Gossypol derivatives, production method thereof and uses of same

Abstract

The present invention relates to compounds of general formula (1): in which, independently of each other, R 1 and R 2 represent: —OH, or —CH 2 —O—R 3 , or —CH 2 —S—R 3 , or R 3 , R 4 , R 5 and R 6 representing, independently of each other, —H or a carbon-containing group with 1 to 10 carbon atoms, saturated or unsaturated, optionally substituted with one or more heteroatomic groups. The invention also relates to pharmaceutical compositions containing these compounds, and their uses, in particular in the context of the treatment of cancer.

1 . A method of treating cancer, parasites, such as malaria, viruses or graft rejections, or for male contraception, comprising admininistering to a patient in need thereof a compound corresponding to the general formula (1) 
       
         
           
           
               
               
           
         
         in which, independently of each other, R 1  and R 2  represent: 
         —OH, or 
         —CH 2 —O—R 3 , or 
         —CH 2 —S—R 3 , or 
       
       
         
           
           
               
               
           
         
         R 3 , R 4 , R 5  and R 6  representing, independently of each other, —H or a carbon-containing group with 1 to 10 carbon atoms, saturated or unsaturated, optionally comprising one or more heteroatomic groups, or their pharmaceutically acceptable salts. 
       
     
     
         2 . The method according to  claim 1 , wherein said compound corresponds to the general formula (1), in which, independently of each other, R 3 , R 4 , R 5  and R 6  represent:
 —H, an alkyl group, a heteroalkyl group, such as a thioalkyl, a hydroxyalkyl, an aminoalkyl, a halogenoalkyl or an alkoxyalkyl, a cycloalkyl group, an alkenyl group, a heteroalkenyl group, an aryl group, a heteroaryl group, such as a thioaryl, a hydroxyaryl, an aminoaryl, a halogenoaryl or an alkoxyaryl or an arylalkyl group.   
     
     
         3 . The method according to  claim 1 , wherein said compound corresponds to the general formula (1), in which R 5  and R 6 , independently of each other, represent an alkyl group with 1 to 8 carbon atoms. 
     
     
         4 . The method according to  claim 1 , wherein said compound corresponds to the general formula (1), in which R 1  and R 2  are identical. 
     
     
         5 . The method according to  claim 1 , wherein said compound corresponds to the general formula (1), in which R 5  represents a methyl group and R 6  represents an isopropyl group. 
     
     
         6 . The method according to  claim 1 , wherein said compound corresponds to the general formula (2): 
       
         
           
           
               
               
           
         
         in which R 3  is as defined in  claim 1 . 
       
     
     
         7 . The method according to  claim 1 , wherein said compound corresponds to the general formula (3): 
       
         
           
           
               
               
           
         
         in which R 3  represents —H or a carbon-containing group with 1 to 10 carbon atoms, saturated or unsaturated, optionally comprising one or more heteroatomic groups. 
       
     
     
         8 . The method according to  claim 1 , wherein said compound corresponds to the following formula: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . A method of treating cancers, such as melanomas, colon cancers, lung cancers, glioblastomas, adenocarcinomas, prostate cancers or breast cancers, comprising administering to a patient in need thereof, compound (4): 
       
         
           
           
               
               
           
         
         and/or of the compound (14):