Synthesis and regioselective substitution of 6-halo- and 6-alkoxy nicotine derivatives

Abstract

The present invention provides active compounds for modulating nicotinic acetylcholine receptors and methods of making the same. The methods of preparing the active compounds utilize different intermediate compounds.

1 .- 10 . (canceled) 
     
     
         11 . A compound of Formula A: 
       
         
           
           
               
               
           
         
       
       wherein:
 n is 2; 
 R 2  is selected from the group consisting of H, alkyl, aryl, alkoxy and halo, 
 R 4 , R 5  and R 6  is selected from the group consisting of H, alkyl, aryl, heteroaryl, alkenyl, alkynyl, alkoxy, aryloxy, halo, SiR 20 R 21 R 22 , SnR 20 R 21 R 22  wherein R 20 , R 21  and R 22  are each independently alkyl, aryl, halo, hydroxy or alkoxy; 
 R 7  is H, alkyl, aryl, amino, alkoxy, cyano or acyl; 
 subject to the proviso that either R 4  and R 5 , or R 5  and R 6 , together form a fused ring, 
 and pharmaceutically acceptable salts and prodrugs thereof. 
 
     
     
         12 . A compound of  claim 11 , wherein R 4  and R 5  together form a fused ring. 
     
     
         13 . A compound of  claim 11 , wherein R 5  and R 6  together form a fused ring. 
     
     
         14 . (canceled) 
     
     
         15 . A composition comprising a compound of  claim 11  in a pharmaceutically acceptable carrier.