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US 2006/0148860 A1Published application
Substituted p-phenyl carbamates
AssigneeNovo Nordisk A/S
InventorsPer Vedso, Soren Ebdrup, Poul Jacobsen
Life of this patent
Estimating the term…
Abstract
Novel substituted p-phenyl carbamates, pharmaceutical compositions comprising them and use thereof in the treatment and/or prevention of diseases and disorders related to hormone sensitive lipase. More particularly, the compounds are useful for the treatment and/or prevention of diseases and disorders in which modulation of the activity of hormone sensitive lipase is beneficial.
Claims60
A compound of formula (I):
- wherein
- R1 is selected from hydroxy, sulfanyl, sulfo, C1-6alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl and C3-10-cycloalkyl, wherein each of hydroxy, sulfanyl, sulfo, C1-6alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl and C3-10-cycloalkyl may optionally be substituted with one or more substituents independently selected from hydroxy, sulfanyl, oxo, halogen, amino, sulfo, C1-6alkyl, C1-6alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl, and C3-10-cycloalkyl, wherein each of hydroxy, sulfanyl, sulfo, C1-6-alkyl, C1-6alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl and C3-10-cycloalkyl may optionally be substituted with one or more substituents independently selected from hydroxy, sulfanyl, oxo, halogen, amino, sulfo, perhalomethyl, perhalomethoxy, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl, and C3-10-cycloalkyl;
- R2 is selected from hydrogen, hydroxy, sulfanyl, amino, halogen, sulfo, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl and C3-10-cycloalkyl, wherein each of hydroxy, sulfanyl, amino, sulfo, C1-6-alkyl, C1-6alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8m-heterocyclyl and C3-10-cycloalkyl may optionally be substituted with one or more substituents independently selected from hydroxy, sulfanyl, oxo, halogen, amino, sulfo, C1-6alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl, and C3-10-cycloalkyl, wherein each of hydroxy, sulfanyl, amino, sulfo, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl and C3-10-cycloalkyl may optionally be substituted with one or more substituents independently selected from hydroxy, sulfanyl, oxo, halogen, amino, sulfo, perhalomethyl, perhalomethoxy, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, aryl, heteroaryl, C3-8-heterocyclyl, and C3-10-cycloalkyl;
- with the proviso that said compound is not
- Methyl-phenyl-carbamic acid 4-(3-chloro-5-trifluoromethyl)-pyridine-2-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-cyano-ethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-pentyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-methoxy-ethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(4-chloro-phenyl)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(4-hydroxy-benzyl)-phenyl ester,{2-[4-(Methyl-phenyl-carbamoyloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester,
- Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(toluene-4-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(3,4-difluoro-benzenesulfonylamino)-ethyl]-phenyl ester,
- 2-{2-[4-(Methyl-phenyl-carbamoyloxy)-phenyl]-ethylsulfamoyl}-benzoic acid methyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(2,5-dichloro-thiophene-3-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(5-pyridin-2-yl-thiophene-2-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(1-methyl-1H-imidazole-4-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-ethyl]-phenyl,
- Methyl-phenyl-carbamic acid 4-[2-(4-nitro-benzenesulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(6-chloro-imidazo[2,1-b]thiazole-5-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(2-trifluoromethoxy-benzenesulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-dimethylaminomethanesulfonylamino-ethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-methanesulfonylamino-ethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(6-morpholin-4-yl-pyridine-3-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(6-phenoxy-pyridine-3-sulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-{2-[4-(4-methyl-piperazin-1-yl)-benzenesulfonylamino]-ethyl}-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(4-dimethylamino-benzenesulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-benzenesulfonylamino]-ethyl}-phenyl ester,
- Methyl-phenyl-carbamic acid 4-pyridin-2-ylmethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-pyridin-3-ylmethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(4-trifluoromethyl-benzyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-thiophen-3-ylmethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-thiophen-2-ylmethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(4-amino-benzenesulfonylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-{2-[(pyridine-3-carbonyl)-amino]-ethyl}-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(2-dimethylamino-acetylamino)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 2-(toluene4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl ester,
- Methyl-phenyl-carbamic acid 4-[4-(2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-{2-[(1-methyl-piperidine-4-carbonyl)-amino]-ethyl}-phenyl ester,
- 3,3-Dimethyl-4-{2-[4-(methyl-phenyl-carbamoyloxy)-phenyl]-ethylcarbamoyl}-butyric acid,
- Methyl-phenyl-carbamic acid 4-{2-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-ethyl}-phenyl ester,
- Methyl-phenyl-carbamic acid 4-{2-[4-(4-methyl-piperazin-1-ylmethyl)-benzoylamino]-ethyl}-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(4,4-dimethyl-2,6-dioxo-piperidin-1-yl)-ethyl]-phenyl ester,
- 3,3-Dimethyl-4-{2-[4-(methyl-phenyl-carbamoyloxy)-phenyl]-ethylcarbamoyl}-butyric acid ethyl ester,
- Methyl-phenyl-carbamic acid 4-hydroxymethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-hydroxy-ethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(4-dimethylamino-pyridin-2-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(4-imidazol-1-yl-phenoxymethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[4-(2-dimethylamino-ethyl)-phenoxymethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(pyrazol-1-yloxymethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(imidazol-1-yloxymethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-oxo-2H-pyridin-1-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(pyridin-2-yloxy)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(4-imidazol-1-yl-phenoxy)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-{2-[4-(2-dimethylamino-ethyl)-phenoxy]-ethyl}-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(pyrazol-1-yloxy)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(imidazol-1-yloxy)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(5-methyl-pyridin-2-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(4-oxo-4H-pyridin-1-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(pyridin-3-yloxy)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-oxo-2H-pyridin-1-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(pyridin-3-yloxymethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(1,3-dioxo-1,3-dihydro-pyrrolo[3,4-]pyridin-2-yl)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(1-methyl-1H-imidazol-2-ylsulfanylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-tetrazol-1-ylmethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2,5-dioxo-pyrrolidin-1-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(2-thioxo-2H-pyridin-1-yl)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(1,3-dioxo-1,3-dihydro-pyrrolo[3,4)pyrid in-2-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[1,2,4]triazol-1-ylmethyl-phenyl ester,
- Methyl-phenyl-carbamic acid 4-(2-thioxo-2H-pyridin-1-ylmethyl)-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(1-methyl-1H-imidazol-2-ylsulfanyl)-ethyl]-phenyl ester,ethyl-phenyl-carbamic acid 4-(2-tetrazol-1-yl-ethyl)-phenyl ester, Methyl-phenyl-carbamic acid 4-[2-(pyrimidin-2-yloxy)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(pyridin-4-ylsulfanyl)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(1-pyridin-3-yl-1H-imidazol-2-ylsulfanyl)-ethyl]-phenyl ester,
- Methyl-phenyl-carbamic acid 4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-phenyl ester, and
- Methyl-phenyl-carbamic acid 4-benzyl-phenyl ester;
- as well as diastereomers, enantiomers or tautomeric forms thereof, mixtures of these, pharmaceutically acceptable salts thereof, pharmaceutically acceptable solvates thereof, or polymorphs.
76 more elements
Dependencies are inferred from the claim text.