US 12,227,510 B2
Crystal form of acid addition salt of furopyrimidine compound
Hee Sook Oh, Hwaseong-si (KR); Jae Hyuk Jung, Hwaseong-si (KR); Ji Young Jeon, Hwaseong-si (KR); Sun Young Jang, Hwaseong-si (KR); and Tae Hee Ha, Hwaseong-si (KR)
Assigned to HANMI PHARM. CO., LTD., Hwaseong-si (KR)
Appl. No. 17/599,044
Filed by HANMI PHARM. CO., LTD., Hwaseong-si (KR)
PCT Filed Mar. 20, 2020, PCT No. PCT/KR2020/003850
§ 371(c)(1), (2) Date Sep. 28, 2021,
PCT Pub. No. WO2020/204426, PCT Pub. Date Oct. 8, 2020.
Claims priority of application No. 10-2019-0037060 (KR), filed on Mar. 29, 2019.
Prior Publication US 2022/0177483 A1, Jun. 9, 2022
Int. Cl. C07D 491/04 (2006.01)
CPC C07D 491/04 (2013.01) [C07B 2200/13 (2013.01)] 5 Claims
 
1. A crystalline form of an acid addition salt of the following compound of Formula 1:

OG Complex Work Unit Chemistry
wherein the crystalline form is selected from:
a crystalline form of dihydrochloride trihydrate (2HCl·3H2O) of the compound of Formula 1 and has an X-ray powder diffraction (XRPD) spectrum comprising peaks at diffraction angles (2θ±0.2°) of 6.4°, 7.1°, 12.8°, 15.6°, and 21.2°, when irradiated with a Cu-Kα light source;
a crystalline form of monohydrochloride dihydrate (1HCl·2H2O) of the compound of Formula 1 and has an X-ray powder diffraction (XRPD) spectrum comprising peaks at diffraction angles (2θ±0.2°) of 7.0°, 7.9°, 15.8°, 17.2°, 18.6°, 20.6°, 21.3°, and 23.2°, when irradiated with a Cu-Kα light source;
a crystalline form of monohydrochloride anhydrous (1HCl) of the compound of Formula 1 and has an X-ray powder diffraction (XRPD) spectrum comprising peaks at diffraction angles (2θ±0.2°) of 4.9°, 14.8°, and 21.2°, when irradiated with a Cu-Kα light source;
a crystalline form of methanesulfonic anhydride (1MsOH) of the compound of Formula 1 and has an X-ray powder diffraction (XRPD) spectrum comprising peaks at diffraction angles (2θ±0.2°) of 11.8°, 17.2°, 19.0°, 20.0°, 22.8°, and 24.0°, when irradiated with a Cu-Kα light source;
a crystalline form of methanesulfonate monohydrate (1MsOH·1H2O) of the compound of Formula 1 and has an X-ray powder diffraction (XRPD) spectrum comprising peaks at diffraction angles (2θ±0.2°) of 7.6°, 15.2°, 17.0°, 18.7°, 20.8°, and 22.8°, when irradiated with a Cu-Kα light source; or
a crystalline form of ethanesulfonic anhydride (1EsOH) of the compound of Formula 1 and has an X-ray powder diffraction (XRPD) spectrum comprising peaks at diffraction angles (2θ+0.2°) of 17.1°, 18.6°, 21.3°, 22.3°, 23.0°, and 23.6°, when irradiated with a Cu-Kα light source.