Crystalline forms of a Bruton's tyrosine kinase inhibitor
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 pharmaceutical composition comprising
a crystalline form of ibrutinib and a pharmaceutically acceptable excipient, wherein said crystalline form of ibrutinib is produced by a process, comprising combining a solvent solution comprising alcohol with a crystalline ibrutinib having 2-theta peaks at 7.0±0.1°, 14.0±0.1°, 15.7±0.1°, and 18.2±0.1°; and
a pharmaceutically acceptable excipient.
2. The pharmaceutical composition of claim 1 , wherein the alcohol is selected from the group consisting of: methanol and ethanol.
3. The pharmaceutical composition of claim 1 , wherein the alcohol is ethanol.
4. The pharmaceutical composition of claim 1 , wherein the alcohol is methanol.
5. The pharmaceutical composition of claim 3 , wherein the crystalline form of ibrutinib has 2-theta peaks at 5.7±0.1°, 13.6±0.1°, 16.1±0.1°, 18.9±0.1°, and 21.3±0.1°.
6. The pharmaceutical composition of claim 3 , wherein the solvent solution further comprises water.
7. The pharmaceutical composition of claim 6 , wherein the crystalline form of ibrutinib has 2-theta peaks at 5.2±0.1°, 10.2±0.1°, 16.5±0.1°, 18.5±0.1°, and 20.8±0.1°.
8. The pharmaceutical composition of claim 1 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.
9. The pharmaceutical composition of claim 2 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.
10. The pharmaceutical composition of claim 3 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.
11. The pharmaceutical composition of claim 4 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.
12. The pharmaceutical composition of claim 5 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.
13. The pharmaceutical composition of claim 6 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.
14. The pharmaceutical composition of claim 7 , wherein the crystalline form of ibrutinib is recovered from the solvent solution.