaine, caffeine, 2-diethylaminoethanol, 2-
dimethylaminoethanol, N-ethyhnorpholine, N-ethylpiperidine, glucamine, glucosamine,
hydrabamine, isopropylamine, methylglucamine, morpholine, piperazine, piperidine,
procaine, purines, theobromine, triethylamine, trimethylamine, tripropylamine,
tromethamine, diethanolamine, meglumine, ethylenediamine, N,N"-
diphenyiethylenediamine, N,N"-dibenzyIethylenediamine, N-benzyl phenylethylamine, choline, choline hydroxide, dicyclohexylamine, metformin, benzylamine, phenylethylamine, dialkylamine, trialkylamine, thiamine, aminopyrimidine, aminopyridine, purine, spermidine, and the like; chiral bases like alkylphenylamine, glycinol, phenyl glycinol and the like, salts of natural amino acids such as glycine, alanine, valine, leucine, isoleucine, norleucine, tyrosine, cystine, cysteine, methionine, proline, hydroxy proline, histidine, ornithine, lysine, arginine, serine, threonine, phenylalanine; unnatural amino acids such as D-isomers or substituted amino acids; guanidine, substituted guanidine wherein the substituents are selected from nitro, amino, alkyl such as methyl, ethyl, propyl and the like; alkenyl such as ethenyl, propenyl, butenyl and the like; alkynyl such as etiiynyl, propynyl and the like; ammonium or substituted ammonium salts and aluminum salts. Salts may include acid addition salts where appropriate which are, sulphates, nitrates, phosphates, perchlorates,

borates, halides, acetates, tartrates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, salicylates, hydroxynaphthoates, benzenesulfonates, ascorbates, glycerophosphates, ketoglutarates and the Uke. Pharmaceutically acceptable solvates may be hydrates or comprising other solvents of crystallization such as alcohols.
Particularly useful compounds according to this invention include:
l-(3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethanol, its salts;
l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-tria2oI-4-yhnethanol, its salts;
l-[3,5-Difluoro-4-(4-thiomorpholiny])phenyl]-li/-l,2,3-triazol-4-ylmethanoI, hs salts;
l-[3,5-Difiuoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-5-ylmethanol, itssahs;
l-[3-Fluoro-4-{4-thiomorpholinyl)phenyl]-l^-l,2,3-triazol-4-yImethanol, its salts;
l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-lH-I,2,3-triazol-5-ylmethanoI, its salts;
l-(3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmetbylmethanesulfonate, its
salts; . l-(3-Fluoro-4-morpholinophenyl)-l/f-l,2,3 triazoI-4-ylinethyl methanesulfonate, its salts; l-[3,5-Difluoro-4-(4-thiomorphoIinyI)phenyl]-lH-I,2,3-triazol-4-ylmethylmethanesulfonate, its salts;
l-[3,5-Difiuoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-5-ylmethylmethanesulfonate, its salts;
l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethylmethanesuIfonate, its salts; l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-5-yhnethylmethane sulfonate,
its salts;
l-{3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3 triazoM-yhnethyl azide, its salts; l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl azide, its salts; l-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyI]-lH-l,2,3-tria2ol-4-ylmethyl azide, its salts; l-[3,5-Difluoro-4-(4-thiomorpho\inyl)phenyl>lH-l,2,3-triazol-5-yhnethyl azide, its salts; l-[3-Fluoro-4-(4-thiomorphoIinyI)phenyl]-lH-l,2,3-triazol-4-ylmethyl azide, its salts; l-[3-Fluoro-4-{4-thiomorpholinyl)phenyl]-l^-l,2,3-triazol-5-ybnethyl azide, its salts; l-{3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazoI-4-yhnethanamine, its salts; l-(3-Fluoro-4-morpholinophenyl)-li/-l,2,3-triazol-4-ybBethanamine, its salts; l-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyl]-l/f-l,2,3-triazol-4-ylmethanamine, its salts;

l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-lH-I,2,3-triazoI-4-yImelhanamine, its salts; l-[3,5-Difluoro-4-(l-oxo-4-thiomorphoIinyl)phenyl]-lH-l,2,3-triazol-4-ylmethylazide, its salts;
l-[3,5-Difluoro-4-(l,l-dioxo-4-thiomorpholinyI)phenyl]-l/f-l,2,3-triazol-4-ylmethylazide, its salts;
l-[3-Fluoro-4-(l-oxo-4-thiomorpholinyl)phenyi]-l/f-l,2,3-tria2ol-4-ylmethyl azide, its salts; l-[3-Fluoro-4-(l,I-dioxo-4-thiomorpholinyl)phenyI]-lH-l,2,3-triazol-4-ylmethylazide, its salts;
l-[3-Fluoro-4-(l-oxo-4-thiomorphoiinyl)phenyl]-l^-l,2,3-triazol-4-ylmethanamine, its
salts;
l-[3,5-Difluoro-4-(l-oxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethanamiiie,
its salts;
l-[3,5-Difluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl]-l/f-l,2,3-triazol-4-yImethanamine,
its salts;
l-[3-Fluoro-4-(l,l-dioxo-4-lhiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethanamine,
its salts;
l-(3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-yImethylisothiocyanate, its salts;
l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazoIe-4-ylmethyl isothiocyanate, its salts;
I-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyl]-l-ff-l,2,3-triazol-4-ylmethylisothiocyanate,
,ts salts;
I-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-\H-1,2,3-triazol-4-ylmethyl isothiocyanate, its
;alts;
l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-yknethyI isothiocyanate, its
ialts; l-[3,5-Difluoro-4-(l-oxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-tria2ol-4-ylmethyl
sothiocyanate, its salts;
[-[3,5-Difluoro-4-{l,l-dioxo-4-thiomorpholinyl)phenyl]-li/-l,2,3-tria2oI-4-ylmethyl sothiocyanate, its salts; l-[3-FIuoro-4-(l,l-dioxo-4-thiomorphoIinyl)phenyl]-lH-l,2,3-triazol-4-ylmethyI
sothiocyanate, its salts; Vl[l-(3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ybnethyI]acetamide, its salts;

,M[l-(3-Fluoro-4-morpholinophenyl)-li/-l,2,3-triazol-4-yimethyl]acetamide, its salts;
M-[l-{3,5-Difluoro-4-{4-thiomorpholinyl)phenyl}-l/f-l,2,3-triazol-4-ylmethyl]acetamide, its salts;
M-[l-{3,5-Difluoro-4-{l-oxo-4-thiomorpholinyl)phenyl}-lff-l,2,3-triazol-4-ylmethyl] acetamide, its salts;
M-[l-{3,5-Difluoro-4-(l,I-dioxo-4-thiomorphoIinyl)phenyi}-lH-I,2,3-triazol-4-ylmethyl] acetamide, its salts;
M-[l-{4-(4-Thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-ylmethyl]acetamide, its salts;
Nl-[l- {3-Fluoro-4-( 1 -oxo-4-thiomorpholinyI)phenyl} - \H-1,2,3-triazol-4-
ylmethyl] acetamide, its salts;
A^l-[l-{3-Fluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-l/f-l,2,3-triazoI-4-ylm ethyl]
acetamide, its salts;
l-[l-(3,5-Difuoro-4-morpholinophenyl-lH-l,2,3-triazol-4-ylmethylamine]-l-elhanethione,
its salts;
l-[l-(3-Fluoro-4-morphoIinophenyl-li:f-l,2,3-triazoI-4-ylmethylamine]-l-ethanethione,
its salts;
0-Methyl-[l-{3,5-difluoro-4-morpholinophenyl)-l/?-l,2,3-triazol-4-
ylmethyljthiocarbamate, its salts;
0-Methyl-[ 1 -(3-fluoro-4-morpholinophenyl)- IH-1,2,3-triazol-4-ylmethyl]thiocarbamate,
its salts;
0-Methyl-[l-{3,5-difluoro-4-{4-thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-ylmethyl]thio
carbamate, its salts;
0-Methyl-[l-{3,5-difluoro-4-(l-oxo-4-thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-
ylmethyl] thiocarbamate, its salts;
0-Methyl-[l-{3,5-difluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-li/-l,2,3-triazol-4-yl
methyl]thiocarbamate, its salts;
0-Methyl-[l-{3-fluoro-4-(4-thiomcrpholinyl)phenyI}-Ii/-l,2,3-triazol-4-yImethyl]
thiocarbamate, its salts; 0-Methyl-[l-{3-fluoro-4-{l-oxo-4-thiomorpholmyl)phenyl}-lH-l,2,3-triazol-4-ylmethyI]
tiiiocarbamate, its salts;

0-Methyl-[l-{3-fluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-yl methyl]thiocarbamate, its salts;
l-(3,5-Difluoro-4-morphoiinophenyl)-l/:f-l,2,3-triazole-4-yImethylaminomethyl-aminomethanethione, its salts;
S"-Methyl-[l-(3-fluoro-4-moiphoIinophenyl)-l/:^-l,2,3-triazol-4-ylmethyl]dithiocarbamate, its salts;
5-Methyl-[l - {3-fluoro-4-( 1 -oxo-4-thiomorpholinyl)phenyl} -17/-1,2,3-triazol-4-ylm ethyl ]
dithiocarbamate, its salts;
5-Methyl-[l-{3-fluoro-4-{l,l-dioxo-4-thiomorpholinyl)phenyl}-lW-l,2,3-triazol-4-
yimethyl] dithiocarbamate, its salts;
l-(3-Fluoro-4-moipholinophenyl)-4-phenylcarboxamido(thioxo)methylaminomethyl-L¥-
1,2,3-triazole, its salts;
A"2-[l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-yhnethyl]-2-pyrazine
carboxamide, its salts;
5-Methyl-0-[l-(3-fluoro-4-morpholinophenyl)-lH^-l,2,3-triazol-4ylmethyl]dithiocarbaniale,
its salts;
I-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl 2-pyridyl ether, its salts;
l-[l-(3-fluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl]-!,2-dihydro-2-pyridinone,
its salts;
Aminc-l-(3-fluoro-4-moipholinophenyl)-lH-l,2,3-triazol-4ylmethylaminomethanethione,
its sails and M-[l-{3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-ylmethyI]-2,2-dichloro-
acetamide, its salts.
The present invention also relates to a process for the preparation of the compound of formula (I) where R1 represents azido and all other symbols are as defined earlier, which comprises: (i) reacting the compound of formula (la)



where R1^ represents (C1-C6)alkyl group such as methyl, ethyl, n-propyl, iso-propyl and the like; Z, Y", Y^ Y\ R^ and R^ are as defined earUer,

(v) reducing the compound of formula (10, to give a compound of formula (I)

where R1 represents hydroxy group; Z, Y", Y^ Y\ R^ and R^ are as defined earlier,
(vi) converting the compound of formula (I), v^-here R1 represents hydroxy group, to a
compound of formula (I), where R1 represents OR"* wherein R1" represents S(0)2(CrC6)aikyl
or S(0)2aryl group and all other symbols are as defined earlier, and
(vii) converting the compound of formula (I) where R1 represents OR1" wherein R^
represents S(0)2(C1-C6)atkyl or S(0)2aryl group, to a compound of formula (I) where R1
represents azido group and all other symbols are as defined earlier.
The compound of formula (Ic) may be prepared by reacting a compound of formula
(la) with a compound of formula (lb) by using a base such as KOH, NaOH, K2CO3,
Na2C03, NaH, KH, triethylamine, diisopropylethyl amine and the like. The reaction may be
carried out using a solvent such as DMSO, DMF, THF, acetonitrile, chloroform,
nitrobenzene and the like or mixtures thereof The reaction may be carried out in inert
atmosphere, which may be maintained using inert gases such as N2 or Ar. The reaction may
r be carried out at a temperature in the range of 20 to 100 "C, preferably at a temperature in
the range of ambient-80 "C. The reaction time may range fi-om 1 to 15 h, preferably from 6
to 12 h.
The reduction of a compound of formula (Ic) to produce a compound of formula (Id)
may be carried out in the presence of reducing agents such as NiCh/NaBHj, lithium
alimiinium hydride (LAH), gaseous hydrogen and a catalyst such as Ru, Pd, Rh, Pt, Ni on
solid beads such as charcoal, alumina, asbestos and the like. The reduction may be carried
out in the presence of a solvent such as dioxane, acetic acid, ethyl acetate, THF, alcohol
such as methanol, ethanol and the like or mixtures thereof A pressure between atmospheric
pressure to 60 psi may be used. The reaction may be carried out at a temperature fi-om 0 to
60 °C, preferably at 0 to room temperature. The reaction time ranges fi-om 0.5 to 48 h,
preferably in the range of 0.5 to 5 h. The reduction may also be carried out by employing
metal in mineral acids such Sn/HCI, Fe/HCl, Zn/HCI, Zn/CHiCOiH and the like.
I

" The compound of formula (Id) may be converted to a compound of formula (le) by using NaNOi in the presence of HCl or CH3COOH followed by NaNs. The solvent used in the reaction may be selected from methanol, ethanol, ethylacetate, THF, ether, dioxan and the like. The temperature of the reaction may be maintained in the range of ^0 "C to boihng temperature, preferably in the range of 0 "C to room temperature. The duration of the reaction may be in the range of 0.5 to 15 h, preferably in the range of 0.5 to 5 h.
The compound of formula (If) may be prepared by heating a compound of formula (le) with (C1-C6)a!kyl ester of propiolic acid. The solvent used in the reaction may be selected from benzene, toluene, xylene, methyl cyanide, THF and the like. The temperature of the reaction may be maintained in the range of 10 to 200 "C, preferably in the range of room temperature to the boihng temperature of the solvent. The duration of the reaction may be in the range of 1 to 25 h, preferably 5 to 20 h.
The conversion of compound of formula (If) to a compound of formula (I), where R1 represents hydroxy may be carried out by using reducing agents such as LAH, lithiumborohydride (LiBPij) or NaBH4/l2. The reaction may be carried out in the presence of a solvent such as methanol, ethanol, THF, EtiO, dioxane and the like, or mixtures thereof The temperature of the reaction may be in the range of -80 to 100 °C, preferably 0 "C to boiling temperature of the solvent. The duration of the reaction may be in the range of 0.5 to 10 h.
The compotmd of formula (I) where R1 represents OH may be converted to compound of formula (I) where R1 represents OR"* wherein R"* represents S(0)2(C1-C6)alky! or S(0)2aryl group, by treating with alkylsulfonylchloride or arylsulfonylchloride such as methanesulfonyl chloride, p-toluenesulfonyl chloride and the like. The reaction may be carried out in the presence of chloroform, dichloromethane, THF, dioxane and the hke or mixtures thereof. The base used in the reaction may be selected from Et3N, diisopropyl ethylamine, Na2C03, K2CO3 and the like. The temperature of the reaction may be mamtained in the range of 0 to 50 °C, preferably in the range o"f 0 to room temperature. The duration of the reaction may be in the range of 1 to 12 h, preferably in the range of 1 to 4 h.
The compound of formula (I) where R1 represents OR1" wherein R1" represents S(0)2(C1-C6)alkyl or S(0)2aryl group may be converted to compound of formula (I) wherein R1 represents azido group, by treatmg with NaN3. The solvent used in the reaction may be

selected from dimethylformamide (DMF), dimethyl sulfoxide (DMSO), methylcyanide, nitromethane and the like. The tempearature of the reaction may be maintained in the range of room temperature to 120 °C, preferably room temperature to 80 "C. The duration of the reaction may be in the range of 1 to 12h, preferably 1 to 4 h.
Alternatively, the compound of formula (I) whrein R1 represents hydroxy can be converted to a compound of formula (I) wherein R1 represents azido group without isolating and characterizing the alkylsulfonylor arylsulfonyl intermediate-formed.
Another embodiment of the present invention provides an aUemate process for the preparation of the compound of formula (I) where R1 represents azido and all other symbols are as defined earlier, which comprises: (i) converting the compound of formula (le)

where Z, Y", Y^, Y"", R^ and R^ are as defined earHer, to a compound of formula (I)

where R1 represents hydroxy; Z, Y", Y^, Y\ R^ and R^ are as defined earlier and (ii) reacting the compound of formula (I) where R1 represents hydroxy group, with MsCl, triethylamine and sodium azide to a give a compound of formula (1) where R1 represents azido group,
where R1 represents azido; Z, Y", Y^ Y\ R^ and R^ are as defined earlier.
The compound of formula (le) may be converted to a compound of formula (I), where R1 represents hydroxy group, by treating with propargyl alcohol. The solvent used in the reaction may be selected from benzene, toluene, xylene, methylcyanide, THF and the

like. The temperature of the reaction may be maintained in the range of 10 to 200 °C, preferably room temperature to the boiling temperature of the solvent. The duration of the reaction may be in the range of 1 to 25 h, preferably in the range of 5 to 20 h.
The compound of formula (I) where R1 represents hydroxy group may be converted to a compound of formula (I) where R1 represents azido group was carried out in two steps. hi step (1) the compound of formula (I) where R1 represents OH is converted to compound of formula (I) where R1 represents leaving group such as halogen atom, by treating with CBr4/PPh3, PBr3, SOCI2 and the like. The reaction may be carried out in the presence of chloroform, dichloromethane, THF, dioxane and the like or mixtures thereof The reaction may be carried out in the presence or absence of a base such as EtjN, diisopropyl ethyiamine, Na2C03, K2CO3 and the like. The temperature of the reaction may be maintained in the range of 0 to 80 "C, preferably in the range of 0 to 50 "C. The duration of the reaction may be in the range of l-12h, preferably in the range of l-4h. In step (2), the compound of formula (I) where R1 represents halogen atom may be converted to compound of formula (I) where R1 represents azido group by treating with NaN3, LiNj, trialkylsilylazide and the like. The solvent used in the reaction may be selected from acetone, THF, DMF, dimethyl sulfoxide (DMSO), methylcyanide and the like. The tempearature of the reaction may be maintained in the range ofroom temperature to 120 "C, preferably room temperature to 80 °C. The duration of the reaction may be in the range of 1 to 12 h, preferably 1 to 4 h.
Yet another embodiment of the present invention provides an alternate process for the preparation of compound of fomiula (I), where R1 represents azido group, which comprises: (i) converting the compound of formula (le)

where Z, Y", Y^, Y"*, R^ and R^ are as defmed earlier, to a compound of formula (I)


where R1 represents halogen atom such as chlorine, bromine and the like, and all other
symbols are as defined earher and
(ii) converting the compound of formula (I) where R1 represents halogen atom such as
chlorine, bromine and the like, to a compound of formula (I), wherein R1 represents azido
group.
The compound of formula (I), where R1 represents halogen atom such as chlorine, bromine and the like, may be prepared from a compound of formula (le) by using propargyl halide such as propargylchloride, propargyl bromide or propargyl iodide. The solvent used in the reaction may be selected from benzene, toluene, xylene, methylcyanide, THF and the like. The temperature of the reaction may be maintained in the range of 10 to 200 "C, preferably room temperature to the boiling temperature of the solvent. The duration of the reaction may be in the range of 1 to 25 h, preferably in the range of 5 to 20 h.
The conversion of a compound of formula (I) where R1 represents halogen atom such as chlorine, bromine and the like, to a compound of formula (I) where R represents azido group, may be carried out in the presence of one or more equivalents of metal azide such as LiNa, NaNj or trialkyl silylazide. The reaction may be carried out in the presence of solvent such as THF, acetone, DMF, DMSO and the like or mixtures thereof The reaction may be carried out in inert atmosphere, which may be maintained using N2 or Ar. The reaction may be carried out at a temperature in the range of ambient temperature to reflux temperature of the solvent, preferably at a temperature in the range of 50 to 80 "C. The reaction time may be in the range from 0.5 to 18 h, preferably 1 to 4 h.
Another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents azido group, Z represents -SOn-, where n represents 1 or 2, which comprises: (i) oxidizing the compound of formula (I),


where R1 represents azido group; Z represents -SOn-, where n represents zero, to obtain a compound of formula (I) where R1 represents azido group, Z represents -SOn-, where n represents 1 or 2; and Y", Y^, Y^, R^ and R^ are as defined earlier.
The conversion of compound of formula (I) where R1 represents azido group; Z represents -SOn-, where n represents zero, to a compoimd of formula (I) where R1 represents azido group, Z represents -SOn- where n represents 1 or 2, may be carried out by using oxidizing agents such as m-CPBA, hydrogen peroxide and the like. The solvent used in the reaction may be selected fi-om dichloromethane, chloroform and the like. The temperature of the reaction may be maintained in the range of-40 to 50 "C, preferably in the range of 0 °C to room temperature. The duration of the reaction may be in the range from 0.2 to 10 h, preferably m the range of 0.5 h to 5 h.
Another embodiment of the present invention provides a process for the preparation of compound of formula (I) where R1 represents NHR"* wherein R"* represents hydrogen atom, which comprises: (i) converting the compound of formula (If)

where R"^ represents (C1-C6)alkyl group such as methyl, ethyl, n-propyl, iso-propyl and the like; and all other symbols are as defined earlier, to a compound of formula (Ig)

where all symbols are as defined earlier and

(ii) reducing the compound of formula (Ig), to produce a compound of formula (I) where R1 represents NHR1* wherein R1* represents hydrogen atom and all other symbols are as defined earlier.
The conversion of compoimd of formula (If) to a compound of formula (Ig) may be carried out in the presence of ammonia solution in water or alcohol. The temperature of the reaction may be in the range of-40 to 50 °C, preferably of 0 "C to room temperature. The duration of the reaction may be in the range of 0.5 to 12 h, preferably 0.5 to 4 h.
The reduction of compound of formula (Ig) to a compound of formula (I), where R1 represents NHR"* wherein R^ represents hydrogen atom, may be carried out by using borane complex in THF, diethylether, SMe; or amine. The solvent used in the reaction may be selected from THF, diethylether, dioxane and the like. The temperature of the reaction may be in the range of -20 to 70 °C, preferably 0 to boiUng temperature of the solvent. The duration ofthe reaction may be in the range of 1 to 15 h, preferably 1 to6h.
Yet another embodiment of the present invention provides an alternate process for the preparation of compoimd of formula (I) where R1 represents NHR1" wherein R* represents hydrogen atom, which comprises;
(i) reducing the compound of formula (I) wherein R1 represents azido group, to produce compound of formula (I)

where R1 represents NHR"* wherein R** represents hydrogen atom; Y", Y^, Y"", R^, R^ and Z are as defined earlier.
The reduction of a compound of formula (I) where R1 represents azido group, to produce a compound of formula (I) where R1 represents NHR1" wherein R"* represents hydrogen atom, may be carried out in the presence of gaseous hydrogen and a catalyst sucfi as Ru, Pd, Rh, Pt, Ni on solid beads such as charcoal, alumina, sabestos and the like. The reduction may be carried out in the presence of a solvent such as dioxane, acetic acid, ethyl acetate, THF, alcohol such as methanol, ethanol and the like of mixtures thereof A pressure between atmospheric pressure to 60 psi may be used. The reaction may be carried out at a

.temperature in the range of 25 to 60 °C, preferably at room temperature. The duration of the reaction may be in the range of 2 to 48 h. The reduction may also be carried out by employing PPhs in water.
Another embodiment of the present invention provides a process for the preparation of compound of formula (I) where R1 represents hydroxy group, which comprises: (i) converting the compound of formula (le),

where Z, Y", Y^ Y\ R^ and R^ are as defined earlier, to obtain a compound of formula (I),

where R1 represents OR1" wherein R** represents substituted or unsubstituted acyl group, and all other symbols are as defined earlier and
(ii) hydrolysis of the compound of formula (I) where R1 represents OR1" wherein R1" is as defined above, to a compound of formula (I), where R1 represents hydroxy group and ail other symbols are as defined earlier.
The conversion of compound of formula (le) to a compound of formula (I) where R1 represents OR1" wherein R1" is as defined above, may be carried out in the presence of esters ((C1-C6)allcyl or aryl)of propargyl alcolhol. The solvent used in the reaction may be selected fi-om benzene, toluene, xylene, methylcyanide, THF and the like. The temperature of the reaction may be maintained in the range of 10 to 200 "C, preferably room temperature to the boiling temperature of the solvent. The duration of the reaction may be in the range of 1 to 25 h, preferably in the range of 5 to 20 h.
The hydrolysis of compound of formula (I) where R1 represents OR1" wherein R1" is as defined above, to a compound of formula (I), where R1 represents hydroxy group, may be carried out by using conventional ester hydrolysis procedures.

Yet another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents NHR\ wherein R" represents acetyl group and all other symbols are as defined earlier, irom a compound of formuJa (I) where R1 represents azido group,

where Z, Y", Y^ Y^ R^ and R^ are as defined earher.
The compound of formula (I), where R1 represents NHR"*, wherein R1" represents acetyl group may be prepared from compound of formula (I), where R1 represents azido group may be carried out by using thioacetic acid with or. without using solvent such as THF, DMF, toluene and the like. The reaction may be carried out at a temperature in the range of 25 to 40 "C, preferably at room temperature. The duration of the reaction may be in the range irom 3 to 24 h, preferably from 4 to 12 h.
Still another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents NHR"*, where R1* represents -C(=S)-R1"S wherein R"" represents (C|-C6)alkyl, halo(C,-C6)alkyl, -C(=0)-(C|-C6)alkoxy, -C(=0)-aryloxy, -C(=S)-(C1-C6)alkyl or -C(=S)-aryl; from compound of formula (I), where R1 represents NHR"*, where R"* represents -C(=0)-R1"*, wherein R"*^ represents (C1-C6)alkyl, halo(C1-C6)alkyl, -C(=0)-(C|-C6)alkoxy, -C(=0)-aryloxy, -C(=S)-(C,-C6)alkyl or -C(=S)-aryl.

where all symbols are as defined earlier.
The compound of formula (I), where R1 represents NHR"*, wherein R* represents -C(=S)-R^^ from compound of formula (I), where R1 represents NHR1", wherein R" represents -C(=0)-R1"^, wherein R1^" is as defined above, may be carried out by taking a solution of the amide and Lawesson"s reagent (2,4-bis(methoxyphenyl)-l,3-dithia-2,4-diphosphetane-2,4-

.disulfide) in dry dioxane, toluene, THF, DMF and the like. The reaction may be earned out at a temperature in the range of room temperature to 130 "C, preferably in the range of 55 to 90 °C. The duration of the reaction may be in the range from 3 to 24 h, preferably from 3 to 10 h.
Another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents NHR1", wherein R"* represents -C(=S)-OR*, wherein R^"" represents (C1-C6)alkyl, cyclo(C3-C6)alkyl, -{C=0)-(CrC6)aIkyl group substituted with fluorine; aryl, halo(C|-C6)alkyI, hydroxy(C|-C6)alkyl, (C1-C6)alkoxy(Cr C6)alkyl or (C2-C6)alkenyl, which comprises: (i) reacting compound of formula (I)

where R1 represents azido group; and all other symbols are as defined earlier, with
triphenylphosphine/water or H2-Pd/C, to produce a compound of formula (1), where R1
represents NHR1", wherein R"* represents hydrogen atom and all other symbols are as defined
earlier,
(ii) reacting compound of formula (I), where R1 represents NHR"*, wherein R"* represents
hydrogen atom, with thiophosgene or carbon disulfide and cfiloromethylformate, in the
presence of a base to produce a compound of formula (I)

where R1 represents isothiocyanate group; and all symbols are as defined earlier, (iii) converting compound of formula (I) where R1 represents isothiocynate group, to a compound of formula (I), where R1 represents NHR1", wherein R1" represents -C(=S)-OR1"", wherein R^*" is as defined above and all other symbols are as defined earlier.
The conversion of compound of formula (I), where R1 represents azido to a comoound of formula (1), where R1 represents NHR1*, wherein R1" represents hydrogen atom

may be carried out in the presence of gaseous hydrogen and a. catalyst such as Ru, Pd, Rh, Pt, Ni on solid beads such as charcoa], alumina, asbestos and the like. The reduction may be conducted in the presence of a solvent such as dioxane, acetic acid, ethyl acetate, THF, alcohol such as methanol, ethanol and the like or mixtures thereof. A pressure between atmospheric pressure to 60 psi may be used. The reaction may be carried out at a temperature in the range of 25 to 60 "C, preferably in the range of room temperature to 80 "C. The duration of the reaction may be in the range of 2 to 48 h, preferably in the range of 5 to 15 h. The reduction may also be carried out by employing PPh3 and water.
The compound of formula (I), where R1 represents NHR1", wherein R*" represents hydrogen atom may be converted to a compound of formula (I) where R1 represents isothiocyanate group, by using thiophosgene or carbon disulfide and chloromethylformate in the presence of a base such as EtjN, K2CO3, NaOH and the like. The reaction may be carried out in the presence of a solvent such as ethanol, methanol, isopropanol, CH2CI2, CHjCN, CHCI3, DMF, THF and the like. The reaction may be carried at a temperature in the range of 0 to 60 °C, preferably at 0 "C. The reaction may be carried out in an inert atmosphere using argon or any other inert gas. The dilation of the reaction may be in the range of 1 to 24 h, preferably 2 to 10 h.
The conversion of compound of formula (I) where R represents isothiocyanate group, to a compound of formula (I), where R1 represents NHR"*, wherein R1^ represents -C(=S)-OR1"", wherein R1"" is as defined above, may be carried out by using respective alcohol such as methanol, ethanol, propanol, cyclohexanol and the like, in the absence or presence of a base such as NaH, KH and the like. The reaction may be carried out in the presence of a solvent such as THF, toluene, DMF and the like. The reaction may be carried out at a temperature in the range of room temperature to 130 "C, preferably at reflux temperature of the solvent used. The duration of the reaction may be in the range of 6 to 24 h.
Another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R^ represents NHR1*, where R1* represents -C(=S)-N{R1R"), wherein R1 represents hydrogen, (C1-C6)alkyt, (C2-C6)alkenyl, substituted or unsubstituted aralkyl, heteroaralkyi, hydroxy(C1-C6)alkyl, R" represents hydrogen or (C1-

C6)alkyl or the two R1 and R" grojups together form a 5 or 6 membered cychc structures containing one or two hetero atoms; from a compound of formula (I) where R1 represents isothiocyanate group,
where all symbols are as defined earlier.
The compound of formula (I), where R1 represents NHR1", wherein R"* represents -C(=S)-N(R1R"), wherein R1 and R" independently represent hydrogen, may be prepared by passing ammonia gas into a solution of compound of formula (I) where R1 represents isothiocyanate group, in the presence of a solvent such as THF, toluene, and the like. The reaction may be carried out at a temperature in the range of -10 °C to room temperature, preferably at -10 °C. The duration of the reaction may be in the range from 20 min to 4 h, preferably 30 min.
The compound of formula (I), where R1 represents NHR1", wherein R"* represents -C{=S)-N(R1R"), wherein R1 represents hydrogen, (C|-C6)alkyl, (C2-C6)alkenyl, substituted or unsubstituted aralkyl, heteroaralkyi, hydroxy(C1-C6)alkyl, R" represents (C1-Cejalkyl or R1 and R" groups together form a 5 or 6 membered cyclic structures containing one or two hetero atoms, may be carried out by treating a compound of formula (I) where R1 represents isothiocyanate group with appropriate amine such as metbyJamine, ethylamine, diemthylamine, diethylamine, benzylamine, aniline, proline, morpholine, thiomorpholine, pyridiylmethylamine and the like, in the presence of a solvent such as THF, DMF, toluene, and the like. The reaction may be carried out at a temperature in the range of room temperature to 140 "C, preferably at room temperature to 100 °C. The duration of the reaction may be in the range of 0.5 to 24 h, preferably 0.5 to 12 h.
Yet another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents NHR*, wherein R represents -CC=S)-SR*", wherem R*" represents (C1-C6)alkyl gorup, from compound of formula (I), where R1 represents NHR"*, wherein R* represents hydrogen atom,


(-here all other symbols are as defined earlier.
The compound of fomula (I), where R1 represents NHR^ wherein R"* represents -)(=S)- SR1"^ wherein R**" is as defined above, may be prepared from compound of formula ;), where R1 represents NHR1*, wherein R1* represents hydrogen atom, by using CS2 in the resence of a base such as EtaN, diisopropyl ethylamine, K2CO3, NaH, t-BuOK and the like, he reaction may be carried out in the presence of alkyl halide such as methyliodide, :hylbromide, propyibromide and the like. The solvent used in the reaction may be selected om ethanol, methanol, isopropanol, THF, diethylether, CH3CN and the like, or mixtures lereof. The reaction may be carried out at a temperature in the range of room temperature I 60 "C, preferably at room temperature. The duration of the reaction may be in the range of to 24 h.
Another embodiment of the present invention provides a process for the preparation "compound of formula (I), where R1 represents NHR1", wherein R1"represents -C(=S)-NH-***, wherein R1*^ represents benzoyl group, from compound of formula (I), where R1 presents NHR1^, wherein R represents hydrogen atom,

here all other symbols are as defined earlier.
The compound of fomula (I), where R1 represents NHR"*, wherein R"* represents -^=S)-NH-R1""" wherein R1""" is as defined above, may be prepared from compound of formula I, where where R1 represents NHR1", wherein R"* represents hydrogen atom by using inzoylisothiocyanate. The solvent used in the reaction may be selected from acetone, lianol, methanol, isopropanol, THF, diethylether, methylcyanide and the like. The uperature of the reaction may be maintained in the range of 0 to 80 "C, preferably in the

range of room temperature to 60 "C. The duration of the reaction may be in the range of 1 to 20 h, preferably in the range of 1 to 10 h.
Yet another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents NHR^ wherein R** represents -{C=0)-heteroaryl, from a compound of formula (I), where R1 represents NHR1*, wherein R"* represents hydrogen atom,

where all other symbols are as defined earlier.
The compound of fomula (I), where R1 represents NHR", wherein R"* represents -(C=0)-heteroaryl, may be prepared from compound of formula (I), where R1 represents NHR1*, wherein R"* represents hydrogen atom by treating with corresponding heteroaryl acid chloride and base such such as pyridine, triethylamine or diisopropylamine. The reaction may also be carried out by using corresponding heteroaryl acid and DCC in the presence of dimethylaminopyridine (DMAP). The solvent used in the reaction may be selected from acetonitrile, THF, methylcyanide, Et20 and the like. The temperature of the reaction may be maintained in the range of-5 to 100 "C, preferably in the range of 0 to 80 °C. The duration ofthe reaction may be in the range of 1 to 15 h, preferably in the range of 2 to 12 h.
Another embodiment ofthe present invention provides a process for the preparation of compound of formula (I), where R1 represents OR"*, wherein R1" represents heteroaryl (or) R1 represents NCR"*):, wherein two R^s together represent six membered heterocycle optionally having one or two hetero atoms, from compound of formula (I), where R1 represents OR"*, wherein R"* represents S(0)2(C|-C6)alkyI or S(0)2aryl group,

where all other symbols are as defined earlier.

The compound of fomula (I), where R1 represents OR1", wherein R"^ represents heteroaryl (or) R1 represents N(R%, wherein two R1"s together represent six membered heterocycle optionally having one or two hetero atoms, may be prepared from compound of formula (I), where R1 represents represents OR1", wherein R1^ represents S(0)2(C1-C6)alkyl or S(0)2aryi group, by using 2-pyridinol. The solvent used in the reaction may be selected from DMF, THF, diethylether, methyl cyanide and the like. The base used in the reaction may be selected from NaH, K2CO3, t-BuOK and the like. The temperature of the reaction may be in the range of 0 to 150 °C, preferably in the range of room temperature to 90 "C. The duration of the reaction may be in the range of 0.5 to 10 h, preferably in the range of 1 to 6 h.
Still another embodiment of the present invention provides a process for the preparation of compound of formula (I), where R1 represents NHR1* where R"* represents -(C=0)-R1" wherein R""" represents (C,-C6)alkyl, (C1-C6)a!koxy, {C2-C6)alkenyl, haIo(Cr C6)alkyl, aryloxy, (C2-C6)aIkenyloxy, (C1-C6)alkylcarbonyl, atylcarbonyl, aryloxycarbonyl or (C|-C6)alkoxycarbonyl; from a compound of formula (I), where R1 represents NHR**, wherein R"" represents hydrogen atom,

where all other symbols are as defined earlier.
The compound of formula (I), where R1 represents NHR"*, wherein R1" represents -C(=0)-R1"*, wherein R"*^ is as defined above, may be prepared from compound of formula (I), where R1 represents NHR1", wherein R* represents hydrogen atom, by treating with appropriate acid halide such as acetyl chloride, propionyl chloride and the like; alkylchloroformate like methylchlcroformate, ethylchloroformate and the like; aralkylchloroformate like benzylchloroformate and the like; or anhydride of the corresponding acid such as acetic anhydride. The reaction may be carried out in the presence of a solvent such as CHzCb, CHCI3, toluene, THF and the like or mixtures thereof The reaction may also be carried out in the presence of a base like EtsN, diisopropyl ethylamine, pyridine, K2CO3, NaH, t-BuOK and the like. The temperature of the reaction may be

.maintained in the range of-20 to 60 "C, preferably in the range of 0 to room temperature. The duration of the reaction may be in the range of 1 to 12 h, preferably from I to 4 h.
Another embodiment of the present invention provides -a process for the preparation of compound of formula (I), where R1 represents OR*, wherein R" represents -C(=S)-SR■*^ wherein R**^ represents (CrC6)alkyl gorup, from a compound of formula (I), where R1 represents OR1", wherein R"* represents hydrogen atom,

where all other symbols are as defined earlier.
The compound of formula (I), where R1 represents OR"*, wherein R"* represents -C(=S)- SR1""^, wherein R1""^ is as defined above, may be prepared from compound of formula (I), where R1 represents OR*, wherein R* represents hydrogen -atom by treating with a base such as pyridine, EtsN, K2CO3, NaOMe, t-BuOK, NaH and the like. The solvent used in the reaction may be selected from THF, methylcyanide, DMF and the like. The reaction may be carried out in the presence of reagents CS2 and alkyl halide. The temperature of the reaction may be maintained in the range of -20 to 80 "C, preferably in the range of 0 to room temperature. The duration of the reaction may be in the range of 0.5 to 10 h, preferably in the range of 1 to 5 h.
Yet another embodiment of the present invention provides a process for the preparation of compound of formula (I) where R1 represents NHR* where R* represents -(C=NH)-NH2, by reacting a compoimd of formula (I), where R1 represents NHR* wherein R* represents hydrogen atom, with di-teii-hutoxy carbonyl thiourea,

where all other symbols are as defined earlier.

The compound of formula (I) where R1 represents NHR" where R" represents -(C=NH)-NH2, may be prepared by reacting the compound of formula (I), where R1 represents NHR1" where R1* represents hydrogen atom, with di-/ert-butoxy carbonyl thiourea in two steps. In the first step, the reaction may be carried out in the presence of solvents such as DMF, acetone, THF, dichloromethane and the like. The base used in the reaction may be selected from triethylamine, diisopropylethylamine, pyridine and the like. The temperature of the reaction may be in the range of 0 to 120 °C, preferably in the range of 0 to 90 °C. The duration of the reaction may be in the range of 0.2 to 15 h, preferably in the range of 0.5 to 10 h. In the second step, the compound obtained in the first step may be reacted with trifluoroacetic acid in the presence of a solvent such as dichloromethane, chloroform, THF and the like. The temperature of the reaction may be in the range of 0 to 110 "C, preferably in the range of 0 to 90 °C. The duration of the reaction may be in the range of 0.5 to 60 h, preferably in the range of 0.5 to 54 h.
Another embodiment of the present invention provides an alternate process for the preparation of compound of formula (I) where R1 represents NHR"* where R1* represents -{C=NH)-NH2, by reacting a compoimd of formula (I), where R1 represents NHR"* wherein R"*represents S{0)2(C1-C5)aIkyl or S(0)2aryl group, with guanidine hydrochloride,

where all other symbols are as defined earlier.
The compound of formula (I) where R1 represents NHR where R represents -(C=NH)-NH2, may be prepared by reacting the compound of formula (I), where R1 represents NHR"* wherein R"* represents S(0)2(C1-C6)alkyr or S(0)2aryl group, with guanidine hydrochloride. The solvent used in the reaction may be seleceted form t-butyl alcohol. The base used in the reaction may be selected from NaH, KH, sodium hexamethyldisilazide (Na-HMDS) and the like. The temperature of the reaction may be in the range of 0 "C to boiling temperature of the solvent used. The duration of the reaction may be in the range of 1 to 30 h, preferably in the range of 1 to 24 h.

Still another embodiment of the present invention proviaes a process tor the preparation of compound of formula (I) where R1 represents NHR" where R1* represents -(C=NH)-(C1-C6)alkyl or -{C=NH)-aryl, which comprises: (i) reacting the compound of formula (li)

v/here all symbols are as defined earlier, with di /ert-butoxy carbonyi ether [(B0C)20], to produce a compound of formula (Ij)

where all symbols are as defined earlier and
(ii) reacting the compound of formula (Ij), with a compound of formula (Ik)
R-NH2 (Ik)
where R represents (C1-C6)alkyl or aryl group, to produce a compound of formula (I) where R1 represents NHR" where R"^ represents -(C=NH)-(C1-C6)alkyl or -(C=NH)-aryl group and all other symbols are as defined earlier.
The conversion of the compound of formula (Ii) to a compound of formula (Ij) may be carried out by reacting with (B0C)20, in the presence of solvent such as THF, diethylether and the like. The base used in the reaction may be selected fi-om NaH, KH, Na-HMDS and the like. The temperature of the reaction may be in the range of 0 to boiling temperature of the solvent. The duration of the reaction may be in the range of 0.5 to 14 h, preferably in the range of 0.5 to 10 h.
The conversion of the compound of formula (Ij) to a compound of formula (I) may be carried out by reacting with the compound of formula (Be) in two steps. In the first step, the reaction may be carried out in the presence of a solvent such as DMF, THF, chlorofomi, dichloromethane and the like. The base used in the reaction may be selected from

triethylamine, diisopropylethylamine, pyridine and the like. The temperature of the reaction may be in the range of 0 to 120 "C, preferably in the range of 0 to 90 "C. The duration of the reaction may be in the range of 0.5 to 24 h, preferably in the range of 0.5 to 20 h. In the second step, the compound obtained in the first step may be reacted with trifluoroacetic acid in the presence of a solvent such as dichloromethane, chloroform, THF and the like. The temperature of the reaction may be in the range of 0 to 110 "C, preferably in the range of 0 to 90 °C. The duration of the reaction may be in the range of 0.5 to 60 h, preferably in the range of 0.5 to 54 h.
Another embodiment of the present invention provides a process for the preparation of compound of formula (I), Z represents -SOn-, where n represents 1 or 2, which comprises: (i) oxidizing the compound of formula (I),

where Z represents -SOn-, where n represents zero, to obtain, a compound of formula (I) where Z represents -SOn-, where n represents 1 or 2; and Y", Y^, Y\ R1, R^ and R"" are as defined earlier.
The conversion of compoimd of formula (I) where 2 represents -SOn-, where n represents zero, to a compound of formula (I) where Z represents -SOn- where n represents 1 or 2, by using m-chloroperoxybenzoic acid (m-CPBA), hydrogen peroxide and the like. The solvent used in the reaction may be selected fi-om CHjCh, CHCI3, THF and the like. The temperature of the reaction may be maintained in the range of-5 to 60 "C, preferably in the range of 0 °C to room temperature. The duration of the reaction may be in the range of 0.2 to 8 h, preferably in the range of 0.5 to 5 h.
Yet another embodiment of the present invention provides a process for the preparation of a compound of formula (I) where R1 represents halogen, fi-om compound of formula (I) where R1 represents hydroxy group.


where all other symbols are as defined above.
The compound of formula (I) where R1 represents halogen is prepared from compound of formula (I) where R1 represents hydroxy group may be carried out by treating with SOCI2, PCI5, PBr3, tetrahalomethane group such as CBr4, CCI4 and the like, in the presence of PPhs, P(alkyi)3 and the like. The reaction may be carried out in the presence of a solvent such as dry dichloromethane, chloroform, tetrachloromethane, benzene, DMF, DMSO, THF and the like. The temperature of the reaction may be maintained in the range of 0 to 60 "C, preferably at room temperature. The duration of the reaction may be in the range of 0.5 to 24 h, preferably I to 13h.
Still another embodiment of the present invention provides a process for the preparation of a compound of formula (I) where R1 represents *SH",

where all other symbols are as defined above, which comprises:
(i) reacting the compound of formula (I) where R1 represents halogen atom, to produce
a compound of formula (Ih),

where all other symbols are as defined earlier, with a base and thioacetic acid,
(ii) reacting the compound of formula (Hi), to produce a compoimd of formula (1) where
R1 represents "SH" group and all other symbols are as defined earlier, with base.
The compound of formula (Ih) is prepared fi^m compound of formula (I) where R1 represents hydroxy group may be prepared by using thioacetic acid in the presence of a base such as triethylamine, di-isopropylamine, di-isopropylethylamine, pyridine, piperidine,

DMAP, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), lithium diisopropylamide (LDA), potassium bis-(trimethyl silyl)amide, BuLi, Na2C03, K2CO3, NaOH, KOH, NaOMe, NaOEt, NaOiPr, t-BuOK, NaH, KH and the like. The solvent used in the reaction may be seleceted from THF, benzene, dioxane and the like. The temperature of the reaction may be maintained in the range of room temperature to reflux temperature, preferably at reflux temperature. Thedm^tionof the reaction may be in the range of 2 to 24 h, preferably 6 h.
The compound of formula (I), where R represents " SH*. group may be prepared from a compound of formula (Ih) by reacting with a base such as K2CO3, NaOH, KOH, BuLi and the like. The reaction may be carried out at a temperature in the range of room temperature to reflux tempratuie. The duration of the reaction may be in the range of 1 to 24 h.



where Z, Y", Y^ Y\ R^ and R^ are as defined earlier, to a compound of formula (le)
The compound of formula (Ic) may be prepared by reacting a compound of formula (la) with a compound of formula (lb) by using a base such as KOH, NaOH, K2CO3, Na2C03, NaH, KH, triethylamine, diisopropylethyl amine and the like. The reaction may be carried out using a solvent such as DMSO, DMF, THF, acetonitrile, chlorofomi, nitrobenzene and the like or mixtures thereof The reaction may be carried out in inert atmosphere, which may be maintained using inert gases such as N2 or Ar. The reaction may be carried out at a temperature in the range of 20 to 100 °C, preferably at a temperature in the range of ambient-80 "C. The reaction time may range from 1 to 15 h, preferably from 6 to 12 h.
The reduction of a compound of formula (Ic) to produce a compound of formula (Id) may be carried out in the presence of reducing agents such as NiCb/NaBJl], lithium aluminium hydride (LAH), gaseous hydrogen and a catalyst such as Ru, Pd, Rh, Pt, Ni on solid beads such as charcoal, alumina, asbestos and the like. The reduction may be carried out in the presence of a solvent such as dioxane, acetic acid, ethyl acetate, THF, alcohol such as methanol, ethanol and the like or mixtures thereof A pressure between atmospheric

pressure to 60 psi may be used. The reaction may be carried out at a temperature from 0 to 60 "C, preferably at 0 to room temperature. The reaction time ranges from 0.5 to 48 h, preferably in the range of 0.5 to 5 h. The reduction may also be carried out by employing metal in mineral acids such Sn/HCl, Fe/HCl, Zn/HCl, Zn/CHiCOjH and the like.
The compound of formula (Id) may be converted to a compound of formula (le) by using NaNOz in the presence of HCl or CH3COOH followed by NaNs- The solvent used in the reaction may be selected from methanol, ethanol, ethylacetate, THF, ether, dioxan and the like. The temperature of the reaction may be maintained in the range of-40 "C to boiling temperature, preferably in the range of 0 °C to room temperature. The duration of the reaction may be in the range of 0.5 to 15 h, preferably in the range of 0.5 to 5 h.



where R*^ represents (C]-C6)alkyl group such as methyl, ethyl, n-propyl, iso-propyl and the like; Z, Y", Y^, Y"*, R^ and R^ are as defined earHer, to a compound of formula (If)-
The compound of formula (Ic) may be prepared by reacting a compound of formula (la) with a compound of formula (lb) by using a base such as KOH, NaOH, K2CO3, NazCOs, NaH, KH, triethylamine, diisopropylethyl amine and the like. The reaction may be carried out using a solvent such as DMSO, DMF, THF, acetonitrile, chloroform, nitrobenzene and the like or mixtures thereof The reaction may be carried out in inert atmosphere, which may be maintained using inert gases such as N2 or Ar. The reaction may be carried out at a temperahire in the range of 20 to 100 "C, preferably at a temperature in

me range or amment-su "C me reaction time may range trom I to 15 h, preferably from 6 tol2h.
The reduction of a compound of formula (Ic) to produce a compound of formula (Id) may be carried out in the presence of reducing agents such as NiCh/NaBHi, lithium aluminium hydride (LAH), gaseous hydrogen and a catalyst such as Ru, Pd, Rh, Pt, Ni on solid beads such as charcoal, alumina, asbestos and the like. The reduction may be carried out in the presence of a solvent such as dioxane, acetic acid, ethyl acetate, THF, alcohol such as methanol, ethanol and the like or mixtures thereof A pressure between atmospheric pressure to 60 psi may be used. The reaction may be carried out at a temperature from 0 to 60 "C, preferably at 0 to room temperature."The reaction tirpe ranges from 0.5 to 48 h, preferably in the range of 0.5 to 5 h. The reduction may also be carried out by employing metal in mineral acids such Sn/HCl, Fe/HCl, Zn/HCl, Zn/CHjC02H and the like.
The compound of formula (Id) may be converted to a compound of formula (le) by using NaN02 in the presence of HCl or CH3COOH followed by NaNs. The solvent used in the reaction may be selected from methanol, ethanol, ethylacetate, THF, ether, dioxan and the like. The temperature of the reaction may be maintained in the range of—40 °C to boiling temperature, preferably in the range of 0 "C to room temperature. The duration of the reaction may be in the range of 0.5 to 15 h, preferably in the range of 0.5 to 5 h.
The compound of formula (If) may be prepared by heating a compound of fonnula (le) with esters ((Cj-C6)alkyl or aryl). The solvent used in the reaction may be selected from benzene, toluene, xylene, methylcyanide, THF and the like. The temperature of the reaction may be maintained in the range of 0 to 200 "C, preferably in the range of room temperature to boiling temperature of the solvent. The duration of the reaction may be in the range of 2 to 25 h, preferably 3 to 15 h.
Another embodiment of the present invention provides a novel intermediate of the formula (Ig),
where all symbols are as defmed earlier.

Yet another embodiment of the present invention provides a process for the preparation of novel intermediate of formula (Ig), which comprises:
(i) converting a compound of formula (If)

where R1 represents (CrC6)alkyl group such as methyl, ethyl, propyl and the like; and all other symbols are as defined earlier, to produce a compound of formula (Ig) and

where all symbols are as defined earlier.
The conversion of compound of formula (If) to a compound of formula (Ig) may be carried out in the presence of ammonia solution in water or alcohol. The temperature of the reaction may be in the range of -40 to 50 "C, preferably of 0 "C to room temperature. The duration of the reaction may be in the range of 0.5 to 12 h, preferably 0.5 to 4 h.
It is appreciated that in any of the above-mentioned reactions, any reactive group in the substrate molecule may be protected according to conventional chemical practice. Suitable protecting groups in any of the above mentioned reactions are tertiarybutyldimethylsilyl, methoxymethyl, triphenyl methyl, benzyloxycarbonyl, tetrahydropyran(THP) etc, to protect hydroxyl or phenolic hydroxy group; N-tert-butoxycarbonyl (N-Boc), N-benzyloxycarbonyl (N-Cbz), N-9-fluorenyl methoxy carbonyl (-N-FMOC), benzophenoneimine, propargyloxy carbonyl (POC) etc, for protection of amino or anilino group, acetal protection for aldehyde, ketal protection for ketone and the like. The methods of formation and removal of such protecting groups are those conventional methods appropriate to the molecule being protected.
The enantiomers may be prepared by using reactants in their single enantiomeric form in the process wherever applicable or by conducting the reaction in the presence of reagents or catalysts m their single enantiomeric form. The single enantiomers may also be

prepared by resolving the racemic mixture by conventional methods. The stereoisomers of the compounds forming part of this invention may be prepared by using reactants in their single enantiomeric form in the process wherever possible or by conducting the reaction in the presence of reagents or catalysts in their single enantiomer form or by resolving the mixture of stereoisomers by conventional methods. Some of the preferred methods include use of microbial resolution, resolving the diastereomeric salts formed with chiral acids such as mandelic acid, camphorsulfonic acid, tartaric acid, lactic acid, and the like wherever applicable or chiral bases such as brucine, cinchona alkaloids and their derivatives and the like, Commonly used methods are compiled by Jaques et al in "Enantiomers, Racemates and Resolution" (Wiley Interscience, 1981). Where appropriate the compounds of formula (I) may be resolved by treating with chiral amines, aminoacids, aminoalcohols derived from aminoacids; conventional reaction conditions may be employed to convert acid into an amide; the diastereomers may be separated either by fractional crystallization or chromatography and the stereoisomers of compound of formula (I) may be prepared by hydrolyzing the pure diastereomeric amide.
The pharmaceutically acceptable salts are prepared by reacting the compounds of formula (I) wherever applicable with 1 to 4 equivalents of a base such as sodium hydroxide, sodium methoxide, sodium hydride, potassium t-butoxide, calcium hydroxide, magnesium hydroxide and the like, in the presence of a solvent like ether, THF, methanol, t-bulanol, dioxane, isopropanol, ethanol etc. Mixture of solvents may be used. Organic bases like lysine, arginine, diethanolamine, choline, tromethamine, guanidine and their derivatives etc. may also be used. Alternatively, acid addition salts wherever applicable are prepared by treatment with acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, p-toluenesulphonic acid, methanesulfonic acid, acetic acid, citric acid, maleic acid salicylic acid, hydroxynaphthoic acid, ascorbic acid, palmitic acid, succinic acid, benzoic acid, benzenesulfonic acid, tartaric acid and the like in the presence of a solvent like ethyl acetate, ether, alcohols, acetone, THF, dioxane etc. Mixture of solvent may also be used. The salts of amino acid groups and other groups may be prepared by reacting the compounds of formula (I) with the respective groups in the presence of a solvent like alcohols, ketones, ether etc. Mixture of solvents may be used.

Various polymorphs of a compound of general foraiula (I) forming part of this invention may be prepared by crystallization of compound of formula (I) under different conditions. For example, using different solvents commonly used or their mixtures for recrystallization; crystallizations at different temperatures; various modes of cooling, ranging from very fast to very slow cooling during crystallizations. Heating or melting the compound followed by gradual or fast cooling may also obtain polymorphs. The presence of polymorphs may be determined by solid probe nmr spectroscopy, IR spectroscopy, differential scanning calorimetry, powder X-ray diffraction or such other techniques.
The present invention also provides ph^maceutical compositions, containing compounds of the general formula (I), as defined above, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts or their pharmaceutically acceptable solvates in combination with the usual pharmaceutically employed carriers, diluents and the like. The pharmaceutical compositions according to this invention can be used for the treatment of bacterial infections. They can also be used for the treatment of bacterial infections associated with multidrug resistance,
Pharmaceutically acceptable solvates of compound of formula (I) forming part of this invention may be prepared by conventional methods such as dissolving the compounds of formula (I) in the presence of a solvent such as water, methanol, ethanol etc., preferably water and recrystallizing by using different crystallization techniques.
The regioisomers of compound of formula (I) may be prepared by modifying the reaction conditions, use of reagents like acid to base or base to acid or by reaction with free base hydrazine instead of its salt with diketone. The molar proportion also can change the regioisomer foimation.
The pharmaceutical compositions may be in the forms normally employed, such as tablets, capsules, powders, syrups, solutions, suspensions and the like, may contain flavorants, sweeteners etc. in suitable solid or liquid carriers or diluents, or in suitable sterile media to form injectable solutions or suspensions. Such compositions typically contam from 1 to 20 %, preferably 1 to 10 % by weight of active compound, the remainder of the composition bemg pharmaceutically acceptable carriers, diluents or solvents.
Suitable pharmaceutically acceptable carriers include solid fillers or diluents and sterile aqueous or organic solutions. The active compounds will be present in such

pharmaceutical compositions in the amounts sufficient to provide the desired dosage in the range as described above. Thus, for oral administration, the compounds can be combined with a suitable solid, liquid earner or diluent to form capsules, tablets, powders, syrups, solutions, suspensions and the like. The pharmaceutical compositions, may, if desired, contain additional components such as flavorants, sweeteners, excipients and the like. For parenteral administration, the compounds can be combined with sterile aqueous or organic media to form injectable solutions or suspensions. For example, solutions in sesame or peanut oil, aqueous propylene glycol and the like can be used, as well as aqueous solutions of water-soluble pharmaceutical!y-acceptable acid addition salts or salts with base of the compounds. The injectable solutions prepared in this manner can then be administered intravenously, intraperitoneally, subcutaneously, or intramuscularly, with intramuscular administration being preferred in humans.
In addition to the compounds of formula (I) the pharmaceutical compositions of the present invention may also contain or be co-administered with one or more known drugs selected from other clinically useful antibacterial agents such as p-lactams or aminoglycosides. These may include penicillins such as oxacillin or flucloxacillin and carbapenems such as meropenem or imiphenem to broaden the therapeutic effectiveness against, for example, methicillin-resistant staphylococci, Compounds of the formula (I) of the present invention may also contain or be co-admistered with bactericidal/permeability-increasing protein product (BPI) or efflux pump inhibitors to improve activity against gram negative bacteria and bacteria resistant to antimicrobial agents.
The compounds of the formula (I) as defined above are clinically administered to mammals, including human beings, via either oral or parenteral routes. Administration by the oral route is preferred, bemg more convenient and avoiding the possible pain and irritation of injection. However, in circumstances where the patient cannot swallow the medication, or absorption following oral administration is impaired, as by disease or other abnormality, it is essential that the drug be administered parenterally. By either route, the dosage is in the range of about 5 mg/kg to about 20 mg / kg body weight of the subject per day administered singly or as a divided dose. However, the optimum dosage for the individual subject being treated will be determined by the person responsible for treatment.

generally smaller doses being administered initially and thereafter increments made to determine the most suitable dosage.
The invention is explained in detail in the examples given below which are provided by way of illustration only and therefore should not be construed to limit the scope of the invention.
Preparation 1 4-(2,6-difluoro-4-nitropheQyl)morpholine

Morpholine (1.2 g, 14.12 mmol) was added to a stirring solution of 3,4,5-trifluoronitro benzene (1 g, 5.65 mmol) in acetonitrile (15 mL) and the reaction mixture was refluxed for 5 h. Yellow solid of the product separated out upon concentration followed by the addition of crushed ice into it. The solid was filtered off and dried under reduced pressure to yield the title compound (1.2 g, 88%).
"H NMR (CDCI3): 8 7.90-7.70 (m, 2H), 3.90-3.70 (m, 4H), 3.50-3.30 (m, 4H) MS (m/e): 245 (M*+l), 230,215. Preparation 2 4-(2-Fluoro-4-nitropheDyl)morpholine

The title compound (1.2 g, 84%) was prepared from 3,4-difiuoro nitrobenzene (1.0 g, 6.29 mmol) and morpholine (1.0 g, 12.5 mmol) by a procedure similar to that described in preparation 1.
"HNMR (CDCI3): 5 8.05-7.80 (m, 2H), 6.90 (t, /= 8.8 Hz, IH), 3.95-3.80 (m, 4H), 3.35-3.20 (m, 4H). MS (m/e): 226 (M^, 168,138.

Preparation 3 4-(2,6-Difluoro-4-iiitrophenyl)thiomorpholine

Thiomorpholine (728 mg, 7.06 mmol) was added to a stirring solution of 3,4,5-trifluoronitro benzene (500 mg, 2.82 mmol) in acetonitrile (15 mL) and the reaction mixture was refluxed for 5 h. Evaporation of the solvent in a rotavapor under reduced pressure left a pasty mass which was dissolved in ethylacetate (50 mL). The ethylacetate portion was washed with water (30 mL x 2) followed by brine (30 mL) and dried over sodium sulfate. Removal of the volatiles yielded the title compound as yellow solid (650 mg, 85%), "H NMR (CDCI3): 5 7.90-7.70 (m, 2H), 3.60-3.40 (m, 4H), 2.80-2.60 (m, 4H). MS(m/e):261 (MVI), 186. Preparation 4 4-(2-Fluoro-4-nitrophenyl)thiomorphoiin e

The title compound (650 g, 86%) was prepared from thiomorpholine (810 g, 7.86 nmol) and 3,4-difluoronitrobenzene (500 mg, 3.4 mmol) by a procedure similar to that lescribed in preparation 3.
H NMR (CDCI3): 6 8.05-7.80 (m, 2H), 6.90 (t, J =8.79 Hz, IH), 3.70-3.50 (m, 4H), 2.90-1.70 (m, 4H).
s/lS (m/e): 243 (M^+1), 168. "reparation 5 t,5-Difluoro-4-morpholinoaniline

NiClz (2.32 g, 9.83 mmol) was added to a solution of 4-(2,6-difluoro-4-litrophenyOmorpholine (1.2 g, 4.92 mmol), obtained in preparation 1, dissolved in methanol 50 mL). NaBH4 (749 mg, 19.6 mmol) was added to the reaction mixture in portion and the

reaction mixture was allowed to stir at room temperature for 0.5 h. It was diluted with
ethylacetate (100 mL) and the ethylacetate portion was washed with water (60 mLx2)
followed by brine (50 mL) and dried over sodium sulfate. Evaporation of the volatiles
produced a solid (0.95 g, 90%).
"HNMR (CDCI3): 5 6.30-6.10 (m, 2H), 3.90-3.70 (m, 4H), 3.1Q-2.90 (m, 4H).
MS(m/e):215(Nr+l),
Preparation 6
3-Fluoro-4-morpholinoanilme

The title compound (0.96 g, 96%) was prepared from 4-(2-fluoro-4-nitrophenyl)morphoiine (1.2 g, 5.30 mmol), obtained in prepartion 2, by a procedure similar to that described in preparation 5.
"H NMR (CDCI3): 8 7.0-6.80 (m, IH), 6.50-6.30 (m, 2H), 3.90-3.70 (br.s, 4H), 3.10-2.90 (br.s, 4H).
Preparation 7 3,5-Difluoro-4-thiomorpholinoanilme

NaBIii (285 mg, 7.5 mmol) was added to a stirring solution of NiCU (1.16 g, 5.0 mmol) and 4-(2,6-difluoro-4-mtrophenyI)thiomorpholine in methanol (30 mL). The reaction mixture was diluted with ethylacetate (50 mL) after 0.5 h and the organic portion was washed with water {30 mLx2) followed by brine (30 mL) and dried over sodium sulfate. Evaporation of the volatiles yielded a solid (400 mg, 70%). "H NMR (CDCI3): 6 6.30-6.10 (m, 2H), 3.40-3.20 (m, 4H), 2.80-2.60 (m, 4H). MS{m/e):231(M^+l), 156.

Preparation 8 3-FIuoro-4-(4-thiomorpholmyl)aniline

The title compound (0.41 g, 71%) was prepared from 4-{2-fluoro-4-nitrophenyl)thiomorpholine (0.5 g, 2.06 mmol), obtained in prepartion 4, by a similar procedure to that described in preparation 7.
"H NMR (CDCI3): 6 6.80 (t. 7= 9.04 Hz, IH), 6.50-6.30 (ra, 2H), 3.30-3.10 (m, 4H), 2.S0-2.70 (m, 4H).
MS (m/e); 213 (M^+1), 212, 138. Preparation 9 4-(4-Azido-2,6-dif1uorophenyl)niorpholine

Sodium nitrite (0.91 g, 13.3 mmol) was added to an ice-cooled solution of 3,5-difluoro-4-morpholinoaniline (0.95 g, 4.4 mmol), obtained in preparation 5, in 6 N HCl (30 mL) and the resulting yellow solution was stirred at 0 "C for 2 h. The reaction mixture was quenched with an aqueous solution of sodium azide (0.575 g, 8.86 mmol) and sodium acetate (57.5 g, 88.6 mmol). The reaction mixture was then extracted with ethylacetate (50mLx2) and the combined extracts were washed with 5% sodium bicarbonate solution followed by brine and dried over sodium sulfate. Removal of solvent gave a brown solid (1 g, 96 %).
"HNMR (CDCI3): 5 6.70-6.50 (m, 2H), 3.90-3.70 (m, 4H), 3.20-3.0 (4H). MS (m/e): 241 (M^+1), 212 (-N2X 154, 91. Preparation 10 4-(4-Azido-2-fluorophenyl)morpholine


The title compound (1.03 g, 91%) was prepared from 3-fluoro-4-morpholmoanilme (1 g, 5.10 mmol), obtained in preparation 6, by a procedure similar to that described in preparation 9.
"HNMR (CDCI3): 6 6.98 (t, /= 8.7 Hz, IH), 6.80-6.70 (m, 2H), 4.0-3.80 (m, 4H). 3.20-3.0 (m, 4H).
MS(nVe):223(M*+l), 195. Preparation 11 4-(4-Azido-2,6-difluoropheQyl)thiomorpboline

Sodium nitrite (1.19 g, 17.2 mmol) was added to a cooled solution (0 "C) of 3,5-difluoro-4-thiomorpholinoamline (2 g, 8.69 mmol), obtained in preparation 7, in 6 N HCl (20 mL) and allowed to stir at the same temperature for 1 h. An aqueous solution of sodium azide (1.13 g, 17.2 mmol) and sodium acetate (15.6 g, 188 mmol) was added to the above reaction mixture dropwise and stirred for a while. The reaction mixture was extracted with ethylacetate (50 mLx2) and the combined ethylacetate portion was washed with brine and dried over sodium sulfate. Evaporation of the volatiles in a rotavapor under reduced pressure yielded the title compound as yellow solid (2.0 g, 90%). "H NMR (CDCI3): 5 6.60-6.40 (m, 2H), 3.40-3.20 (m, 4H), 2.80-2.60 (m, 4H). MS (m/e): 257 (MVI), 228 (-Nz), 154. PrepartioD 12 4-(4-Azido-2-fluorophenyl)thiomorpholine

The title compound (2.1 g, 93%) was prepared from 3,5-difluoro-4-(4-thiomorpholinyl)aniline (2 g, 9.4 mmol), obtained in preparation 8, by a procedure similar to that described in preparation 11.
"H NMR (CDCI3): 5 7.00-6.90 (t, 7= 8.92 Hz, IH), 6.90-6.80 (m, 2H), 3.40-3.20 (m, 4H), 2.90-2.70 (m. 4H). MS (m/e): 239 (M^+1), 210 (-N2).

Prep ration 13 Ethyl-l-(3,5-difluoro-4-morpholinophenyl)-l/M,2,3-triazol-4-carboxylate

A solution of 4-(4-azido-2,6-difluorophenyl)morphoIine (1 g, 4.16 mmol), obtained in preparation 9, and ethyl propiolate (1.2 g, 12.5 mmol) in benzene (50 mL) was refluxed for 16 h.The precipitate of the required isomer was collected after the reaction mixture was cooled down to room temperature to yield 0.8 g (60%) of the title compound. "HNMR (CDCI3): 5 8.42 (s. IH), 7.40-7.30 (m, 2H), 4.60-4.40 (q, J= 7.33 Hz, 2H), 3.90-3.70 (m, 4H), 3.40-3.20 (br.s, 4H), 1.44 (t, J= 7.33 Hz, 3H). MS(m/e):339(MVl). Preparation 14 Ethyl-l-(3-nuoro-4-morpholinophenyl)-lH-l,23-triazole-4-c^boxylate

The title compound (0.9 g, 60%) was prepared from 4-(4-azido-2-fluorophenyl)morpholine (1.03 g, 4.63 mmol), obtained in preparation 10, by a procedure similar to that described in preparation 13.
"H NMR (CDCI3): 6 8.44 (s, IH), 7.60-7.40 (m, 2H), 7.06 (t, J = 8.7 Hz, IH), 4.50 (q, J = 7.33 Hz, 2H), 4.0-3.80 (m, 4H), 3.30-3.10 (m, 4H), 1.44 (t, J= 7.33 Hz, 3H). MS (m/e): 321 (M*+l), 234,162.
Example 1 l-(3,5-Difluoro-4-morphoiinophenyi)-lff-l,2,3-triazoI-4-ylmethanoI

A solution of ethyI-l-(3,5-difluoro-4-morphoUnophenyl)-lH-l,2,3-triazo!e-4-carboxylate (0.8 g, 2.3 mmol), obtained in preparation 13, in anhydrous THF (30 mL) was

treated with lithium borohydride (0.1 g, 4.73 mmol) and the reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture was then extracted with ethylacetate (70 mLx2) after the addition of saturated ammonium chloride solution (1.0 mL). Combined ethylacetate portion was washed with brine and dried over sodium sulfate. Evaporation of soJvent afforded an oil which was purified by column chromatography (silica gei, 80 g;






A stirring solution of l-(3,5-difluoro-4-morpholinophenyl)-l/f-l,2,3-triazol-4-ylmethyl methanesuifonate (0.7 g, 1.87 mmol), obtained in example 5, and sodium azide (0.3 g, 5.61 mmol) in dimethylformamide (30 mL) was wanned to 60 "C for 3 h. DMF was removed under reduced pressure. The residue was dissolved in ethylacetate and the resulting solution was washed with water followed by brine and dried over sodium sulfate.


(100 mL X 2) followed by brine (50 mL) and dried over sodium sulfate. Removal of solvent and purification of the residual material through a silica gel column (60-120, 1:9-3:7 ethylacetate/hexane) yielded compounds l-[3,5-dJfluoro-4-(4-thiomorpholinyI)phenyI]-li¥-l,2,3-triazol-4-ylmethyl azide (llA) (800 mg, 45%) and l-[3,5-difluoro-4-(4-


Example 13 l-(3,5-Difluoro-4-morpholinophenyl)-l/f-l,2,3-triazol-4-ylmethanainine

A mixture of l-(3,5-difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl azide (0.5 g, 1.55 mmol), obtained in example 9, and triphenylphosphine (0.45 g, 1.71 mmol) in THF (25 mL) was stirred at room temperature for 4 h. It was then warmed to 40 "C after the addition of 2 mL of water and allowed to stir at the same temperature for 16 h. The reaction mixture was diluted with water and extracted with ethylacetate (30 mLx2). The combined ethylacetate extract was washed with water followed by brine and dried over sodium sulfate. Evaporation of volatiles and purification of the resulting residue by column chromatography (CHCb/MeOH, 9:1) yielded the title compound as pale yellow crystals (0.3 g, 66Vo). "HNMR (CDCI3): 5 7.94 (s, IH), 7,40-7.20 (m, 2H), 4.77 (s, 2H), 3.90-3.70 (m, 4H), 3.30-3.10 (m,4H).
MS (m/e): 296 (M^l), 251, 238. Example 14 l-(3-FIuoro-4-morpholinopbenyl)-lff-l,2,3-triazol-4-ylmethanamine

The title compound (0.36 g, 80%) was prepared from l-(3-fluoro-4-morphoiinophenyl)-lH-l,2,3 triazol-4-ylmethyl azide (0.5 g, 1.65 mmol), obtained in example 10, by a procedure similar to that described in Example 13.
"HNMR (CDCI3): 5 7.82 (s, IH), 7.60-7.40 (m, 2H), 7.10-6.95 (t, 7= 8.74 Hz, IH), 4.07 (s, 2H), 4.0-3.80 (m, 4H), 3.30-3.10 (m, 4H). MS (m/e): 278 (M^+1).

Example 15 l-[3,5-Dmuoro-4-(4-thiomorphoUDyl)phenyl]-lH-l,2,3-triazol-4-ylmethanaiiiine

A mixture of l-[3,5-difluoro-4-(4-thiomorpholinyI)phenyi]-lH-l,2,3-triazol-4-yimethyi azide (0.53 g, 1.55 mmol), obtained in example 11, and triphenylphosphine (0.45 g, 1.71 mmol) in THF (25 mL) was stirred at room temperature for 4 h. It was then wanned to 40 "C after the addition of 2 mL of water and allowed to stir at the same temperature for 16 h. The reaction mixture was diluted with water and extracted with ethylacetate (30 mLx2). The combined ethylacetate extract was washed with water followed by brine and dried over sodium sulfate. Evaporation of volatiles and purification of the resulting residue by column chromatography (CHCb/MeOH, 9:1) yielded the title compound as pale yellow crystals (0.33 g, 70%).
"HNMR (CDCb): 5 7.95 (s, IH), 7.40-7.20 (m, 2H), 4.80 (s, 2H), 3.55-3.35 (m, 4H), 2.90-2.70 (m, 4H).
MS (m/e); 312 (M^"+l), 267, 254. Example 16

thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-yImethyl azide (0.8 g, 2.5 mmol), obtained in
example 12, by a procedure similar to that described in Example 15.
"H NMR (CDCI3): 5 7.83 (s, IH), 7.55-7.35 (m, 2H). 7.10-6.95 (t, 7 = 8.75 Hz, IH), 4.08 (s,
2H), 3.50-3.30 (m, 4H), 2.90-2.70 (m, 4H).
MS (m/e): 294 (M^+1).





A solution of triphenyl phosphine (749 mg, 2.85 mmol) in THF (20 mL) was added dropwise to a solution of l-[3-fluoro-4-(l-oxo-4-thiomorphollnyl)phenyl]-l/:f-l,2,3-triazol-4-ylmethyl azide (800 mg, 2.38 mmol), obtained in example 19, in tetrahydrofuran (5 mL) and the reaction mixture was stirred at room temperature for 4 h. It was then warmed to 40 "C after the addition of 1 mL of water and kept stirring at the same temperature overnight. Evaporation of solvent and purification of the resuUing semisolid through a silica gel (60-120) column (MeOH.-CHCb, 1:4) yielded l-E3-Fluoro-4-(l-oxo-4-thiomorpho]inyJ)-pheny)]-



Thiophosgene (62 [iL 0.74 mmol) was added into a white suspension, obtained by stirring a mixture of satd. NaHCOa solution {10 mL) and l-(3,5-difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylniedianamine (0.2 g,. 0.677 mmol), obtained in

example 13, in chloroform (10 mL). After stirring for 30 min. the reaction mixture was diluted with chloroform (20 mL) and the chloroform portion was washed with water followed by brine. Upon drying over sodium sulfate and concenfration, a light brown compound was obtained (0.2 g, 70%).



stirring a mixture of satd. NaHCOj solution {10 mL) and l-[3,5-difluoro-4-(l-oxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethanamine (500 mg, 1.5 mmol), obtained in example 22, in chloroform {10 mL). After stirring for 5 min. the reaction mixture was diluted with chloroform (20 mL) and the chloroform portion was washed with water followed by brine. Upon drying over sodium sulfate and concentration, a light brown compound 0.485 g, 85%) was obtained.
"H NMR (CDCI3): 5 8.0 (s, IH), 7.40-7.20 (m, 2H), 4.90 (s, 2H), 4.20-4.0 (m, 2H), 3.40-3.20 (m, 2H), 3.10-2.90 (m, 4H). MS Cm/e); 370 (M^+l), 352. 283,193.


0.93 mmol), obtained in example 9, was dissolved in thioaceticacid (3 mL) and allowed to stir at room temperature for 15 h. The reaction mixture was adsorbed on silica gel and purified by column chromatography with ethylacetate as eluent to produce a crystalline white sohd (0.28 g, 80%). Mp. 218 "C.


(0.32 g, 0.93 mmol), obtained in example 11, was dissolved in thioaceticacid (3 mL) and
allowed to stir at room temperature for 15 h. The reaction mixture was adsorbed on silica
gel and purified by column chromatography with ethylacerate as eluent to produce a
crystalline white solid (0.29 g, 80%). Mp. 210 "C.
"HNMR (CDCb): 5 7.94 (s, IH), 7.30-7.20 (m, 2H), 6.90 (br. s, IH), 4.54 (d, /= 5.85 Hz,
2HX 3.50-3.53 (m, 4H), 2.90-2.70 (m, 4H), 2.0 {s, 3H).
MS (m/e): 354 (M^+1), 325, 229.



The title compound (0.163 g, 78%) was prepared from l-[3-fluoro-4-(4-thiomorpholmyl)phenyl]-l/7-l,2,3-triazol-4-ylmethyl azide (0.2 g, 0.626 mmol), obtained in example 12, by a procedure similar to that described in Example 35. Mp. 207 "C.



morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl]acetamide (0.3 g, 0.94 mmol), obtained example in 34, by a procedure similar to that described in Example 41. Mp. 192 "C-"HNMR (CDCI3): 5 10.35 (br. s, IH), 8.45 (s, IH), 7.70-7.50 (m. 2H), 7.10 {l,J= 8.74 Hz, IH), 4.89 (d, J= 4.88 Hz, 2H). 3.90-3.75 (m, 4H). 3.20-3.05 (m, 4H), 2.50 (s, 3H). MS (m/e): 335 (M^, 307, 274.




isothiocyanate, obtained in example 30, was refluxed in methanol for 15 h. Evaporation of the solvent and purification of the resulting material through a silica gel (60-120) column with methanol/chloroform (5/95) yielded a white solid (400 mg, 75%) as rotamers (3:1).











To a mixture of pyrazine 2-carboxy!ic acid (0.09 g, 0".72 mmol) and DCC (0.2 g, 1.08 nunol) in dry acetonitrile (20 mL) catalytic amount of TV^Ttf-dimethylaminopyridine (DMAP) was added and stirred for 15 min. l-(3-fluoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-ylmethanamine (0.2 g, 0.72 mmol), obtained in example 14, in dry acetonitrile (5 mL) was added to the reaction mixture and stirred for 4 h. After removal of acetonitrile in a rotavapor it was poured into crushed ice to obtam white solid. The solid was further purified by column chromatography. Yield-^.15 g, 60%. Mp. 215 °C.



2-Pyridinol (0.11 g, 1.21 mmol) was added to a suspension of sodium hydride (23 mg, 0.97 mmol) in dry DMF (5 mL) and allowed to stir for 10 min. l-(3-fluoro-4-raorpholinophenyl)-li:f-l,2,3 triazol-4y!-methyI methanesulfonate (0.3 g, 0.81 mmol), obtained in example 6, in dry DMF (2 mL) was added to the above suspension and heated to 60""C for 2 h. The reaction mixture was diluted with ethyl acetate (30 mL) and ethyl acetate portion was washed with water followed by brine and dried over sodium sulfate. Evaporation of volatiles and column chromatographic purification of the resulting material yielded compound (58A) first followed by compound (58B).

To a solution of l-{3-fluoro-4-morpholinopheny])-l/f-l,2,3-triazoI-4-ylmethyl isothiocyanate (0.1 g, 0.313 mmol), obtained in example 26, in methanol (5 mL) was added ammonia solution (18%, 1 mL) and stirred at RT for 5 h. The reaction mixture was then diluted with ethylacetate (40 mL) and the organic portion was washed successively with water, satd. NaHCOB solution and brine. Upon drying over sodium sulfate and concentration


To a mixture of l-{3-fluoro-4-morpholinophenyl)-lH-l,2,3-triazoie-4-ylmethanamine (0.2 g, 0.72 mmol), obtained in example 14, and triethylamine (0.14 g, 1.44 mmol) in anhydrous THF (10 mL) was added dichloroacetyl chloride (0.16 g, 1.08 mmol) at 0°C. It was brought to RT gradually and allowed to stir for 1 h. It was then diluted with ethylacetate (40 mL) and the organic portion was washed with, water followed by brine and dried over sodium sulfate. Evaporation of volatiles and column chromatographic purification of the resulting material yielded the title compound (0.2 g, 70%) as rotamers. Mp. 190 "C. "HNMR (CDCI3): 5 7.96 (s, IH), 7.60-7.20 (m, 2H), 7.05 (t, J= Z.ll Hz, IH), 5.98 (s, IH), 4.68 (d, y= 5.86 Hz, 2H), 4.0 - 3.80 (m, 4H), 3.25-3.05 (m, 4H). MS (m/e); 388 (M^, 354, 271, 233.
In vitro Data:
Minimum Inhibiton Concentrations (MICs) were determined by broth microdilution technique as per the guidelines prescribed om the fifth edition of Approved Standards, NCCLS document M7-A5 Vol 20 - No 2, 2000 Villinova. PA.
Initial stock solution of the test compound was prepared in DMSO. Subsequent two fold dilutions were carried out in sterile Mueller Hinton Broth (Difco) (MHB).
Frozen cultures stocks were inoculated into 50 mL sterile MHB in 250 mL Erlyn Meyer flasks.

Composition of MHB is as follows: Beef Extract Powder - 2.0 g/Iitre Acid Digest of Casein -17.5 g/ litre Soluble Starch -1.5 g/litre Final pH 7.3 ±0.1
Flasks were incubated for 4 to 5 h at 35 °C on a rotary shaker at 150 rpm. Inoculum was prepared by diluting the culture in sterile MHB to obtain a turbidity of 0.5 McFarland standard. This corresponds to 1-2 x 10^ CFU/mL. The stock was further diluted in sterile broth to obtain 1-2 X 10"^ CFU/mL. 50 |il of the above diluted inoculum was added from 1-10 wells. The plates were incubated overnight at 37 "C.
MIC is read as the lowest concentration of the compound that completely inhibits growth of the organism in the microdilution wells as detected by the unaided eye.






We Claim
1. A compound of formula (I)

where R" represents halo, azido, thioalcohol, isothiocyanate, OR"*, NHR"* or N(R"")2, where
R represents hydrogen atom, or substituted or unsubstituted groups selected from (C1-
C6)alkyl, acyl, thioacyl, (C1-C6)alkoxycarbonyl, (Cs-C6)cycloalkoxythiocarbonyl, (C2-
C6)alkenyloxycarbonyl, (C2-C6)alkenylcarbonyl, heteroaryl, aryloxycarbonyl,
heteroarytcarbonyl, (C1-C6)alkoxythiocarbonyl, (C2-C6)alkenyloxythiocarbonyl,
aryloxythiocarbonyl, -C(=0)-C(=0)-(C1-C6)alkyl, -C(=0)-C(=0)-aryl, -C(=0)-C(=0)-(C1-
C6)aIkoxy, -C(=0)-C{=0)-aryloxy, -(C=S>S-(C1-C6)alkyl, -(C=S)-NH2, -(C=S)-NH-(C,-
C6)alkyl, -C(=S)-N-((C1-C6)aIkyI)2, -C(=S)-NH-(C2-Q)aIkenyI, (C=S)-(C=0)- (C1-
C6)alkoxy, -(C=S)-{C=0)-aryloxy, -C(-S)-0-(C=OHC1-C6)alkyl, C(=S)-C(=S)-(C1-
C6)alkyi, -C(=S)-C(-S)-aryi, -C(=S)-NH-C(=0)-aryI, -(C=NH)-NH2, -(C=NH)-(C1-
C6)alkyl, -(C=NH)-aryl, S(0)2(C1-C6)alkyl, S(0)2aryl, thiomorpholinylthiocarbonyl,
pyrrolidinylthiocarbonyl or two R"* s together represent 5 or 6 member heterocycle ring
optionally having one or two hetero atoms; R and R are same or different and
independently represent hydrogen, halogen atom, (C1-C6)a]kyl group, ha]o(C1-C6)a]ky],
cyano, nitro, SR", NR^, OR* where R* represents substituted or unsubstituted (C1-C6)alkyl
group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or (C1-
C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and Y"" may be same or different and
independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or
substituted or unsubstituted groups selected from (C1-C6)alkyl, hydroxy{C1-C6)alkyl, (C1-
C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)aikyl, (C1-C6)alkylsulfonyl,
(C1-C6)aIkylcarbonylamino(C1-C6)alky!, arylcarbonylamino(C1-C6)alkyl, (C1-
C6)alkylcarbonyloxy(C1-C6)a!kyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl orheterocycloalkyi; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or

unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its phamiaceutically acceptable salts or its pharmaceutically acceptable solvates.
2. The compound according to claim 1, wherein the heterocyclic ring formed by two R"*s together is selected from substituted or unsubstituted pyrroiidinyl, pyrrolyl, morpholinyl, thiomorpholinyl, benzothiazole, benzoimidazolyl, pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl.
3. The compound according to claims 1 and 2, wherein the substituents on R"^ and heterocycles formed by two R""s are selected from halogen atom, hydroxy, amino, cyano, nitro, (C1-C6)alkyl, (C1-C6)alkoxy, =0, =S, aryl, hydroxyaryl, pyridyl, hydroxy(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, (C1-C6)alkoxyaryl or carboxyl and its derivatives.
4. The compound according to claims 1-3, wherein the substituents on R^ are selected from hydroxy, halogen, nitro, amino, (C1-C6)alkoxy, carboxyl or cyano group.
5. The compound according to claims 1-4, wherein the cyclic structure formed by any
two of Y", Y2or Y2 when present on adjacent carbon atoms is selected from substituted or
unsubstituted benzene, pyridine, pyrrolidine, fliran, thiophene, morpholine, piperazine or
pyrrole.
6. The compound according to claims 1-5, wherein the substituents on Y , Y , Y and
cyclic structure formed by Y", Y or Y2 are selected from hydroxy, nitto, cyano, amino, tert-
butyldimethylsilyloxy, halogen atom, {C1-C6)all^l, (C1-C6)alkoxy, (C3-C6)cycloalkyl, aryl,

l-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-5-ylmethanol, its salt: l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethanol, its salts; t-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-l/y-l,2,3-triazol-5-ylmethanol, its salts; l-{3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethylmethanesulfonate,

its salts; "
l-{3-FIuoro-4-morphoIinophenyI)-IH-l,2,3 triazol-4-yImethyl methanesulfonate, its salts;
l-[3,5-Difluoro-4-(4-thiomorphofinyl)phenyI]-IH-I,2,3-triazoI-4-
ylmethylmethanesulfonate, its salts;
l-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyl]-l/f-I,2,3-triazoi-5-
ylmethylmethanesulfonate, its salts;
l-[3-Fluoro-4-(4-thiomorpholinyI)phenyI]-li7-l,2,3-triazol-4-ylmethylmethanesulfonate, its salts;
l-[3-Fluoro-4-(4-thiomorpholinyl)phenyi]-lH-l,2,3-triazol-5-ylmethyImethane sulfonate, its salts;
l-(3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3 triazol-4-ylmethyl azide, its salts; l-{3-FIuoro-4-morphoHnophenyl)-lH-l,2,3-triazol-4-ylmethyI azide, its salts; l-[3,5-Difluoro-4-(4-thiomorpholinyi)phenyl]-li/-l,2,3-triazdl-4-ylmethyl azide, its salts; l-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-5-ylmethyl azide, its salts; l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-l/f-l,2,3-triazol-4-ylmethyl azide, its salts, l-[3-Fluoro-4-{4-thiomorpholinyl)phenyl]-l^-l,2,3-triazol-5-ylmethyl azide, its salts; l-(3,5-Difluoro-4-morpholinophenyl)-l/7-l,2,3-triazol-4-ylmethanamine, its salts; l-(3-Fluoro-4-morpholinophenyl)-l/f-l,2,3-triazol-4-ylmethanamine, its salts; l-[3,5-Difiuoro-4-(4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylinethanamine, its salts; l-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-l/f-l,2,3-triazol-4-yknethanamine, its salts; l-[3,5-Difluoro-4-(l-oxo-4-thiomoi-pholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethylazide, its salts;
l-[3,5-Difluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethyl azide, its salts;
l-[3-Fluoro-4-(l-oxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethyl azide, its salts;
I -[3-F]uoro-4-(l, I -dioxo-4-thiomoipholinyI)pheny!]-1 A"-1,2,3-triazoI-4-yImethyIazide,
its salts;
l-[3-Fluoro-4-(l-oxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-triazol-4-ylmethanamine, its
salts; l-[3,5-Difluoro-4-(l-oxo-4-thiomorpholinyl)phenyl]-lH-l,2,3-tria2ol-4-ylmethanamine,
its salts;

l-[3,5-Diiluoro-4-(l,I-dioxo-4-thiomorpholinyI)phenyl]-lH-l,2,3-triazo]-4-ylmethanamine, its salts;
1 -[3-Fluoro-4-( 1,1 -dioxo-4-thiomorpholinyl)pheny]]- I/f-1,2,3-triazol-4-ylmethanamine, its salts;
l-(3,5-Dinuoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-ylmethylisothiocyanate, its salts;
l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-ylmethyl isothiocyanate, its salts; l-[3,5-Difluoro-4-(4-thiomorpholinyl)phenyl]-lH-I,2,3-triazol-4-ylmethylisothiocyanate, its salts;
l-[3-Fluoro-4-(4-thiomorpholinyI)phenyl]-lH-I,2,3-triazol-4-ylmethyt isothiocyanate, its salts;
l-[3-FIuoro-4-(4-tliiomorpholinyl)phenyi]-l^-l,2,3-triazol-4-ylmethyl isothiocyanate, its
salts;
l-[3,5-DifIuoro-4-(l-oxo-4-thiomorpholiny!)phenyl]-lH-l,2,3-triazol-4-ylmethyl
isothiocyanate, its salts;
l-[3,5-Difluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl]-l/f-l,2,3-triazoI-4-ylmethyI
isothiocyanate, its salts;
1 -[3-Fluoro-4-( 1,1 -dioxo-4-thiomorpholinyl)phenyl]-1^-1,2,3-triazol-4-yhnethyl
isothiocyanate, its salts;
iVl[l-(3,5-Difluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl]acetamide, its salts;
M[l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl]acetamide, its salts;
A^l-[l-{3,5-Difluoro-4-(4-thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-yhnethyl]acetamide,
its salts;
M-[ 1 - {3,5-Difluoro-4-( 1 -oxo-4-thiomorpholinyl)phenyl} -1H-1.2,3-triazol-4-ylmethyl]
acetamide, its salts;
M-[l-{3,5-Difluoro-4-(l,l-dioxo-4-thiomorphotinyl)phenyl}-lH-l,2,3-triazol-4-yknethyl]
acetamide, its salts;
7\^.[l.{4-{4-Thiomorpholinyl)phenyl}-li/-l,2,3-triazol-4-ylmethyl]acetamide, its salts;
M-[l-{3-Fluoro-4-{l-oxo-4-thiomorpholinyl)phenyl}-l/M,2,3-triazol-4-
ylmethyljacetamide, its salts;
Aa-[l-{3-Fluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-17/-l,2,3-tria2ol-4-yUnethyl]
acetamide, its salts;

l-[l-{3,5-Difuoro-4-morphoiinophenyI-lH-l,2,3-triazol-4-yimeihylamine]-I-ethanethione, its salts;
l-[l-{3-FIuoro-4-morpholinophenyl-lH-I,2,3-triazol-4-ylmethylamine]-i-eihanethione, its salts;
0-Methyl-[l-(3,5-difluoro-4-morpholinophenyl)-l^-l,2,3-triazol-4-ylmethyljtfaiocarbamate, its salts;
0-Methyl-[l-{3-fluoro-4-morpholinophenyl)-li/-l,2,3-tria2ol-4-ylmethyl]thiocarbamate, its salts;
0-Methyl-[l-{3,5-difluoro-4-(4-thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-ylmethyl]thio carbamate, its salts;
0-Methyl-[l-{3,5-difluoro-4-(l-oxo-4-thiomoipholinyl)phenyl}-l/^-l,2,3-tria2ol-4-ylmethyl] thiocarbamate, its salts;
0-Methyl-[l-{3,5-difluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-l/f-l,2,3-triazoI-4-yl methyljthiocarbamate, its salts;
0-Methyl-[l-(3-fluoro-4-(4-thiomorphoUnyl)phenyl}-lif-l,2,3-triazol-4-ylmethyl] thiocarbamate, its salts;
0-Methyi-[l-{3-fluoro-4-(l-oxo-4-thiomorpholinyl)plienyl}-lH-I,2,3-triazol-4-ylmethy!] thiocarbamate, its salts;
0-Methyl-[l-{3-fluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-lH-l,2,3-triazot-4-yl methyl]thiQcarbamate> its salts;
l-{3,5-Diflucro-4-morpholinophenyl)-lif-l,2,3-triazole-4-ylmethyIaminomethyl-aminomethanethione, its salts; 5-Methyl-[l-{3-fluoro-4-morpholinophenyl)-li/-l,2,3-triazol-4-ylmethyI]dithiocarbamate,
its salts; 5-Methyl-[l-(3-fluoro-4-{l-oxo-4-thiomorpholinyl)phenyl}-li/-l,2,3-triazol-4-ylmethyl]
dithiocarbamate, its salts; 5"-Methyl-[l-{3-fluoro-4-(l,l-dioxo-4-thiomorpholinyl)phenyl}-lH-l,2,3-triazol-4-
yhnethyl] dithiocarbamate, its salts;
l-(3-Fluoro-4-morpholinophenyl)-4-phenylcarboxamido(thioxo)melhyiaminomethyl-lH-1,2,3-triazole, its salts;

7V2-[I-{3-Fluoro-4-morpholinophenyi)-I/f-l,2,3-tria2ole-4-ylmethyi]-2-pyra2ine carboxamide, its salts;
5"-Methy!-0-[l-{3-fluoro-4-morpholmophenyi)-l/f-l,2,3-triazoi-4ylmethyl]dithiocarbamate,
its salts;
l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazol-4-ylmethyl 2-pyridyl ether, its salts;
1 -[ 1 -{3-fluoro-4-morpholinophenyI)-1H-1,2,3-triazol-4-ylmethyI]-1,2-dihydro-2-pyridiiione,
its salts;
Amino-l-(3-f]uoro-4-raorpholinophenyl)-l/f-l,2,3-triazol-4ylmethylaminomethanethione, its salts and
jVl-[l-(3-Fluoro-4-morpholinophenyl)-lH-l,2,3-triazole-4-ylmethyl]-2,2-dichloro-acetamide, its salts.
8. A compound according to claims 1 or 7, wherein the pharmaceutlcally acceptable salt is selected from Li, Na, K, Ca, Mg, Fe, Cu, Zn, Mn; salts of organic bases, chiral bases, natural amino acids, unnatural amino acids, substituted amino acids, guanidine, substituted guanidine salts; ammonium, substituted ammonium salts, aluminum salts and acid audition salts.
9. Pharmaceutically acceptable salt according to claim 8, wherein the salts of organic bases are selected from N,N"-diacetylethylenediamine, betaine, caffeine, 2-diethylaminoethanol, 2-dimethylaminoethanol, N-ethylmorpholine, N-ethylpiperidine. glucamine, glucosamine, hydrabamine, isopropylamine, methylglucamine, morpholine, piperazine, piperidine, procaine, purines, theobromine, triethylamine, trimethylamine, tripropylamine, tromethamine, diethanolamine, meglumine, ethylenediamine, N,N"-diphenylethylenediamine, N,N"-dibenzylethylenediamine, N-benzyl phenyiethylamine, choline, choline hydroxide, dicyclohexylamine, metformin, benzylamine, phenyiethylamine, dialkylamine, trialkylamine, thiamine, aminopyrimidine, aminopyridine, purine, spermidine.
10. Pharmaceutically acceptable salt according to claim 8 wherein_the salts of chiral bases lare selected from alkylphenylamine, glycinol, phenyl glycinol.
11. Pharmaceutically acceptable salt according to claim 8 wherein the salts of natural amino acids are selected from glycine, alanine, valine, leucine, isoleucine, norleucine, tyrosine, cystine, cysteine, methionine, proline, hydroxy proline, histidine, ornithine, lysine, arginine, serine, threonine, phenylalanine.

12. Pharmaceutically acceptable salt according to claim 8 wherein the salts of unnatural amino acid, substituted amino acids are selected from D-isomers, guanidine, substituted guanidine wherein the substituents are selected from nitro, amino, alkyl such as methyl, ethyl, propyl and the like; alkenyl such as ethenyl, propenyl, butenyl and the like; alkynyl such as ethynyl, propynyl.
13. Pharmaceutically acceptable salt according to claim 8 wherein the acid addition salts are selected fromsulphates, nitrates, phosphates, perchlorates, borates, halides, acetates, tartrates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, salicylates, hydroxynaphthoates, benzenesulfonates, ascorbates, glycerophosphates, ketoglutarates.
14. A process for the preparation of the compound of formula (I)

where R" represents azido group; R^ and R"" are same or different and independently
represent hydrogen, halogen atom, {C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR^,
NR*, OR^ where R^ represents substituted or unsubstituted (C1-C6)a!kyl group; Z represents
S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or CC1-C6)aJkyI, S(0)„ where
n represents 0-2; Y , Y2 and Y2 may be same or different and independently represent
hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted
groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-
C6)alkoxycarbonyl, carboxy{C1-C6)alkyl, {C1-C6)alkylsulfonyl, (C1-
C6)alkylcarbonylamino(C1-C6)alkyl, arylcarbonylamino(C1-C6)alkyl, {C1-
C6)alkylcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkyIamino, aryiamino, (C1-C6)aIkoxy, aryl, aryioxy, aralkyl, heteroaryi, heteroaraikyi, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y"represents =0 or =S group; or any two of Y .. Y2 or Y present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its £malogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:


where Z, Y", Y2 Y2 R^ and R^ are as defined above, to a compound of formula (le) (iv) converting the compound of formula (le), to a compound of formula (If)




(ii) converting the compound of formula (I) where R" represents halogen atom, to a compound of formula (I), wherein R" represents azido group.

(iii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods.
17. A process for the preparation of compound of formula (I)

where R" represents azido group, R^ and R^ are same or different and independently
represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitre, SR^,
NR°, OR^ where R* represents substituted or unsubstituted (C1-C6)alkyl group; Z represents -
SOn-, where n represents 1 or 2; Y", Y2 and Y2 may be same or different and independently
represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or
unsubstituted groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-
C6)alkyl, (C1-C6)alkoxycarbonyl, carbcxy(C[-C6)alkyl, (C1-C6)alkylsulfonyl, (C1-
C6)aiky!carbonyIamino(C1-C6)aIkyl, aryIcarbonyIamino(C1-C6)aIkyI, (C[-
C6)alkylcarbonyloxy(C1-C6)alkyl, aimno(C1-C6)alkyl, mono(C1-C6)alkylamino, di{C1-C6)alkytamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y , Y or Y present on adjacent carbon atoms together also form a substituted or imsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises; (i) oxidizing the compound of formula (1)
where R" represents azido group; Z represents -SOn-, where n represents zero and all other symbols are as defined above, by using m-chloroperoxybenzoic acid (m-CPBA) or hydrogen peroxide.
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods.
18. A process for the preparation of compound of formula (I)



(ii) reducing the compound of formula (Ig), to produce a compound of formula (I) where R" represents NHR"* wherein R"" represents hydrogen atom and all other symbols are as defined above
(iii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods.

hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR*, NR", OR^ where R^ represents substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y", Y and Y may be same or different and independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted

groups selected from (C1-C6)aJkyl, hydroxy(C,-C6)aIkyl, (C,-C6)aIkoxy(C1-C6)a]ky], (C1-
C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsuIfonyI, (C1-
C6)alkylcarbonylamino(C1-C6)alkyl, arylcarbonylammo(Cr-C6)aIkyl, (C1-
C6)alkylcarbonyloxy{C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-QJalkylamino, arylamino, (C1-C6)aIkoxy, aryl, aryloxy, araikyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y" , Y2 or Y2 represents =0 or =S group; or any two of Y\ Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:





where R" represents OR*" wherein R** represents substituted or unsubstituted acyl group, and
all other symbols are as defined above and
(ii) hydrolysis of the compound of formula (I) where R" represents OR^ wherein R*^ is as
defined above, to a compound of formula (I), where R" represents hydroxy group and all
other symbols are as defined above.
(iii) and if desire converting the compound obtained in to its derivatives, its anolagous, its
tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its
pharmaceutically solvates by conventionals methods.
23. A process for the preparation of compound of formula (I)


where R" represents NHR^, wherein R"* represents acetyl group; R^ and R^ are same or
different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-
Cfijalkyl, cyano, nitro, SR^ NR^ OR" where R" represents substituted or unsubstituted (C1-
C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen
or (C1-C6)alky], S(0)n where n represents 0-2; Y", Y2 and Y2 may be same or different and
independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or
substituted or unsubstituted groups selected from (C1-Cfi)alkyl, hydroxy(C1-C6)alkyl, (C1-
C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsulfonyl,
(C1-C6)alkylcarbonylamino(C1-C6)alkyl, arylcarbonylamino(C1-C6)alkyl, (Cp
C6)alkylcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y , Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its pojymoiphs, its pharmaceutically acceptable salts or its pharraaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I) where R" represents azido group and all other symbols are as defined above, with thioacetic acid.
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods. 24. A process for the preparation of compound of formula (I)


where R^ represents NHR"", where R"* represents -C(=S)-R""^, wherein R""" represents (C1-
C6)a]kyl, ha]o(C,-C6)a]kyl, -C(=0)-(C,-C6)a]koxy, -C(=0)-aiyIoxy, -C(=S)-(C,-C6)a]ky] or -
C(=S)-aryl; R^ and R^ are same or different and independently represent hydrogen, halogen
atom, (C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR^ NR^, OR*" where R* represents
substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR
wherein R represents hydrogen or (C1-Cs^alkyl, S(0)n where n represents 0-2; Y", Y2 and
Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitro,
formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl,
hydroxy(C1-C6)alky], (C,-C6)aJkoxy(C1-C6)a!ky], (C[-C6)alkoxycarbonyl, carboxy(C(-
C6)alkyl, (C1-C6)a!kylsulfonyl, {C1-C6)alkylcarbonylammo(C1-C6)alkyl,
arylcarbonylamino(C1-C6)alkyl, (C1-C6)alky!carbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylaraino, di(C1-C6)alkylamino, arylamino, (d-C6)alkoxy, aryl, aryloxy, aralkyi, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloatkyl; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I) where R" represents NHR"", where R"* represents -C(-0)-R""", wherein R"" represents (C1-C6)alkyl, halo(C1-C6)alkyI, -C(=0)-(C1-C6)alkoxy, -C(=0)-aryloxy, -C(=S)-(C1-C6)alkyI or -C(=S)-aryl and all other symbols are as defined above, with a solution of amide and Lawesson"s reagent (2,4-bis(methoxyphenyl)-l,3-dithia-2,4-diphosphetane-2,4-disuifide}.
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or hs pharmaceutically solvates by conventionals methods. 25. A process for the preparation of compotmd of formula (I)


where R" represents NHR"*, wherein R""represents-C(=S)-OR*^ wherein R""^ represents (C1-
Csjalkyl, cyclo(C3-C6)alkyl, -(C=0)-(C1-C6)alkyl group substituted with fluorine; aryl,
halo(C,-C6)alkyl, hydroxy{C1-C6)alkyl, (C1-C6)aIkoxy(C,-C6)aIkyl or (C2-C6)alkenyl; R^
and R^ are same or different and independently represent hydrogen, halogen atom, (C1-
C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR", NR", OR" where R" represents
substituted or unsubstituted {C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR
wherein R represents hydrogen or (C1-Ceialkyl, S(0)n where n represents 0-2; Y", Y2 and
Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitre,
formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-^6)alkyl,
hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy{C1-
C6)aikyl, (C1-C6)aIkyIsuIfonyI, (C1-C6)aIkyIcarbonyIamino(C1-C6)aIkyl,
arylcarbonylamino(C1-C6)alkyl, (C1-C6)alkylcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyi, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyi; any one ofY", V^ orY2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises: (i) reacting compound of formula (I)

where R" represents azido group; and all other symbols are as defined above, with
triphenylphosphine/water or Hi-Pd/C, to produce a compoimd of formula (I), where R"
represents NHR*, wherein R* represents hydrogen atom and all other symbols are as defined
above,
(ii) reacting compound of formula (I), where R" represents NHR"*, wherein R"" represents
hydrogen atom, with thiophosgene or carbon disulfide and chloromethylformate, to produce
a compound of formula (I)


where R" represents NHR"*, where R"" represents -C(=S)-N(R"R"), wherein R" represents
hydrogen, (C1-C6)a!kyl, (C2-C6)alkenyl, substituted or unsubstituted aralkyl, heteroaralkyl,
hydroxy{C1-C6)alkyl, R" represents hydrogen or (C1-C6)alkyl or the two R" and R" groups
together form a 5 or 6 membered cyclic structures containing one or two hetero atoms; R
and R are same or different and independently represent hydrogen, halogen atom, (C1-
C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR\ NR^, OR^ where R" represents
substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR
wherein R represents hydrogen or (C[-C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and
Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitro,
formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl,
hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(Cr
Q)alky), (C, -C6)alky]sulfony], (C, -C6)a]kylcarbonylamino(C, -C6)a]ky],
arylcarbonylamino(C1-C6)alkyl, (C1-C6)alkylcarbonyIoxy(C1-Cs)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyi; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y present on adjacent carbon atoms

together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic
cyclic structure, optionEilly containing one or two hetero atoms; its derivatives, its analogs,
its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts
or its pharmaceutically acceptable solvates, which comprises:
(i) reacting a compound of formula (I) where R represents isothiocyanate group and all
other symbols are as defined above, with ammonia gas or appropriate amine
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its
tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its
pharmaceutically solvates by conventionals methods.
27. A process for the preparation of compound of formula (I)

where R" represents NHR"", wherein R^ represents -C{=S)-SR*^ wherein R"*"" represents (Cr C6)alkyl group; R and R are same or different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR"*, NR", OR* where R" represents substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C,-C6)alkyl, hydroxy(C1-C6)alkyl, (C,-C6)alkoxy(C,-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylcarbonylamino(C1-C6)alkyl, arylcarbonyiamino(C1-C6)alkyl, (C1-C6)alkylcarbonyIoxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)aIkylamino, di(C1-C6)alky!amino, arylamino, (C1-C6)aIkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one ofY",Y2 orY" represents =0 or =S group; or any two of Y", Y or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:

(i) reacting the compound of formula (I), where R" represents NHR"*, wherein R""
represents hydrogen atom and all other symbols are as defmed above, with CS2 and
alkylhalide
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its
tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its
pharmaceutically solvates by conventionals methods.
28. A process for the preparation of compound of formula (I)

where R represents NHR , wherein R represents -C(=S)-NH-R , wherein R"" represents benzoyl group; R^ and R"" are same or different and independently represent hydrogen, halogen atom, (C1-C6)alkyI group, ha]o(C1-C6)a!kyl, cyano, nitro, SR^ NR^ OR"* where R"* represents substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y , Y and Y may be same or different and independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C,-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)aIkyl, (C1-C6)aIkylsuIfonyl, (C[-C6)aIkyIcarbonylamino(C1-C6)aJkyl, arylcarbonylamino(C1-C6)alkyl, {C1-C6)alkylcarbonyIoxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di{C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyi, heteroaryl, heteroaralkyl, heterocyclyl or heterocycJoalkyJ; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or hs pharmaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I), where R" represents NHR"*, wherein R"* represents hydrogen atom and all other symbols are as defined above, with benzoylisothiocyanate

(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods.
29. A process for the preparation of compound of formula (I)

where R" represents NHR"", wherein R"* represents -(C=0)-heteroaryl; R^ and R^ are same or
different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-
C6)alkyl, cyano, nitro, SR", NR*, OR" where R" represents substituted or unsubstituted (C1-
C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen
or (C,-C6)alkyl, S{0)n where n represents 0-2; Y", Y2 and Y" may be same or different and
independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or
substituted or unsubstituted groups selected from (C1-C6)alky!, hydroxy(C1-C6)aIkyl, (C[-
C6)alkoxy{C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsulfonyl,
(C1-C6)alkylcarbonylamino(C1-C6)alkyl, arylcarbonylamino(C1-C6)alkyl, (C[-
C6)alkylcarbonyloxy(C!-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocycly] or heterocycloalkyi; any one of Y\ Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its phannaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I), where R" represents NHR"*, wherein R"" represents hydrogen atom and all other symbols are as defined above, with heteroaryl acid chloride
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods.
30. A process for the preparation of compound of formula (I)


where R" represents OR"*, wherein R"* represents heteroaryl (or) R" represents N(R"")2, wherein two R"*s together represent six membered heterocycle optionally having one or two hetero atoms; R^ and R^ are same or different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C,-C6)alkyl, cyano, nitro, SR\ NR^ OR^ where R* represents substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or {C1-C6)alkyl, S(0)n where n represents 0-2; Y , Y and Y may be same or different and independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, {C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-Q)aIkyI, (C1-C6)aIkyIsulfonyl, (C1-C6)aIkyIcarbonyIamino(C1-C6)alkyI, arylcarbonylamino(C1-C6)alkyl, (C1-C6)alkylcarbonyloxy(C1-C6)alkyl, amino{C1-C6)alkyl, mono{C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I), where R" represents OR"", wherein R"" represents S(0)2(C1-C6)alkyl or S(0)2aryl group and all other symbols are as defined above, 2-pyridinol
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its mtomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods. 31. A process for the preparation of compound of formiila (I)


where R" represents NHR"" where R^ represents -(C=0)-R""^ wherein R"*" represents (C1-
C6)alkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, halo{C1-C6)aIkyl, aryloxy, (C2-C6)alkenyloxy, (C1-
C6)alkylcarbonyl, arylcarbonyl, aryloxycarbonyl or (C1-C6)alkoxycarbonyl; R^ and R^ are
same or different and independently represent hydrogen, halogen atom, (C1-CsjalkyI group,
haIo(C1-C6)alkyi, cyano, nitro, SR^ NR^, OR^ where R^ represents substituted or
unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R
represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and Y2 may be
same or different and independently represent hydrogen, halogen, cyano, nitro, formyl,
hydroxy, amino or substituted or unsubstituted groups selected from {C1-C6)alkyl,
hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C[-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-
C6)alkyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylcarbonylamino(C1-C6)alkyl,
arylcarbonyIamino(C1-C6)alkyl, (C1-C6)alkyIcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkyiamino, di(C1-C6)aIkyIamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y"" represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises;
(i) reacting the compound of formula (I), where R" represents NHR"*, wherein R"" represents hydrogen atom and all other symbols are as defined above, with acid halide, alkylchloroformate or anhydride of acid
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods. 32. A process for the preparation of compound of formula (1)


where R" represents OR"", wherein R^ represents -C(=S)-SR""*", wherein R"*"^ represents {C1-C6)alkyl gorup; R^ and R^ are same or different and independently represent hydrogen, halogen atom, (C1-C6)alkyt group, ha!o(C1-C6)aikyi, cyano, nitre, SR*, NR*, OR^ where R^ represents substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C,-C6)aIky!, (C1-Q}a]kylsulfonyJ, (C1-C6)a]ky]carbonylamino(C1-C6)alkyl, arylcarbonyIamino(C1-C6)alkyl, (C1-C6)alkylcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono{C1-C6)alkyIamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y2 represents =0 or -S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I), where R" represents OR^, wherein R"* represents hydrogen atom and all other symbols are as defined above, with CS; and alky haiide
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods. 33. A process for the preparation of compound of formula (I)


where R" represents NHR"" where R"* represents -(C=NH)-NH2; R^ and R"* are same or
different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-
C6)alkyl> cyano, nitro, SR^ NR^ OR* where R" represents substituted or unsubstituted (C1-
C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR wherein R represents hydrogen
or (C1-C6)alkyJ, S(0)n where n represents 0-2; Y", Y2 and Y2 may be same or different and
independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or
substituted or unsubstituted groups selected from (C1-C6)aikyi, hydroxy(C1-C6)alky!, (C1-
C6)alkoxy{C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsulfonyl,
(C1-C6)aIkylcarbonyIamino(C1-C6)alkyI, aryIcarbonylamino(C1-C6)aIkyI, (Cp
C6)alkylcarbonyloxy{C1-C6)alkyl, amino{C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y" , Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:
(a) reacting a compound of formula (I), where R" represents NHR"* wherein R"* represents hydrogen atom and all other symbols are as defined above, with di-tert-hutoxy carbonyl thiourea
(b) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods.
34. A process for the preparation of compound of formula (1)

wherein all symbols are as defined in claim 33, which comprises:
(a) reacting compound of formula (I), where R" represents NHR"" wherein R"* represents S(0)2(C1-C6)alkyl or S(0)2aryt group and all other symbols are as defined above, with guanidine hydrochloride.

(b) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceulically acceptable salts or its pharmaceutically solvates by conventionals methods. 35. A process for the preparation of compound of formula (I)

where R" represents NHR" where R"^ represents -(C=NH)-(C1-C6)alkyl or -(C=NH)-aryl; R^
and R^ are same or different and independently represent hydrogen, halogen atom, (C1-
C6)a]kyl group, halo(C(-Cfi)a]ky], cyano, nilro, SR^ NR^ OR* where R^ represents
substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S-NR, S(-0)=NR
wherein R represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and
Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitro,
formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl,
hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, {C1-C6)alkoxycarbonyl, carboxy(C1-
C6)alkyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylcarbonylamino(C1-C6)alkyI,
aryicarbonylamino(C1-C6)alkyl, (C1-C6)alkyIcarbonyloxy(C1-C6)aIkyl, amino(C1-C6)alkyl, mono(C1-C6)aIkylamino, di(C1-C6)aIkyIamino, arylamino, (C1-C6)aIkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloatkyl; any one of Y", Y or Y represents =0 or =S group; or any two of Y , Y or Y present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises; (i) reacting the compound of formula (li)


where all symbols are as defined above, with di lert-butoxy carbonyl ether [(B0C)20], to produce a compound of formula (Ij)

where all symbols are as defined above and
(ii) reacting the compound of formula (Ij), with a compound of formula (Ik)
R-NH2 ak)
where R represents (C1-C6)alkyl or aryl group, to produce a compound of formula (1) where
R" represents NHR" where R" represents -(C=NH)-(C1-C6)alkyl or -(C=NH)-aryl group and
all other symbols are as defined above
(iii) and if desire converting the compound obtained in to its derivatives, its anolagous, its
tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its
pharmaceutically solvates by conventionals methods.
36. A process for the preparation of compound of formula (I)

where R" represents halo, azido, thioalcohol, isothiocyanate, OR"", NHR^ or N(R^)2, where
R"* represents hydrogen atom, or substituted or unsubstifuted groups selected from (C1-
C6)alkyl, acyl, thioacyl, (C1-C6)alkoxycarbonyl, (C3-C6)cycloalkoxythiocarbonyl, (C2-
Cs)alkenyloxycarbonyl, (C2-C6)alkenyl carbonyl, heteroaryl, aryloxycarbonyl,
heteroarylcarbonyl, (C1-C6)alkoxythiocarbonyl, (C2-C6)alkenyloxythiocarbonyl,
aryloxythiocarbonyl, -C(-0)-C(=0)-(C1-C6)alkyl, -C(=0)-C(=0)-aryl, -C(=0)-C(=0)-(C,-C6)alkoxy, -C(=0)-C(=0)-aryloxy, -(C=S)-S-(C1-C6)alkyl, -(C=S)-NH2, -(C=S)-NH-(C1-C6)alkyl, -C(=S)-N-((C,-C6)alkyl)2, -C(=S).NH-{C2-C6)alkenyl, (C=S)-(C=0)- (C,-C6)alkoxy, -(C=S)-(C=0)-aryloxy, -C(=S)-0-(C=0)-(C,-C6)alkyl, C(=S)-C(=S)-(C1-C6)alkyl, -C(=S)-C{=S)-aryl, -CC=S)-NH-C(=0)-aryl, -(C=NH)-NH2, -(C=NH)-(C r C6)alkyl, -(C=NH)-aryl, S(0)2(C1-C6)alkyl, S(0)2aryl, thiomorpholinylthiocarbonyl.

pyrrolidinylthiocarbonyl or two R"" s together represent 5 or 6 member heterocycle ring optionally having one or two hetero atoms; R and R are same or different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, haIo(C[-C6)aIky!, cyano, nitro, SR^, NR^ OR" where R" represents substituted or unsubstituted (C1-C6)alkyl group; 2 represents -SOn-, where n represents J or 2; Y", Y2 and Y2 may be same or different and independently represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted groups selected ftom (C1-C6)alkyi, hydroxy(C1-C6)alkyl, {C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, {C1-C6)alkyIsulfonyi, (C1-C6)aIkylcarbonylamino(C1-C6)aIky!, aryIcarbonyIamino(C,-C6)aikyI, (C1-C6)aIkylcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, (C1-C6)aikoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyi, heterocyclyl or heterocycloalkyl; any one of Y , Y or Y represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:
(i) oxidizing the compound of formula (I) where Z represents -SOn-, where n represents zero and all other symbols are as defined above, by using m-chloroperoxybenzoic acid (m-CPBA) or hydrogen peroxide
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically solvates by conventionals methods. 37. A process for the preparation of compound of formula (I)

where R" represents halogen atom; R^ and R^ are same or different and independently represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR^, NR*, OR" where R" represents substituted or unsubstituted (C1-C6)alkyl group; Z represents -SOn-, where n represents 1 or 2; Y , Y and Y may be same or different and independently

represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or
unsubstituted groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)atkoxy(C1-
C6)alkyl, (C1-C6)a]koxycarbonyI, carboxy(C,-C6)aIkyI, (C1-C6)alkylsuIfonyI, (C1-
C6)aIkylcarbonylamino(C1-C6)alkyI, arylcarbonylaniino(C1-C6)alkyt, (C1-
C6)alkylcarbonyloxy(C1-C6)alkyl, amino(C[-C6)alkyI, mono(C1-C6)alkyl amino, di(C1-C6)aIkylamino, arylamino, (C1-C6)aIkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y" , Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y"* present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable soivates, which comprises:
(i) converting the compound of formula (I) where R" represents hydroxy group and all other symbols are as defined above, with SOCh, PCls/PBra, tetrahalomethane, in the presence of PPha or P(aikyJ)3
(ii) and if desire converting the compound obtained in to its derivatives, its anolagous, its tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceuticaily solvates by conventionais methods. 38. A process for the preparation of compound of formula (I)

where R" represents "SH" group; R^ and R^ are same or different and independently
represent hydrogen, halogen atom, (C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR^,
NR", OR" where R" represents substituted or unsubstituted (C1-C6)alkyl group; Z represents -
SOn", where n represents 1 or 2; Y", Y2 and Y2 may be same or different and independently
represent hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or
unsubstituted groups selected from (C1-C6)a!kyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-
C6)alkyl, (C1-C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsulfonyl, (Cp
C6)alkylcarbonyIamino(C1-C6)alkyl, arylcarbonylamino(C1-C6)alkyl, (C1-
C6)alkyJcarbonyIoxy(C1-C6)alkyI, amino(C1-C6)aIkyl, mono(C1-C6)aIkyIamino, di(C1-

C6)alkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one of Y" , Y2 or Y2 represents =0 or =S group; or any two of Y , Y or Y present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms; its derivatives, its analogs, its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates, which comprises:
(i) reacting the compound of formula (I) where R" represents halogen atom, to produce a compound of formula (Ih),

where all other symbols are as defined above, with a base and thtoacetic acid^
(ii) reacting the compound of formula (Ih), to produce a compound of formula (I) where
R^ represents "SH" group and all other symbols are as defined above, with base
(iii) and if desire converting the compound obtained in to its derivatives, its anolagous, its
tutomaric form, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its
pharmaceutically solvates by conventionals methods.
39. A pharmaceutical composition comprising a compound of formula (I)

as claimed in claim 1 and a pharmaceutically acceptable carrier, diluent, excipient or solvate.
40. A pharmaceutical composition as claimed in claim 39, in the form of a tablet, capsule, powder, syrup, solution or suspension.
41. A pharmaceutical composition comprising a compound as claimed in claim 7 and a pharmaceutically acceptable carrier, diluent, excipient or solvate.
42. A pharmaceutical composition as claimed in claim 41, in the form of a tablet, capsule, powder, syrup, solution or suspension.

43. A compound of formula (le)

where R and R are same or different and independently represent hydrogen, halogen atom,
(C1-C6)alkyl group, halo(C1-C6)alkyl, cyano, nitro, SR\ NR^ OR^ where R" represents
substituted or unsubstituted (C1-C{,)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR
wherein R represents hydrogen or (C1-C6)alkyl, S(0)n where n represents 0-2; Y", Y2 and
Y"* may be same or different and independently represent hydrogen, halogen, cyano, nitro,
formyl, hydroxy, amino or substituted or unsubstituted groups selected from (C1-C6)alkyl,
hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)aIkyl, (CpC6)alkoxycarbonyl, carboxy(C1-
C6)a!kyl, (C1-C6)alkylsulfonyl, {C1-C6)alkylcarbonylamino(C1-C6)alkyl,
arylcarbonylaniino{C1-C6)alkyl, (C1-C6)alkylcarbonyloxy(C1-C6)alkyl, amino{C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, arylamino, {C1-C6)alkoxy, aryl, aryloxy, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocycloalkyl; any one ofY",Y2 orY2 represents =0 or =S group; or any two of Y", Y"^ or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms.
44. A compound of formula (If)
«>.
where R*^ represents (C1-C6)alkyl group; R^ and R^ are same or different and independently
represent hydrogen, halogen atom, (C1-C6)alkyi group, halo(C1-C6)alkyl, cyano, nitro, SR^
NR^, OR^ where R^ represents substituted or unsubstituted (C1-C6)alkyl group; Z represents
S, O, -CH2, S=NR, S(=0)=NR wherem R represents hydrogen or (C1-C6)alkyl, S(0)n where
n represents 0-2; Y", Y2 and Y2 may be same or different and independently represent
hydrogen, halogen, cyano, nitro, formyl, hydroxy, amino or substituted or unsubstituted
groups selected from (C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-
C6)alkoxycarbonyl, carboxy(C1-C6)alkyl, (C1-C6)alkylsulfonyI, (Cp

C6)alkylcarbonylamino(C1-C6)alkyl, arylcarbonylamino(C1-C6)alkyl, (C1-
C6)alkylcarbonyloxy(C1-C6)alkyl, ammo(C1-C6)alkyl, mono(C1-C6)alkyl amino, di(C1-Csjalkylamino, arylamino, (C1-C6)alkoxy, aryl, aryloxy, aralkyi, heteroaryl, heteroaralkyi, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y" present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms. 45. A compound of formula (Ig)

where R^ and R are same or different and independently represent hydrogen, halogen atom,
(C1-C6)aikyl group, halo(C1-C6)alkyI, cyano, nitro, SR", NR", OR* where R" represents
substituted or unsubstituted (C1-C6)alkyl group; Z represents S, O, -CH2, S=NR, S(=0)=NR
wherein R represents hydrogen or (C1-C6)alkyl, S(0)„ where n represents 0-2; Y", Y2 and
Y may be same or different and independently represent hydrogen, halogen, cyano, nitro,
formyl, hydroxy, amino or substituted or unsubstituted groups selected from {C1-C6)alkyl,
hydroxy(C1-Ct,)alkyl, (C1-C6)alkoxy(C1-C6)alkyI, (C1-C6)alkoxycarbonyl, carboxy(C1-
C6)alkyl, {C,-C6)alkylsulfonyl, (C1-C6)alkylcarbonyIamino(C1-C6)alkyl,
arylcarbonylamino(C1-C6)alkyl, (C1-C6)alkylcarbonyloxy(C1-C6)alkyl, amino(C1-C6)alkyl, mono(C1-C6)alkylamino, di(C1-C6)a!kylamino, arylamino, {C1-C6)alkoxy, aryl, aryloxy, aralkyi, heteroaryl, heteroaralkyi, heterocyclyl or heterocycloalkyl; any one of Y", Y2 or Y2 represents =0 or =S group; or any two of Y", Y2 or Y2 present on adjacent carbon atoms together also form a substituted or unsubstituted 5 or 6 membered aromatic or non-aromatic cyclic structure, optionally containing one or two hetero atoms.

Documents:

0042-mas-2002 assignment.pdf

0042-mas-2002 correspondence-others.pdf

0042-mas-2002 correspondence-po.pdf

0042-mas-2002 description(complete).pdf

0042-mas-2002 form-1.pdf

0042-mas-2002 form-13.pdf

0042-mas-2002 form-18.pdf

0042-mas-2002 form-3.pdf

0042-mas-2002 form-6.pdf

0042-mas-2002 abstract-duplicate.pdf

0042-mas-2002 abstract.jpg

0042-mas-2002 abstract.pdf

0042-mas-2002 claims-duplicate.pdf

0042-mas-2002 claims.pdf

0042-mas-2002 description(complete)-duplicate.pdf

42mas2002.jpg


Patent Number 202817
Indian Patent Application Number 42/MAS/2002
PG Journal Number 05/2007
Publication Date 02-Feb-2007
Grant Date 13-Nov-2006
Date of Filing 18-Jan-2002
Name of Patentee Dr. REDDY'S LABORATORIES LTD
Applicant Address 7-1-27 AMEERPET, HYDERABAD 500016
Inventors:
# Inventor's Name Inventor's Address
1 JAGATTARAN DAS Dr. REDDY'S RESEARCH FOUNDATION 7-1-27 AMEERPET, HYDERABAD 500016
2 NATESAN SELVAKUMAR Dr. REDDY'S RESEARCH FOUNDATION, 7-1-27 AMEERPET, HYDERABAD 500016
3 SANJAY TREHAN Dr. REDDY'S RESEARCH FOUNDATION 7-1-27 AMEERPET, HYDERABAD 500016
4 JAVED IQBAL Dr. REDDY'S RESEARCH FOUNDATION 7-1-27 AMEERPET, HYDERABAD 500016
5 MAGADI SITARAM KUMAR Dr. REDDY'S RESEARCH FOUNDATION 7-1-27 AMEERPET, HYDERABAD 500016
6 MAMIDI NAGA VENKATA SRINIVASA RAO Dr. REDDY'S RESEARCH FOUNDATION 7-1-27 AMEERPET, HYDERABAD 500016
7 RAMANUJAM RAJAGOPALAN Dr. REDDY'S RESEARCH FOUNDATION 7-1-27 AMEERPET, HYDERABAD 500016
PCT International Classification Number A61K 31/4192
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA