Aminoquinoline derivatives and their use as adenosine a3 ligands

Abstract

The present invention relates to an adenosine A 3 receptor ligand of the general formula (VI″), (VII″) and (VIII″) and their preparation.

1 . A compound of formula (VI″): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 4″  and R 5″  independently stand for hydrogen atom,
 C 3-6  cycloalkyl, straight or branched C 1-4  alkyl, each of which is optionally substituted by a hydroxy, a carboxy, straight or branched C 1-4  alkoxy, amino, or amino substituted with one or two straight or branched C 1-4  alkyl, 
 or protective group; 
 
 R 4″  stands for hydrogen atom or a straight or branched C 1-4  alkyl or a benzyl, and 
 R 5″  stands for hydrogen atom, —SO 2 OH, straight or branched C 1-4  acyl or protective group, or 
 R 4″  and R 5′  taken together with the nitrogen atom to which they are attached form a group of the general formula a″.) 
 
       
         
           
           
               
               
           
         
         R 7″  and R 8″  independently stand for hydrogen atom, straight or branched C 1-4  alkyl or C 3-6  cycloalkyl; 
         Z″ stands for oxygen atom, sulphur atom, —CHR 10″ — or —NR 11″ —; 
         R 10″  stands for hydrogen atom, straight or branched C 1-4  alkyl, or C 3-6  cycloalkyl; 
         R 11″  stands for hydrogen atom, straight or branched C 1-4  alkyl, C 3-6  cycloalkyl, —SO 2 OH, straight or branched C 1-4  acyl or protective group; 
         m″ represents 1, 2, or 3; 
         o″ represents 1, 2, or 3; 
         p″ represents zero or 1; and 
         r″ represents zero or 1. 
       
     
     
         2 . A compound of formula (VII″): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 4″  and R 5″  independently stand for hydrogen atom,
 C 3-6  cycloalkyl, straight or branched C 1-4  alkyl, each of which is optionally substituted by a hydroxy, a carboxy, straight or branched C 1-4  alkoxy, amino, or amino substituted with one or two straight or branched C 1-4  alkyl, 
 or protective group; 
 
 R 4″  stands for hydrogen atom or a straight or branched C 1-4  alkyl or a benzyl, and 
 R 5″  stands for hydrogen atom, —SO 2 OH, straight or branched C 1-4  acyl or protective group, or 
 R 4″  and R 5′  taken together with the nitrogen atom to which they are attached form a group of the general formula a″.) 
 
       
         
           
           
               
               
           
         
         R 7″  and R 8″  independently stand for hydrogen atom, straight or branched C 1-4  alkyl or C 3-6  cycloalkyl; 
         Z″ stands for oxygen atom, sulphur atom, —CHR 10″ — or —NR 11″ —; 
         R 10″  stands for hydrogen atom, straight or branched C 1-4  alkyl, or C 3-6  cycloalkyl; 
         R 11″  stands for hydrogen atom, straight or branched C 1-4  alkyl, C 3-6  cycloalkyl, —SO 2 OH, straight or branched C 1-4  acyl or protective group; 
         m″ represents 1, 2, or 3; 
         o″ represents 1, 2, or 3; 
         p″ represents zero or 1; and 
         r″ represents zero or 1. 
       
     
     
         3 . A compound of formula (VIII″): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 4″  and R 5′  taken together with the nitrogen atom to which they are attached form morpholinyl, 4-methyl-piperazin-1-yl, piperazinyl, or 4-benzyl-piperzin-1-yl.