US 12,221,414 B2
Quaternary ammonium salt compound, preparation method therefor and use thereof
Bowen Ke, Sichuan (CN); Jin Liu, Sichuan (CN); Wensheng Zhang, Sichuan (CN); and Jun Yang, Sichuan (CN)
Assigned to WEST CHINA HOSPITAL, SICHUAN UNIVERSITY, Sichuan (CN)
Appl. No. 17/427,521
Filed by WEST CHINA HOSPITAL, SICHUAN UNIVERSITY, Sichuan (CN)
PCT Filed Jan. 21, 2020, PCT No. PCT/CN2020/073387
§ 371(c)(1), (2) Date Jul. 30, 2021,
PCT Pub. No. WO2020/156359, PCT Pub. Date Aug. 6, 2020.
Claims priority of application No. 201910102803.0 (CN), filed on Feb. 1, 2019.
Prior Publication US 2022/0135526 A1, May 5, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 211/60 (2006.01); C07D 205/04 (2006.01); C07D 207/16 (2006.01); C07D 223/06 (2006.01); C07D 413/06 (2006.01); C07D 413/12 (2006.01)
CPC C07D 211/60 (2013.01) [C07D 205/04 (2013.01); C07D 207/16 (2013.01); C07D 223/06 (2013.01); C07D 413/06 (2013.01); C07D 413/12 (2013.01)] 12 Claims
 
1. A compound of formula I, or a pharmaceutically acceptable salt thereof, or a stereoisomer thereof, or a solvate thereof,

OG Complex Work Unit Chemistry
wherein,
each of X and Y is independently selected from O and NR10, wherein R10 is selected from H, deuterium, and C1-C4 alkyl;
Z− is a pharmaceutically acceptable anion;
R1 is selected from n1 R11-substituted aryls; and
R2 is selected from n1′ R11′-substituted aryls;
wherein,
n1 and n1′ are each independently selected from an integer of 0 to 5, and R11 and R11′ are each independently selected from deuterium, C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro, cyano, hydroxyl, carboxyl, and amino;
when the dotted line between R3 and R4 in Formula I is none, R3 is selected from substituted C1-C10 alkyl and unsubstituted C5-C10 alkyl, and R4 is a substituted or unsubstituted C1-C10 alkyl, wherein said substituted C1-C10 alkyl or said substituted C1-C4 alkoxy is substituted with one or more substituent selected from deuterium, C1-C4 alkoxy substituted with hydroxyl, unsubstituted C1-C4 alkoxy, halogen, nitro, cyano, hydroxyl, carboxy, amino, ester, C1-C6 alkylthio, and mercapto;
when the dotted line between R3 and R4 in formula I is a bond, R3 and R4 are independently selected from C1-C4 alkylenes that are unsubstituted or substituted with one or more substituent selected from C1-C3 alkyls, the main chain of each of the C1-C4 alkylenes contains 0 to 4 heteroatoms selected from O, S, and NR12, wherein said R12 is selected from hydrogen, deuterium, and C1-C4 alkyls;
L1 is selected from C1-C14 alkylenes that are unsubstituted or substituted with one or more substituent selected from deuterium, C1-C4 alkyls, C1-C4 alkoxys, and halogen; wherein the main chain of each of the C1-C14 alkylenes contains 0 to 4 heteroatoms selected from O, S, and NR12, wherein said R12 is selected from the group hydrogen, deuterium, C1-C4 alkyls, and C1-C4 alkoxys; and
the dotted line connected to L2 is a bond, and L2 is selected from C1-C8 alkylenes that are unsubstituted or substituted with one or more substituent selected from deuterium, C1-C4 alkyls, C1-C4 alkoxys, and halogen.