Xanthine Oxidase Inhibitor

Abstract

The invention relates to compounds of the following formula (I) or their salts: in which R 1 represents OR 4 or others, in which R 4 is an alkyl group having 1-8 carbon atoms which may have a substituent or the like; R 2 is halogen, nitro, cyano, carboxyl, or the like; R 3 is hydrogen, halogen, hydroxyl, amino, carboxyl, or the like; X is NR 11 , oxygen, or sulfur, in which R 11 is hydrogen, or an alkyl group having 1-8 carbon atom which may have a substituent; and each of Y and Z is CR 12 or nitrogen, in which R 12 has the same meaning as R 3 above, and a xanthine oxidase inhibitor containing the compound as an active ingredient.

1 . Compounds of the following formula (I) or salts thereof  
     
       
         
         
             
             
         
       
       in which  
       R 1  represents an alkyl group having 1-8 carbon atoms, an alkyl group substituted  
       with 1-3 halogen atoms, OR 4 , CO 2 R 5 , or S(O),  n R 6 ; wherein R 4  is hydrogen, or an alkyl group having 1-8 carbon atoms, an aralkyl group having an aryl moiety of 6-10 carbon atoms and an alkyl moiety of 1-4 carbon atoms, an alkylcarbonyl group having 2-9 carbon atoms, an arylcarbonyl group having an aryl moiety of 6-10 carbon atoms, an aralkylcarbonyl group having an aryl moiety of 6-10 carbon atoms and an alkylcarbonyl moiety of 2-5 carbon atoms or an aryl group having 6-10 carbon atoms which may have a substituent selected from the group consisting of halogen, hydroxyl, nitro and cyano; each of R 5  and R 6  is hydrogen or an alkyl group having 1-8 carbon atoms, an aralkyl group having an aryl moiety of 6-10 carbon atoms and an alkyl moiety of 1-4 carbon atoms, or an aryl group having 6-10 carbon atoms which may have a substituent selected from the group consisting of halogen, hydroxyl, nitro, cyano and amino; and n is an integer of 0 to 2;  
       R 2  is hydrogen, halogen, nitro, cyano, formyl, an alkyl group having 1-8  
       carbon atoms, an alkyl group having 1-8 carbon atoms which is substituted with one to three halogens, or CO 2 R 7  wherein R 7  has the same meaning as R 5  above;  
       R 3  is hydrogen, halogen, hydroxyl, amino, CO 2 R 8 , PO 3 H, PO(OH)(OR′),  
       S(O) m R 10 , or an alkyl group having 1-8 carbon atoms or an alkylaminocarbonyl group having alkyl of 1-8 carbon atoms which may have a substituent selected from the group consisting of halogen, hydroxyl, nitro, cyano and amino; wherein each of R 8 , R 9 , and R 10  has the same meaning as R 5  above; m has the same meaning as n above;  
       X is NR 11 , oxygen, or sulfur, wherein R 11  is hydrogen, or an alkyl group having  
       1-8 carbon atom which may have a substituent selected from the group consisting of halogen, hydroxyl, nitro, cyano and amino; and  
       each of Y and Z is CR 12  or nitrogen, wherein R 12  has the same meaning as R 3  above.  
     
   
   
       2 . The compounds or salts thereof according to  claim 1 , wherein R 1  is OR 4 .  
   
   
       3 . The compounds or salts thereof according to  claim 1 , wherein R 1  is an alkoxy group having 1-5 carbon atoms.  
   
   
       4 . The compounds or salts thereof according to  claim 1 , wherein R 1  is isobutoxy.  
   
   
       5 . The compounds or salts thereof according to one of claims  1 - 4 , wherein R 2  is nitro, cyano, halogen, or carboxyl.  
   
   
       6 . The compounds or salts thereof according to one of claims  1 - 4 , wherein R 2  is nitro or cyano.  
   
   
       7 . The compounds or salts thereof according to one 10 of claims  1 - 6 , wherein R 3  is hydrogen, amino, hydroxyl, halogen, or carboxyl.  
   
   
       8 . The compounds or salts thereof according to one of claims  1 - 7 , wherein X is NH or oxygen, and each of Y and Z are nitrogen.  
   
   
       9 . The compounds or salts thereof according to one of claims  1 - 7 , wherein X is sulfur, oxygen, or NH, Y is CH, C—OH, or C—CO 2 H, and Z is CH.  
   
   
       10 . The compounds or salts thereof according to one of claims  1 - 7 , wherein X is NH, and one of Y and Z is nitrogen and other is CH.  
   
   
       11 . A xanthine oxidase inhibitor containing as an active ingredient the compound or a salt thereof according to one of claims  1 - 10 .  
   
   
       12 . An agent for treating hyperuricemia containing as an active ingredient the compound or a salt thereof according to one of claims  1 - 10 .