Cephalosporin compositions and methods of manufacture

Abstract

Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising the conversion of a protected 7-amino group into a 7-carboxamide moiety in a single step.

1 - 13 . (canceled) 
     
     
         14 . A composition comprising a compound of formula (V), or a salt thereof, selected from the compounds of Table 2, or salts thereof, prepared according to the method of claim  5 . 
     
     
         15 . The composition of  claim 14 , comprising:
 (a) the compound of formula (V-1), or a salt thereof:   
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (b) the compound of formula (V-2), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (c) the compound of formula (V-3), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (d) the compound of formula (V-5), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (e) the compound of formula (V-6), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (f) the compound of formula (V-9), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (g) the compound of formula (V-26), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof; or
 (h) the compound of formula (V-16), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       and 0.3-0.5% of one or more compound selected from: 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and 
       
         
           
           
               
               
           
         
       
       or a salt thereof. 
     
     
         16 . A method of treating a bacterial infection in a patient, comprising the step of administering to the patient a composition of  claim 15 . 
     
     
         17 . A composition comprising two or more compounds selected from the group consisting of:
 the compound of formula (II-1), or a salt thereof   
       
         
           
           
               
               
           
         
         the compound of formula (III-1), or a salt thereof 
       
       
         
           
           
               
               
           
         
         the compound of formula (IIc), or a salt thereof 
       
       
         
           
           
               
               
           
         
         the compound of formula (IV-1), or a salt thereof 
       
       
         
           
           
               
               
           
         
       
       and the compound of formula (IVb), or a salt thereof 
       
         
           
           
               
               
           
         
       
     
     
         18 . The composition of  claim 17 , further comprising the compound having the structure: 
       
         
           
           
               
               
           
         
       
       or a salt thereof. 
     
     
         19 . A compound selected from formula (III-1) and formula (IV-1): 
       
         
           
           
               
               
           
         
       
     
     
         20 - 21 . (canceled)