Polysubstituted 1,1-pyridylaminocyclopropanamine compounds

Abstract

A compound selected from those of formula (1): wherein: n represents an integer from 1 to 6 inclusive, R 1 and R 2 represent a hydrogen atom, a (C 1 -C 6 )alkyl group or an aryl-(C 1 -C 6 )alkyl group, R 3 and R 4 represent a hydrogen atom or a (C 1 -C 6 )alkyl group, R 5 and R 6 represent a hydrogen atom or a (C 1 -C 6 )alkyl, halogen, hydroxy, (C 1 -C 6 )alkoxy, cyano, nitro, (C 2 -C 6 )acyl, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )trihaloalkyl or (C 1 -C 6 )-trihaloalkoxy group or an optionally substituted amino group, R 7 represents a hydrogen atom, a (C 1 -C 6 )alkyl group or an arylalkyl group, its enantiomers, diastereoisomers and additional salts thereof with a pharmaceutically acceptable acid or base. Medicinal products containing the same which are useful in the treatment of conditions requiring a specific nicotinic ligand of α4β2 receptors.

1 . A method for treating a living animal body, including a human, afflicted with a condition requiring a specific nicotinic ligand of α4β2 receptors comprising the step of administering to the living animal body, including a human, a therapeutically effective amount of a compound selected from those of formula (I): 
       
         
           
           
               
               
           
         
       
       wherein:
 n represents an integer from 1 to 6 inclusive, 
 R 1  and R 2 , which may be identical or different, each independently of the other represent a hydrogen atom, a linear or branched (C 1 -C 6 )alkyl group or an aryl-(C 1 -C 6 )alkyl group in which the alkyl moiety may be linear or branched, 
 R 3  and R 4 , which may be identical or different, each independently of the other represent a hydrogen atom or a linear or branched (C 1 -C 6 )alkyl group, 
 R 5  and R 6 , which may be identical or different, each independently of the other represent a hydrogen atom or a linear or branched (C 1 -C 6 )alkyl, halogen, hydroxy, linear or branched (C 1 -C 6 )alkoxy, cyano, nitro, linear or branched (C 2 -C 6 )acyl, linear or branched (C 1 -C 6 )alkoxycarbonyl, linear or branched (C 1 -C 6 )trihaloalkyl or linear or branched (C 1 -C 6 )trihaloalkoxy group or an amino group optionally substituted by one or two linear or branched (C 1 -C 6 )alkyl groups, 
 R 7  represents a hydrogen atom, a linear or branched (C 1 -C 6 )alkyl group or an aryl-(C 1 -C 6 )alkyl group in which the alkyl moiety may be linear or branched, 
 it being understood that an aryl group means phenyl, biphenyl, naphthyl, dihydronaphthyl, tetrahydronaphthyl, indanyl or indenyl group, each of the groups being optionally substituted by one or more identical or different groups selected from halogen, linear or branched (C 1 -C 6 )alkyl, hydroxy, cyano, nitro, linear or branched (C 1 -C 6 )alkoxy, linear or branched (C 2 -C 7 )acyl, linear or branched (C 1 -C 6 )alkoxycarbonyl, linear or branched (C 1 -C 6 )trihaloalkyl and linear or branched (C 1 -C 6 )trihaloalkoxy groups and amino groups optionally substituted by one or two linear or branched (C 1 -C 6 )alkyl groups, 
 its enantiomers, diastereoisomers and additional salts thereof with a pharmaceutically acceptable acid or base, which is effective for alleviation of the condition. 
 
     
     
         2 . The method of  claim 1 , wherein n is an integer having the value 1. 
     
     
         3 . The method of  claim 1 , wherein R 1  and R 2 , which may be identical or different, each independently of the other represent a hydrogen atom or a linear or branched (C 1 -C 6 )alkyl group. 
     
     
         4 . The method of  claim 1 , wherein R 3  and R 4  represent a hydrogen atom. 
     
     
         5 . The method of  claim 1 , wherein R 5  and R 6 , which may be identical or different, each independently of the other represent a hydrogen atom or a linear or branched (C 1 -C 6 )alkyl group. 
     
     
         6 . The method of  claim 1 , wherein R 7  represents a hydrogen atom or a linear or branched (C 1 -C 6 )alkyl group. 
     
     
         7 . The method of  claim 1 , wherein the compound of formula (I) is selected from: 
       N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, 
       N-methyl-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, 
       N-[(1-aminocyclopropyl)methyl]pyridin-3-amine, 
       N-{[1-(dimethylamino)cyclopropyl]methyl}pyridin-3-amine, 
       N-[(1-aminocyclopropyl)methyl]-N-methylpyridin-3-amine, 
       N-{[1-(dimethylamino)cyclopropyl]methyl}-N-methylpyridin-3-amine, 
       6-chloro-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, 
       6-chloro-N-methyl-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, 
       6-bromo-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, 
       6-bromo-N-methyl-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, 
       6-methyl-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine, and 
       N,6-dimethyl-N-{[1-(methylamino)cyclopropyl]methyl}pyridin-3-amine,
 its enantiomers, diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base. 
 
     
     
         8 . The method of  claim 1 , wherein the condition is selected from cognitive disorders associated with cerebral ageing and with neurodegenerative diseases, and also for the treatment of depression, Tourette's syndrome, tobacco withdrawal and pain. 
     
     
         9 . The method of  claim 1 , wherein the condition is selected from cognitive disorders associated with Alzheimer's disease, and frontal lobe and subcortical dementias.