Fused cyclic compounds

Abstract

The present invention provides a compound represented by the formula (I): wherein each symbol is as defined in the description, or a salt thereof. The compound or a salt thereof or a prodrug thereof has a GPR40 receptor function modulating action and is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.

1 . A compound represented by the formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         R is R 6 —SO 2 — (wherein R 6  is a substituent) or an optionally substituted 1,1-dioxidotetrahydrothiopyranyl group; 
         X is a bond or a divalent hydrocarbon group; 
         R 2  and R 3  are the same or different and each is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; 
         R 4  and R 5  are the same or different and each is a C 1-6  alkyl group optionally substituted by hydroxy group(s); 
         ring A is a benzene ring optionally further having substituent(s) selected from a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted hydroxy group and an optionally substituted amino group; 
         ring B is a 5- to 7-membered ring; 
         Y is a bond or CH 2 ; and 
         R is an optionally substituted hydroxy group, 
         or a salt thereof. 
       
     
     
         2 . The compound of  claim 1 , wherein R 1  is R 6 —SO 2 — (wherein R 6  is a substituent). 
     
     
         3 . The compound of  claim 2 , wherein R 6  is a C 1-6  alkyl group. 
     
     
         4 . The compound of  claim 1 , wherein X is a C 1-6  alkylene group. 
     
     
         5 . The compound of  claim 1 , wherein R 2  and R 3  are the same or different and each is a hydrogen atom, a halogen atom or a C 1-6  alkyl group. 
     
     
         6 . The compound of  claim 1 , wherein R 4  and R 5  are the same or different and each is a C 1-6  alkyl group. 
     
     
         7 . The compound of  claim 1 , wherein ring A is an unsubstituted benzene ring. 
     
     
         8 . The compound of  claim 1 , wherein ring B is tetrahydrofuran. 
     
     
         9 . The compound of  claim 1 , wherein Y is CH 2 . 
     
     
         10 . The compound of  claim 1 , wherein R is a hydroxy group. 
     
     
         11 . The compound of  claim 1 , which is selected from
 [(3S)-6-({4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid,   [(3S)-6-({2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid,   [(3S)-6-({3′-fluoro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid,   [(3S)-6-({3′-chloro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid,   [(3S)-6-({3′,5′-dichloro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid, and   [(3S)-6-({2′,6′-diethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid.   
     
     
         12 . A prodrug of the compound of  claim 1 . 
     
     
         13 . A GPR40 receptor function modulator comprising the compound of  claim 1  or a prodrug thereof. 
     
     
         14 . A pharmaceutical agent comprising the compound of  claim 1  or a prodrug thereof. 
     
     
         15 . The pharmaceutical agent of  claim 14 , which is an agent for the prophylaxis or treatment of diabetes. 
     
     
         16 . A method for the prophylaxis or treatment of diabetes in a mammal, which comprises administering an effective amount of the compound of  claim 1  or a prodrug thereof to the mammal. 
     
     
         17 . Use of the compound of  claim 1  or a prodrug thereof for the production of an agent for the prophylaxis or treatment of diabetes. 
     
     
         18 . (6-Hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetic acid or a salt thereof. 
     
     
         19 . A production method of an optically active form of a compound represented by the formula (III): 
       
         
           
           
               
               
           
         
         wherein 
         Z is a halogen atom or an optionally substituted hydroxy group; and 
         R is an optionally substituted hydroxy group, 
         or a salt thereof, which comprises subjecting a compound represented by the formula (II): 
       
       
         
           
           
               
               
           
         
         wherein each symbol is as defined above, 
         or a salt thereof to an asymmetric reduction reaction.