Novel crystal form of an organic compound and process for the preparation thereof

Abstract

The present invention relates to novel crystalline Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione, (also known as CDB-4124), processes for the preparation thereof and pharmaceutical composition comprising it. Form II can be crystallized from different medium such as esters of C1-C4 alcohols and carboxylic acids, ketones, cyclohexane, acetonitrile, dimethylformamide, dimethyl sulfoxide, water and any mixture thereof.

1 .- 13 . (canceled) 
     
     
         14 . A pharmaceutical composition comprising a crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it provides one or more of:
 a) a characteristic X-ray powder diffractions with peaks at 6.8, 11.0, 11.6, 14.9, 19.1±0.2[°]2θ; 
 b) a characteristic FT Raman absorption bands at about 3054, 2963, 2850, 1604, 1195, 1159±4 cm −1 ; and 
 c) a  13 C solid-state NMR spectrum comprising characteristic resonances at about 196.7, 172.4, 169.3, 20.7, 20.1, 17.7±0.1 ppm. 
 
     
     
         15 . The composition of  claim 14 , wherein the crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it has an X-ray powder diffraction pattern as shown in  FIG. 1 . 
     
     
         16 . The composition of  claim 14 , wherein the crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it has an FT Raman spectrum as shown in  FIG. 2 . 
     
     
         17 . The composition of  claim 14 , wherein the crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it has a  13 C solid-state NMR spectrum in accordance with  FIG. 3 . 
     
     
         18 . A method of treating a tumorous disorder, the method comprising administering a therapeutically effective amount of a composition comprising a crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it provides one or more of:
 a) a characteristic X-ray powder diffractions with peaks at 6.8, 11.0, 11.6, 14.9, 19.1±0.2[°]2θ; 
 b) a characteristic FT Raman absorption bands at about 3054, 2963, 2850, 1604, 1195, 1159±4 cm −1 ; and 
 c) a  13 C solid-state NMR spectrum comprising characteristic resonances at about 196.7, 172.4, 169.3, 20.7, 20.1, 17.7±0.1 ppm. 
 
     
     
         19 . The method of  claim 18 , wherein the tumorous disorder is fibroma. 
     
     
         20 . The composition of  claim 18 , wherein the crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it has an X-ray powder diffraction pattern as shown in  FIG. 1 . 
     
     
         21 . The composition of  claim 18 , wherein the crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it has an FT Raman spectrum as shown in  FIG. 2 . 
     
     
         22 . The composition of  claim 18 , wherein the crystalline anhydrate Form II of 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione characterized in that it has a 13C solid-state NMR spectrum in accordance with  FIG. 3 .