US 12,479,822 B2
AHR agonists
Lacie Marie Chauvigne-Hines, Plainfield, IN (US); Christian Alexander Clarke, Fishers, IN (US); Douglas Linn Gernert, Fishers, IN (US); Steven James Green, Indianapolis, IN (US); and Brian Morgan Watson, Carmel, IN (US)
Assigned to ELI LILLY AND COMPANY, Indianapolis, IN (US)
Filed by Eli Lilly and Company, Indianapolis, IN (US)
Filed on Sep. 13, 2022, as Appl. No. 17/943,554.
Claims priority of provisional application 63/261,794, filed on Sep. 29, 2021.
Claims priority of provisional application 63/261,118, filed on Sep. 13, 2021.
Prior Publication US 2023/0159493 A1, May 25, 2023
Int. Cl. C07D 401/12 (2006.01); C07D 215/54 (2006.01); C07D 417/12 (2006.01); C07D 471/04 (2006.01); C07D 471/06 (2006.01)
CPC C07D 401/12 (2013.01) [C07D 215/54 (2013.01); C07D 417/12 (2013.01); C07D 471/04 (2013.01); C07D 471/06 (2013.01)] 20 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
R1 is selected from phenyl optionally substituted with 1-2 Ri, 5- to 6-membered heteroaryl optionally substituted with Rk and C3-C6 cycloalkyl optionally substituted with Rj;
Ri is independently selected from halogen, C1-C4 alkyl, CF3, OH, O(C1-C4 alkyl), O(C1-C3)OCH3 and NH(C1-C3 alkyl)N(CH3)2;
Rk is selected from halogen, C1-C4 alkyl, nitrile, CF3 and O(C1-C4 alkyl);
Rj is O(C1-C4 alkyl);
X is selected from N and —C(R4)—;
R2 is C1-C3 alkyl, or together with R4 it forms a 5- to 6-membered heterocyclic fused ring;
R4 is hydrogen, halogen, NH(C1-C3 alkyl)N(CH3)2, or together with R2 it forms a 5- to 6-membered heterocyclic fused ring, and
R3 is selected from C3-C6 cycloalkyl, NH(C1-C3 alkyl), N(C1-C3 alkyl)2, NH(C1-C3 alkyl)OH, NH(C1-C3 alkyl)N(C1-C3 alkyl)2 and O(C1-C3 alkyl)OH;
or a pharmaceutically acceptable salt thereof.