US 12,410,176 B2
Crystalline forms of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile
Pasit Phiasivongsa, Hillsborough, CA (US); Kolbot By, San Ramon, CA (US); and Jean Baum, San Bruno, CA (US)
Assigned to Principia Biopharma Inc., Bridgewater, NJ (US)
Filed by Principia Biopharma Inc., Bridgewater, NJ (US)
Filed on Oct. 6, 2023, as Appl. No. 18/482,278.
Application 18/482,278 is a continuation of application No. 17/154,452, filed on Jan. 21, 2021, granted, now 11,814,390.
Claims priority of provisional application 62/964,378, filed on Jan. 22, 2020.
Prior Publication US 2024/0182484 A1, Jun. 6, 2024
Int. Cl. C07D 487/14 (2006.01)
CPC C07D 487/14 (2013.01) [C07B 2200/13 (2013.01)] 1 Claim
 
1. A process of preparing crystalline Form C of Compound (I):

OG Complex Work Unit Chemistry
wherein C* is a stereochemical center and
wherein crystalline Form C is characterized by an X-ray powder diffractogram having a signal at at least three two-theta values chosen from 9.8±0.2, 10.2±0.2, 15.6±0.2, 16.6±0.2, 18.6±0.2, 18.9±0.2, 19.6±0.2, and 21.6±0.2, the process comprising:
adding acetonitrile to amorphous (R)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile to form a solution;
seeding the solution with crystalline Form B of Compound (I) to form a mixture and stirring the mixture to obtain a slurry, wherein the crystalline Form B is characterized by an X-ray powder diffractogram having a signal at at least three two-theta values chosen from 10.8±0.2, 15.3±0.2, 16.3±0.2, 17.9±0.2, 18.4±0.2, 18.7±0.2, 22.0±0.2, and 22.9±0.2; and
isolating crystalline Form C by filtering the slurry.