US 12,312,326 B2
Substituted benzimidazole derivatives as D-amino acid oxidase (DAAO) inhibitors
Yufeng Jane Tseng, Stafford, VA (US); Yu-Li Liu, Miaoli County (TW); Chung-Ming Sun, Hsinchu (TW); Wen-Sung Lai, Taipei (TW); Chih-Min Liu, Taipei (TW); and Hai-Gwo Hwu, Taipei (TW)
Assigned to Yufeng Jane Tseng, Stafford, VA (US); National Taiwan University, Taipei (TW); National Yang Ming Chiao Tung University, Hsinchu (TW); and National Health Research Institutes, Miaoli County (TW)
Filed by NATIONAL TAIWAN UNIVERSITY, Taipei (TW); NATIONAL YANG MING CHIAO TUNG UNIVERSITY, Hsinchu (TW); NATIONAL HEALTH RESEARCH INSTITUTES, Miaoli County (TW); and Yufeng Jane Tseng, Stafford, VA (US)
Filed on May 4, 2022, as Appl. No. 17/736,924.
Application 17/736,924 is a continuation of application No. 16/332,628, granted, now 11,370,775, previously published as PCT/US2017/051610, filed on Sep. 14, 2017.
Claims priority of provisional application 62/394,479, filed on Sep. 14, 2016.
Prior Publication US 2022/0267301 A1, Aug. 25, 2022
Int. Cl. C07D 401/12 (2006.01); A61P 25/18 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/14 (2006.01)
CPC C07D 401/12 (2013.01) [A61P 25/18 (2018.01); C07D 401/14 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/14 (2013.01)] 7 Claims
 
1. A compound of formula (I),

OG Complex Work Unit Chemistry
wherein n is 0 or 1,
X is —S—;
A is N;
Ra is —C(═O)ORa1; wherein
Ra1 is H or linear or branched C1-15alkyl;
Rb is linear or branched C5-15alkyl, linear or branched C2-15alkenyl, C1-3alkoxy-C1-15alkyl-, -T′-C3-10cycloalkyl, -T′-C3-10cycloalkenyl, -T′-C6-10 aryl or -T′-C5-10heteroaryl;
Rc each is independently linear or branched C1-15alkyl, linear or branched C1-15alkoxyl, hydroxyl group, or —C1-10alkylene-Y—C6-10heteroaryl wherein —Y— is —CH2—, —NH—, —O— or —S—;
m is an integer from 0 to 4;
-T′- is C1-3alkylene or C2-3alkenylene; 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 C1-15 alkyl, or linear or branched C1-15 alkoxy or C3-10cycloalkyl;
or a pharmaceutically acceptable salt thereof.