US 12,304,898 B2
Quinolyl-containing compound and pharmaceutical composition, and use thereof
Wei Wu, Beijing (CN); Li Zhu, Beijing (CN); Yanqing Yang, Beijing (CN); Wei Hu, Beijing (CN); Hui Zhang, Beijing (CN); and Changxin Dong, Beijing (CN)
Assigned to PrimeGene (Beijing) Co., Ltd., Beijing (CN)
Appl. No. 17/594,039
Filed by PrimeGene (Beijing) Co., Ltd., Beijing (CN)
PCT Filed Mar. 30, 2020, PCT No. PCT/CN2020/082041
§ 371(c)(1), (2) Date Sep. 30, 2021,
PCT Pub. No. WO2020/200160, PCT Pub. Date Oct. 8, 2020.
Claims priority of application No. 201910266681.9 (CN), filed on Apr. 3, 2019.
Prior Publication US 2022/0162184 A1, May 26, 2022
Int. Cl. C07D 409/12 (2006.01); A61K 31/47 (2006.01); A61K 31/4709 (2006.01); C07D 215/22 (2006.01); C07D 215/233 (2006.01); C07D 401/12 (2006.01); C07D 417/12 (2006.01)
CPC C07D 401/12 (2013.01) [C07D 215/22 (2013.01); C07D 409/12 (2013.01); C07D 417/12 (2013.01)] 10 Claims
 
1. A compound represented by formula (I) or (II), or a pharmaceutically acceptable salt, or stereoisomer thereof,

OG Complex Work Unit Chemistry
wherein,
A represents

OG Complex Work Unit Chemistry
or —NR3R4;
X represents hydrogen, halogen or substituted or unsubstituted C1-8 alkyl;
Y represents a substituted or unsubstituted C3-8 cycloalkyl, C3-8 heterocyclyl containing one or more heteroatoms selected from the group consisting of O, S and N, C6-20 aryl or C2-20 heteroaryl containing one or more heteroatoms selected from the group consisting of O, S and N;
Z represents —O— or —S—;
L represents linear —(CH2)n—, n represents an integer from 3 to 10, wherein optionally one or more —CH2— are replaced with one or more of —NR5—, —(CO)—, —(CS)—, and —CR5R6—, and/or optionally one or more of —CH2CH2— are replaced with —CH═CH—;
R1 represents C1-6 alkoxy, C1-6 alkylsulfanyl or —(CO)NR7R8;
R2 represents substituted or unsubstituted hydrogen, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylsulfanyl, C1-8 haloalkyl, C3-8 cycloalkyl, C3-8 heterocyclyl containing one or more heteroatoms selected from the group consisting of N, O and S, C6-20 aryl, C2-20 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S, —(CO)R9, —(CS)R9, or R2 is connected with one of —CH2— in L group so that R2, S and —CH2— together form C3˜8 heterocyclic group optionally containing additional one or more N, O and S, or C2-20 heteroaryl optionally containing additional one or more N, O and S;
R3 and R4 independently represent substituted or unsubstituted hydrogen, C1˜8 alkyl, C1˜8 alkoxyl, C1˜8 alkylsulfanyl, C1˜8 haloalkyl, C3˜8 cycloalkyl, C3−8 heterocyclyl containing one or more heteroatoms selected from the group consisting of O, S and N, C6˜20 aryl or C2˜20 heteroaryl containing one or more heteroatoms selected from the group consisting of O, S and N;
R5 and R6 independently represent substituted or unsubstituted hydrogen, C1˜8 alkyl, C1˜8 alkoxyl, C1˜8 alkylsulfanyl, C1˜8 haloalkyl, hydroxyl, mercapto, carboxyl, amino or cyano;
R7 and R8 independently represent substituted or unsubstituted hydrogen or C1˜8 alkyl;
R9 represents substituted or unsubstituted C1˜8 alkyl, C1˜8 alkoxyl, C1˜8 alkylsulfanyl, C1˜8 haloalkyl, C1˜6 alkylsulfonyl, C1˜6 alkylamino, C3˜8 cycloalkyl, C3˜8 heterocyclyl containing at least one N atom, C6˜20 aryl, C2˜20 heteroaryl containing at least one N atom, C1˜6 alkylene C3˜8 cycloalkyl, C1˜6 alkylene C3˜8 heterocyclyl containing at least one N atom, C1˜6 alkylene C6−20 aryl, C1˜6 alkylene C2˜20 heteroaryl containing at least one N atom, hydroxyl, mercapto, nitro, amino, cyano, or R9 is connected with anyone of —CH2— in the L group, so that —(CO) R9 or —(CS)R9 together with S and —CH2— forms C3˜8 heterocyclyl optionally containing additional one or more N, O and S, or C2˜20 heteroaryl optionally containing additional one or more N, O and S;
The substituents of the above groups, if any, are selected from halogen, C1˜8 alkyl, C2˜8 alkenyl, C2˜8 alkynyl, C1˜8 haloalkyl, C1˜8 alkoxyl, C1˜8 alkylsulfanyl, C3˜8 cycloalkyl, C3˜8 heterocyclyl, C6˜20 aryl, C2˜20 heteroaryl, C1˜6 alkoxycarbonyl, C1˜6 alkanoyl, C1˜6 alkylamino, C1˜6 alkylsufonyl, amino, hydroxyl, mercapto, carboxyl, nitro, carboxamido, or cyano.