Claims for Patent: 9,796,721
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Summary for Patent: 9,796,721
Title: | Crystal forms of (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-- yl)-N-(pyridin-2-yl)benzamide |
Abstract: | In some embodiments, the invention relates to crystalline solid forms, including hydrates, polymorphs, and salt forms, of (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-- yl)-N-(pyridin-2-yl)benzamide. In some embodiments, the invention relates to amorphous solid forms of (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-- yl)-N-(pyridin-2-yl)benzamide. In some embodiments, the invention also relates to pharmaceutical compositions containing the solid forms, and methods for treating conditions or disorders by administering to a subject a pharmaceutical composition that includes the forms, including pharmaceutical compositions and methods for overcoming the effects of acid reducing agents. |
Inventor(s): | Blatter; Fritz (Reinach, CH), Ingallinera; Tim (San Francisco, CA), Barf; Tjeerd (Ravenstein, NL), Aret; Edwin (Almere, NL), Krejsa; Cecile (Seattle, WA), Evarts; Jerry (Bellevue, WA) |
Assignee: | Acerta Pharma B.V. (Oss, NL) |
Application Number: | 15/200,875 |
Patent Litigation and PTAB cases: | See patent lawsuits and PTAB cases for patent 9,796,721 |
Patent Claims: |
1. A crystal form of (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-- yl)-N-(pyridin-2-yl)benzamide characterized by a reflection X-ray powder diffraction
pattern comprising peaks at 6.4.degree..+-.0.2.degree. 2.theta., 8.6.degree..+-.0.2.degree. 2.theta., 10.5.degree..+-.0.2.degree. 2.theta., 11.6.degree..+-.0.2.degree. 2.theta. and 15.7.degree..+-.0.2.degree. 2.theta..
2. The crystal form of claim 1, wherein the reflection X-ray powder diffraction pattern further comprises peaks at 10.9.degree..+-.0.2.degree. 2.theta., 12.7.degree..+-.0.2.degree. 2.theta., 13.4.degree..+-.0.2.degree. 2.theta., 14.3.degree..+-.0.2.degree. 2.theta., 14.9.degree..+-.0.2.degree. 2.theta. and 18.2.degree..+-.0.2.degree. 2.theta.. 3. The crystal form of claim 2, wherein the reflection X-ray powder diffraction pattern comprises one or more peaks at 11.3.degree..+-.0.2.degree. 2.theta., 15.1.degree..+-.0.2.degree. 2.theta., 16.1.degree..+-.0.2.degree. 2.theta., 17.3.degree..+-.0.2.degree. 2.theta., 19.2.degree..+-.0.2.degree. 2.theta., 19.4.degree..+-.0.2.degree. 2.theta., 19.8.degree..+-.0.2.degree. 2.theta., 20.7.degree..+-.0.2.degree. 2.theta., 21.1.degree..+-.0.2.degree. 2.theta., 21.4.degree..+-.0.2.degree. 2.theta., 21.6.degree..+-.0.2.degree. 2.theta., 21.9.degree..+-.0.2.degree. 2.theta., 22.6.degree..+-.0.2.degree. 2.theta., 23.3.degree..+-.0.2.degree. 2.theta., 23.6.degree..+-.0.2.degree. 2.theta., 24.9.degree..+-.0.2.degree. 2.theta., 25.2.degree..+-.0.2.degree. 2.theta., 25.4.degree..+-.0.2.degree. 2.theta., 25.7.degree..+-.0.2.degree. 2.theta., 26.1.degree..+-.0.2.degree. 2.theta., 26.4.degree..+-.0.2.degree. 2.theta., 26.8.degree..+-.0.2.degree. 2.theta., 26.9.degree..+-.0.2.degree. 2.theta., 27.7.degree..+-.0.2.degree. 2.theta., 28.6.degree..+-.0.2.degree. 2.theta., 29.1.degree..+-.0.2.degree. 2.theta., 29.4.degree..+-.0.2.degree. 2.theta., 30.1.degree..+-.0.2.degree. 2.theta., 30.5.degree..+-.0.2.degree. 2.theta., 31.7.degree..+-.0.2.degree. 2.theta., 31.9.degree..+-.0.2.degree. 2.theta., 32.2.degree..+-.0.2.degree. 2.theta., 32.6.degree..+-.0.2.degree. 2.theta., 33.1.degree..+-.0.2.degree. 2.theta., 33.4.degree..+-.0.2.degree. 2.theta..degree..+-.0.2.degree. 2.theta., 34.5.degree..+-.0.2.degree. 2.theta., 35.9.degree..+-.0.2.degree. 2.theta., 36.1.degree..+-.0.2.degree. 2.theta., 36.8.degree..+-.0.2.degree. 2.theta., 37.4.degree..+-.0.2.degree. 2.theta., 38.1.degree..+-.0.2.degree. 2.theta., 38.9.degree..+-.0.2.degree. 2.theta. and 39.5.degree..+-.0.2.degree. 2.theta.. 4. The crystal form of claim 2, wherein the reflection X-ray powder diffraction pattern further comprises peaks at 11.3.degree..+-.0.2.degree. 2.theta., 15.1.degree..+-.0.2.degree. 2.theta., 16.1.degree..+-.0.2.degree. 2.theta., 17.3.degree..+-.0.2.degree. 2.theta., 19.2.degree..+-.0.2.degree. 2.theta., 19.4.degree..+-.0.2.degree. 2.theta., 19.8.degree..+-.0.2.degree. 2.theta., 20.7.degree..+-.0.2.degree. 2.theta., 21.1.degree..+-.0.2.degree. 2.theta., 21.4.degree..+-.0.2.degree. 2.theta., 21.6.degree..+-.0.2.degree. 2.theta., 21.9.degree..+-.0.2.degree. 2.theta., 22.6.degree..+-.0.2.degree. 2.theta., 23.3.degree..+-.0.2.degree. 2.theta., 23.6.degree..+-.0.2.degree. 2.theta., 24.9.degree..+-.0.2.degree. 2.theta., 25.2.degree..+-.0.2.degree. 2.theta., 25.4.degree..+-.0.2.degree. 2.theta., 25.7.degree..+-.0.2.degree. 2.theta., 26.1.degree..+-.0.2.degree. 2.theta., 26.4.degree..+-.0.2.degree. 2.theta., 26.8.degree..+-.0.2.degree. 2.theta., 26.9.degree..+-.0.2.degree. 2.theta., 27.7.degree..+-.0.2.degree. 2.theta., 28.6.degree..+-.0.2.degree. 2.theta., 29.1.degree..+-.0.2.degree. 2.theta., 29.4.degree..+-.0.2.degree. 2.theta., 30.1.degree..+-.0.2.degree. 2.theta., 30.5.degree..+-.0.2.degree. 2.theta., 31.7.degree..+-.0.2.degree. 2.theta., 31.9.degree..+-.0.2.degree. 2.theta., 32.2.degree..+-.0.2.degree. 2.theta., 32.6.degree..+-.0.2.degree. 2.theta., 33.1.degree..+-.0.2.degree. 2.theta., 33.4.degree..+-.0.2.degree. 2.theta..degree..+-.0.2.degree. 2.theta., 34.5.degree..+-.0.2.degree. 2.theta., 35.9.degree..+-.0.2.degree. 2.theta., 36.1.degree..+-.0.2.degree. 2.theta., 36.8.degree..+-.0.2.degree. 2.theta., 37.4.degree..+-.0.2.degree. 2.theta., 38.1.degree..+-.0.2.degree. 2.theta., 38.9.degree..+-.0.2.degree. 2.theta. and 39.5.degree..+-.0.2.degree. 2.theta.. 5. The crystal form of claim 2, wherein the crystal form is a crystalline anhydrate. 6. The crystal form of claim 1, 2, 3, 4 or 5, wherein the peaks are present when the reflection x-ray powder diffraction is carried out using Cu--K.sub..alpha. radiation. 7. The crystal form of claim 1, 2, 3, 4 or 5, wherein the peaks are present when the reflection x-ray powder diffraction is carried out using a Bruker D8 Advance powder X-ray diffractometer equipped with a LynxEye detector and operating in Bragg-Brentano reflection geometry, a tube voltage of 40 kV and current of 40 mA, a variable divergence slit with a 3.degree. window, a step size of 0.02.degree. 2.theta., sample rotation of 0.5 rps, and a step time of 37 seconds. 8. A pharmaceutical composition comprising the crystal form of any of claim 1, 2, 3, 4 or 5 and at least one pharmaceutically acceptable excipient. 9. The pharmaceutical composition of claim 8, wherein the pharmaceutical composition further comprises an extragranular acidulant. 10. The pharmaceutical composition of claim 9, wherein the extragranular acidulant is selected from the group consisting of fumaric acid, succinic acid, D-tartaric acid, L-tartaric acid, (.+-.)-tartaric acid, ascorbic acid, isoascorbic acid, alginic acid, a salt of alginic acid, Protacid F 120 NM, Protacid AR 1112 and Carbopol 971P, or a combination thereof. 11. The pharmaceutical composition of claim 9, wherein the extragranular acidulant is selected from the group consisting of alginic acid, a sodium salt of alginic acid and a potassium salt of alginic acid. 12. A method of inhibiting Bruton's tyrosine kinase activity in a human, comprising administering to said human a therapeutically effective amount of the pharmaceutical composition of claim 8. 13. The method of claim 12, wherein the human suffers from a hyperproliferative disease. 14. The method of claim 13, wherein the hyperproliferative disease is chronic lymphocytic leukemia. 15. The method of claim 13, wherein the hyperproliferative disease is small lymphocytic lymphoma. 16. The method of claim 13, wherein the hyperproliferative disease is mantle cell lymphoma. 17. The method of claim 13, wherein the hyperproliferative disease is Waldenstrom's macroglobulinemia. |
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