US 11,939,307 B2
Phenylmethyl-piperazine derivatives and antiviral uses thereof
Yanping Li, Beijing (CN); Zhuorong Li, Beijing (CN); Zonggen Peng, Beijing (CN); Xinbei Jiang, Beijing (CN); Yixuan Wang, Beijing (CN); Jianrui Li, Beijing (CN); and Jiali Tan, Beijing (CN)
Assigned to INSTITUTE OF MEDICINAL BIOTECHNOLOGY, CHINESE ACADEMY OF MEDICAL SCIENCES, Beijing (CN)
Appl. No. 17/780,160
Filed by INSTITUTE OF MEDICINAL BIOTECHNOLOGY, CHINESE ACADEMY OF MEDICAL SCIENCES, Beijing (CN)
PCT Filed Nov. 29, 2019, PCT No. PCT/CN2019/000232
§ 371(c)(1), (2) Date May 26, 2022,
PCT Pub. No. WO2021/102600, PCT Pub. Date Jun. 3, 2021.
Prior Publication US 2023/0024612 A1, Jan. 26, 2023
Int. Cl. C07D 295/135 (2006.01); C07D 205/04 (2006.01); C07D 207/14 (2006.01); C07D 207/325 (2006.01); C07D 211/56 (2006.01); C07D 211/58 (2006.01); C07D 213/36 (2006.01); C07D 233/61 (2006.01); C07D 241/04 (2006.01); C07D 241/12 (2006.01); C07D 401/06 (2006.01)
CPC C07D 295/135 (2013.01) [C07D 205/04 (2013.01); C07D 207/14 (2013.01); C07D 207/325 (2013.01); C07D 211/56 (2013.01); C07D 211/58 (2013.01); C07D 213/36 (2013.01); C07D 233/61 (2013.01); C07D 241/04 (2013.01); C07D 241/12 (2013.01); C07D 401/06 (2013.01)] 20 Claims
 
1. A compound having the structure as shown in the formula I or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein R1 is alkyl containing 1 to 4 carbons or H;
R2 is H, alkyl, cycloalkyl, aryl, heteroaryl, or, aryl or heteroaryl substituted with 1, 2 or 3 substituents, wherein, the substituent is selected from the group consisting of alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, phenylthio, halogen, cyano, and haloalkyl; when being alkyl or cycloalkyl, R2 is alkyl containing 1 to 6 carbon atoms, or cycloalkyl containing 3 to 6 carbon atoms, and the alkyl and cycloalkyl are optionally substituted with halogen;
R3 is cyano or trifluoromethyl;
X is N or CH;
Y is CH;
Aryl is a benzene or aza-aromatic ring, or a benzene or aza-aromatic ring containing 1-3 substituents selected from the group consisting of alkyl, cycloalkyl, alkyloxy, phenoxy or substituted phenoxy, alkylthio, phenylthio or substituted phenylthio, haloalkyl, cyano, and halogen;
R4 is substituted alkyl or substituted heterocycloalkyl, and when R4 is substituted alkyl, the substituent is selected from the group consisting of alkylamino, dialkylamino, and saturated or unsaturated heterocyclyl containing one nitrogen or two nitrogens; when R4 is substituted heterocycloalkyl, the heterocycloalkyl contains at least one nitrogen atom, and the substituent is selected from the group consisting of alkyl, alkylamino and dialkylamino;
R5 is hydrogen or alkyl containing 1-4 carbons;
alternatively, R4, R5, and the nitrogen atom to which they are attached jointly form a cyclic structure containing 1 or 2 nitrogen atoms or cyclic structure substituted with a substituent selected from the group consisting of alkyl containing 1 to 6 carbons, alkylamino, dialkylamino, cycloalkyl, and heterocyclic groups.