US 12,459,940 B2
Oxazole compound as multi-targeted inhibitor of IRAK4 and BTK
Jianfei Wang, Shanghai (CN); Haizhong Tan, Shanghai (CN); Jie Li, Shanghai (CN); Yang Zhang, Shanghai (CN); Jian Li, Shanghai (CN); and Shuhui Chen, Shanghai (CN)
Assigned to Shanghai Fosun Pharmaceutical Industrial Development Co., Ltd., Shanghai (CN)
Appl. No. 17/625,599
Filed by SHANGHAI FOSUN PHARMACEUTICAL INDUSTRIAL DEVELOPMENT CO., LTD., Shanghai (CN)
PCT Filed Jul. 10, 2020, PCT No. PCT/CN2020/101369
§ 371(c)(1), (2) Date Jan. 7, 2022,
PCT Pub. No. WO2021/004533, PCT Pub. Date Jan. 14, 2021.
Claims priority of application No. 201910619602.8 (CN), filed on Jul. 10, 2019; application No. 201911240843.8 (CN), filed on Dec. 6, 2019; and application No. 202010470469.7 (CN), filed on May 28, 2020.
Prior Publication US 2022/0267322 A1, Aug. 25, 2022
Int. Cl. C07D 471/04 (2006.01); A61P 35/00 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 35/00 (2018.01)] 18 Claims
 
1. A compound represented by formula (II) or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein,
R1 is selected from H, F, Cl, Br, I, OH, NH2, CN, C1-6 alkyl, cyclopropyl and —C(═O)—NH2, wherein the C1-6 alkyl, cyclopropyl and —C(═O)—NH2 are optionally substituted by 1, 2 or 3 Ra;
R2 is selected from thienyl, phenyl, pyridyl, cyclopropyl, cyclohexyl and

OG Complex Work Unit Chemistry
wherein the thienyl, phenyl, pyridyl, cyclopropyl, cyclohexyl and

OG Complex Work Unit Chemistry
are optionally substituted by 1, 2, 3, 4 or 5 Rb;
T1 is selected from CH2, NH and O;
R3 is selected from C1-6 alkyl, wherein the C1-6 alkyl is optionally substituted by 1, 2 or 3 Rc;
Ra is each independently selected from F, OH, NH2 and CN;
Rb is each independently selected from H, D, F, Cl, Br, I, OH, NH2, CN, C1-3 alkyl, COOH, —C(═O)—C1-3 alkyl, —C(═O)—O—C1-3 alkyl and —C(═O)—NH2, wherein the OH, NH2, C1-3 alkyl, COOH, —C(═O)—C1-3 alkyl, —C(═O)—O—C1-3 alkyl and —C(═O)—NH2 are optionally substituted by 1, 2 or 3 R;
Rc is each independently selected from F, OH, NH2, CN, CH3, COOH and —SO2CH3;
R is each independently selected from F, OH, NH2 and CH3.