US 11,993,594 B2
IRAK inhibitors and method for making and using
Hui Li, Santa Clara, CA (US); Thilo Heckrodt, San Francisco, CA (US); Yan Chen, Foster City, CA (US); Ryan Kelley, Pacifica, CA (US); Darren McMurtrie, Daly City, CA (US); Kin Tso, San Francisco, CA (US); Vanessa Taylor, San Francisco, CA (US); Rajinder Singh, Belmont, CA (US); Rose Yen, San Francisco, CA (US); and Jack Maung, Daly City, CA (US)
Assigned to Rigel Pharmaceuticals, Inc., South San Francisco, CA (US)
Filed by Rigel Pharmaceuticals, Inc., South San Francisco, CA (US)
Filed on Sep. 27, 2022, as Appl. No. 17/953,570.
Application 16/444,093 is a division of application No. 15/793,770, filed on Oct. 25, 2017, granted, now 10,370,367.
Application 17/953,570 is a continuation of application No. 17/184,182, filed on Feb. 24, 2021, granted, now 11,492,349.
Application 17/184,182 is a continuation of application No. 16/444,093, filed on Jun. 18, 2019, granted, now 10,941,140.
Claims priority of provisional application 62/413,217, filed on Oct. 26, 2016.
Prior Publication US 2023/0062818 A1, Mar. 2, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 413/14 (2006.01); A61P 29/00 (2006.01)
CPC C07D 413/14 (2013.01) [A61P 29/00 (2018.01)] 17 Claims
 
1. A compound, having a formula 1

OG Complex Work Unit Chemistry
or a salt thereof, wherein:
at least one of R1 and R2 is a nitrogen-containing heteroaryl, and the remaining R1 or R2 is H, alkyl, haloalkyl, nitro, cyano, amide, amino, hydroxyl, carboxyl, carboxyl ester, or acyl;
R3 is H, aliphatic, heteroaliphatic, heterocyclyl, amide, aromatic, or araliphatic;
R4 is H, aliphatic, heteroaliphatic, or one of R1 or R2 together with R4, and together with the atoms to which they are attached, form a heterocyclic ring;
R5 is H or alkyl; and
ring A is a heterocyclic ring.