Pyridinylpyrazolopyrimidinone derivatives as pde 7 inhibitors

Abstract

To provide the compounds inhibiting PDE 7 selectively, and therefore, enhance cellular cAMP level. Consequently, the compound is useful for treating various kinds of disease such as allergic disease, inflammatory disease or immunologic disease. The compound is pyridinylpyrazolopyrimidinone compound represented by the following formula (IA) or (IB): especially, R 1 is cyclohexyl or cycloheptyl group, R 2 is methyl; R 3 is a group: —NR 5 R 6 or —S(O) 0-2 R 8 ; hydrogen atom; nitro group; cyano group; a halogen atom; heteroaryl group; and R 4 is methoxy or ethoxy group.

1 . Pyridinylpyrazolopyrimidinone derivative represented by the following formula (IA) or (IB):  
       
         
           
           
               
               
           
         
         wherein:  
         R 1  is a substituted or unsubstituted C 3 -C 8  cycloalkyl group or tert-butyl group;  
         R 2  is a hydrogen atom or C 1 -C 3  alkyl group;  
         R 3  is a group: —NR 5 R 1 , —C(=O)R 7  or —S(O) 0-2 R 8 ;  
         R 4  is a hydrogen atom or C 1 -C 3  alkoxyl group which is unsubstituted or substituted by one or more fluorine atom(s);  
         R 5  and R 6  are, same or different from each other, a hydrogen atom, substituted or unsubstituted C 1 -C 6  alkyl group, substituted or unsubstituted acyl group, substituted or unsubstituted heterocycloalkyl group, and substituted or unsubstituted heterocycloalkyl ring formed with a nitrogen atom which is binding R 5  and R 6 ;  
         R 7  is a group: —OR 9  or —NR 5 R 6 ;  
         R 8  is a hydrogen atom, a halogen atom, a group: —NR 5 R 6 , substituted or unsubstituted C 1 -C 6  alkyl group, or substituted or unsubstituted aryl group;  
         R 9  is a hydrogen atom or substituted or unsubstituted C 1 -C 6  alkyl group; or pharmaceutically acceptable salts or solvates thereof.  
       
     
     
         2 . The compound represented by the formula (IA) according to  claim 1 .  
     
     
         3 . The compound represented by the formula (IB) according to  claim 1 .  
     
     
         4 . The compound according to  claim 1 , in which R 1  is a cyclohexyl group or cycloheptyl group.  
     
     
         5 . The compound according  claim 1 , in which R 2  is a methyl group.  
     
     
         6 . The compound according to  claim 1 , in which R 4  is a methoxy or ethoxy group.  
     
     
         7 . The compound according to  claim 1 , in which R 3  is a group —NR 5 R 6 .  
     
     
         8 . A pharmaceutical composition comprising a compound according to  claim 1  or pharmaceutically acceptable salts or solvates thereof as active ingredient.  
     
     
         9 . A PDE 7 inhibitor comprising a compound according to  claim 1  or pharmaceutically acceptable salts or solvates thereof as active ingredient.