Crystalline forms of a Bruton's tyrosine kinase inhibitor
View Patent ↗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.
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°.