US 11,746,109 B2
Crystalline forms of 2-[(2S)-1-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one hemihydrate
Kentaro Iwata, Kanagawa (JP); Masahiro Mizuno, Osaka (JP); Kazuhiro Maeda, Osaka (JP); Tsuneo Yasuma, Osaka (JP); Misaki Homma, Kanagawa (JP); Yuya Oguro, Kanagawa (JP); Naohiro Taya, Kanagawa (JP); Lei Zhu, Bedford, MA (US); John Daniel Bailey, Cambridge, MA (US); Marianne Langston, Cambridge, MA (US); Siddhesh Dinanath Patil, Cambridge, MA (US); Shruti Gour, Watertown, MA (US); and Lilly Roy, Boston, MA (US)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (JP)
Appl. No. 16/88,096
Filed by TAKEDA PHARMACEUTICAL COMPANY LIMITED, Osaka (JP)
PCT Filed Mar. 27, 2017, PCT No. PCT/US2017/024226
§ 371(c)(1), (2) Date Sep. 25, 2018,
PCT Pub. No. WO2017/172565, PCT Pub. Date Oct. 5, 2017.
Claims priority of provisional application 62/367,842, filed on Jul. 28, 2016.
Claims priority of provisional application 62/314,080, filed on Mar. 28, 2016.
Prior Publication US 2023/0102273 A1, Mar. 30, 2023
Int. Cl. C07D 471/08 (2006.01); A61K 9/48 (2006.01)
CPC C07D 471/08 (2013.01) [A61K 9/485 (2013.01); A61K 9/4858 (2013.01); C07B 2200/13 (2013.01)] 20 Claims
 
1. A crystalline form of 2-[(2S)-l-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one hemihydrate (Compound 1), or a tautomer or a combination thereof, wherein Compound 1 is represented by the structure

OG Complex Work Unit Chemistry
wherein the crystalline form of Compound 1 is characterized by an X-ray powder diffraction pattern having characteristic peaks expressed in degrees 2θ at 15.2±0.2, 17.8±0.2, and 27.6±0.2.