Melatonin derivatives and medicine containing same

Abstract

The invention concerns melatonin derivatives of formula (I) wherein: R 1 represents H, a C 1 -C 4 alkyl group or a C 1 -C 4 alkoxy group; R 2 represents H or a C 1 -C 4 alkyl group; R 3 represents H, methyl or a halogen atom; R 4 , R 5 represent individually H or a halogen atom; R 6 represents H or a C 1 -C 4 alkyl group, or a pharmaceutically acceptable salt thereof. The invention also concerns a medicine comprising said derivatives.

1 . Melatonin derivative of formula:  
       
         
           
           
               
               
           
         
         in which: 
 R 1  represents H, a C 1  to C 4  alkyl group or a C 1  to C 4  alkoxy group,  
 R 2  represents H or a C 1  to C 4  alkyl group,  
 R 3  represents H, methyl or a halogen atom,  
 R 4  and R 5  individually represent H or a halogen atom,  
 R 6  represents H or a C 1 -C 4  alkyl group, or a pharmaceutically acceptable salt of the latter.  
 
       
     
     
         2 . Melatonin derivative according to  claim 1 , characterized in that R 2 =H, R 6 =CH 3  and R 1 =CH 3 .  
     
     
         3 . Melatonin derivative according to  claim 2  of formula:  
       
         
           
           
               
               
           
         
         N1-nitrosomelatonin (Niomel)  
       
     
     
         4 . Melatonin derivative according to one of  claims 1  to  3 , for its application as therapeutically active substance.  
     
     
         5 . Melatonin derivative according to one of claims  1  to 3, for its application as therapeutically active substance in the treatment of cardiovascular diseases, ischemia reperfusion injuries, parasitic diseases, inflammatory diseases, neurodegenerative diseases, in particular Alzheimer's disease, myopathies or falciform anemias.  
     
     
         6 . Pharmaceutical composition, characterized in that it comprises a melatonin derivative of formula I and an active pharmaceutical excipient.  
     
     
         7 . Process for the preparation of a melatonin derivative according to  claim 1 , characterized in that a precursor of formula:  
       
         
           
           
               
               
           
         
         in which R 1  to R 6  have the same meanings as in  claim 1 ,  
         is brought into contact, in protic organic solution, with an aqueous sodium nitrite solution and then the mixture is basified, so as to obtain a derivative according to one of  claims 1  to  3 .