US 11,897,863 B2
Indazole amine derivative, preparation method therefor and medical use thereof
Yongping Lu, Zhejiang (CN); Cheng Ye, Zhejiang (CN); Wenjian Qian, Zhejiang (CN); Taishan Hu, Zhejiang (CN); and Lei Chen, Zhejiang (CN)
Assigned to ZHEJIANG HISUN PHARMACEUTICAL CO., LTD., Zhejiang (CN)
Appl. No. 17/267,771
Filed by ZHEJIANG HISUN PHARMACEUTICAL CO., LTD., Zhejiang (CN)
PCT Filed Aug. 15, 2019, PCT No. PCT/CN2019/100760
§ 371(c)(1), (2) Date Feb. 10, 2021,
PCT Pub. No. WO2020/035019, PCT Pub. Date Feb. 20, 2020.
Claims priority of application No. 201810937427.2 (CN), filed on Aug. 17, 2018.
Prior Publication US 2021/0309636 A1, Oct. 7, 2021
Int. Cl. C07D 401/12 (2006.01); C07D 401/14 (2006.01)
CPC C07D 401/12 (2013.01) [C07D 401/14 (2013.01)] 18 Claims
 
1. A compound of formula (I), or stereoisomers, tautomers or pharmaceutically acceptable salts thereof:

OG Complex Work Unit Chemistry
wherein:
R1 and R2 are independently selected from hydrogen or C 1-C6 alkyl;
R3 is selected from halogen, cyano, carboxyl, —CONRARB, haloalkyl or heteroaryl; wherein the heteroaryl is optionally further substituted by one or more substituents selected from halogen, hydroxyl, cyano, carboxyl, —CONRARB or haloalkyl;
W is azetidinyl, nitrogen-containing aromatic heterocyclic ring group or nitrogen-containing aromatic heterocyclic ring group bonded via a single methylene group; wherein the azetidinyl is optionally further substituted by one or more substituents selected from —CORC, —SO2RD, C1-C6 alkyl or C 3-C6 cycloalkyl; wherein the nitrogen-containing aromatic heterocyclic ring group is optionally further substituted by one or more substituents selected from halogen, cyano, carboxyl, —CONRARB and haloalkyl;
or, W has a structure of formula (II):

OG Complex Work Unit Chemistry
* represents bonding site of the group to rest of the molecule;
Ra is selected from hydrogen, C 1-C6 alkyl or C 3-C6 cycloalkyl; wherein the C 1-C6 alkyl or C 3-C6 cycloalkyl is optionally further substituted by one or more substituents selected from halogen, hydroxyl, carboxyl and —SO2NRERF;
Rb and Rc are independently selected from hydrogen, —CORC, —SO2RD, C1-C6 alkyl or C3-C6 cycloalkyl; or, any two of R a, R b and Rc together with the atoms to which they are attached form a 4-8 membered nitrogen-containing heterocyclic ring, wherein the nitrogen-containing heterocyclic ring may be further substituted by one or more oxo groups (O═);
RA, R B, R E and R F are independently selected from hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl; wherein the alkyl or cycloalkyl is optionally further substituted by one or more substituents selected from halogen, hydroxyl, cyano or haloalkyl;
RC and R D are independently selected from C1-C6 alkyl or C 3-C6 cycloalkyl; wherein the alkyl or cycloalkyl is optionally further substituted by one or more substituents selected from halogen, hydroxyl, cyano or haloalkyl.