Benzoquinoline inhibitors of vesicular monoamine transporter 2

Abstract

The present invention relates to new benzoquinoline inhibitors of vesicular monoamine transporter 2 (VMAT2), pharmaceutical compositions thereof, and methods of use thereof.

What is claimed is: 
     
         1 . A mixture of about 90% or more by weight of the (3R,11bR)-enantiomer [the (+)-enantiomer] and about 10% or less by weight of the (3S,11bS)-enantiomer [the (−)-enantiomer] of the compound having the structural formula: 
       
         
           
           
               
               
           
         
         or a salt thereof, wherein each position represented as D has deuterium enrichment of no less than about 10%. 
       
     
     
         2 . The composition as recited in  claim 1  wherein each position represented as D has deuterium enrichment of no less than 50%. 
     
     
         3 . The composition as recited in  claim 1  wherein each position represented as D has deuterium enrichment of no less than 90%. 
     
     
         4 . The composition as recited in  claim 1  wherein each position represented as D has deuterium enrichment of no less than 98%. 
     
     
         5 . A pharmaceutical composition comprising a compound as recited in  claim 1  together with a pharmaceutically acceptable carrier. 
     
     
         6 . A compound having the structural formula: 
       
         
           
           
               
               
           
         
         or a salt thereof, wherein:
 the compound is the (3R,11bR)-enantiomer; and 
 each position represented as D has deuterium enrichment of no less than about 10%. 
 
       
     
     
         7 . The composition as recited in  claim 6  wherein each position represented as D has deuterium enrichment of no less than 50%. 
     
     
         8 . The composition as recited in  claim 6  wherein each position represented as D has deuterium enrichment of no less than 90%. 
     
     
         9 . The composition as recited in  claim 6  wherein each position represented as D has deuterium enrichment of no less than 98%. 
     
     
         10 . A pharmaceutical composition comprising a compound as recited in  claim 6  together with a pharmaceutically acceptable carrier.