Oxazolidinone derivatives as pontential antimicrobials

Abstract

The present invention relates to certain substituted phenyl oxazolidinones and to processes for the synthesis of the same. This invention also relates to pharmaceutical compositions containing the compounds of the present invention as antimicrobials. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bacteroides spp. and Clostridium spp. species, and acid fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.

1 . A compound having the structure of Formula I,  
       
         
           
           
               
               
           
         
       
       and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxide, polymorphs, pharmaceutically acceptable solvates, prodrugs or metabolites, wherein 
 ring D is a five membered heterocyclic ring;  
 ring C is four to eight membered in size or larger which has either two or three carbon atoms between each nitrogen atoms or ring C is a bridged bicyclic system and is optionally substituted by the substituents Y and Z independently selected from alkyl groups, cycloakyl groups, fluoro group, carboxylic groups and corresponding esters or amides;  
 Q 1  is selected from O, S, NR 11 ;  
 Q 2  is selected from N or C;  
 G, J, L are independently selected from H, C 1-6  alkyl, F, Cl, Br, I, —CN, COR 5 , COOR 5 , N(R 6 , R 7 ), NHCOC(R 5 , R 8 , R 9 ), —NHCOOR 5 , CON(R 6 , R 7 ), CH 2 NO 2 , NO 2 , CH 2 R 8 , CHR 9 , —CH═N—OR 10 , —C═CH—R 5 , OR 5 , SR 5 , —C(R 9 )═C(R 9 )NO 2 , C 1-12  alkyl substituted with one or more of F, Cl, Br, I, OR 4 , SR 4 ; wherein R 5  is selected from H, C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl substituted with one or more of F, Cl, Br, I or OH, aryl, heteroaryl; R 6  and R 7 , are independently selected from H, optionally substituted C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy; R 8  and R 9  are independently selected from H, C 1-6  alkyl, F, Cl, Br, I, C 1-12  alkyl substituted with one or more of F, Cl, Br, I, OR 5 , SR 5 , N(R 6 , R 7 ); R 10 =H, optionally substituted C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl, aryl, heteroaryl; except when W is C═O, Q 1 =S, Q 2 =C, and G, J, L=H;  
 R 1  is selected from the group consisting of —NHC(═O)R 2 , N(R 3 , R 4 ), —NR 2 C(═S)R 3 , —NR 2 C(═S)SR 3 , wherein R 2  is hydrogen, C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl substituted with one or more of F, Cl, Br, I or OH; R 3 , R 4  are independently selected from hydrogen, C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl substituted with one or more of F, Cl, Br, I or OH;  
 U and V are independently selected from hydrogen, optionally substituted C 1-6  alkyl, F, Cl, Br, C 1-12  alkyl substituted with one or more of F, Cl, Br, I;  
 X is selected from C, CH, CH—S, CH—O and N;  
 Y and Z are independently selected from hydrogen, C 1-6  alkyl, C 3-12  cycloalkyl and C 0-3  bridging groups;  
 W is selected from the group CH 2 , CO, CH 2 NH, —NHCH 2 , —CH 2 NHCH 2 , —CH 2 —N(R 11 )CH 2 —, CH 2 (R 11 )N—, CH(R 11 ), S, CH 2 (CO), NH, O, N(R 11 ), (CO)CH 2 , N(R 11 )CON(R 11 ), N(R 11 )C(═S)N(R 11 ), SO 2 , SO, wherein R 11  is hydrogen, optionally substituted C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl, C 1-6  alkylcarbonyl, C 1-6  alkylcarboxy, aryl, heteroaryl;  
 n is an integer ranging from 0 to 3.  
 
     
     
         2 . The compound of Formula I according to  claim 1  wherein ring C is four to eight membered in size or the larger size which have either two or three carbon atoms between each nitrogen atom, comprising of  
       
         
           
           
               
               
           
         
       
       or ring C is bridged to form a bicyclic system as shown below,  
       
         
           
           
               
               
           
         
       
       ring C is optionally substituted by Y and Z, independently selected from alkyl groups, cycloalkyl groups, fluoro group, carboxylic and corresponding esters, amides, substituted alkyls or bridging alkyl groups which are as shown below:  
       
         
           
           
               
               
           
         
       
       the five or six membered ring C (when X is —CH—(NHR), or >CCH 2 (NHR—) is selected from the group consisting of the following rings,  
       
         
           
           
               
               
           
         
       
       and the bicyclic bridged ring C is selected from the group consisting of the following rings,  
       
         
           
           
               
               
           
         
       
     
     
         3 . The compound of Formula I according to  claim 1  wherein ring D is selected from the group consisting of furanyl, thienyl, pyrrolyl and pyrazolyl.  
     
     
         4 . The compound of Formula I according to  claim 1  wherein Q 1 =NR 11  and Q 2 =N shown as Formula II below  
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of Formula II according to  claim 4  selected from the group consisting of: 
 (S)-N-[[3-[3-Fluoro-[N-1-[4-{3-pyrazolecarbonyl-(4-nitro)}]piperazinyl]phenyl-]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{3-pyrazolecarbonyl-(5-nitro)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide.  
 
     
     
         6 . The compound of Formula I according to  claim 1  wherein Q 1 =NR 11  and Q 2 =C shown as Formula III below,  
       
         
           
           
               
               
           
         
       
     
     
         7 . The compound of Formula III according to  claim 6  selected from the group consisting of: 
 (S)-N-[[-[3-Fluoro-4-[N-1-[4-{2-pyrrole-(1-methyl-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-pyrrole-(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide  
 
     
     
         8 . The compound of Formula I according to  claim 1  wherein Q 1 =S and Q 2 =C shown as Formula IV below,  
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of Formula IV according to  claim 8  selected from the group consisting of: 
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophen-(4-nitro)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl-(5-nitro)}]homopiperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[1-{2-thiophenyl-(5-nitro)}-1-ethyl]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[2-methyl-4-{2-thiophenoyl-(5-nitro)}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-(3-Fluoro-4-[4-{N-ethyl-2-thiophenoyl-(5-nitro)}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1,{3-{[N-methyl)[N-{2-thiophenoyl(5-nitro)}]amino pyrrolidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 
     
     
         10 . The compound of Formula I according to  claim 1  wherein Q 1 =O and Q 2 =C shown as Formula V below,  
       
         
           
           
               
               
           
         
       
     
     
         11 . The compound of Formula V according to  claim 10  selected from the group consisting of: 
 (S)-N-[[3-[3-Fluoro-4-[N-1-[-4-{2-furoyl-(3-methyl)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furoyl-(3-methyl-5-nitro)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[1-{2-furyl-(5-nitro)}]ethyl]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,  
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-difluoroacetamide,  
 (S)-N-[[3-[-Fluoro-4-[4-[N-2-furyl-(5-nitro)methyl}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide  
 
     
     
         12 . A compound selected from the group consisting of: 
 (S)-N-[[3-[3-Fluoro-4-[N-1-[4-(2-furyl-carbonylmethyl)]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-(2-thiophenoyl-methyl)]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl{5-(4-chloro-2-nitro-)-phenyl}methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophen-(4-bromo-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-(3-methyl-5-nitro)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[(3-[3-Fluoro-4-[N-1-[4-{2-thiophene-(4-cyano-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-(5-(4-chloro)phenyl)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl],    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{3-furyl(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-(4-bromo)phenyl)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-methyl)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-(3-Fluoro-4-[N-1-[4-{2-pyrrole-(1-methyl-4-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-(3-Fluoro-4-N-1-[4-{2-pyrrole-(1-methyl-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-pyrrole-(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophen-(4-nitro-)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-(5-methoxy)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-{5-O-(2-nitro-4-fluoro-phenyloxy)}methyl]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-chloro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{3-furyl(2-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophen-(4-dimethylamino-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophene-(4-morpholino-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-(5-methylsulphonyl-)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-(4-nitro)-phenyl)-methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-(3-nitro-)phenyl-)methyl}]piperazinyl]phenyl]2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2-furyl(5-(2-nitro)-phenyl)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4[N-1-[4-{2-Furyl-4-bromo-(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4[N-1-4-{2-Furyl-(4-isopropyl)methyl}]piperazinyl]phenyl]2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4[N-1-[4-{2-Furyl-4-isopropyl-(5-nitro)methyl}]piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[2-furoyl-(5-methoxy)methyl]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl-(5-acetamido)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{3-pyrazolecarbonyl-(4-nitro)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{3-pyrazolecarbonyl(5-nitro)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-4-{2-thiophenoyl-(5-tert-butoxy-carboxamido)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl}acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl(5-trifuoroacetamido)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl],    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl(5-amino)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furoyl{5-(4-chloro-2-nitro-)-phenyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl],    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furoyl-(3-methyl)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furoyl-(3-methyl-5-nitro)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl-(4-dimethylamino-5-nitro)}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-Furoyl-(5-nitro)acrylic}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl-(5-nitro)acrylic}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    Iodide (S)-N-[[3-[3-Fluoro-4-[N-1-[4-N-methyl-4-{2-furyl-(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-fluoroacetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophen(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]fluoroacetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophen(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]difluoroacetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]difluoroacetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]monochloroacetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[2-thiophenyl-5-nitro)methyl}],    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[2-thiophenyl-4-bromo-(5-nitro)methyl}]piperazinyl]-phenyl]2-oxo-5-oxazolidinyl]methyl]monochloroacetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1[4-[2-thiophenyl-(5-nitro)methyl}]piperazinyl]phenyl]2-oxo-5-oxazolidinyl]methyl]-2-chloropropionamide,    (S)-N-[[3-[3-Fluoro-4-[N-1[4-[2-Furyl-(5-nitro)methyl}]piperazinyl]-phenyl]2-oxo-5-oxazolidinyl]methyl]-2-chloropropionamide,    (S)-N-[[3-[3-Fluoro-4-[N-1[4-[2-thiophenyl-4-bromo-(5-nitro)methyl}]piperazinyl]-phenyl]2-oxo-5-oxazolidinyl]methyl]-2-chloropropionamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-furyl-(5-nitro)methyl}]homopiperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-{4-(3-furoyl)}homopiperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophenoyl-(5-nitro)}]homopiperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-[[3-[3-Fluoro-4-[N-1-[4-{2-furoyl(5-nitro)}]homopiperazinyl]phenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-{2-methyl-4-(t-butoxycarbonyl)}piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2-methyl-4-{2-thiophen-(5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2-methyl-4-{2-furyl(5-nitro)methyl}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2-methyl-4-{2-furoyl(5-nitro)}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2-methyl-4-{2-thiophenoyl-(5-nitro)}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-{2-furoyl-}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-{2-furyl-(5-formyl)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-{2-furyl-(5-nitro)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-{2-furyl-(5-hydroxymethyl)methyl-}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-{2-furyl-(aldoxime)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-(2-thienylacetyl)]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[2,6-dimethyl-4-{2-furyl-(5-cyano)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[3-methyl-4-{2-thienylacetyl-}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[3-methyl-4-{2-furoyl-(5-nitro)}]-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[3-methyl-4-{2-thienoyl-(5-nitro)}]-piperazinyl]phenyl-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{3-methyl-2-furyl-(5-formyl)methyl-}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-acetyl-N-2-furyl-(5-nitro)methyl-}]aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[{3-methyl-4-(N-methyl-N-thiophenacetyl-)}aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[[3-methyl-4-{N-methyl-2-furoyl(5-nitro)}]aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[[3-methyl-4-{N-methyl-2-thienoyl-(5-nitro)}]aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[{3-methyl-4-(N-methyl-N-2-furoyl)}-aminopiperidine-1-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[[3-methyl-4-{N-methyl-N-2-furyl(5-nitro)}]aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[[3-methyl-4-{N-methyl-N-2-thienyl-(5-nitro)}]aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-ethyl-2-thienoyl-(5-nitro)}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-ethyl-2-furoyl-(5-nitro)}aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-ethyl-N-2-furoyl}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-ethyl-N-2-thiophenacetyl}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-ethyl-N-2-thiophenyl-(5-nitro)methyl}aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-thienyl-(5-nitro)methyl}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{2-furyl-(5-nitro)methylene}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-2-furyl-(5-nitro)methyl}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-methyl-N-2-pyrrole-(5-nitro)methyl}aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-methyl-N-2-furyl-(5-acetoxymethyl)methyl}aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-{N-methyl-N-2-furoyl-(5-nitro)}-aminopiperidine-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1,3-[N-methyl[N-{2-thiophenyl-(5-nitro)methyl}]aminopyrodinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1,{3-[[N-methyl)[N-{2-thiophenoyl(5-nitro)}]aminopyrrolidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-{[3-[3-Fluoro-4[N-1[3-{(N-methyl)[N-2-furoyl(5-nitro)}]aminopryrolidinyl]phenyl]2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1[4-{N-methyl)-N-2-furyl-(5-nitro)-methyl}]aminomethylpiperidine-1-yl]-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[4-N-1(N-methyl){N-2-thiophenyl-(5-nitro)-methyl}]aminomethylpiperidine-1-yl]-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-{N-1[4-N-methyl)-N-2-furoyl(5-Nitro)-methyl}]aminomethylpiperidine-1-yl]-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-{3-Fluoro-4-(3-oxopiperidin-1-yl)-phenyl}-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[3-{3-Fluoro-4-[N-1-[3-N-methyl]-N-2-furyl(5-nitro)methyl}]aminopiperidinyl]-phenyl]2-oxo-5-oxazolidinyl]methyl]acetamidezolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[3-{2-furyl-(5-nitro)-methylene}aminomethyl]-3-azabiyclo(3.1.0)hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4[N-1[3N-2-furyl-(5-nitro)methyl}-aminomethyl]-3-azabicyclo[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[1-{2-thiophenyl-(5-nitro)}-1-ethyl]]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-[1-{2-furyl-(5-nitro)}-1-ethyl]]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophene-(4-(4-t-butoxycarbonyl)piperazinyl-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophene-(4N-piperazinyl-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    (S)-N-[[3-[3-Fluoro-4-[N-1-[4-{2-thiophene-(4-(4-methyl)piperazinyl-5-nitro)methyl}]piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide,    
     
     
         13 . A pharmaceutical composition comprising the compound of  claim 1  or  12  and a pharmaceutical acceptable carrier, diluent, excipient or solvate.  
     
     
         14 . A pharmaceutical composition comprising a pharmaceutically effective amount of a compound according to claims  1  or  12 , or a physiologically acceptable acid additional salt thereof with a pharmaceutically acceptable carrier for treating microbial infections.  
     
     
         15 . A method of treating or preventing microbial infection in a mammal comprising administering to said mammal the pharmaceutical composition according to  claim 14 .  
     
     
         16 . A process for preparing a compound of Formula I,  
       
         
           
           
               
               
           
         
       
       and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxide, polymorphs, pharmaceutically acceptable solvates prodrugs or metabolites, wherein 
 ring D is a five membered heterocyclic ring;  
 ring C is four to eight membered in size or larger which has either two or three carbon atoms between each nitrogen atoms or ring C is a bridged bicyclic system and is optionally substituted by the substients Y and Z independently selected from alkyl groups, cycloakyl groups, fluoro group, carboxylic groups and corresponding esters or amides;  
 Q 1  is selected from O, S, NR 11 ;  
 Q 2  is selected from N or C;  
 G, J, L are independently selected from H, C 1-6  alkyl, F, Cl, Br, I, N, —CN, COR 5 , COOR 5 , N(R 6 , R 7 ), NHCOC(R 5 , R 8 , R 9 ), —NHCOOR 5 , CON(R 6 , R 7 ), CH 2 NO 2 , NO 2 , CH 2 R 8 , CHR 9 , —CH═N—OR 10 , —C═CH—R 5 , OR 5 , SR 5 , —C(R 9 )═C(R 9 )NO 2 , C 1-12  alkyl substituted with one or more of F, Cl, Br, I, OR 4 , SR 4 ; wherein R 5  is selected from H, C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl substituted with one or more of F, Cl, Br, I or OH, aryl, heteroaryl; R 6  and R 7 , are independently selected from H, optionally substituted C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy; R 8  and R 9  are independently selected form H, C 1-6  alkyl, F, Cl, Br, I, C 1-12  alkyl substituted with one or more of F, Cl, Br, I, OR 5 , SR 5 , N(R 6 , R 7 ); R 10 =H, optionally substituted C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl, aryl, heteroaryl; except when W is C═O, Q 1 =S, Q 2 =C, and G, J, L=H;  
 R 1  is selected from the group consisting of —NHC(═O)R 2 , N(R 3 , R 4 ), —NR 2 C(═S)R 3 , —NR 2 C(═S)SR 3 , wherein R 2  is hydrogen, C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl substituted with one or more of F, Cl, Br, I or OH; R 3 , R 4  are independently selected from hydrogen, C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl substituted with one or more of F, Cl, Br, I or OH;  
 U and V are independently selected from hydrogen, optionally substituted C 1-6  alkyl, F, Cl, Br, C 1-12  alkyl substituted with one or more of F, Cl, Br, I,  
 X is selected from C, CH, CH—S, CH—O and N;  
 Y and Z are independently selected from hydrogen, C 1-6  alkyl, C 3-12  cycloalkyl and C 0-3  bridging groups;  
 W is selected from the group CH 2 , CO, CH 2 NH, —NHCH 2 , —CH 2 NHCH 2 , —CH 2 —N(R 11 )CH 2 —, CH 2 (R 11 )N—, CH(R 11 ), S, CH 2 (CO), NH, O, N(R 11 ), (CO)CH 2 , N(R 11 )CON(R 11 ), N(R 11 )C(═S)N(R 11 ), SO 2 , SO, wherein R 11  is hydrogen, optionally substituted C 1-12  alkyl, C 3-12  cycloalkyl, C 1-6  alkoxy, C 1-6  alkyl, C 1-6  alkylcarbonyl, C 1-6  alkylcarboxy, aryl, heteroaryl;  
 n is an integer ranging from 0 to 3;  
 which comprises reacting an amine compound of Formula VI  
                     
 with a heterocyclic compound of Formula VII  
                     
 wherein Q 1 , Q 2 , G, J, L, W, X Y, Z, U, V, R 1  and n are the same as defined above and M 1  in amine of Formula VI is defined as NH, CH(NHR 13 ), CH—CH 2 NHR 13 , CCH 2 NHR 13  wherein R 13  is H, methyl, ethyl, isopropyl, acetyl, cyclopropyl, alkoxy or acetyl;  
 R 12  is a suitable leaving group or suitable functional group.  
 
     
     
         17 . The process according to  claim 16  wherein the suitable leaving group R 12  is selected from the group comprising of fluoro alkyl, chloro alkyl, bromo alkyl SCH 3 , —SO 2 CH 3 , —SO 2 CF 3  and OC 6 H 5 .  
     
     
         18 . The process according to  claim 16  wherein the suitable functional group is carboxaldehyde or carboxylic acid.  
     
     
         19 . The process according to  claim 16  for preparing a compound of Formula I wherein reaction of compounds of Formula VI and VII is carried out in a suitable solvent selected from the group consisting of N,N-dimethylformamide, dimethylacetamide, dimethylsulfoxide, ethanol and ethylene glycol.  
     
     
         20 . The process according to  claim 19  wherein the reaction is carried out in the presence of a base selected from the group consisting of triethylamine, diisopropylamine, potassium carbonate and sodium carbonate.  
     
     
         21 . The process according to  claim 16  for preparing a compound of Formula I wherein a compound of Formula VII is a heterocyclic aldehyde.  
     
     
         22 . The process according to  claim 16  wherein the reductive amination of the compound of Formula VI with the heterocyclic aldehyde of Formula VII is performed with a reducing agent selected from the group consisting of sodium triacetoxyborohydride and sodium cyanoborohydride to give a compound of Formula I wherein W=CH 2 .  
     
     
         23 . The process according to  claim 16  wherein the compound of Formula VII is a heterocyclic carboxylic acid.  
     
     
         24 . The process according to  claim 16  wherein the reaction of amine of Formula VI with carboxylic acid of Formula VII is carried out in the presence of a suitable condensing agent.  
     
     
         25 . The process according to  claim 24  wherein the suitable condensing agent is selected from the group consisting of 1,3-dicyclohexylcarbodiimide (DCC) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC).  
     
     
         26 . The process according to  claim 16  for preparing a compound of Formula I wherein the compounds of Formula I having carbonyl link are prepared by reacting heteroaromatic compound of Formula VII with a compound of Formula VI is in the presence of triphosgene and phosgene.  
     
     
         27 . The process according to  claim 22  wherein compound of Formula VII is N-methyl pyrrole.  
     
     
         28 . The process according to  claim 16  for preparing a compound of Formula I wherein W=CO comprising reacting 3-bromothiophene (Formula VII) and amine of Formula VI with carbon monoxide.  
     
     
         29 . The process according to  claim 16  for preparing a compound of Formula I  
       
         
           
           
               
               
           
         
       
       when G=R 15  shown as Formula IX  
       
         
           
           
               
               
           
         
       
       wherein R 15  is a subset of G comprising of amine and acetamide,  
       comprising converting compound of Formula VIII (Formula I, when G=R 14  wherein R= 14  is also a subset of G comprising carbamate)  
       
         
           
           
               
               
           
         
       
       to a compound of Formula IX (Formula I, when G=R 15 ).  
     
     
         30 . The process according to  claim 16  for preparing a compound of Formula I when G=NHCOCF 3 , Q 1 =S, Q 2 =C, G=J=L=H, W=CO, X=N, Y=Z=H, n=1, U=H, V=F, R 1 =NHCOCH 3 ) shown as Formula XI  
       
         
           
           
               
               
           
         
       
       comprising reacting compound of Formula X with trifluoroacetic acid.  
       
         
           
           
               
               
           
         
       
     
     
         31 . The process according to  claim 16  for preparing a compound of Formula I when G=NH 2 , Q 1 =S, Q 2 =C, G=J=L=H, W=CO, X=N, Y=Z=H, n=1, U=H, V=F, R 1 =NHCOCH 3 ) shown as Formula XII  
       
         
           
           
               
               
           
         
       
       comprising reacting compound of Formula X  
       
         
           
           
               
               
           
         
       
       with trifluoroacetic acid followed by potassium carbonate in a suitable solvent.