Solid state forms of sitagliptin salts

Abstract

Solid state forms of Sitagliptin salts, processes for preparing the solid state forms, and pharmaceutical compositions thereof, are provided.

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         5 . A crystalline form of sitagliptin acetate, designated Form E1, characterized by data selected from: a powder X-ray diffraction pattern with peaks at 6.2°, 11.1°, 12.5°, 17.7°, and 18.4°±0.2° 2θ; a powder X-ray diffraction pattern as shown in  FIG. 9   a : a solid-state  13 C NMR spectrum with signals at 122.3, 150.5 and 167.4±0.2 ppm; a solid-state  13 C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 190 ppm of 18.5, 46.7 and 63.6±0.1 ppm; and a  13 C NMR spectrum as depicted in  FIG. 9   c  and  FIG. 9   d ; and combinations thereof. 
     
     
         6 . A crystalline form of sitagliptin L-malate, designated Form I1, characterized by data selected from: a powder X-ray diffraction pattern with peaks at 6.0°, 8.0°, 12.8°, 18.0° and 20.4°±0.2° 2θ; a powder X ray diffraction pattern shown in  FIG. 4   f ; a solid-state  13 C NMR spectrum with signals at 121.7, 150.8 and 173.0±0.2 ppm; a solid-state  13 C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 190 ppm of 17.2, 46.3 and 68.5±0.1 ppm; and a  13 C NMR spectrum as depicted in  FIG. 4   d  and  FIG. 4   e ; and combinations thereof. 
     
     
         7 . A crystalline form of sitagliptin quinate, designated Form Q1, characterized by data selected from a powder X-ray diffraction pattern with peaks at 7.3°, 8.6°, 10.5°, 12.6° and 13.9°±0.2° 2θ; a powder X-ray diffraction pattern as shown in  FIG. 6   a ; a solid-state  13 C NMR spectrum with signals at 121.5, 169.0 and 180.3±0.2 ppm; a solid-state  13 C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 190 ppm of 16.8, 64.3 and 75.6±0.1 ppm; and a  13 C NMR spectrum is depicted in  FIG. 6   b  and  FIG. 6   c ; and combinations thereof. 
     
     
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         12 . A pharmaceutical composition comprising a crystalline form of  claim 5 , and at least one pharmaceutically acceptable excipient. 
     
     
         13 . A pharmaceutical composition comprising a crystalline form of  claim 6 , and at least one pharmaceutically acceptable excipient. 
     
     
         14 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form of sitagliptin sulfate, designated Form S2 characterized by data selected from: a powder X-ray diffraction pattern with peaks at 9.3°, 9.7°, 15.2°, 15.6° and 25.4°±0.2° 2θ; a powder X-ray diffraction pattern as shown in  FIG. 1   b ; a solid-state  13 C NMR spectrum with signals at 119.2, 150.3 and 170.6±0.2 ppm; a solid-state  13 C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 180 ppm of 13.7, 44.8 and 65.1±0.1 ppm; a  13 C NMR spectrum as depicted in  FIG. 1   m  and  FIG. 1   n ; and combinations thereof. 
     
     
         15 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form of sitagliptin sulfate, designated Form S6, characterized by a powder X-ray diffraction pattern as shown in  FIG. 1   f.    
     
     
         16 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form of sitagliptin sulfate isopropanol solvate, designated Form S7, characterized by data selected from a powder X-ray diffraction pattern with peaks at 5.2°, 15.6°, 16.6°, 18.7° and 21.1°±0.2° 2θ; a powder X-ray diffraction pattern as shown in  FIG. 1   g ; a solid-state  13 C NMR spectrum with signals at 120.4, 149.1 and 171.2±0.2 ppm a solid-state  13 C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 180 ppm of 15.1, 43.8 and 65.9±0.1 ppm; and a  13 C NMR spectrum as depicted in  FIG. 1   i  and  FIG. 1   j ; and combinations thereof. 
     
     
         17 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form sitagliptin sulfate designated Form S1, characterized by data selected from: a powder X-ray diffraction pattern with peaks at 11.8°, 13.7°, 14.4°, 17.0° and 17.5°±0.2° 2θ; a powder X-ray diffraction pattern as shown in  FIG. 1   a ; and combinations thereof. 
     
     
         18 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form of  claim 5 . 
     
     
         19 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form of  claim 6 . 
     
     
         20 . A method of treating type 2 diabetes mellitus comprising administering an effective amount of a crystalline form of  claim 7 .