US 12,264,150 B2
NR4A1 ligands, pharmaceutical compositions, and related methods of use
Stephen Safe, College Station, TX (US)
Assigned to The Texas A&M University System, College Station, TX (US)
Filed by The Texas A&M University System, College Station, TX (US)
Filed on Oct. 26, 2021, as Appl. No. 17/510,904.
Application 17/510,904 is a continuation of application No. 16/638,101, abandoned, previously published as PCT/US2018/046115, filed on Aug. 9, 2018.
Claims priority of provisional application 62/543,761, filed on Aug. 10, 2017.
Prior Publication US 2022/0332703 A1, Oct. 20, 2022
Int. Cl. C07D 403/06 (2006.01); A61P 3/10 (2006.01); A61P 35/00 (2006.01)
CPC C07D 403/06 (2013.01) [A61P 3/10 (2018.01); A61P 35/00 (2018.01)] 37 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
or a salt thereof,
wherein,
R1, and R1′ are each independently selected from the group consisting of hydrogen, a linear alkyl group containing one to about ten carbon atoms, and a branched alkyl group containing one to about ten carbon atoms;
R2 and R2′ are each hydrogen;
R3, R4, R5, R6, R3′, R4′, R5′, and R6′ are each independently selected from the group consisting of hydrogen, a halogen, a linear alkyl group containing one to about ten carbon atoms, a branched alkyl group containing one to about ten carbon atoms, an alkoxy group containing one to about ten carbon atoms, and a nitro group;
R7 is selected from the group consisting of hydrogen, a linear alkyl group containing one to about ten carbon atoms, a branched alkyl group containing one to about ten carbon atoms, a cycloalkyl group containing one to about ten carbon atoms, and an aryl group;
R8 is OH;
R9, is selected from the group consisting of H, a fluoro, a chloro, an iodo, a linear alkyl group containing one to about ten carbon atoms, a branched alkyl group containing one to about ten carbon atoms, an alkoxy group containing one to about ten carbon atoms, a haloalkyl group containing one to about ten carbon atoms, a nitro group, a phenyl, a cyano, and a haloalkoxy group containing one to about ten carbon atoms;
R10 is selected from the group consisting of H, a fluoro, a bromo, an iodo, a linear alkyl group containing one to about ten carbon atoms, a branched alkyl group containing one to about ten carbon atoms, an alkoxy group containing one to about ten carbon atoms, a haloalkyl group containing one to about ten carbon atoms, a nitro group, a phenyl, a cyano, and a haloalkoxy group containing one to about ten carbon atoms;
R11 is selected from the group consisting of a linear alkyl group containing one to about ten carbon atoms, a haloalkyl group containing one to about ten carbon atoms, a hydroxyl group, a phenyl, a cyano, and a haloalkoxy group containing one to about ten carbon atoms; and
R12 is selected from the group consisting of H, a halogen, a linear alkyl group containing one to about ten carbon atoms, a branched alkyl group containing one to about ten carbon atoms, an alkoxy group containing one to about ten carbon atoms, a haloalkyl group containing one to about ten carbon atoms, a hydroxyl group, a nitro group, a phenyl, a cyano, and a haloalkoxy group containing one to about ten carbon atoms.