US 11,932,628 B2
Selective small molecule peptidomimetic melanocortin ligands
Carrie Haskell-Luevano, Minneapolis, MN (US); Skye Ross Doering, Minneapolis, MN (US); Marcello A. Giulianotti, Port St. Lucie, FL (US); Clemencia Pinilla, Port St. Lucie, FL (US); Radleigh G. Santos, Port St. Lucie, FL (US); and Richard A. Houghten, Port St. Lucie, FL (US)
Assigned to REGENTS OF THE UNIVERSITY OF MINNESOTA, Minneapolis, MN (US)
Filed by REGENTS OF THE UNIVERSITY OF MINNESOTA, Minneapolis, MN (US); and TORREY PINES INSTITUTE FOR MOLECULAR STUDIES, Port St. Lucie, FL (US)
Filed on Jan. 3, 2022, as Appl. No. 17/567,201.
Claims priority of provisional application 63/133,571, filed on Jan. 4, 2021.
Prior Publication US 2022/0213068 A1, Jul. 7, 2022
Int. Cl. C07D 403/14 (2006.01); A61K 9/20 (2006.01); A61K 9/48 (2006.01); A61P 3/04 (2006.01)
CPC C07D 403/14 (2013.01) [A61K 9/2013 (2013.01); A61K 9/2027 (2013.01); A61K 9/2054 (2013.01); A61K 9/2059 (2013.01); A61K 9/485 (2013.01); A61K 9/4858 (2013.01); A61K 9/4866 (2013.01); A61P 3/04 (2018.01)] 22 Claims
 
1. A compound of formula I:

OG Complex Work Unit Chemistry
wherein:
R1 is H, or C1-30 alkyl; wherein the C1-30 alkyl is optionally substituted with one or more groups selected from the group consisting of halo, hydroxy, nitro, cyano, C1-6 alkoxy, —NRa2, —NHC(═NH)NRa2, —C(═O)NRa2, —COORa, and —SRa;
R2 is H, C1-8 alkyl or -L2-A2; wherein the C1-8 alkyl is optionally substituted with one or more groups selected from the group consisting of halo, hydroxy, nitro, cyano, C1-6 alkoxy, —NRb2, —NHC(═NH)NRb2, —C(═O)NRb2, —COORb, and —SRb;
R3 is H, or C1-30 alkyl; wherein the C1-30 alkyl is optionally substituted with one or more groups selected from the group consisting of halo, hydroxy, nitro, cyano, C1-6 alkoxy, —NRc2, —NHC(═NH)NRc2, —C(═O)NRc2, —COORc, and —SRc;
R4 is H, C1-30 alkyl or -L4-A4; wherein the C1-30 alkyl is optionally substituted with one or more groups selected from the group consisting of halo, hydroxy, nitro, cyano, C1-6 alkoxy, —NRd2, —NHC(═NH)NRd2, —C(═O)NRd2, —COORd, and −SRd;
L2 is absent or C1-4 alkylene;
L4 is absent or C1-4 alkylene;
A2 is cycloalkyl, aryl, or heteroaryl; wherein the cycloalkyl, aryl, and heteroaryl are optionally substituted with one or more groups selected from the group consisting of halo, hydroxy, nitro, cyano, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, and phenyl;
A4 is cycloalkyl; wherein the cycloalkyl is optionally substituted with one or more groups selected from the group consisting of halo, hydroxy, nitro, cyano, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6haloalkoxy, and phenyl;
each Ra is independently H or C1-6 alkyl;
each Rb is independently H or C1-6 alkyl;
each Rc is independently H or C1-6 alkyl; and
each Rd is independently H or C1-6 alkyl;
or a salt thereof.