US 12,459,941 B2
Tricyclic IRAK inhibitors
Zhushou Luo, South San Francisco, CA (US); Simon Shaw, South San Francisco, CA (US); Ihab Darwish, South San Francisco, CA (US); Esteban Masuda, South San Francisco, CA (US); and Chrystelle Lamagna, South San Francisco, CA (US)
Assigned to Rigel Pharmaceuticals, Inc., South San Francisco, CA (US)
Filed by Rigel Pharmaceuticals, Inc., South San Francisco, CA (US)
Filed on Mar. 30, 2023, as Appl. No. 18/192,813.
Claims priority of provisional application 63/325,957, filed on Mar. 31, 2022.
Prior Publication US 2023/0312568 A1, Oct. 5, 2023
Int. Cl. C07D 471/04 (2006.01); C07F 7/08 (2006.01)
CPC C07D 471/04 (2013.01) [C07F 7/0812 (2013.01)] 13 Claims
 
1. A compound according to Formula I

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt or solvate thereof,
wherein:
Y is O(CH2)n;
n is 1, or 2;
Z1 is N;
Z2 and Z3 are CR5;
R1 is H, halo, cyano, —SO2alkyl, N3, Si(C1-6alkyl)3, heterocycloalkyl, heteroaryl, or Ra;
R2 is pyrrolidi-2-one, optionally substituted with a halogen and/or C1-C4 alkyl;
R3 is H or Ra;
each R5 is H;
each Ra is independently selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, aralkyl, or C3-8 cycloalkyl, and may be optionally substituted with 1, 2, or 3 Rb;
each Rb is independently selected from OH, —ORa, halo, oxo, —NRcRc, —C(O)ORd, —C(O)NRcRc, —N(Rd)C(O)ORa, or —N(Rd)C(O)NRcRc;
each Rc is independently selected from Rd or two Rc, together, with the nitrogen atom to which they are attached, form a C2-8 heterocyclyl optionally having one or two additional heteroatoms selected from O and NRd and optionally substituted with one or more of the same or different Ra or Rb, and
each Rd is independently selected from hydrogen and C1-6 alkyl.