New substituted pyridine or piperidine compounds

Abstract

The invention relates to a compound of formula (I): wherein A represents pyridine, pyridinium or piperidine R 1 , R 2 , R 3 and R 4 are as defined in the description R 5 represents hydrogen, a nitrogen-containing heterocycle or a group of formula (II): R 6 represents hydrogen or linear or branched (C 1 -C 6 )alkyl. and medicinal products containing the same which are useful in treating pain or deficiencies in memory.

We claim:  
     
         1 . A compound of formula (I):  
       
         
           
           
               
               
           
         
       
       wherein: 
 A represents pyridine, pyridinium or piperidine,  
 R 2  represents hydrogen and R 3  represents hydroxy, or R 2  and R 3  together form oxo,  
 R 4  represents unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl or unsubstituted or substituted heteroaryl,  
 R 1  represents hydrogen,  
 or R 1  and R 4 , together with the two carbon carrying them, form a ring containing 6 carbon,  
 or R 1  and R 2  form an additional bond and, in that case, R 3  represents a 5- or 6-membered heterocycle that contains nitrogen atom by which it is bound and that may contain another hetero atom selected from sulphur, oxygen and nitrogen,  
 R 5  represents: 
 a 5- or 6-membered heterocycle that contains nitrogen atom by which it is bonded to the ring A and that may contain another hetero atom selected from sulphur, oxygen and nitrogen,  
 a group of formula (II):  
                     
 wherein R′ 1 , R′ 2 , R′ 3  and R′ 4  may have the same meanings as R 1 , R 2 , R 3  and R 4 , respectively, or hydrogen and, in that case, R 4  cannot represent unsubstituted phenyl, unsubstituted naphthyl or heteroaryl,  
 
 R 6  represents hydrogen or linear or branched (C 1 -C 6 )alkyl, the group R 6  being present or absent depending on the nature of the ring A,  
 heteroaryl being understood to mean any aromatic, mono- or bi-cyclic, 5- to 10-membered group containing from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulphur,  
 the term “substituted” used in respect of the expressions “phenyl”, “naphthyl” or “heteroaryl” being understood to mean that the groups concerned may be substituted by one or more groups, which may be the same or different, selected from linear or branched (C 1 -C 6 )alkyl, linear or branched (C 1 -C 6 )alkoxy, mercapto, linear or branched (C 1 -C 6 )-alkylthio, amino, linear or branched (C 1 -C 6 )alkylamino, di-(C 1 -C 6 )alkylamino in which each alkyl moiety is linear or branched, linear or branched (C 1 -C 6 )polyhaloalkyl and hydroxy and halogen,  
 it being understood that:  
 when R 2  and R 3  together form oxo and simultaneously R 5  represents hydrogen and R 6  represents hydrogen or does not exist, then R 4  is other than phenyl substituted by one group selected from hydroxy, alkoxy, CF 3  and halogen (except for bromine when A represents piperidine), or by several groups selected from hydroxy and alkoxy,  
 when R 2  represents hydrogen and R 3  represents hydroxy and simultaneously R 5  represents hydrogen and R 6  represents hydrogen or does not exist, then R 4  is other than phenyl substituted by one group selected from hydroxy, linear or branched (C 1 -C 6 )alkoxy, linear or branched (C 1 -C 6 )alkyl and chlorine, or by several groups selected from hydroxy and alkoxy,  
 the compound of formula (I) may not represent 1-(1,3-benzodioxol-5-yl)-2-(2-pyridinyl)ethanol nor 2-(2-pyridinyl)cyclohexanone,  
 their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
 
     
     
         2 . A compound of formula (I) according to  claim 1 , wherein the group  
       
         
           
           
               
               
           
         
       
       represents piperidinyl or N-methylpiperidinyl their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         3 . A compound of formula (I) according- to  claim 1 , wherein the group  
       
         
           
           
               
               
           
         
       
       represents pyridinyl or N-methylpyridinium their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         4 . A compound of formula (I) according to  claim 1 , wherein R 4  represents substituted phenyl, their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         5 . A compound of formula (I) according to  claim 1 , wherein R 5  represents hydrogen, their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         6 . A compound of formula (I) according to  claim 1 , wherein R 5  represents a group of formula (II), their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         7 . A compound of formula (I) according to  claim 1 , wherein R 2  and R 3  together form oxo, their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         8 . A compound of formula (I) according to  claim 1 , wherein R 2  represents hydrogen and R 3  represents hydroxy, their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         9 . A compound of formula (1) according to  claim 1  which is 1-(4-bromophenyl)-2-(1-methyl-2-piperidinyl)-1-ethanone, its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         10 . A compound of formula (I) according to  claim 1  which is (R)-2-1-methyl-2-piperidinyl)-1-(4-bromophenyl)-1-ethanone and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         11 . A compound of formula (I) according to  claim 1  which is (S)-2-(1-methyl-2-piperidinyl)-1-(4-bromophenyl)-1-ethanone and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         12 . A compound of formula (I) according to  claim 1  which is 1-(4-bromophenyl)-2-(1-methyl-2-piperidinyl)-1-ethanol, its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         13 . A compound of formula (I) according to  claim 1  which is (S,S)-1-(4-bromophenyl)-2-(1-methyl-2-piperidinyl)-1-ethanol, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         14 . A compound of formula (I) according to  claim 1  which is (R,R)-1-(4-bromophenyl)-2-(1-methyl-2-piperidinyl)-1-ethanol, and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         15 . A compound of formula (I) according to  claim 1  which is 1-methyl-2-[2-oxo-2-(4-bromophenyl)ethyl]pyridinium iodide and addition salts thereof with a pharmaceutically acceptable acid or base.  
     
     
         16 . A method for treating a living body afflicted with pain and deficiencies in memory associated with cerebral ageing and with neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, Korsakoff's disease and frontal lobe and subcortical dementias comprising the step of administering to the living body an amount of a compound to  claims 1  to  15  which is effective for the alleviation for said condition.  
     
     
         17 . A pharmaceutical composition useful for treating pain and deficiencies in memory associated with cerebral ageing and with neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, Korsakoff's disease and frontal lobe and subcortical dementias comprising, as active principle an effective amount of a compound as claimed in  claims 1  to  15 , together with one or more pharmaceutically acceptable excipients or vehicles.