US 11,987,572 B2
Therapeutic compounds and methods of use thereof
Joseph J. Topczewski, Minneapolis, MN (US); William C. K. Pomerantz, Minneapolis, MN (US); Angela S. Carlson, Minneapolis, MN (US); Huarui Cui, Minneapolis, MN (US); and Anand Divakaran, Minneapolis, MN (US)
Assigned to REGENTS OF THE UNIVERSITY OF MINNESOTA, Minneapolis, MN (US)
Filed by REGENTS OF THE UNIVERSITY OF MINNESOTA, Minneapolis, MN (US)
Filed on Jun. 3, 2020, as Appl. No. 16/892,072.
Claims priority of provisional application 62/856,617, filed on Jun. 3, 2019.
Prior Publication US 2020/0377474 A1, Dec. 3, 2020
Int. Cl. C07D 401/14 (2006.01); C07D 403/14 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 403/14 (2013.01)] 3 Claims
 
1. A compound of formula (Ic):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 is selected from H, halo, aryl, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, and (C2-C6)alkynyl, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, and (C2-C6)alkynyl of R1 is optionally substituted with one or more groups independently selected from the group consisting of halo, oxo, —OH, cyano, (C3-C6)cycloalkyl, and (C1-C6)alkoxy; and wherein any aryl of R1 is optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, cyano, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy group on an aryl of R1 is optionally substituted with one or more groups independently selected from the group consisting of halo and —OH;
R2 is aryl that is optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, cyano, (C1-C6)alkyl, (C3-C6)cycloalkyl, and (C1-C6)alkoxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, and (C1-C6)alkoxy of R2 is optionally substituted with one or more groups independently selected from the group consisting of halo, and (C1-C6)alkoxy;
R3 is selected from the group consisting of H, —C(═N(Ra))NRaRb, and (C1-C6)alkyl that is optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, cyano, (C3-C6)cycloalkyl, (C1-C6)alkoxy, —C(═N(Ra))NRaRb, and —NRaRb;
each Ra and Rb is independently selected from the group consisting of H, (C1-C6)alkyl, (C1-C6)alkanoyl, and (C3-C6)cycloalkyl; or Ra and Rb together with the nitrogen to which they are attached form a 4-6 membered ring heterocycle;
F is O, S, or NRc;
G is CH or N; and
Rc is H or (C1-C6)alkyl.