Granted Patent B2

US 12,312,326 · App. 17/736,924 · Granted May 27, 2025

Inventors: Yufeng Jane Tseng (Stafford, VA); Yu-Li Liu (Miaoli County, TW); Chung-Ming Sun (Hsinchu, TW); Wen-Sung Lai (Taipei, TW); Chih-Min Liu (Taipei, TW); Hai-Gwo Hwu (Taipei, TW)

Assignees: Yufeng Jane Tseng; National Taiwan University; National Yang Ming Chiao Tung University; National Health Research Institutes

C07D401/12A61P25/18C07D401/14C07D405/14C07D409/14C07D413/14

Abstract

Claims (24)

1. A compound of formula (I),

wherein n is 0 or 1,

X is —S—;

A is N;

R a is —C(═O)OR a1 ; wherein

R a1 is H or linear or branched C 1-15 alkyl;

R b is linear or branched C 5-15 alkyl, linear or branched C 2-15 alkenyl, C 1-3 alkoxy-C 1-15 alkyl-, -T′-C 3-10 cycloalkyl, -T′-C 3-10 cycloalkenyl, -T′-C 6-10 aryl or -T′-C 5-10 heteroaryl;

R c each is independently linear or branched C 1-15 alkyl, linear or branched C 1-15 alkoxyl, hydroxyl group, or —C 1-10 alkylene-Y—C 6-10 heteroaryl wherein —Y— is —CH 2 —, —NH—, —O— or —S—;

m is an integer from 0 to 4;

-T′- is C 1-3 alkylene or C 2-3 alkenylene; and

wherein the heteroaryl contains at least one heteroatom, each heteroatom being independently S, N or O;

wherein the alkyl, alkenyl, alkoxy, cycloalkyl, aryl, heteroaryl, alkylene and alkenylene are each independently unsubstituted or substituted with at least one substituent; and

wherein the substituent is each independently a halogen, amino, nitro, nitroso, linear or branched C 1-15 alkyl, or linear or branched C 1-15 alkoxy or C 3-10 cycloalkyl;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein n is 0.

3. The compound of claim 1 , wherein m is an integer from 0 to 3.

4. The compound of claim 1 , wherein R a is —C(═O)OH, or —C(═O)OC 1-4 alkyl.

5. The compound of claim 1 , wherein R e each is independently halogen, linear or branched C 1-6 alkyl, linear or branched C 1-6 alkoxyl, or —C 1-10 alkenylene-Y—C 6-10 heteroaryl; wherein Y is S and C 6-10 heteroaryl is unsubstituted or substituted by C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, —OH, —NH 2 , —NO 2 or halogen.

6. The compound of claim 1 , which is selected from the group consisting of:

12082: Methyl 1-(2-(cyclohex-1-en-1-yl)ethyl)-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole-5-carboxylate

12083: 1-(2-(cyclohex-1-en-1-yl)ethyl)-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole-5-carboxylic acid, and

12088: methyl 2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1-octyl-1H-benzo[d]imidazole-5-carboxylate,

or a pharmaceutically acceptable salt thereof.

7. A pharmaceutical composition, comprising a compound of claim 1 .

Assignments (5)

Continuity (3)

References Cited (68)