Polymorphs of bicifadine hydrochloride

Abstract

A new polymorphic crystalline form of bicifadine hydrochloride, designated form B, which is more thermodynamically stable than the previously known polymorphic form of bicifadine hydrochloride, designated as form A, methods for preparing said crystalline form B and pharmaceutical compositions containing said crystalline form B.

1 - 52 . (canceled)  
   
   
       53 . A method for obtaining the (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane of claim  1 , comprising the steps of: 
 (a) passing a solution of an organic eluent and (:±:)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane over a chiral polysaccharide stationary phase to provide a first fraction containing (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane; and    (b) passing the first fraction over the chiral polysaccharide stationary phase to provide a second fraction containing (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane substantially free of its corresponding (+)-enantiomer.    
   
   
       54 . The method of  claim 53 , further comprising the step of (c) concentrating the second fraction.  
   
   
       55 . A method for obtaining the (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane of claim  1 , comprising the steps of: 
 (a) passing a solution of an organic eluent and (±)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane over a chiral polysaccharide stationary phase to provide a first fraction containing (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane;    (b) concentrating the first fraction to provide a residue; and    (c) passing a solution of an organic eluent and the residue over a chiral polysaccharide stationary phase to provide a second fraction containing (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane substantially free of its corresponding (+)-enantiomer.    
   
   
       56 . The method of  claim 55 , further comprising the step of (d) concentrating the second fraction.