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US 12,473,262 B2Granted
Aryl hydrocarbon receptor activators
AssigneeOregon State University
InventorsSiva Kumar Kolluri, Nancy I. Kerkvliet, Sebastian Bernales, Jit Chakravarty, Brahmam Pujala, Pasha Khan, Varun Kumar, Abhinandan Danodia, Gonzalo Ureta
Life of this patent
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Abstract
Small molecule AhR ligands are disclosed. The ligands can induce the differentiation of Tr1 cells to suppress pathogenic immune responses without inducing nonspecific immune suppression. Methods of treatment of autoimmune diseases using the AhR ligands are also disclosed.
Claims10
A compound of the formula:
- 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.
9 more elements
A compound of the formula:
- or a tautomer thereof, a stereoisomer thereof, a hydrate thereof, or a pharmaceutically acceptable salt thereof,
- wherein R2 and R3, independently, F, Cl, Br, O(C1-C5 alkyl), SCF3, OCF3, CO2H, CO2(C1-C5 alkyl), or CONR5R6, wherein R5 and R6 are independently H, optionally substituted C1-C10 alkyl, optionally substituted C3-C10 cycloalkyl, or R5 and R6, together with the nitrogen atom to which they are attached, form an optionally substituted morpholinyl;
- and
- 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.
5 more elements
Dependencies are inferred from the claim text.