US 12,466,832 B2
Monohydrate and crystalline forms of 6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-3-tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one
Suzanne Buttar, Cambridge (GB); Mateusz Pitak, Cambridge (GB); Adam Ross Patterson, Cambridge (GB); Samuel Alexander Stratford, Cambridge (GB); Ioana Sovago, Cambridge (GB); Jun Xu, Changzhou (CN); Peng Zhou, Changzhou (CN); Haojuan Wei, Changzhou (CN); and Kuangchu Dai, Changzhou (CN)
Assigned to Cardurion Pharmaceuticals, Inc., Burlington, MA (US)
Filed by Cardurion Pharmaceuticals, Inc., Burlington, MA (US)
Filed on Mar. 4, 2024, as Appl. No. 18/594,898.
Application 18/594,898 is a continuation of application No. 17/110,000, filed on Dec. 2, 2020, granted, now 12,006,319.
Application 17/110,000 is a continuation of application No. PCT/US2019/033835, filed on May 23, 2019.
Claims priority of provisional application 62/788,323, filed on Jan. 4, 2019.
Claims priority of provisional application 62/676,381, filed on May 25, 2018.
Prior Publication US 2024/0199627 A1, Jun. 20, 2024
Int. Cl. C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) [C07B 2200/13 (2013.01)] 11 Claims
 
1. A process for preparing Monohydrate Form 1 (MH1) of Compound 1:

OG Complex Work Unit Chemistry
wherein the MH1 has an XRPD pattern comprising peaks at 9.1, 11.5, 16.2, 16.7, 18.2, 18.9, 19.8, 22.6, and 26.4 degrees 2θ, each ±0.2 degrees 2θ, comprising:
(i) dissolving Compound 1 in a first solvent to get a solution;
(ii) adding a second solvent to get a mixture; and
(iii) filtering the mixture to get a solid,
wherein the first and second solvent is each individually selected from isopropyl acetate, ethanol, tetrahydrofuran, water, dichloromethane, acetonitrile, anisole, methylisobutyl ketone, nitromethane, 1,2-dimethoxyethane, methylethyl ketone, n-heptane, 1,4-dioxane, n-propyl acetate, 2-propanol, acetone, cumene, N,N-dimethylformamide, dimethyl sulfoxide, and a combination thereof.