Phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings

Abstract

A process for preparing a compound of the formula I: or pharmaceutical acceptable salts thereof wherein X is —NR 1 —, —S(O) g —, or —O—; R 1 is —H, C 1-6 alkyl optionally substituted with one or more —OH, —CN, or halo, or R 1 is —(CH 2 ) h -aryl, —COR 1-1 , —COOR 1-2 , —CO—(CH 2 ) h —COR 1-1 , C 1-6 alkyl sulfonyl, —SO 2 —(CH 2 ) h -aryl, or —(CO) i -Het; R 2 is —H, C 1-6 alkyl, —(CH 2 ) h -aryl, or halo; R 3 and R 4 are the same or different and are —H or halo; R 5 is —H, C 1-12 alkyl optionally substituted with one or more halo, C 3-12 cycloalkyl, C 1-6 alkoxy. The compounds are useful antimicrobial agents.

1 - 18 . (canceled)  
     
     
         19 . A compound of formula VI as an intermediate for preparing oxazolidinones useful as antimicrobial agents  
       
         
           
           
               
               
           
         
         wherein X 2  is —NH—, protected —NH—, —S(O) g —, or —O—;  
         R 2  is H, OH or C 1 alkyl;  
         R 3  and R 4  are independently H or halo;  
         B is NH 2 , protected NH 2 , N 3 , or —OSO 2 C 1-4  alkyl;  
         the dotted line   in the ring system is a single or a double bond;  
         G is 0, 1, or 2; m is 0, 1, 2, 3, 4, or 5; n is 0, 1, 2, 3, 4, or 5; and with the proviso that m and n taken together are 1, 2, 3, 4 or 5.  
       
     
     
         20 . A compound of formula VI of  claim 19  which is an optically pure enantiomer having the S-configuration at C5 of the oxazolidinone ring as shown below:  
       
         
           
           
               
               
           
         
       
     
     
         21 . A compound of formula VI of  claim 20  wherein 
 X 2  is —NH—, protected —NH—, —S(O) g —, or —O—;    R 2  is H or OH;    R 3  and R 4  are independently H or F;    B is, NH 2 , N 3 , or —OSO 2 C 1-4  alkyl.    
     
     
         22 . A compound of formula VI as an intermediate for preparing oxazolidinones useful as antimicrobial agents  
       
         
           
           
               
               
           
         
         wherein X 2  is —NH—, protected —NH—, —S(O) g —, or —O—;  
         R 2  is H, OH or C 1  alkyl;  
         R 3  and R 4  are independently H or halo;  
         B is NH 2 , protected NH 2 , N 3 , or —OSO 2 C 1-4  alkyl;  
         the dotted line   in the ring system is a single or a double bond;  
         G is 0, 1, or 2; and  
         m is 0 and n is 3; m is 1 and n is 2; or m is 3 and n is 0.  
       
     
     
         23 . A compound of formula VI of  claim 22  which is an optically pure enantiomer having the S-configuration at C5 of the oxazolidinone ring as shown below:  
       
         
           
           
               
               
           
         
       
     
     
         24 . A compound of formula VI of  claim 22  wherein 
 X 2  is —NH—, —S(O) g —, or —O—;    R 2  is H or OH;    R 3  and R 4  are independently H or F;    B is NH 2 , N 3 , or —OSO 2 C 1-4  alkyl.    
     
     
         25 . A compound of  claim 19  wherein B is NH 2 , protected NH 2 , N 3 , or —OSO 2 C 1-4 alkyl.