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US 2026/0022099 A1Published application
Aryl hydrocarbon receptor agonists and uses thereof
AssigneeNexys Therapeutics, Inc.
InventorsTom Yao-Hsiang WU, Qihui JIN
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Abstract
The present invention relates to pharmaceutical compounds of Formula (I): as further described herein, and pharmaceutical compositions containing such compounds, as well as methods of using these compounds to modulate the activity of aryl hydrocarbon receptor (AhR) and to treat conditions comprising inflammation inside the intestinal tract and certain disorders of the central nervous system affected by the gut-brain axis, including IBD, ulcerative colitis, Crohn's disease, Huntington's disease, and multiple sclerosis.
Claims25
A compound of Formula (I):
- wherein:
- one of Z1 and Z2 is —N═N—Ar, and the other of Z1 and Z2 is H;
- wherein Ar is selected from phenyl, naphthyl, and
- wherein each phenyl and naphthyl is optionally substituted with up to three groups selected from —OR, COOR, C1-4 alkyl, C1-4haloalkyl, C1-4haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, and halo;
- R3 is selected from H, CN, halo, C1-4 alkyl, C1-4 haloalkyl, and C1-4 haloalkoxy;
- each R1 and R4 is independently selected from —OR, COOR, C1-4 haloalkyl, C1-4 haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, halo, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkyl, —CN, and —NR′2;
- each R2 and R5 is independently selected from halo, —OR, COOR, C1-4 haloalkyl, C1-4 haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkyl, —CN, and —NR′2;
- each R is independently selected from H, C1-4 haloalkyl, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4haloalkoxy, C1-4haloalkyl, —CN, and —NR′2;
- each R′ is independently selected from H and C1-3 alkyl;
- each m, n, p, and q is independently selected from 0, 1 and 2;
- and
- [N] represents the attachment of Ar to N in —N═N—Ar;
- or a pharmaceutically acceptable salt thereof.
10 more elements
A pharmaceutical composition comprising a compound of Formula (I):
- wherein:
- one of Z1 and Z2 is —N═N—Ar, and the other of Z1 and Z2 is H;
- wherein Ar is selected from phenyl, naphthyl, and
- wherein each phenyl and naphthyl is optionally substituted with up to three groups selected from —OR, COOR, C1-4 alkyl, C1-4haloalkyl, C1-4haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, and halo;
- R3 is selected from H, CN, halo, C1-4 alkyl, C1-4 haloalkyl, and C1-4 haloalkoxy;
- each R1 and R4 is independently selected from —OR, COOR, C1-4 haloalkyl, C1-4 haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, halo, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkyl, —CN, and —NR′2;
- each R2 and R5 is independently selected from halo, —OR, COOR, C1-4 haloalkyl, C1-4 haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkyl, —CN, and —NR′2;
- each R is independently selected from H, C1-4 haloalkyl, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4haloalkoxy, C1-4haloalkyl, —CN, and —NR′2;
- each R′ is independently selected from H and C1-3 alkyl;
- each m, n, p, and q is independently selected from 0, 1 and 2;
- and
- [N] represents the attachment of Ar to N in —N═N—Ar;
- or a pharmaceutically acceptable salt thereof;
- admixed with at least one pharmaceutically acceptable excipient.
11 more elements
A method to treat a condition affecting the intestinal tract or modulated through the gut-brain axis, wherein the method comprises administering to a subject in need of such treatment an effective amount of a compound of Formula (I):
- wherein:
- one of Z1 and Z2 is —N═N—Ar, and the other of Z1 and Z2 is H;
- wherein Ar is selected from phenyl, naphthyl, and
- wherein each phenyl and naphthyl is optionally substituted with up to three groups selected from —OR, COOR, C1-4 alkyl, C1-4haloalkyl, C1-4haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, and halo;
- R3 is selected from H, CN, halo, C1-4 alkyl, C1-4 haloalkyl, and C1-4 haloalkoxy;
- each R1 and R4 is independently selected from —OR, COOR, C1-4 haloalkyl, C1-4 haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, halo, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkyl, —CN, and —NR′2;
- each R2 and R5 is independently selected from halo, —OR, COOR, C1-4 haloalkyl, C1-4 haloalkoxy, —NR2, CN, —PO3R2, —SO2R, —SO3R, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkyl, —CN, and —NR′2;
- each R is independently selected from H, C1-4 haloalkyl, and C1-4 alkyl optionally substituted with one or two groups selected from —OR′, COOR′, C1-4 alkoxy, C1-4haloalkoxy, C1-4haloalkyl, —CN, and —NR′2;
- each R′ is independently selected from H and C1-3 alkyl;
- each m, n, p, and q is independently selected from 0, 1 and 2;
- and
- [N] represents the attachment of Ar to N in —N═N—Ar;
- or a pharmaceutically acceptable salt thereof.
10 more elements
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Dependencies are inferred from the claim text.