US 12,492,195 B2
Preparation method for and crystal form of 3-aryloxy-3-five-membered heteroaryl-propylamine compound
Juan Yu, Fujian (CN); Youxin Wang, Shanghai (CN); Tingting Yin, Fujian (CN); Jinxiang Zeng, Fujian (CN); Lingling Zhang, Shanghai (CN); and Qiang Ding, Shanghai (CN)
Assigned to ZHANGZHOU PIEN TZE HUANG PHARMACEUTICAL CO., LTD., Fujian (CN); and SHANGHAI LEADO PHARMATECH CO. LTD., Shanghai (CN)
Appl. No. 17/799,487
Filed by Zhangzhou Pien Tze Huang Pharmaceutical Co., Ltd., Fujian (CN); and Shanghai Leado Pharmatech Co. Ltd., Shanghai (CN)
PCT Filed Feb. 9, 2021, PCT No. PCT/CN2021/076337
§ 371(c)(1), (2) Date Aug. 12, 2022,
PCT Pub. No. WO2021/160134, PCT Pub. Date Aug. 19, 2021.
Claims priority of application No. 202010093694.3 (CN), filed on Feb. 14, 2020.
Prior Publication US 2023/0339920 A1, Oct. 26, 2023
Int. Cl. C07D 409/12 (2006.01)
CPC C07D 409/12 (2013.01) [C07B 2200/13 (2013.01)] 15 Claims
 
1. A crystal form of a salt of the compound of formula Ic-1

OG Complex Work Unit Chemistry
wherein the crystal form of the salt is selected from the group consisting of:
(a) a crystal form A of the hydrochloride salt of a compound of formula Ic-1,
wherein the X-ray powder diffraction pattern of the crystal form A of the hydrochloride salt has characteristic peaks at 2θ angles of 18.27±0.2°, 21.27±0.2°, and 22.89±0.2°;
(b) a crystal form B of the maleate salt of a compound of formula Ic-1,
wherein the X-ray powder diffraction pattern of the crystal form B of the maleate salt has characteristic peaks at 2θ angles of 19.23±0.2°, 24.04±0.2°, and 24.70±0.2°;
(c) a crystal form C of the oxalate salt of a compound of formula Ic-1,
wherein the X-ray powder diffraction pattern of the crystal form C of the oxalate salt has characteristic peaks at 2θ angles of 14.64±0.2°, 22.05±0.2°, and 25.61±0.2°;
(d) a crystal form D of the mucate salt of a compound of formula Ic-1,
wherein the X-ray powder diffraction pattern of the crystal form D of the mucate salt has characteristic peaks at 2θ angles of 3.79±0.2°, 11.28±0.2°, and 19.48±0.2°;
(e) a crystal form E of the fumarate salt of a compound of formula Ic-1,
wherein the X-ray powder diffraction pattern of the crystal form E of the fumarate salt has characteristic peaks at 2θ angles of 14.17±0.2°, 18.95±0.2°, and 23.76±0.2°;
(f) a crystal form F of the D-glucuronate salt of a compound of formula Ic-1,
wherein the X-ray powder diffraction pattern of the crystal form F of the D-glucuronate salt has characteristic peaks at 2θ angles of 4.77±0.2°, 16.13±0.2°, and 19.53±0.2°.