Crystalline forms of 2-[3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile
Crystalline forms of Compound (I): are disclosed. Pharmaceutical compositions comprising the same, methods of inhibiting BTK using the same, and methods for making crystalline forms of Compound (I) are also disclosed.
1. Crystalline Form (I) of Compound (I):
wherein crystalline Form (I) is characterized by an X-ray powder diffractogram comprising at least one signal at a value (°2θ) chosen from 6.3°±0.2 °2θ, 12.6°±0.2 °2θ, 16.2°±0.2 °2θ, 17.6°±0.2 °2θ, 18.2°±0.2 °2θ, 18.4°±0.2 °2θ, and 22.1°±0.2 °2θ.
2. The crystalline Form (I) according to claim 1 , wherein the crystalline Form (I) is further characterized by an X-ray powder diffractogram comprising at least three signals at values (°2θ) chosen from 6.3°±0.2 °2θ, 12.6°±0.2 °2θ, 16.2°±0.2 °2θ, 17.6°±0.2 °2θ, 18.2°±0.2 °2θ, 18.4°±0.2 °2θ, and 22.1°±0.2 °2θ.
3. The crystalline Form (I) according to claim 1 , wherein the crystalline Form (I) is further characterized by any one of the following:
(i) a differential scanning calorimetry thermogram showing onset of melting at about 174.8° C. to about 175.2° C.; or
(ii) a differential scanning calorimetry thermogram having an endothermic peak at about 177° C. to about 178° C.; or
(iii) a differential scanning calorimetry thermogram showing onset of melting at about 174.8° C. to about 175.2° C. and a differential scanning calorimetry thermogram having an endothermic peak at about 177° C. to about 178° C.
4. The crystalline Form (I) according to claim 1 , wherein at least 95% by weight of the crystalline Form (I) of Compound (I) is the (R) enantiomer.
5. The crystalline Form (I) according to claim 1 , wherein at least 95% by weight of the crystalline Form (I) of Compound (I) is the (E) diastereomer.
6. A pharmaceutical composition comprising at least one pharmaceutically acceptable excipient and the crystalline Form (I) according to claim 1 .