Crystalline sulfonamide-containing indole compound and process for preparing the same

Abstract

A crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having a diffraction peak at a diffraction angle (2θ±0.2°) of 19.1° in a powder X-ray diffraction.

1 . A crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having peaks at chemical shifts of approximately 143.4 ppm, 137.7 ppm, 136.9 ppm, 134.2 ppm, 131.1 ppm, 128.5 ppm, 126.4 ppm, 125.8 ppm, 124.3 ppm, 120.0 ppm, 118.8 ppm, 115.8 ppm, 111.0 ppm, 84.5 ppm and 19.4 ppm in a  13 C solid state NMR spectrum. 
     
     
         2 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide according to  claim 1 , comprising crystallizing N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide using a simple solvent selected from the group consisting of n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, s-butyl alcohol, t-butyl alcohol and water, or a mixed solvent thereof as a crystallization solvent. 
     
     
         3 . The process according to  claim 2 , wherein the crystallization solvent is a simple solvent of isopropyl alcohol or s-butyl alcohol, or a mixed solvent of s-butyl alcohol and water or a mixed solvent of isopropyl alcohol and water. 
     
     
         4 . The process according to  claim 2 , wherein the crystallization solvent is a mixed solvent of s-butyl alcohol and water (volume ratio=3:1-5:1) or a mixed solvent of isopropyl alcohol and water (volume ratio=9:1-10:1). 
     
     
         5 . The process according to  claim 2 , wherein the crystallization solvent is a mixed solvent of s-butyl alcohol and water (volume ratio=3.9:1-4.1:1). 
     
     
         6 . The process according to  claim 2 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated and dissolved in a solvent and then crystallized. 
     
     
         7 . The process according to  claim 2 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated and dissolved in a solvent and then crystallized by gradual cooling. 
     
     
         8 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide according to  claim 1 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated at 80-130° C. 
     
     
         9 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide according to  claim 1 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated and stirred in water at 60-90° C. 
     
     
         10 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide according to  claim 1 , wherein a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide hydrate is heated at 80-130° C. 
     
     
         11 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide according to  claim 1 , wherein a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide hydrate is heated and stirred in water at 60-90° C. 
     
     
         12 . A crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having the  13 C solid state NMR spectrum substantially as depicted in  FIG. 5 . 
     
     
         13 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having the X-ray diffraction pattern substantially as depicted in  FIG. 3 , comprising:
 crystallizing N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide using a simple solvent selected from the group consisting of n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, s-butyl alcohol, t-butyl alcohol and water, or a mixed solvent thereof as a crystallization solvent.   
     
     
         14 . The process according to  claim 13 , wherein the crystallization solvent is a simple solvent of isopropyl alcohol or s-butyl alcohol, or a mixed solvent of s-butyl alcohol and water or a mixed solvent of isopropyl alcohol and water. 
     
     
         15 . The process according to  claim 13 , wherein the crystallization solvent is a mixed solvent of s-butyl alcohol and water (volume ratio=3:1-5:1) or a mixed solvent of isopropyl alcohol and water (volume ratio=9: 1-10:1). 
     
     
         16 . The process according to  claim 13 , wherein the crystallization solvent is a mixed solvent of s-butyl alcohol and water (volume ratio=3.9:1-4.1:1). 
     
     
         17 . The process according to  claim 13 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated and dissolved in a solvent and then crystallized. 
     
     
         18 . The process according to  claim 13 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated and dissolved in a solvent and then crystallized by gradual cooling. 
     
     
         19 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having the X-ray diffraction pattern substantially as depicted in  FIG. 3 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated at 80-130° C. 
     
     
         20 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having the X-ray diffraction pattern substantially as depicted in  FIG. 3 , wherein N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide is heated and stirred in water at 60-90° C. 
     
     
         21 . A process for preparing a crystalline N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having the X-ray diffraction pattern substantially as depicted in  FIG. 3 , wherein a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide hydrate is heated at 80-130° C. 
     
     
         22 . A process for preparing a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide having the X-ray diffraction pattern substantially as depicted in  FIG. 3 , wherein a crystalline form of N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide hydrate is heated and stirred in water at 60-90° C.