IP Library › Granted Patent US 12709619
Granted Patent B2
US 12709619 · App. 17/605,186 · Granted Aug 18, 2026

Selective ligands of human constitutive androstane receptor

Inventors: Radim Nencka (Roztoky, CZ); Ivana Mejdrova (Prague, CZ); Petr Pavek (Hradec Kralove, CZ); Jan Dusek (Prelouc, CZ)
Assignees: USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; UNIVERZITA KARLOVA
C07D513/04A61P3/00C07D471/04C07D487/04
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Quick Facts
Patent No.
US 12709619
App. No.
17/605,186
Granted
Aug 18, 2026
Kind
B2
Abstract

A structurally novel class of heterocyclic compounds of general formula I wherein L1 is heteroaryl and L2 is heteroaryl or aryl is disclosed. The novel compounds are useful in a method of prevention or treatment of a condition that is mediated by the action, or by loss of action of Constitutive androstane receptor (CAR) receptor or its endogenous ligands. The present invention provides the novel compounds for medicinal use as well as pharmaceutical composition containing the compounds.

Claims (74)

1 . A compound of general formula I, selected from the group consisting of:

2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

6-(4-Chlorophenyl)-5-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole,

5-(1-(3,4-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)-6-phenylimidazo[2,1-b]thiazole,

6-(4-Chlorophenyl)-5-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole,

2-(4-Chlorophenyl)-3-(1-(3,4-dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

2-(4-Chlorophenyl)-3-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

3-(1-Benzyl-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,

2-(4-Chlorophenyl)-3-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-(4-chlorophenyl)imidazo[2,1-b]thiazole,

6-(4-Chlorophenyl)-5-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole,

3-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,

5-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)-6-(4-chlorophenyl)imidazo[2,1-b]thiazole,

3-Benzyl-5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)isoxazole,

4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile,

2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-b]pyridazine,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(3,4-dichlorophenyl)imidazo[1,2-a]pyridine,

5-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-6-(3,4-dichlorophenyl)imidazo[2,1-b]thiazole,

3-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine,

5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-3-(3,4-dichlorobenzyl)-1,2,4-oxadiazole,

2-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-(3,4-dichlorobenzyl)-1,3,4-oxadiazole,

5-(6-(4-Chlorophenyl)imidazo[2,1-b]thiazol-5-yl)-3-(3,4-dichlorobenzyl)-1,2,4-oxadiazole,

2-(4-Chlorophenyl)-3-(5-(3,4-dichlorobenzyl)-1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine,

6-(4-Chlorophenyl)-5-(2-(3,4-dichlorobenzyl)thiazol-4-yl)imidazo[2,1-b]thiazole,

4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-2-(3,4-dichlorobenzyl)thiazole,

2-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-(3,4-dichlorobenzyl)-1,3,4-thiadiazole,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(p-tolyl)imidazo[1,2-a]pyridine,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(2,4-dichlorophenyl)imidazo[1,2-a]pyridine,

4-(3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridin-2-yl)benzonitrile,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)imidazo[1,2-a]pyridine,

3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-ethylphenyl)imidazo[1,2-a]pyridine,

Methyl2-chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzoate,

(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) phenyl)methanol,

2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine, 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-pyrrol-2-yl)imidazo[1,2-a]pyridine,

2-(4-Chlorophenyl)-3-(1-(3,4-dichlorophenethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) benzamide,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N,N-dimethylbenzamide,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N-methoxy-N-methylbenzamide,

1-(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)ethan-1-one,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N-methylbenzamide,

1-(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)propan-1-one,

2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)-N,N-dimethylbenzamide,

2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)-N,N-dimethylbenzothioamide,

2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methyl)-N-methylbenzothioamide,

2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methyl)-N-methylbenzamide,

2-(4-Chlorophenyl)-3-(1-(4-(methylsulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

2-(4-Chlorophenyl)-3-(1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

2-(4-Chlorophenyl)-3-(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)aniline,

2-Chloro-5-(1-(4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)ethyl)benzamide,

2-(4-Chlorophenyl)-3-(1-(4-(methylthio)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

2-Chloro-5-((4-(2-(4-chlorophenyl)-8-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) benzamide,

2-Chloro-5-((4-(2-(4-chlorophenyl)-7-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) benzamide,

2-Chloro-5-((4-(2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzamide,

2-Chloro-5-((4-(2-(4-chlorophenyl)-6,8-difluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzamide,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) benzaldehyde,

(E)-2-chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) benzaldehyde oxime,

N-(4-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)acetamide,

3-(1-(4-Chloro-3-nitrobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl) aniline,

3-(4-Benzylphenyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,

3-(6-Benzylpyridin-3-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,

2-(4-Chlorophenyl)-3-(6-(1-phenylvinyl)pyridin-3-yl)imidazo[1,2-a]pyridine,

2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-iodo-1H-1,2,3-triazol-1-yl)methyl)benzamide,

2-(4-Chlorophenyl)-3-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,

3-(4-Benzylcyclohex-1-en-1-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,

4-Benzyl-1-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)cyclohexan-1-ol,

1-(5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)-1-phenylethane-1,2-diol,

(5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)(phenyl)methanone, and

2-Chloro-5-((4-(2-(pyridine-4-yl)imidazo[1,2-a]pyridine-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzamide.

2 . A pharmaceutical composition characterized in that it comprises as an active ingredient the compound according to claim 1 or its pharmaceutically acceptable salt or solvate, and one or more pharmaceutically acceptable carriers, polymers and/or excipients.

3 . The pharmaceutical composition according to claim 2 , characterized in that it comprises one or more additional therapeutic agents.