US 12,269,816 B2
Benzothiophene compound, preparation method therefor and use thereof
Jinming Liu, Sichuan (CN); Yun Ren, Sichuan (CN); Qiang Tian, Sichuan (CN); Hongmei Song, Sichuan (CN); Tongtong Xue, Sichuan (CN); and Jingyi Wang, Sichuan (CN)
Assigned to SICHUAN KELUN-BIOTECH BIOPHARMACEUTICAL CO., LTD., Sichuan (CN)
Appl. No. 17/435,031
Filed by SICHUAN KELUN-BIOTECH BIOPHARMACEUTICAL CO., LTD., Sichuan (CN)
PCT Filed Apr. 20, 2020, PCT No. PCT/CN2020/085525
§ 371(c)(1), (2) Date Aug. 30, 2021,
PCT Pub. No. WO2020/221038, PCT Pub. Date Nov. 5, 2020.
Claims priority of application No. 201910359616.0 (CN), filed on Apr. 30, 2019.
Prior Publication US 2022/0162199 A1, May 26, 2022
Int. Cl. C07D 409/12 (2006.01); C07D 409/14 (2006.01)
CPC C07D 409/12 (2013.01) [C07D 409/14 (2013.01)] 29 Claims
OG exemplary drawing
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
wherein
both X1 and X3 are —O—;
X2 is C1-6 alkylene, wherein the C1-6 alkylene, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-6 alkyl and C1-6 alkoxy;
L1 is —(C(R8)2)p—;
L2 is —C(O)—;
L3 is —(C(R9)2)q—;
A1 is —C(O)—ORa;
R1 and R4 are H;
R2 and R3 are the same or different, and are each independently selected from the group consisting of H, halogen, cyano, —ORa, —SRa, —S(O)Ra, —S(O)2Ra, —NRaRb, —C(O)—NRaRb, —NRa—C(O)—Ra, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, 3-6 membered heterocyclyl, C6-10 aryl and 5-10 membered heteroaryl, wherein the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, 3-6 membered heterocyclyl, C6-10 aryl and 5-10 membered heteroaryl are each optionally substituted with one or more substituents independently selected from the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, cyano, hydroxy and C1-6 alkoxy;
R5 is selected from the group consisting of H, C1-6 alkyl, C3-10 cycloalkyl and 3-10 membered heterocyclyl, wherein the C1-6 alkyl, C3-10 cycloalkyl and 3-10 membered heterocyclyl are each optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-6 alkyl, C3-10 cycloalkyl, 3-10 membered heterocyclyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, —NRaRb, —CO2Ra and —S(O)2Ra;
R6 is ORa or —C(O)2R7;
R7 is selected from the group consisting of H and C1-6 alkyl;
R8 is each independently selected from the group consisting of H and C1-6 alkyl;
R9 is each independently selected from the group consisting of H and C1-6 alkyl;
Ra and Rb are each independently selected from the group consisting of H and C1-6 alkyl wherein the C1-6 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of hydroxy, halogen and C1-6 alkyl;
m and n are each independently selected from the group consisting of 0, 1, 2 and 3; and
p and q are each independently selected from the group consisting of 1, 2, and 3,
or a pharmaceutically acceptable salt, a stereoisomer, a tautomer, a polymorph, a solvate, an N-oxide, or an isotope-labeled compound thereof.