US 11,957,683 B2
Bicyclic compounds
Sandrine Vendeville, Brussels (BE); Pierre Jean-Marie Bernard Raboisson, Wavre (BE); David McGowan, Brussels (BE); and Yannick Debing, Bilzen (BE)
Assigned to Aligos Therapeutics, Inc., South San Francisco, CA (US)
Filed by Aligos Therapeutics, Inc., South San Francisco, CA (US)
Filed on Jun. 15, 2022, as Appl. No. 17/807,057.
Claims priority of provisional application 63/269,017, filed on Mar. 8, 2022.
Claims priority of provisional application 63/264,496, filed on Nov. 23, 2021.
Claims priority of provisional application 63/264,434, filed on Nov. 22, 2021.
Claims priority of provisional application 63/212,369, filed on Jun. 18, 2021.
Prior Publication US 2023/0051483 A1, Feb. 16, 2023
Int. Cl. A61K 31/522 (2006.01); A61K 31/513 (2006.01); A61K 31/519 (2006.01); A61K 31/675 (2006.01); A61K 31/7072 (2006.01); A61K 31/7088 (2006.01); A61K 38/21 (2006.01); A61P 31/14 (2006.01); C07D 471/04 (2006.01); C07D 519/00 (2006.01)
CPC A61K 31/519 (2013.01) [A61K 31/513 (2013.01); A61K 31/522 (2013.01); A61K 31/675 (2013.01); A61K 31/7072 (2013.01); A61K 31/7088 (2013.01); A61K 38/212 (2013.01); A61P 31/14 (2018.01); C07D 471/04 (2013.01); C07D 519/00 (2013.01)] 46 Claims
 
1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

OG Complex Work Unit Chemistry
wherein:
n is 0 or 1;
Z1 is —C(═O)—or —NH—C(═O)—;
R1 is selected from the group consisting of an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl, an optionally substituted aryl(C1-4 alkyl), an optionally substituted heteroaryl(C1-4 alkyl) and an optionally substituted heterocyclyl(C1-4 alkyl);
R2 and R3 are independently selected from the group consisting of hydrogen, an optionally substituted C1-4 alkyl, an optionally substituted C2-4 alkenyl, an optionally substituted C2-4 alkynyl, an unsubstituted C1-4 haloalkyl, an optionally substituted monocyclic C3-6 cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl, an optionally substituted aryl(C1-4 alkyl), an optionally substituted heteroaryl(C1-4 alkyl) and an optionally substituted heterocyclyl(C1-4 alkyl);
R4 and R5 are independently selected from the group consisting of hydrogen, an unsubstituted C1-4 alkyl, an unsubstituted C1-4 haloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl, an optionally substituted aryl(C1-4 alkyl), an optionally substituted heteroaryl(C1-4 alkyl) and an optionally substituted heterocyclyl(C1-4 alkyl);
R6 and R7 are independently selected from the group consisting of hydrogen, an unsubstituted C1-4 alkyl and an unsubstituted C1-4 haloalkyl;
R8 is —NR10AR10B or an optionally substituted C2-12 alkynyl, wherein the C2-12 alkynyl is optionally substituted with one or more substituents selected from the group consisting of amino, —NH—C(═O)(an unsubstituted C1-4 alkyl), hydroxy, an unsubstituted C1-4 alkoxy, an unsubstituted C1-4 haloalkyl, an unsubstituted C3-4 monocyclic cycloalkyl, a fluoro-substituted C3-4 monocyclic cycloalkyl, a hydroxy-substituted C3-4 monocyclic cycloalkyl an unsubstituted 4-6 membered monocyclic heterocyclyl, an optionally substituted aryl and an optionally substituted 5-6 membered monocyclic heteroaryl;
R9 is a substituted phenyl, a substituted monocyclic heteroaryl or a substituted fused-bicyclic heteroaryl, wherein the substituted phenyl, the substituted monocyclic heteroaryl or the substituted fused-bicyclic heteroaryl is substituted with one or more substituents selected from the group consisting of halogen, an unsubstituted C1-4 alkyl, a cyano-substituted C1-4 alkyl, an unsubstituted C1-4 haloalkyl, an unsubstituted C1-4 alkoxy, a hydroxy-substituted C1-4 alkoxy, an optionally substituted monocyclic C3-6 cycloalkyl, an optionally substituted monocyclic heteroaryl, an optionally substituted monocyclic heterocyclyl, amino, a mono-substituted amine, a di-substituted amine and —C(═O)NHR11;
R10A is hydrogen, an unsubstituted C1-6 alkyl, a monocyclic C3-6 cycloalkyl optionally substituted with one or two halogens, an optionally substituted 5-6 membered monocyclic heteroaryl, an optionally substituted 4-6 membered monocyclic heterocyclyl or an optionally substituted monocyclic C3-6 cycloalkyl(C1-4 alkyl);
R10B is an optionally substituted C2-8 alkenyl, wherein the C2-8 alkenyl is optionally substituted with one or more substituents selected from the group consisting of amino, hydroxy, an unsubstituted C1-4 alkoxy, an unsubstituted C1-4 haloalkyl, an unsubstituted C3-4 monocyclic cycloalkyl, a fluoro-substituted C3-4 monocyclic cycloalkyl, a hydroxy-substituted C3-4 monocyclic cycloalkyl and an unsubstituted 4-6 membered monocyclic heterocyclyl;
wherein when R10A is an optionally substituted monocyclic C3-6 cycloalkyl(C1-4 alkyl), then R10B cannot be an unsubstituted C2-6 alkenyl; and
R11 is hydrogen, an unsubstituted C1-6 alkyl, an optionally substituted C2-6 alkenyl, an optionally substituted C1-6 alkynyl or an optionally substituted C3-6 monocyclic cycloalkyl.