US 12,065,428 B2
Anti-viral compounds
Dorothée Alice Marie-Eve Bardiot, Leuven (BE); Koen Vandyck, Paal (BE); Sandro Boland, Leuven (BE); Antitsa Dimitrova Stoycheva, Half Moon Bay, CA (US); Arnaud Didier Marie Marchand, Leuven (BE); Pierre Jean-Marie Bernard Raboisson, Wavre (BE); and Leonid Beigelman, San Mateo, CA (US)
Assigned to Aligos Therapeutics, Inc., South San Francisco, CA (US); and Katholieke Universiteit Leuven, Leuven (BE)
Filed by Aligos Therapeutics, Inc., South San Francisco, CA (US); and Katholieke Universiteit Leuven, Leuven (BE)
Filed on Sep. 14, 2022, as Appl. No. 17/932,218.
Claims priority of provisional application 63/367,791, filed on Jul. 6, 2022.
Claims priority of provisional application 63/265,481, filed on Dec. 15, 2021.
Claims priority of provisional application 63/261,339, filed on Sep. 17, 2021.
Prior Publication US 2023/0140238 A1, May 4, 2023
Int. Cl. C07D 401/14 (2006.01); C07D 401/12 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 417/14 (2006.01); C07D 487/04 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 401/12 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 417/14 (2013.01); C07D 487/04 (2013.01)] 23 Claims
 
1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

OG Complex Work Unit Chemistry
wherein:
Ring A1 is

OG Complex Work Unit Chemistry
Ring A2 is an unsubstituted or a substituted monocyclic C3-6 cycloalkyl;
R1 is selected from the group consisting of cyano, an unsubstituted or a substituted C2-5 alkynyl, an unsubstituted or a substituted ketoamide, —CH(OH)—(S(═O)2—O−), —CH(OH)((P═O)(OR6)2) and —C(═O)CH2—O—((P═O)(OR7)2),
R2 is hydrogen, deuterium or halogen;
R3 is an unsubstituted or a substituted C-amido(C1-4 alkyl), an unsubstituted or a substituted monocyclic nitrogen-containing heteroaryl(C1-4 alkyl), an unsubstituted or a substituted monocyclic nitrogen-containing heterocyclyl(C1-4 alkyl), an unsubstituted or a substituted bicyclic nitrogen-containing heteroaryl(C1-4 alkyl) or an unsubstituted or a substituted bicyclic nitrogen-containing heterocyclyl(C1-4 alkyl);
R4 is hydrogen, deuterium or halogen;

OG Complex Work Unit Chemistry
R8a is selected from the group consisting of an unsubstituted or a substituted C2-6 alkyl, an unsubstituted or a substituted C2-6 alkenyl, an unsubstituted or a substituted C2-6 alkynyl, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, an unsubstituted or a substituted bicyclic C5-8 cycloalkyl and an unsubstituted or a substituted monocyclic 4- to 6-membered heterocyclyl,
wherein when the C2-6 alkyl is substituted, the C2-6 alkyl is substituted 1, 2, 3 or 4 times with a substituent independently selected from the group consisting of halogen, cyano, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, an unsubstituted C1-4 alkoxy and an unsubstituted C1-4 haloalkoxy, or the C2-6 alkyl is substituted 1 to 13 times with deuterium;
wherein when the C2-6 alkenyl, the C2-6 alkynyl, the monocyclic C3-6 cycloalkyl, the bicyclic C5-8 cycloalkyl and the monocyclic 4- to 6-membered heterocyclyl are substituted, the C2-6 alkenyl, the C2-6 alkynyl, the monocyclic C3-6 cycloalkyl, the bicyclic C5-8 cycloalkyl and the monocyclic 4- to 6-membered heterocyclyl are substituted 1, 2, 3 or 4 times with a substituent independently selected from the group consisting of halogen, an unsubstituted C1-4 alkyl, an unsubstituted C2-4 alkenyl, an unsubstituted C2-4 alkynyl, an unsubstituted C1-6 haloalkyl, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl and an unsubstituted C1-4 alkoxy; and
R8b is selected from the group consisting of an unsubstituted or a substituted C1-6 alkyl, an unsubstituted or a substituted C1-6 haloalkyl, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, an unsubstituted or a substituted bicyclic C5-6 cycloalkyl, an unsubstituted or a substituted monocyclic heteroaryl and an unsubstituted or a substituted monocyclic heterocyclyl, wherein the substituted C1-6 alkyl is substituted 1 or 2 times with an unsubstituted C1-4 alkoxy, wherein the substituted monocyclic C3-6 cycloalkyl is substituted 1, 2, 3 or 4 times with a substituent independently selected from the group consisting of halogen, an unsubstituted C1-4 alkyl, an unsubstituted C2-4 alkenyl, an unsubstituted C1-4 alkoxy, an unsubstituted C1-4 haloalkyl and an unsubstituted monocyclic C3-6 cycloalkyl, and wherein the substituted C1-6 haloalkyl is substituted 1 or 2 times with an unsubstituted C1-4 alkoxy; and
each R6 and each R7 are independently hydrogen, an unsubstituted C1-6 alkyl, an unsubstituted C2-6 alkenyl, an unsubstituted C1-6 haloalkyl, an unsubstituted or a substituted aryl or an unsubstituted or a substituted aryl(C1-4 alkyl).