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US 10,647,688 B2Granted
Compounds, synthesis method thereof and use of same in medicine and in cosmetics
AssigneeGalderma Research & Development
InventorThibaud Portal
Life of this patent
Estimating the term…
Abstract
Novel compounds, synthesis methods and use of the same in medicine and in cosmetics are disclosed. Also disclosed, are novel compounds and ligands that modulate RARs.
Claims29
A compound of formula (I)
- wherein:
- A represents:
- R1 represents a branched alkyl radical, a substituted cycloalkyl radical, or an NR4R5 radical;
- R2 is a hydrogen atom, a linear or branched alkyl radical, a polyether radical, or a mono or polyhydroxyalkyl radical;
- R3 is a hydrogen atom;
- R4 and R5, identical or different, represent a hydrogen atom, a linear or branched alkyl radical, a substituted alkyl radical, or an acyl radical;
- R4 and R5 taken together can also be linked and form an optionally substituted azetidine, pyrrolidine or piperidine heterocycle with the nitrogen atom with which they are linked;
- W represents O or S;
- X, Y, Z, identical or different represent O, S, N, NR6 or CH;
- the central heterocycle
- corresponds to one of the structures presented below, the dashed bonds may be a single or double bond depending on the nature of atoms X, Y and Z and their covalence
- R6 represents a hydrogen or alkyl radical;
- as well as their addition salts with a pharmaceutically-acceptable acid, their addition salts with a pharmaceutically-acceptable base and their enantiomers.
10 more elements
A compound selected from the group consisting of:
- 4-[3-(3-adamantan-1-yl-4-ethoxymethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-ethoxymethoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2-methoxy-ethoxymethoxy)-phenyl]-[1,3,4]-oxadiazol-2-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-hydroxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-hydroxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2-methoxy-ethoxy)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-[5-(3-tert-butyl-4-hydroxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-methoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-isobutoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-propoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-ethoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-hydroxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-isobutoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2-methoxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2-dimethylamino-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-ethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-propoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-isobutoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2,2-dimethoxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-ethoxymethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{5-[4-(2-methoxy-ethoxymethoxy)-3-(1-methyl-cyclohexyl)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-ethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-5-(3-adamantan-1-yl-4-cyclopropylmethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2,2,2-trifluoro-ethoxy)-phenyl]-[1,3,4]-oxadiazol-2-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-propoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-hydroxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[4-ethoxymethoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-hydroxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2-methoxy-ethoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2-dimethylamino-ethoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-ethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-propoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-isobutoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2,2,2-trifluoro-ethoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-cyclopropylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[3-tert-Butyl-4-(2,2-dimethoxy-ethoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-[1,3]dioxolan-2-ylmethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl)-benzoic acid;
- 4-{5-[4-hydroxy-3-(1-methyl-cyclohexyl)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{5-[4-isobutoxy-3-(1-methyl-cyclohexyl)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{5-[4-methoxy-3-(1-methyl-cyclohexyl)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{5-[3-(1-methyl-cyclohexyl)-4-propoxy-phenyl]-thiazol-2-yl}-benzoic acid,
- 4-{5-[4-cyclopropylmethoxy-3-(1-methyl-cyclohexyl)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{5-[4-ethylcarbamoylmethoxy-3-(1-methyl-cyclohexyl)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-trimethylsilanylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2,2-dimethoxy-ethoxy)-phenyl]-[1,3,4]-oxadiazol-2-yl}-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2-methoxy-ethoxymethoxy)-phenyl]-4H-pyrazol-3-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-propylamino-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-methoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-ethoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-propoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-{5-[3-tert-butyl-4-(2,2,2-trifluoro-ethoxy)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-[5-(3-tert-butyl-4-cyclopropylmethoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-{5-[3-tert-butyl-4-(2-methoxy-ethoxy)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{5-[3-tert-butyl-4-(2,2-dimethoxy-ethoxy)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{5-[3-(1-methyl-cyclohexyl)-4-(2,2,2-trifluoro-ethoxy)-phenyl]-thiazol-2-yl}-benzoic acid;
- 4-{3-[4-methoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-(1-methyl-cyclohexyl)-4-propoxy-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-isobutoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-cyclopropylmethoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-(2,2-dimethoxy-ethoxy)-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-hydroxy-phenyl)-4H-pyrazol-3-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-cyclopropylmethoxy-phenyl)-isoxazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-propoxy-phenyl)-isoxazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-isobutoxy-phenyl)-isoxazol-5-yl]-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2,2-dimethoxy-ethoxy)-phenyl]-isoxazol-5-yl}-benzoic acid,
- 4-[5-(3-tert-butyl-4-ethylcarbamoylmethoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-isobutoxy-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-ethoxy-phenyl)-isoxazol-5-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-([1,3]dioxolan-2-ylmethoxy)-phenyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid;
- 4-{3-[3-(1-methylcyclohexyl)-4-(2,2,2-trifluoroethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-([1,3]dioxolan-2-ylmethoxy)-3-(1-methylcyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-propylamino-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2-hydroxy-ethoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(3-hydroxy-propoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-[5-(3-tert-butyl-4-propoxy-phenyl)-1-methyl-1H-imidazol-2-yl]-benzoic acid;
- 4-[5-(4-allyloxy-3-tert-butyl-phenyl)-[1,3,4]thiadiazol-2-yl]-benzoic acid;
- 4-{4-[3-(1-methyl-cyclohexyl)-4-(pyridin-4-ylmethoxy)-phenyl]-oxazol-2-yl}-benzoic acid;
- 4-[5-(4-ethoxy-3-pyrrolidin-1-yl-phenyl)-4H-[1,2,4]triazol-3-yl]-benzoic acid;
- 4-{5-[3-diethylamino-4-(4-fluoro-benzyloxy)-phenyl]-[1,3,4]-thiadiazol-2-yl}-benzoic acid;
- 4-[5-(3-tert-butyl-4-isobutoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-benzoic acid;
- methyl 4-[3-(3-tert-butyl-4-hydroxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoate;
- 4-[5-(4-butoxy-3-tert-butyl-phenyl)-1-methyl-1H-pyrrol-2-yl]-benzoic acid;
- 4-{5-[4-(2-amino-ethoxy)-3-tert-butyl-phenyl]-thiophen-2-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-((E)-propenyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-propyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-ethylsulfanyl-phenyl)-thiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-cyclopropylmethylsulfanyl-phenyl)-oxazol-2-yl]-benzoic acid;
- 4-[3-(4-cyclopropylmethoxy-3-pyrrolidin-1-yl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(4-hydroxy-3-pyrrolidin-1-yl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[4-(2-hydroxy-ethoxy)-3-pyrrolidin-1-yl-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 3-[5-(3-adamantan-1-yl-4-hydroxy-phenyl)-2-ethyl-2H-pyrazol-3-yl]-benzoic acid;
- 4-{3-[4-diethylamino-3-(3-hydroxy-propoxy)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-[3-(4-diethylamino-3-propoxy-phenyl)-isoxazol-5-yl]-benzoic acid;
- 4-[3-(4-tert-butyl-3-ethylamino-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-(2-[3-(1-methyl-cyclohexyl)-4-(pyridin-4-ylmethoxy)-phenyl]-oxazol-4-yl}-benzoic acid;
- 4-[2-(3-tert-butyl-4-cyclopropylmethylsulfanyl-phenyl)-oxazol-5-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-hydroxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-ethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(4-hydroxy-3-pyrrolidin-1-yl-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- methyl 4-[5-(4-hydroxy-3-pyrrolidin-1-yl-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoate;
- and
- methyl 4-[3-(4-tert-butyl-3-ethylamino-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoate or pharmaceutically acceptable salts thereof.
103 more elements
A compound of formula (I)
- wherein:
- A represents:
- R1 represents a linear or branched alkyl radical, a substituted alkyl radical, a cycloalkyl radical, a substituted cycloalkyl radical, an adamantyl radical, or an NR4R5 radical;
- R2 is a hydrogen atom, a linear or branched alkyl radical, a substituted alkyl radical, a fluorinated alkyl radical, an alkenyl radical, a substituted alkenyl radical, an alkynyl radical, a substituted alkynyl radical, a cycloalkyl-alkyl radical, a polyether radical, a mono or polyhydroxyalkyl radical, an aminoalkyl radical, an aralkyl radical, a substituted aralkyl radical, a heteroaralkyl radical, or a substituted heteroaralkyl radical;
- R3 is a hydrogen or a linear or branched alkyl radical;
- R4 and R5, identical or different, represent a hydrogen atom, a linear or branched alkyl radical, a substituted alkyl radical, an acyl radical;
- R4 and R5 taken together can also be linked and form an optionally substituted azetidine, pyrrolidine or piperidine heterocycle with the nitrogen atom with which they are linked;
- W represents O, S, or NH;
- X, Y, Z, identical or different represent O or N;
- the central heterocycle
- corresponds to one of the structures presented below, the dashed bonds may be a single or double bond depending on the nature of atoms X, Y and Z and their covalence
- as well as their addition salts with a pharmaceutically acceptable acid, their addition salts with a pharmaceutically acceptable base and their enantiomers.
9 more elements
A compound selected from the group consisting of:
- 4-[3-(3-adamantan-1-yl-4-ethoxymethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2-methoxy-ethoxymethoxy)-phenyl]-[1,3,4]-oxadiazol-2-yl}-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-hydroxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-hydroxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-isobutoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2-methoxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2-dimethylamino-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-ethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-propoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-isobutoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[3-adamantan-1-yl-4-(2,2-dimethoxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-ethoxymethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-ethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-cyclopropylmethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2,2,2-trifluoro-ethoxy)-phenyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid;
- 4-[5-(3-adamantan-1-yl-4-propoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-hydroxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[4-ethoxymethoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-hydroxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2-methoxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2-dimethylamino-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-ethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-propoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(3-tert-butyl-4-isobutoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2,2,2-trifluoro-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-cyclopropylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2,2-dimethoxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-([1,3]dioxolan-2-ylmethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-adamantan-1-yl-4-trimethylsilanylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-(2,2-dimethoxy-ethoxy)-phenyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid;
- 4-{3-[4-methoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-(1-methyl-cyclohexyl)-4-propoxy-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-isobutoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-cyclopropylmethoxy-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]-oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-(2,2-dimethoxy-ethoxy)-3-(1-methyl-cyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{5-[3-adamantan-1-yl-4-([1,3]dioxolan-2-ylmethoxy)-phenyl]-[1,3,4]oxadiazol-2-yl}benzoique;
- 4-{3-[3-(1-methyl-cyclohexyl)-4-(2,2,2-trifluoro-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-([1,3]dioxolan-2-ylmethoxy)-3-(1-methylcyclohexyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(2-hydroxy-ethoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[3-tert-butyl-4-(3-hydroxy-propoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- methyl 4-[3-(3-tert-butyl-4-hydroxy-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoate;
- 4-{3-[3-tert-butyl-4-((E)-propenyl)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(3-tert-butyl-4-propyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(4-cyclopropylmethoxy-3-pyrrolidin-1-yl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[3-(4-hydroxy-3-pyrrolidin-1-yl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-{3-[4-(2-hydroxy-ethoxy)-3-pyrrolidin-1-yl-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-{3-[4-diethylamino-3-(3-hydroxy-propoxy)-phenyl]-[1,2,4]oxadiazol-5-yl}-benzoic acid;
- 4-[3-(4-tert-butyl-3-ethylamino-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-hydroxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(3-tert-butyl-4-ethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid;
- 4-[5-(4-hydroxy-3-pyrrolidin-1-yl-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoic;
- methyl 4-[5-(4-hydroxy-3-pyrrolidin-1-yl-phenyl)-[1,3,4]oxadiazol-2-yl]-benzoate;
- and
- methyl 4-[3-(4-tert-butyl-3-ethylamino-phenyl)-[1,2,4]oxadiazol-5-yl]-benzoate or pharmaceutically acceptable salts thereof.
54 more elements
Dependencies are inferred from the claim text.