US 11,891,398 B2
2,3-dihydro-1H-pyrrolizine-7-formamide derivative and application thereof
Haiying He, Shanghai (CN); Jianhua Xia, Shanghai (CN); Zhen Gong, Shanghai (CN); Jian Li, Shanghai (CN); and Shuhui Chen, Shanghai (CN)
Assigned to CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., Jiangsu (CN)
Appl. No. 17/058,308
Filed by CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., Jiangsu (CN)
PCT Filed May 24, 2019, PCT No. PCT/CN2019/088376
§ 371(c)(1), (2) Date Nov. 24, 2020,
PCT Pub. No. WO2019/223791, PCT Pub. Date Nov. 28, 2019.
Claims priority of application No. 201810528259.1 (CN), filed on May 25, 2018; application No. 201810843225.1 (CN), filed on Jul. 27, 2018; and application No. 201811189801.1 (CN), filed on Oct. 12, 2018.
Prior Publication US 2022/0204510 A1, Jun. 30, 2022
Int. Cl. C07D 487/04 (2006.01); A61P 31/20 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 31/20 (2018.01)] 20 Claims
 
1. A compound of formula (II) or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein,
m is 1;
L is selected from

OG Complex Work Unit Chemistry
T1 is selected from the group consisting of N and C (R43);
R2 is selected from the group consisting of H and C1-6 alkyl, wherein the C1-6 alkyl is optionally substituted by 1, 2, or 3 Rb;
R3 is selected from the group consisting of Cl, F, Br, I, OH, NH2, C1-6 alkyl, and C1-3 alkoxy, wherein the C1-6 alkyl and the C1-3 alkoxy are optionally substituted by 1, 2, or 3 Rc;
R41, R42, R43, R44, and R45 are each independently selected from the group consisting of H, Cl, F, Br, I, OH, NH2, CN, COOH, and C1-3 alkyl, wherein the C1-3 alkyl is optionally substituted by 1, 2, or 3 Rd;
R5 is selected from the group consisting of R51, C3-10 cycloalkyl, and 3-6 membered heterocycloalkyl, wherein the C3-10 cycloalkyl and the 3-6 membered heterocycloalkyl are optionally substituted by 1, 2, or 3 R1;
R51 is selected from the group consisting of C1-7 alkyl and C1-6 heteroalkyl, wherein the C1-7 alkyl and the C1-6 heteroalkyl are optionally substituted by 1, 2, or 3 Re;
R1 is each independently selected from the group consisting of H, Cl, F, Br, I, OH, NH2, CN, COOH, C1-6 alkyl, —COO—C1-6 alkyl, and —C1-3 alkyl-COO—C1-6 alkyl, wherein the C1-6 alkyl, the —COO—C1-6 alkyl, and the —C1-3 alkyl-COO—C1-6 alkyl are optionally substituted by 1, 2, or 3 Ra;
Ra is each independently selected from the group consisting of Cl, F, Br, I, NH2, CN, COOH, C1-3 alkyl, and C1-3 alkoxy, wherein the C1-3 is optionally substituted by 1, 2, or 3 R;
Rb is each independently selected from the group consisting of Cl, F, Br, I, OH, NH2, CN, and COOH;
Re is each independently selected from the group consisting of Cl, F, Br, I, OH, NH2, CN, COOH, and C1-3 alkyl, wherein the C1-3 is optionally substituted by 1, 2, or 3 R;
Rd is each independently selected from the group consisting of Cl, F, Br, I, OH, NH2, CN, and COOH;
Re is each independently selected from the group consisting of Cl, F, Br, I, OH, NH2, CN, and COOH;
R is each independently selected from the group consisting of Cl, F, Br, I, OH, NH2, CN, and COOH; and
the C1-6 heteroalkyl and the 3-6 membered heterocycloalkyl each contain 1, 2, 3, or 4 heteroatoms or heteroatom groups independently selected from the group consisting of —NH—, —O—, —S—, and N.