US 11,771,680 B2
Pyrrole compounds
Sandrine Vendeville, Brussels (BE); David Bernard Smith, San Mateo, CA (US); Leonid Beigelman, San Mateo, CA (US); and Vladimir Serebryany, Burlingame, CA (US)
Assigned to Aligos Therapeutics, Inc., South San Francisco, CA (US)
Filed by Aligos Therapeutics, Inc., South San Francisco, CA (US)
Filed on Nov. 16, 2021, as Appl. No. 17/455,178.
Application 17/455,178 is a continuation of application No. 16/837,515, filed on Apr. 1, 2020, granted, now 11,191,747.
Claims priority of provisional application 62/932,686, filed on Nov. 8, 2019.
Claims priority of provisional application 62/828,919, filed on Apr. 3, 2019.
Prior Publication US 2022/0071957 A1, Mar. 10, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/4025 (2006.01); C07D 405/12 (2006.01); A61K 31/40 (2006.01); C07D 207/34 (2006.01); C07D 487/04 (2006.01); C07D 401/12 (2006.01); C07D 403/12 (2006.01); C07D 409/12 (2006.01); A61K 31/4192 (2006.01)
CPC A61K 31/4025 (2013.01) [A61K 31/40 (2013.01); A61K 31/4192 (2013.01); C07D 207/34 (2013.01); C07D 401/12 (2013.01); C07D 403/12 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 487/04 (2013.01)] 19 Claims
 
1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

OG Complex Work Unit Chemistry
wherein:
R1 is an unsubstituted or a substituted C2 alkenyl, an unsubstituted or a substituted C2 alkynyl, wherein when the C2 alkenyl and the C2 alkynyl are substituted, the C2 alkenyl and the C2 alkynyl are independently substituted with one or more substituents selected from the group consisting of halogen, an unsubstituted C1-4 alkyl, an unsubstituted C1-4 haloalkyl, an unsubstituted C1-4 hydroxyalkyl, an unsubstituted monocyclic C3-6 cycloalkyl and a hydroxy-substituted monocyclic C3-6 cycloalkyl;
R2 and R3 are taken together along with the carbon to which R2 and R3 are attached to form an unsubstituted or a substituted monocyclic C3-6 cycloalkyl or an unsubstituted or a substituted monocyclic 3-6 membered heterocyclyl, wherein when the C3-6 cycloalkyl and 3-6 membered heterocyclyl are substituted, the C3-6 cycloalkyl and the 3-6 membered heterocyclyl are independently substituted with 1 or 2 substituents selected from the group consisting of halogen and hydroxy;
R4 and R5 are independently hydrogen, halogen, an unsubstituted C1-4 alkyl, a deuterated C1-4 alkyl or an unsubstituted C2-4 alkenyl;
R6 is hydrogen, an unsubstituted C1-4 alkyl, a deuterated C1-4 alkyl or an unsubstituted C3-4 alkenyl; and
provided that at least one of R4, R5 and R6 is not hydrogen; or
R5 is hydrogen, halogen, an unsubstituted C1-4 alkyl or an unsubstituted C2-4 alkenyl; and
R4 and R6 are taken together to form an unsubstituted or substituted 5-6 membered heterocyclic ring;
X1 is CRA;
R7a, R7c and R7d are each hydrogen;
R7b is cyano or an unsubstituted C1-4 haloalkyl;
R8 is hydrogen; and
RA is F.