US 12,077,542 B2
Indole AHR inhibitors and uses thereof
Alfredo C. Castro, Somerville, MA (US); and Catherine A. Evans, Somerville, MA (US)
Assigned to Ikena Oncology, Inc., Boston, MA (US)
Filed by Ikena Oncology, Inc., Boston, MA (US)
Filed on May 6, 2022, as Appl. No. 17/662,246.
Application 16/668,070 is a division of application No. 15/958,586, filed on Apr. 20, 2018, granted, now 10,570,138, issued on Feb. 25, 2020.
Application 17/662,246 is a continuation of application No. 16/843,606, filed on Apr. 8, 2020, granted, now 11,358,969.
Application 16/843,606 is a continuation of application No. 16/668,070, filed on Oct. 30, 2019, granted, now 10,689,388, issued on Jun. 23, 2020.
Claims priority of provisional application 62/658,454, filed on Apr. 16, 2018.
Claims priority of provisional application 62/592,542, filed on Nov. 30, 2017.
Claims priority of provisional application 62/488,476, filed on Apr. 21, 2017.
Prior Publication US 2023/0028336 A1, Jan. 26, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 487/04 (2006.01); A61P 29/00 (2006.01); A61P 35/00 (2006.01); C07D 401/14 (2006.01); C07D 473/34 (2006.01); C07D 495/04 (2006.01); C07D 519/00 (2006.01); A61K 9/00 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 29/00 (2018.01); A61P 35/00 (2018.01); C07D 401/14 (2013.01); C07D 473/34 (2013.01); C07D 495/04 (2013.01); C07D 519/00 (2013.01); A61K 9/0053 (2013.01)] 20 Claims
 
1. A compound of formula VIII-b:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
X is N or CH;
p is 0, 1, or 2;
each R is independently hydrogen, deuterium, or an optionally substituted group selected from C1-6 aliphatic, a 3-8 membered saturated or partially unsaturated monocyclic carbocyclic ring, phenyl, an 8-10 membered bicyclic aromatic carbocyclic ring; a 4-8 membered saturated or partially unsaturated monocyclic heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 5-6 membered monocyclic heteroaromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered bicyclic heteroaromatic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or two R on the same nitrogen are taken together with their intervening atoms to form a 4-7 membered saturated, partially unsaturated, or aromatic ring having 1-2 heteroatoms in addition to the nitrogen independently selected from oxygen, nitrogen, or sulfur;
each of Rx, Ry, and Rz is independently selected from R, halogen, cyano, nitro, —OR, —SR, —N(R)2, —N(R)C(O)R, —C(O)N(R)2, —C(O)N(R)OR, —N(R)C(O)N(R)2, —N(R)C(O)OR, —OC(O)N(R)2, —N(R)SO2R, —SO2N(R)2, —C(O)R, —C(O)OR, —OC(O)R, —S(O)R, or —SO2R;
m is 1, 2, 3, or 4;
n is 1, 2, 3, 4, or 5;
L1 is a covalent bond or an optionally substituted C1-6 membered straight or branched bivalent hydrocarbon chain wherein a methylene unit of L1 is optionally replaced with —Cy—, —O—, —S—, —NR—, —C(O)—, —C(O)O—, —OC(O)—, —C(O)N(R)—, —N(R)C(O)—, —SO2—, —N(R)SO2—, or —SO2N(R)—S —SO2N(R)—; and
-Cy- is a 3-8 membered bivalent saturated, partially unsaturated, or aromatic monocyclic ring having 0-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered bivalent saturated, partially unsaturated, or aromatic bicyclic ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur.