Crystalline pyrrolo[2,3-d]pyrimidine compounds
AssigneePfizer Inc.
InventorsBrendan J. Murphy, Timothy D. White, Brian P. Chekal, Phillip J. Johnson, Christopher James Foti, Leonid A. Margulis
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Abstract
The present invention discloses novel crystalline and non-crystalline forms of 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-pip-eridin-1-yl)-3-oxopropionitrile, pharmaceutical composition containing the same, preparations thereof and the uses thereof.
Claims28
A crystalline form of 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile, having a powder X-ray diffraction pattern comprising peaks, in terms of 2θ, at 6.4°, 14.3°, and 17.0° 2θ±0.2° 2θ.
A crystalline form of 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile, having a powder X-ray diffraction pattern comprising peaks, in terms of 2θ, at 6.4°, 9.1°, and 11.1° 2θ±0.2° 2θ.
A crystalline form of 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile, having solid state 13C nuclear magnetic resonance chemical shifts at 157.0, 151.0, 102.4, 44.8 and 32.7 ppm±0.2 ppm.
A non-crystalline form of 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile character-ized by a physical or spectroscopic analysis selected from the group consisting of:
- a) a solid state 13C nuclear magnetic resonance spectrum comprising chemical shifts at 161.9, 152.0, 103.3, 31.8, and 26.0 ppm±0.2 ppm.;
- b) a set of Raman bands at 1311, 1506, and 2258 cm−1±2 cm−1;
- and,
- c) a set of infrared bands at 1407, 1554, and 1647 cm−1±2 cm−1.
A pharmaceutical composition comprising:
- 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile;
- one or more penetration enhancer;
- and, a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising:
- about 2.0% 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile by weight, about 2.0% oleyl alcohol, about 20.0% glycerin, at least about 30.0% polyethylene glycol, and about 0.1% butyl hydroxyanisole
A method of topically treating a disease in a mammal, comprising administering by a topical mode of administration to a mammal in need thereof a therapeutically effective amount of 3-((3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl)-3-oxopropionitrile, having a crystalline form or non-crystalline form, or a pharmaceutically acceptable salt thereof, one or more penetration enhancer;
- and a pharmaceutically acceptable carrier, wherein the disease is selected from the group consisting of psoriasis and dermatitis and said penetration enhancer is selected from oleyl alcohol, linoleyl alcohol, γ-linolenyl alcohol, linolenyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid and arachidic acid, palmitoleic acid, oleic acid, cis-vaccenic acid, linoleic acid, γ-linolenic acid, linolenic acid, and arachidonic acid.
Dependencies are inferred from the claim text.