US 12,252,481 B2
Anti-viral compounds
Koen Vandyck, Paal (BE); Dorothée Alice Marie-Eve Bardiot, Leuven (BE); Pierre Jean-Marie Bernard Raboisson, Wavre (BE); Leonid Beigelman, San Mateo, CA (US); Antitsa Dimitrova Stoycheva, Half Moon Bay, CA (US); Sandro Boland, Leuven (BE); and Arnaud Didier Marie Marchand, Leuven (BE)
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 Oct. 13, 2023, as Appl. No. 18/486,759.
Application 18/486,759 is a continuation of application No. 17/811,008, filed on Jul. 6, 2022, granted, now 11,851,422.
Claims priority of provisional application 63/268,052, filed on Feb. 15, 2022.
Claims priority of provisional application 63/265,479, filed on Dec. 15, 2021.
Claims priority of provisional application 63/264,212, filed on Nov. 17, 2021.
Claims priority of provisional application 63/261,480, filed on Sep. 22, 2021.
Claims priority of provisional application 63/203,135, filed on Jul. 9, 2021.
Prior Publication US 2024/0109871 A1, Apr. 4, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/12 (2006.01); A61K 31/14 (2006.01); A61K 31/403 (2006.01); A61K 31/407 (2006.01); A61K 31/4155 (2006.01); A61K 31/4192 (2006.01); A61K 31/422 (2006.01); A61K 31/4245 (2006.01); A61K 31/437 (2006.01); A61K 31/4439 (2006.01); A61K 31/4709 (2006.01); A61K 31/497 (2006.01); A61K 31/519 (2006.01); A61K 31/5377 (2006.01); A61K 31/538 (2006.01); A61K 31/553 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 405/14 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01); C07D 487/04 (2006.01); C07D 491/04 (2006.01); C07D 491/107 (2006.01); C07D 498/04 (2006.01)
CPC C07D 403/12 (2013.01) [C07D 403/14 (2013.01); C07D 405/14 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01); C07D 487/04 (2013.01); C07D 491/107 (2013.01); C07D 498/04 (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 selected from the group consisting of

OG Complex Work Unit Chemistry
 wherein Ring A1 is optionally substituted with one or more moieties independently selected from the group consisting of deuterium, halogen, hydroxy, an unsubstituted C1-4 alkyl and an unsubstituted C1-4 haloalkyl;
R1 is cyano;
R2 is hydrogen or deuterium;
R3 is an unsubstituted or a substituted monocyclic nitrogen-containing heterocyclyl(C1-4 alkyl) or an unsubstituted or a substituted bicyclic nitrogen-containing heterocyclyl(C1-4 alkyl);
R4 is hydrogen or deuterium;
R5 is

OG Complex Work Unit Chemistry
R8 is selected from the group consisting of an unsubstituted or a substituted C2-6 alkyl and an unsubstituted C2-6 alkynyl,
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, an unsubstituted monocyclic C3-6 cycloalkyl and an unsubstituted C1-4 alkoxy; and
R9 is an unsubstituted C1-6 haloalkyl or a substituted monocyclic C3-6 cycloalkyl, 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 C1-4 alkoxy and an unsubstituted C1-4 haloalkyl.