Novel antibacterial agents

Abstract

This invention relates to novel macrolides, to the preparation of novel macrolides, to the use of such novel macrolides preventing, treating, or ameliorating various conditions, and to the use of such novel macrolides as antibacterial agents.

1 .- 17 . (canceled) 
     
     
         18 . A compound of the formula 
       
         
           
           
               
               
           
         
       
       or a salt thereof, wherein:
 Macrolide is an antibiotic or antibiotic scaffold; 
 A is CH 2 , C(O), C(O)O, C(O)NH, S(O) 2 , S(O) 2 NH, or C(O)NHS(O) 2 ; 
 B is alkylene or unsaturated alkylene; and 
 C is hydrogen; or C is hydroxy, alkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, or heteroarylheteroalkyl, each of which is optionally substituted. 
 
     
     
         19 . The compound of  claim 18  wherein A is CH 2 . 
     
     
         20 . The compound of  claim 18  wherein B is (CH 2 ) n , where n is 0 to  10 . 
     
     
         21 . The compound of  claim 18  wherein B is (CH 2 ) n , where n is 1 to 10. 
     
     
         22 . The compound of  claim 18  wherein B is (CH 2 ) n , where n is 3 to 5. 
     
     
         23 . The compound of  claim 18  wherein B is (CH 2 ) 3 . 
     
     
         24 . The compound of  claim 18  wherein C is optionally substituted aryl. 
     
     
         25 . The compound of  claim 18  wherein C is optionally substituted arylalkyl. 
     
     
         26 . A process for preparing a compound of the formula 
       
         
           
           
               
               
           
         
       
       or a salt thereof;
 the process comprising contacting a compound of the formula
   Macrolide-A-B-N 3    
 
 
       with a compound of the formula
   H═C
 
 
       and a copper catalyst;
 wherein Macrolide is an antibiotic or antibiotic scaffold; A is CH 2 , C(O), C(O)O, C(O)NH, S(O) 2 , S(O) 2 NH, or C(O)NHS(O) 2 ; B is alkylene or unsaturated alkylene; 
 and C is hydrogen; or C is hydroxy, alkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, or heteroarylheteroalkyl, each of which is optionally substituted. 
 
     
     
         27 . A process for preparing a compound of the formula 
       
         
           
           
               
               
           
         
       
       or a salt thereof;
 the process comprising contacting a compound of the formula
   Macrolide-A-B-H 
 
 with a compound of the formula
   N 3 —C
 
 
 
       and a copper catalyst;
 wherein Macrolide is an antibiotic or antibiotic scaffold; A is CH 2 , C(O), C(O)O, C(O)NH, S(O) 2 , S(O) 2 NH, or C(O)NHS(O) 2 ; B is alkylene or unsaturated alkylene; and C is hydrogen; or C is hydroxy, alkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, or heteroarylheteroalkyl, each of which is optionally substituted.