US 12,421,245 B2
Pharmaceutically acceptable acid salt of free base of GLP1 receptor agonist, and preparation method therefor
Haiwen Hu, Zhejiang (CN); Li Fang, Zhejiang (CN); Fan Hu, Zhejiang (CN); Xinjie Zhou, Zhejiang (CN); and Fenfen Chen, Zhejiang (CN)
Assigned to Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd., Zhejiang (CN)
Appl. No. 17/995,091
Filed by Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd., Zhejiang (CN)
PCT Filed Mar. 2, 2021, PCT No. PCT/CN2021/078658
§ 371(c)(1), (2) Date Sep. 29, 2022,
PCT Pub. No. WO2021/196951, PCT Pub. Date Oct. 7, 2021.
Claims priority of application No. 2020010248957.3 (CN), filed on Apr. 1, 2020.
Prior Publication US 2023/0174547 A1, Jun. 8, 2023
Int. Cl. C07D 491/056 (2006.01)
CPC C07D 491/056 (2013.01) [C07B 2200/13 (2013.01)] 23 Claims
OG exemplary drawing
 
1. A crystalline form of a salt of (S)-2-(3S,8S)-3-(4-(3,4-dichlorobenzyloxy)phenyl-7-((S)-1-phenylpropyl)-2,3,6,7,8,9-hexahydro-[1,4]-dioxino[2,3-g]isoquinolin-8-ylformylamino)-3-(4-(2,3-dimethylpyridin-4-yl)phenyl)propionic acid (OAD2), selected from the group consisting of the following:
crystal form B of hydrochloride salt of OAD2 (form B),
crystal form C of hydrochloride salt of OAD2 (form C),
crystal form C of p-toluenesulfonate salt of OAD2 (form C),
crystal form C of tartrate salt of OAD2 (form C),
crystal form C of citrate salt of OAD2 (form C),
crystal form C of glycollate salt of OAD2 (form C),
crystal form C of methanesulfonate salt of OAD2 (form C),
crystal form C of hydrobromide salt of OAD2 (form C),
crystal form D of hydrobromide salt of OAD2 (form D), and
crystal form C of sulfate salt of OAD2 (form C).