Derivatives of porphyrins, their process of preparation and their use for treating viral infections

Abstract

The present application provides metallated porphyrin derivatives as ligands of G-quadruplex and their novel use as anti-viral agents. More specifically, this application is related to the use of porphyrin derivatives as G-quadruplex ligands to inhibit viral infections, such as HIV, more particularly to inhibit HIV-1 replication cycle.

1 . A compound of formula (IA): 
       
         
           
           
               
               
           
         
       
       wherein:
 in Formula (IA) - - - represents an optionally present single bond; 
 M represents H 2 , Cobalt (Co), Manganese (Mn) or a Nickel (Ni) atom ; 
 A − represents a counter anion; and 
 
       
         
           
           
               
               
           
         
       
       wherein - - - represents the attachment of X to the phenyl groups in Formula (IA). 
     
     
         2 . The compound according to  claim 1  wherein X represents 
       
         
           
           
               
               
           
         
       
       and M represents a Manganese atom. 
     
     
         3 . The compound of formula (IA) according to  claim 1 , wherein A − represents a halogen ion. 
     
     
         4 . The compound according to  claim 1 , wherein A − is Cl − . 
     
     
         5 . A pharmaceutical composition comprising the compound according to  claim 1 , and at least one pharmaceutically acceptable excipient. 
     
     
         6 . A process for the preparation of the compound according to  claim 1  comprising reacting a compound of formula (II) 
       
         
           
           
               
               
           
         
       
       wherein X is defined as in  claim 1 , and wherein B − represents a counter anion;
 with a gold-containing complex. 
 
     
     
         7 . The process according to  claim 6  wherein the counter anion is trifluoroacetate. 
     
     
         8 . The process according to  claim 6  wherein the gold-containing complex is a complex of formula (III):
   KAu III   A   4   (III)
 
 
       wherein A represents a counter anion.