US 12,071,424 B2
IRE1 small molecule inhibitors
Joseph P. Vacca, Telford, PA (US); Dansu Li, Warrington, PA (US); and Sarah Elizabeth Bettigole, New York, NY (US)
Assigned to Cornell University, Ithaca, NY (US)
Filed by Cornell University, Ithaca, NY (US)
Filed on Feb. 28, 2023, as Appl. No. 18/176,362.
Application 18/176,362 is a continuation of application No. 17/175,940, filed on Feb. 15, 2021, granted, now 11,634,403.
Application 17/175,940 is a continuation of application No. 16/931,203, filed on Jul. 16, 2020, granted, now 10,961,218.
Application 16/931,203 is a continuation of application No. 16/184,916, filed on Nov. 8, 2018, granted, now 10,745,379.
Claims priority of provisional application 62/584,575, filed on Nov. 10, 2017.
Claims priority of provisional application 62/678,723, filed on May 31, 2018.
Prior Publication US 2023/0271935 A1, Aug. 31, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/04 (2006.01); A61K 31/517 (2006.01); A61P 35/00 (2006.01); C07D 217/22 (2006.01); C07D 239/74 (2006.01); C07D 239/84 (2006.01); C07D 239/94 (2006.01); C07D 401/10 (2006.01); C07D 403/04 (2006.01); C07D 403/10 (2006.01); C07D 413/04 (2006.01); C07D 417/04 (2006.01)
CPC C07D 401/10 (2013.01) [A61P 35/00 (2018.01); C07D 217/22 (2013.01); C07D 239/84 (2013.01); C07D 401/04 (2013.01); C07D 403/04 (2013.01); C07D 403/10 (2013.01); C07D 413/04 (2013.01); C07D 417/04 (2013.01)] 21 Claims
 
1. A compound of Formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein
R3 is C1-C4alkyl, or —O—C1-C4alkyl;
R4 is halogen;
each R5 is independently H, halogen;
R6 is H, or C-C4alkyl;
R7 is C1-C4alkyl; and
RA1 and RA2 are each independently H, —C1-C4alkyl; provided that both RA1 and RA2 are not H.