Substituted biphenyl compounds

Abstract

The invention relates to compound of formula (I) wherein: B represents hydrogen, COOR, CONRR′, or (C 1 -C 6 )alkyl substituted by COOR, CONRR′, or OR, G 1 represents —X′—(CH 2 ) n —X—(CH 2 ) m —X″— chain wherein X, X′, X″, n and m are as defined in the description, Cy represents a grouping of formula (II) or (III): G 2 represents alkylene chain as defined in the description, and A represents NRCOR′, NRCSR′, CONRR′, CSNRR′, NRCONR′R″, or NRCSNR′R″. and medicinal products containing the same which are useful in treating or preventing melatoninergic disorders.

1 . A compound selected from those of formula (I):  
     
       
         
         
             
             
         
       
     
     wherein 
 B represents hydrogen, COOR, CONRR′, or linear or branched (C 1 -C 6 )alkyl substituted by COOR, CONRR′, or OR wherein R and R′, which may be identical or different, each represents hydrogen, or linear or branched (C 1 -C 6 )alkyl, linear or branched (C 2 -C 6 )alkenyl, linear or branched (C 2 -C 6 )alkynyl, aryl, aryl-(C 1 -C 6 )alkyl in which the alkyl moiety may be linear or branched, heteroaryl, heteroaryl-(C 1 -C 6 )alkyl in which the alkyl moiety may be linear or branched, polyhalo-(C 1 -C 6 )alkyl in which the alkyl moiety may be linear or branched, (C 3 -C 8 )cycloalkyl or (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl in which the alkyl moiety may be linear or branched, it being possible in addition for R and R′ to form, together with the nitrogen carrying them, morpholinyl, piperidyl, piperazinyl, or pyrrolidinyl,  
 G 1  represents an —X′—(CH 2 ) n —X—(CH 2 ) m —X″— chain wherein 
 X represents CH 2 ,  
 X′ and X″, which may be identical or different, each represents oxygen or sulphur,  
 n and m, which may be identical or different, each represents 0, 1, 2, 3, 4 or 5, it being understood that it is not possible to have two consecutive hetero atoms in the chain and that the chain so defined may contain one or more unsaturations,  
 
 Cy represents a group of formula (II)  
                     wherein D represents phenyl or pyridine, W represents oxygen, sulphur, CH 2 , or NR, wherein R is as defined hereinbefore, R 1  represents halogen, R, OR, or COOR, wherein R is as defined hereinbefore and the representation   denotes that the bond is single or double, it being understood that the valency of the atoms is respected,    
 G 2  represents a 1 to 6 carbon atom chain containing that is optionally substituted by one or more groups selected from R, OR, COR, COOR, wherein R is as defined hereinbefore, and halogen,  
 and A represents NRCOR′, NRCSR′, CONRR′, CSNRR′, NRCONR′R″, or NRCSNR′R″, wherein R and R′ are as defined hereinbefore and R″ may have the same meanings as R and R′,  
 wherein:  
 “aryl” is to be understood as meaning phenyl or naphthyl that is unsubstituted or substituted by one or more identical or different groups selected from R, OR, COR, COOR, NRR′, wherein R and R′ are as defined hereinbefore, nitro, cyano and halogen,  
 “heteroaryl” is to be understood as meaning any mono- or bi-cyclic group having from 5 to 10 ring members and capable of containing from 1 to 3 hetero atoms selected from oxygen, sulphur, and nitrogen, that group being unsubstituted or substituted by one or more identical or different groups selected from R, OR, COR, COOR, NRR′, wherein R and R′ are as defined hereinbefore, nitro, cyano, and halogen,  
 its enantiomers and diastereoisomers, and also addition salts thereof with a pharmaceutically acceptable acid or base.  
 
   
   
       2 . A compound of  claim 1 , wherein B represents COOR.  
   
   
       3 . A compound of  claim 2 , wherein R represents hydrogen.  
   
   
       4 . A compound of  claim 2 , wherein R represents linear or branched (C 1 -C 6 )alkyl.  
   
   
       5 . A compound of  claim 1 , wherein B represents linear or branched (C 1 -C 6 )alkyl substituted by COOR.  
   
   
       6 . A compound of  claim 1 , wherein B represents linear or branched (C 1 -C 6 )alkyl substituted by OR.  
   
   
       7 . A compound of  claim 1 , wherein G 1  represents —O—(CH 2 ) p —O— in which p is an integer such that 0<p<6.  
   
   
       8 . A compound of  claim 1 , wherein A represents NHCOR.  
   
   
       9 . A compound of  claim 1 , which is selected from ethyl 4′-[4-({3-[2-(acetylamino)ethyl]-1-methyl-1H-pyrrolo[3,2-b]pyrid-5-yl}oxy)butoxy]-[1,1′-biphenyl]-4-carboxylate and addition salts thereof with a pharmaceutically-acceptable acid or base.  
   
   
       10 . A method for treating a living animal body, including a human, afflicted with a disorder of the melatoninergic system, comprising the step of administering to the living animal body, including a human, an amount of a compound of  claim 1  which is effective for the alleviation of the disorder.  
   
   
       11 . A pharmaceutical composition comprising as active principle an effective amount of a compound of  claim 1 , together with one or more pharmaceutically-acceptable excipients or vehicles.