US 11,753,374 B2
Compounds for the treatment of acute and chronic kidney disease
Mark J. Suto, Homewood, AL (US); Bini Mathew, Hoover, AL (US); Anupam Agarwal, Mountain Brook, AL (US); and Amie M. Traylor, Talladega, AL (US)
Assigned to Southern Reserach Institute, Birmingham, AL (US); The UAB Research Foundation, Birmingham, AL (US); and The United States Government as represented by the Department of Veterans Affairs, Washington, DC (US)
Filed by Southern Research Institute, Birmingham, AL (US); and UAB Research Foundation, Birmingham, AL (US)
Filed on Nov. 17, 2021, as Appl. No. 17/529,199.
Claims priority of provisional application 63/115,421, filed on Nov. 18, 2020.
Prior Publication US 2022/0153695 A1, May 19, 2022
Int. Cl. C07D 207/416 (2006.01); C07D 405/04 (2006.01); C07D 417/10 (2006.01)
CPC C07D 207/416 (2013.01) [C07D 405/04 (2013.01); C07D 417/10 (2013.01)] 20 Claims
 
1. A compound having a structure represented by a formula:

OG Complex Work Unit Chemistry
wherein n is 0, 1, or 2;
wherein each of R1a, R1b, R1c, R1d, and R1e is independently selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, C1-C4 aminoalkyl, —C(O)R10, —CO2R11, Cy1, and —OCy1;
wherein R10, when present, is selected from hydrogen, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
wherein R11, when present, is selected from hydrogen and C1-C4 alkyl; and
wherein Cy1 is selected from C6 aryl, C2-C5 heteroaryl, C3-C6 cycloalkyl, and C2-C5 heterocycloalkyl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
or wherein two adjoining R1a, R1b, R1c, R1d, and R1e groups are covalently bonded and, together with the intermediate atoms, comprise a 5- or 6-membered cycloalkyl, a 5- or 6-membered heterocycloalkyl, a 6-membered aryl, or a 5- or 6-membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
wherein R2 is selected from hydrogen and C1-C4 alkyl; and
wherein each of R3a, R3b, R3c, and R3d is independently selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl,
provided that when one or two of R1a, R1b, R1c, R1d, and R1e is —OH or C1-C4 alkoxy and the remaining R1a, R1b, R1c, R1d, and R1e groups are hydrogen, then at least two of R3a, R3b, R3c, and R3d are non-hydrogen groups,
provided that when one or two of R1a, R1b, R1c, R1d, and R1e is —OH or C1-C4 alkoxy and at least one of the remaining R1a, R1b, R1c, R1d, and R1e groups is a different non-hydrogen group, then at least one of R3a, R3b, R3c, and R3d are non-hydrogen groups, and
provided that when one of R1a, R1b, R1c, R1d, and R1e is C1-C4 hydroxyalkyl, then at least one of R1a, R1b, R1c, R1d, R1e, R3a, R3b, R3c, and R3d is a non-hydrogen group,
or a pharmaceutically acceptable salt thereof.