US 12,441,686 B2
Heterocyclic g-protein-coupled receptor 52 (GPR52) agonists
Jia Zhou, Galveston, TX (US); John A. Allen, Galveston, TX (US); Pingyuan Wang, Galveston, TX (US); and Daniel E. Felsing, Galveston, TX (US)
Assigned to Board of Regents, The Univeristy of Texas System, Ausitn, TX (US)
Filed by Board of Regents, The University of Texas System, Austin, TX (US)
Filed on Aug. 27, 2023, as Appl. No. 18/238,510.
Application 18/238,510 is a continuation of application No. 17/499,299, filed on Oct. 12, 2021, granted, now 11,773,065.
Claims priority of provisional application 63/090,519, filed on Oct. 12, 2020.
Prior Publication US 2024/0059655 A1, Feb. 22, 2024
Int. Cl. C07D 213/74 (2006.01); C07D 401/04 (2006.01); C07D 401/12 (2006.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 405/12 (2006.01)
CPC C07D 213/74 (2013.01) [C07D 401/04 (2013.01); C07D 401/12 (2013.01); C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 405/12 (2013.01)] 4 Claims
 
1. A compound according to Formula I: or pharmaceutically acceptable salt thereof, wherein:

OG Complex Work Unit Chemistry
or
pharmaceutically acceptable salt thereof;
wherein:
R1 is aryl or heteroaryl;
wherein:
each aryl or heteroaryl optionally is substituted with one or more groups selected independently from: H, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, benzyl, alkoxy, halogen, cyan, nitro, amino, hydroxyl, CF3 or —OCF3;
wherein:
alkyl is optionally substituted with one or more hydroxyl, cyan, amino, or halogen;
X is CT1T2;
wherein:
T1 is independently chosen from: H, OH, alkyl or F; and T2 is independently chosen from:
H or F;
W is CP1
Y is CP1 or N;
Z is CP1 wherein each P1 defined in CP1 for each W, Y and Z above independently is chosen from: H, alkyl, alkoxy, halogen, cyan, amino, hydroxyl, NO2, CF3 or —OCF3;
Q is

OG Complex Work Unit Chemistry
provided that when Q is

OG Complex Work Unit Chemistry
then at least one of W, Y, Z is N;
R2 is H; and
R3 Is selected from: H, alkyl, heteroaryl, heterocyclyl, heterocylclyl-alkyl, and hydroxyl-alkyl; and each group is optionally substituted with one or more groups selected independently from: alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, benzyl, alkoxy, halogen, cyan, nitro, amino, hydroxyl, CF3 or —OCF3;
or R2 and R3together form a 4-12 membered cycloalkyl ring, and the -12 membered cycloalkyl is optionally substituted with one or more groups selected independently from: alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, benzyl, alkoxy, halogen, cyan, nitro, amino, hydroxyl, CF3 or —OCF3; and
R4 is independently chosen from H, alkyl, alkoxy, halogen, cyan, amino, hydroxyl, nitro, CF3 or —OCF3.