US 12,435,093 B2
Free base crystals
Peng Li, New Milford, NJ (US)
Assigned to INTRA-CELLULAR THERAPIES, INC., Bedminster, NJ (US)
Appl. No. 17/997,983
Filed by INTRA-CELLULAR THERAPIES, INC., New York, NY (US)
PCT Filed May 6, 2021, PCT No. PCT/US2021/031197
§ 371(c)(1), (2) Date Nov. 4, 2022,
PCT Pub. No. WO2021/226407, PCT Pub. Date Nov. 11, 2021.
Claims priority of provisional application 63/020,972, filed on May 6, 2020.
Prior Publication US 2023/0174543 A1, Jun. 8, 2023
Int. Cl. C07D 487/14 (2006.01)
CPC C07D 487/14 (2013.01) [C07B 2200/13 (2013.01)] 20 Claims
 
1. A crystal of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one free base (Compound A) as shown by the following chemical formula:

OG Complex Work Unit Chemistry
wherein said free base crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2-theta angle values selected from the group consisting of 3.39, 3.77, 4.74, 7.94, 8.21, 9.41, 10.10, 10.69, 13.61, 14.04, 15.68, 16.68, 17.55, 18.52, 19.26, 19.49, 21.55, 21.95, 22.41, 23.43, 24.98, 25.05, 25.94, 26.57, 28.41, 29.70, 31.48, 31.53, and 31.65 degrees, wherein the XRPD pattern is measured in a diffractometer using copper anode.