Compounds capable of activating cholinergic receptors

Abstract

Compounds incorporating aryl substituted olefinic amine are provided. Representative compounds are (4E)-N-methyl-5-(3-pyridyl)-4-penten-2-amine, (4E)-N-methyl-5-(5-pyrimidinyl)-4-penten-2-amine, (4E)-N-methyl-5-(5-methoxy-3-pyridyl)-4-penten-2-amine, (4E)-N-methyl-5-(6-amino-5-methyl-3-pyridyl)-4-penten-2-amine, (2R)-(4E)-N-methyl-5-(3-pyridyl)-4-penten-2-amine, (2R)-(4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine, (4E)-N-methyl-5-(5-bromo-3-pyridyl)-4-penten-2-amine, (4E)-N-methyl-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine, (2S)-(4E)-N-methyl-5-(3-pyridyl)-4-penten-2-amine, (4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine and (2S)-(4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine.

1 . A compound of Formula I: 
     
       
         
         
             
             
         
       
     
     or a pharmaceutically acceptable salt thereof, wherein:
 X is N, C—H, C—F, C—Cl, C—Br, C—I, C—R′, C—NR′R″, C—CF 3 , C-OH, C—CN, C—NO 2 , C—C 2 R′, C—SH, C—SCH 3 , C—N 3 , C—SO 2 CH 3 , C—OR′, C—SR′, C—C(═O)NR′R″, C—NR′C(═O)R′, C—C(═O)R′, C—C(═O)OR′, C(CH 2 ) q ,OR′, C—OC(═O)R′, COC(═O)NR′R″ or C—NR′C(═O)OR′, wherein R′ and R″ are individually hydrogen or alkyl and wherein 
 q is an integer from 1 to 6; 
 Z′ and Z″ individually represent hydrogen or alkyl, wherein at least one of Z′ and Z″ is hydrogen; and 
 the wavy line in the structure indicates that the compound can have a cis (Z) or trans (E) form. 
 
   
   
       2 . The compound of  claim 1 , wherein X is C—H, C—Br, or C—OR′. 
   
   
       3 . The compound of  claim 2 , wherein R′ is straight chain or branched alkyl. 
   
   
       4 . The compound of  claim 1 , wherein R′ and R″ are C 1 -C 5  alkyl. 
   
   
       5 . The compound of  claim 4 , wherein R′ and R″ are methyl, ethyl, isopropyl or isobutyl. 
   
   
       6 . The compound of  claim 1 , wherein Z′ is hydrogen and Z″ is straight chain or branched alkyl. 
   
   
       7 . The compound of  claim 1 , wherein Z′ is hydrogen and Z″ is C 1 -C 5  alkyl. 
   
   
       8 . The compound of  claim 7 , wherein Z″ is methyl, ethyl, or isopropyl. 
   
   
       9 . A pharmaceutical composition comprising a compound according to  claim 1  or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. 
   
   
       10 . The pharmaceutical composition according to  claim 9 , comprising said compound in an amount effective to treat a central nervous system disorder selected senile dementia of the Alzheimer's type or attention deficit disorder.