US 12,269,798 B2
Second generation GRP94-selective inhibitors
Brian S. J. Blagg, Niles, MI (US); and Vincent Matthew Crowley, Lawrence, KS (US)
Assigned to University of Kansas, Lawrence, KS (US)
Filed by University of Kansas, Lawrence, KS (US)
Filed on Jun. 7, 2021, as Appl. No. 17/341,047.
Application 17/341,047 is a continuation of application No. 16/640,897, granted, now 11,028,041, previously published as PCT/US2018/047820, filed on Aug. 23, 2018.
Claims priority of provisional application 62/550,292, filed on Aug. 25, 2017.
Prior Publication US 2021/0300872 A1, Sep. 30, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 69/94 (2006.01); A61K 31/216 (2006.01); A61K 31/44 (2006.01); A61P 27/02 (2006.01); A61P 35/04 (2006.01); C07C 69/76 (2006.01); C07C 69/78 (2006.01); C07C 69/88 (2006.01); C07C 219/34 (2006.01); C07C 229/52 (2006.01); C07D 213/55 (2006.01); C07D 213/643 (2006.01)
CPC C07C 69/94 (2013.01) [A61K 31/216 (2013.01); A61K 31/44 (2013.01); A61P 27/02 (2018.01); A61P 35/04 (2018.01); C07C 69/76 (2013.01); C07C 69/78 (2013.01); C07C 219/34 (2013.01); C07C 229/52 (2013.01); C07D 213/55 (2013.01); C07D 213/643 (2013.01)] 24 Claims
 
1. A compound of Formula I

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
X1 is Cl or F;
X2 is CH2 or O;
R1, R2, R4, R5, and R6 are each independently H, alkoxy, hydroxyl, thiol, or halo; and
R3 is H, alkoxy, amino, hydroxyl, thiol, or halo.
 
3. A compound of Formula III

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
X3 is Cl or F;
X4 is CH2 or O; and
R7 is alkoxy, hydroxyl, or halo.