Crystalline forms of a Bruton's tyrosine kinase inhibitor

Patent metadata

Field	Value
Publication number	US-10266540-B2
Application number	US-201816035449-A
Country	US
Kind code	B2
Filing date	Jul 13, 2018
Priority date	Jun 4, 2012
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

Described herein is the Bruton's tyrosine kinase (Btk) inhibitor 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one, including crystalline forms, solvates and pharmaceutically acceptable salts thereof. Also disclosed are pharmaceutical compositions that include the Btk inhibitor, as well as methods of using the Btk inhibitor, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions.

First claim

What is claimed is:

1. A crystalline form of 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one that has an X-ray powder diffraction (XRPD) pattern comprising 2-Theta peaks at about 7.0°, about 14.0°, and about 18.2°.

2. The crystalline form of claim 1 , wherein the XRPD pattern further comprises a 2-Theta peak at about 15.7°.

3. The crystalline form of claim 1 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.1°.

4. The crystalline form of claim 1 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.5°.

5. The crystalline form of claim 1 , wherein the XRPD pattern further comprises 2-Theta peaks at about 15.7° and about 19.1°.

6. The crystalline form of claim 1 , wherein the XRPD pattern further comprises 2-Theta peaks at about 15.7° and about 19.5°.

7. The crystalline form of claim 1 , wherein the XRPD pattern further comprises 2-Theta peaks at about 15.7°, about 19.1°, and about 19.5°.

8. The crystalline form of claim 7 , wherein the XRPD pattern further comprises 2-Theta peaks at about 20.3°, about 22.1°, and about 22.9°.

9. A crystalline form of 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one that has an XRPD pattern comprising 2-Theta peaks at about 7.0°, about 15.7°, and about 18.2°.

10. The crystalline form of claim 9 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.1°.

11. The crystalline form of claim 9 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.5°.

12. The crystalline form of claim 9 , wherein the XRPD pattern further comprises 2-Theta peaks at about 19.1° and about 19.5°.

13. The crystalline form of claim 12 , wherein the XRPD pattern further comprises 2-Theta peaks at about 20.3°, about 22.1°, and about 22.9°.

14. A crystalline form of 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one that has an XRPD pattern comprising 2-Theta peaks at about 7.0°, about 14.0°, and about 15.7°.

15. The crystalline form of claim 14 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.1°.

16. The crystalline form of claim 14 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.5°.

17. The crystalline form of claim 14 , wherein the XRPD pattern further comprises 2-Theta peaks at about 19.1° and about 19.5°.

18. The crystalline form of claim 17 , wherein the XRPD pattern further comprises 2-Theta peaks at about 20.3°, about 22.1°, and about 22.9°.

19. A crystalline form of 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one that has an XRPD pattern comprising 2-Theta peaks at about 14.0°, about 15.7° and about 18.2°.

20. The crystalline form of claim 19 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.1°.

21. The crystalline form of claim 19 , wherein the XRPD pattern further comprises a 2-Theta peak at about 19.5°.

22. The crystalline form of claim 19 , wherein the XRPD pattern further comprises 2-Theta peaks at about 19.1° and about 19.5°.

23. The crystalline form of claim 22 , wherein the XRPD pattern further comprises 2-Theta peaks at about 20.3°, about 22.1°, and about 22.9°.

Assignees

• Pharmacyclics Llc

Inventors

• Purro Norbert
• Smyth Mark S
• Goldman Erick
• Wirth David D

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P39/00

  General protective or antinoxious agents · CPC title

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• A61P37/02

  Immunomodulators · CPC title

• A61P37/00

  Drugs for immunological or allergic disorders · CPC title