Novel crystalline forms of (1s,2r)-2-(amino methyl)-n,n-diethyl-1-phenyl cyclopropane carboxamide

Abstract

The present invention relates to novel crystalline forms of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide. Processes for the preparation of this form, compositions containing the form, and methods of use thereof are also described.

What is claimed is: 
     
         1 . A crystalline form of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide having an X-ray powder diffraction pattern comprising characteristic peaks at 12.0, 20.1 and 22.5±0.2 degrees 2θ. 
     
     
         2 . The crystalline form of  claim 1 , wherein the X-ray powder diffraction pattern further comprises a characteristic peak at 32.7±0.2 degrees 2θ. 
     
     
         3 . The crystalline form of  claim 1 , wherein the X-ray powder diffraction pattern further comprises a characteristic peak at 6.0±0.2 degrees 2θ. 
     
     
         4 . A crystalline form of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide having an X-ray powder diffraction pattern comprising characteristic peaks at 6.0, 12.0 and 20.1±0.2 degrees 2θ. 
     
     
         5 . The crystalline form of  claim 4 , wherein the X-ray powder diffraction pattern further comprises a characteristic peak at 22.5±0.2 degrees 2θ. 
     
     
         6 . The crystalline form of  claim 4  having a melting endotherm at about 200° C. as determined by differential scanning calorimetry. 
     
     
         7 . The crystalline form of  claim 4  having a Raman spectrum comprising characteristic peaks at about 695, about 735 and about 1435 cm −1 . 
     
     
         8 . The crystalline form of  claim 4  having an X-ray diffraction pattern further comprising d spacing peaks at 4.0 and 4.4±0.2 Å. 
     
     
         9 . A pharmaceutical composition comprising the crystalline form of  claim 1  and a pharmaceutically acceptable carrier. 
     
     
         10 . A method of treating a disorder that can be managed by inhibition of norepinephrine and serotonin reuptake in a patient in need thereof, by administering to said patient an effective amount of a pharmaceutical compositions that comprises the crystalline form of  claim 1 . 
     
     
         11 . A pharmaceutical composition comprising the crystalline form of  claim 4  and a pharmaceutically acceptable carrier. 
     
     
         12 . A method of treating a disorder that can be managed by inhibition of norepinephrine and serotonin reuptake in a patient in need thereof, by administering to said patient an effective amount of a pharmaceutical compositions that comprises the crystalline form of  claim 4 . 
     
     
         13 . A crystalline form of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide having an X-ray powder diffraction pattern substantially as shown in  FIG. 5 . 
     
     
         14 . A crystalline form of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide having an X-ray powder diffraction pattern comprising characteristic peaks at 6.0, 13.3 and 23.6±0.2 degrees 2θ. 
     
     
         13 . The crystalline form of  claim 14 , wherein the X-ray powder diffraction pattern further comprises a characteristic peak at 12.0±0.2 degrees 2θ. 
     
     
         14 . A pharmaceutical composition comprising the crystalline form of  claim 14  and a pharmaceutically acceptable carrier. 
     
     
         15 . A method of treating a disorder that can be managed by inhibition of norepinephrine and serotonin reuptake in a patient in need thereof, by administering to said patient an effective amount of a pharmaceutical compositions that comprises the crystalline form of  claim 14 . 
     
     
         16 . A crystalline form of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide having an X-ray powder diffraction pattern comprising characteristic peaks at 14.2, 21.6 and 24.6±0.2 degrees 2θ. 
     
     
         17 . A pharmaceutical composition comprising the crystalline form of  claim 16  and a pharmaceutically acceptable carrier. 
     
     
         18 . A method of treating a disorder that can be managed by inhibition of norepinephrine and serotonin reuptake in a patient in need thereof, by administering to said patient an effective amount of a pharmaceutical compositions that comprises the crystalline form of  claim 16 . 
     
     
         19 . A crystalline form of (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide having an X-ray powder diffraction pattern comprising characteristic peaks at 5.9, 18.3 and 36.4±0.2 degrees 2θ. 
     
     
         20 . A pharmaceutical composition comprising the crystalline form of  claim 19  and a pharmaceutically acceptable carrier. 
     
     
         21 . A method of treating a disorder that can be managed by inhibition of norepinephrine and serotonin reuptake in a patient in need thereof, by administering to said patient an effective amount of a pharmaceutical compositions that comprises the crystalline form of  claim 19 . 
     
     
         22 . A process for preparing the crystalline form of  claim 1 , comprising dissolving (1S,2R)-2-(amino methyl)-N,N-diethyl-1-phenyl cyclopropane carboxamide and precipitating the crystalline form.