Crystalline polymorphic forms of an antidiabetic compound
View Patent ↗The present invention relates to polymorphic forms of a compound of formula A: This compound is useful as a glucagon receptor antagonist and serves as a pharmaceutically active ingredient for the treatment of type 2 diabetes and related conditions, such as hyperglycemia, obesity, dyslipidemia, and the metabolic syndrome. Hydrates, hemihydrates, anhydrates and similar polymorphic forms are included.
1. A crystalline polymorphic form of a compound of formula A:
or a pharmaceutically acceptable salt thereof, the polymorphic form being an anhydrous free acid of polymorphic Form III.
2. A crystalline polymorphic compound of Form III in accordance with claim 1 having at least three of the X Ray Powder Diffraction Pattern d-spacings shown in Table 5:
TABLE 5
2 theta
d-spacing [Å]
26.42
3.37
24.90
3.58
24.61
3.62
23.87
3.73
23.21
3.83
22.44
3.96
19.66
4.52
19.43
4.57
17.94
4.94
12.2927
7.20.
3. A crystalline polymorphic compound of Form III in accordance with claim 1 having at least five of the X Ray Powder Diffraction Pattern d-spacings shown in Table 5:
TABLE 5
2 theta
d-spacing [Å]
26.42
3.37
24.90
3.58
24.61
3.62
23.87
3.73
23.21
3.83
22.44
3.96
19.66
4.52
19.43
4.57
17.94
4.94
12.2927
7.20.
4. A crystalline polymorphic compound of crystalline anhydrate Form III, in accordance with claim 1 having at least three C13 NMR peaks selected from the group consisting of: 177.58, 148.52, 146.17, 130.34, 121.11, 113.44, 52.77, 31.30, 21.42 and 14.04 ppm.
5. A pharmaceutical composition comprised of an anhydrous free acid of polymorphic Form III of a compound in accordance with claim 1 in combination with a pharmaceutically acceptable carrier.