Solid state forms of sitagliptin salts
AssigneeTeva Pharmaceutical Industries Ltd.
InventorsGideon PILARSKI, Nurit PERLMAN, Ariel MITTELMAN, Nada KOSUTIC HULITA, Marina KALUJNY, Revital RAMATY
Life of this patent
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Abstract
Solid state forms of Sitagliptin salts, processes for preparing the solid state forms, and pharmaceutical compositions thereof, are provided.
Claims20
Sitagliptin sulfate, designated Form S2, characterized by data selected from:
- a powder XRD pattern with peaks at 9.3°, 9.7°, 15.2°, 15.6° and 25.4°±0.2° 2θ;
- a powder XRD pattern as shown in FIG. 1b;
- a solid-state 13C NMR spectrum with signals at 119.2, 150.3 and 170.6±0.2 ppm;
- a solid-state 13C 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 13C NMR spectrum as depicted in FIGS. 1m and 1n;
- and combinations thereof.
Sitagliptin sulfate, designated Form S6, characterized by a powder XRD diffractogram shown in FIG. 1f.
Sitagliptin sulfate isopropanol solvate, designated Form S7, characterized by data selected from:
- a powder XRD pattern with peaks at 5.2°, 15.6°, 16.6°, 18.7° and 21.1°±0.2° 2θ;
- a powder XRD diffractogram shown in FIG. 1g;
- a solid-state 13C NMR spectrum with signals at 120.4, 149.1 and 171.2±0.2 ppm;
- a solid-state 13C 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 13C NMR spectrum as depicted in FIGS. 1i and 1j;
- and combinations thereof.
Sitagliptin sulfate designated Form S1, characterized by data selected from:
- a powder XRD pattern with peaks at 11.8°, 13.7°, 14.4°, 17.0° and 17.5°±0.2° 2θ;
- a powder XRD diffractogram as shown in FIG. 1a;
- and combinations thereof.
Sitagliptin acetate, designated Form E1, characterized by data selected from:
- a powder XRD pattern with peaks at 6.2°, 11.1°, 12.5°, 17.7°, and 18.4°±0.2° 2θ;
- a powder XRD pattern as shown in FIG. 9a;
- a solid-state 13C NMR spectrum with signals at 122.3, 150.5 and 167.4±0.2 ppm;
- a solid-state 13C 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 13C NMR spectrum as depicted in FIGS. 9c and 9d;
- and combinations thereof.
Sitagliptin L-malate, designated Form I1, characterized by data selected from:
- a powder XRD pattern with peaks at 6.0°, 8.0°, 12.8°, 18.0° and 20.4°±0.2° 2θ;
- a powder XRD diffractogram shown in FIG. 4f;
- a solid-state 13C NMR spectrum with signals at 121.7, 150.8 and 173.0±0.2 ppm;
- a solid-state 13C 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 13C NMR spectrum as depicted in FIGS. 4d and 4e;
- and combinations thereof.
Sitagliptin quinate, designated Form Q1, characterized by data selected from:
- a powder XRD pattern with peaks at 7.3°, 8.6°, 10.5°, 12.6° and 13.9°±0.2° 2θ;
- a powder XRD pattern as shown in FIG. 6a;
- a solid-state 13C NMR spectrum with signals at 121.5, 169.0 and 180.3±0.2 ppm;
- a solid-state 13C 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 13C NMR spectrum is depicted in FIGS. 6b and 6c;
- and combinations thereof.
Dependencies are inferred from the claim text.