US 12,473,262 B2
Aryl hydrocarbon receptor activators
Siva Kumar Kolluri, Corvallis, OR (US); Nancy I. Kerkvliet, Corvallis, OR (US); Sebastian Bernales, San Francisco, CA (US); Jit Chakravarty, Edmond, OK (US); Brahmam Pujala, Greater Noida (IN); Pasha Khan, New Delhi (IN); Varun Kumar, New Delhi (IN); Abhinandan Danodia, Greater Noida (IN); and Gonzalo Ureta, Santiago (CL)
Assigned to Oregon State University, Corvallis, OR (US)
Appl. No. 17/630,763
Filed by Oregon State University, Corvallis, OR (US)
PCT Filed Jul. 30, 2020, PCT No. PCT/US2020/044294
§ 371(c)(1), (2) Date Jan. 27, 2022,
PCT Pub. No. WO2021/022061, PCT Pub. Date Feb. 4, 2021.
Claims priority of provisional application 62/880,478, filed on Jul. 30, 2019.
Prior Publication US 2022/0281824 A1, Sep. 8, 2022
Int. Cl. C07D 235/06 (2006.01); C07D 209/12 (2006.01); C07D 307/80 (2006.01); C07D 401/04 (2006.01); C07D 401/06 (2006.01); C07D 403/04 (2006.01); C07D 405/04 (2006.01); C07D 405/06 (2006.01); C07D 409/04 (2006.01); C07D 471/06 (2006.01); C07D 471/16 (2006.01); C07D 487/04 (2006.01)
CPC C07D 235/06 (2013.01) [C07D 209/12 (2013.01); C07D 307/80 (2013.01); C07D 401/04 (2013.01); C07D 401/06 (2013.01); C07D 403/04 (2013.01); C07D 405/04 (2013.01); C07D 405/06 (2013.01); C07D 409/04 (2013.01); C07D 471/06 (2013.01); C07D 471/16 (2013.01); C07D 487/04 (2013.01)] 10 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
or a tautomer thereof, a stereoisomer thereof, a hydrate thereof, or a pharmaceutically acceptable salt thereof, wherein:
Q1 is an optionally substituted C6-C10 aryl; optionally substituted C5-C10 heteroaryl; optionally substituted C5-C10 heterocyclyl; optionally substituted C1-C10 alkyl, or optionally substituted C3-C10 cycloalkyl;
Z is C;
R1 is H or halogen;
R2, R3, and R4 are independently H, halogen, CN, optionally substituted C1-C10 alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted C1-C6 alkoxy, SO2R5, CO2R5, or CONR5R6, or any one of R1 and R2, R2 and R3, and R3 and R4 pairs, together with the carbon atoms to which they are attached, forms an optionally substituted a five- or six-membered cycloalkenyl, heterocyclenyl, aryl or heteroaryl;
R5 and R6 are independently H, optionally substituted C1-C10 alkyl, or optionally substituted C3-C10 cycloalkyl, or R5 and R6, together with the nitrogen atom to which they are attached, form an optionally substituted 5-membered ring or an optionally substituted 6-membered ring;
R7, at each occurrence, is independently H, halogen, CN, optionally substituted C1-C10 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C1-C10 heteroalkyl, optionally substituted C1-C10 heterocyclyl, optionally substituted C6-C10 aryl, optionally substituted C5-C10 heteroaryl, optionally substituted C1-C6 alkoxy, optionally substituted C1-C6 cycloalkyloxy, OCF3, NR5R6, SCF3, or C(O)NR5R6; and
m is an integer from 1 to 7.