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US 10,370,328 B2Granted
Oxindole compounds and pharmaceutical compositions thereof
AssigneeMUSC Foundation for Research Development
InventorsCraig C. Beeson, Christopher C. Lindsey, Baerbel Rohrer, Yuri Karl Peterson
Life of this patent
Estimating the term…
Abstract
Provided herein are compounds of the formula (I) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of degenerative diseases and disorders.
Claims2
A compound, or a pharmaceutically acceptable salt thereof, wherein said compound is:
- 3-hydroxy-5-methyl-1-(2,2,2-trifluoroethyl)-3-(3,4,5-trimethoxybenzyl)indolin-2-one;
- 2-((3-hydroxy-5-methyl-1-(4-methylpentyl)-2-oxoindolin-3-yl)methyl)-5-methoxyphenyl isonicotinate;
- 2-((3-hydroxy-5-methyl-1-(4-methylpentyl)-2-oxoindolin-3-yl)methyl)-5-methoxyphenyl acetate;
- 2-((3-hydroxy-5-methyl-1-(4-methylpentyl)-2-oxoindolin-3-yl)methyl)-5-methoxyphenyl 2-methoxyacetate;
- 5-chloro-1-ethyl-3-(2-hydroxy-3-methoxybenzyl)-2-oxoindolin-3-yl isonicotinate;
- 5-chloro-1-ethyl-3-(2-hydroxy-3-methoxybenzyl)-2-oxoindolin-3-yl picolinate;
- 5-chloro-1-ethyl-3-(2-hydroxy-3-methoxybenzyl)-2-oxoindolin-3-yl diethyl phosphate;
- 2-((5-chloro-1-ethyl-3-hydroxy-2-oxoindolin-3-yl)methyl)-6-methoxyphenyl 2-methoxyacetate;
- 2-((5-chloro-1-ethyl-3-hydroxy-2-oxoindolin-3-yl)methyl)-6-methoxyphenyl butyrate;
- 5-chloro-1-ethyl-3-(2-hydroxy-3-methoxybenzyl)-2-oxoindolin-3-yl dimethylcarbamate;
- (1,3-dioxolan-4-yl)methyl (5-chloro-1-ethyl-3-(2-hydroxy-3-methoxybenzyl)-2-oxoindolin-3-yl) carbonate;
- 5-chloro-1-ethyl-3-(2-(((2-(2-hydroxyethoxy)ethyl)carbamoyl)oxy)-3-methoxybenzyl)-2-oxoindolin-3-yl benzoate;
- 2-((5-chloro-1-ethyl-2-oxoindolin-3-yl)methyl)-6-methoxyphenyl dimethylcarbamate;
- 3-hydroxy-1,5-dimethyl-3-((1-methyl-1H-indazol-4-yl)methyl)indolin-2-one;
- 1-butyl-3-((1-methyl-1H-indazol-4-yl)methyl)-2-oxoindolin-3-yl benzoate;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-5-chloro-2-oxo-1-propylindolin-3-yl benzoate;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-1-ethyl-3-hydroxy-5-methylindolin-2-one;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-1-butyl-3-hydroxyindolin-2-one;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-3-hydroxy-1-isobutylindolin-2-one;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-1-isopentyl-2-oxoindolin-3-yl benzoate;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-1-isobutyl-5-methyl-2-oxoindolin-3-yl benzoate;
- 3-(benzo[d][1,3]dioxol-4-ylmethyl)-1-isopentyl-5-methyl-2-oxoindolin-3-yl benzoate;
- 3-((1H-benzo[d]imidazol-4-yl)methyl)-5-chloro-1-ethyl-3-hydroxyindolin-2-one,
- 1-ethyl-3-(2-hydroxy-3,4-dimethoxybenzyl)-5-methyl-2-oxoindolin-3-yl dimethylcarbamate;
- 3-((1-benzoyl-1H-indol-3-yl)methyl)-2-oxo-1-propylindolin-3-yl dimethylcarbamate;
- 3-((1H-benzo[d]imidazol-4-yl)methyl)-5-chloro-1-methyl-2-oxoindolin-3-yl dimethylcarbamate;
- 5-chloro-1-ethyl-3-(pyrimidin-4-ylmethyl)indolin-2-one;
- 5-methyl-1-ethyl-3-(pyrimidin-4-ylmethylene)indolin-2-one;
- 5-chloro-1-ethyl-3-hydroxy-3-(pyrazin-2-ylmethyl)indolin-2-one;
- 1-ethyl-5-methyl-3-(pyrazin-2-ylmethylene)indolin-2-one;
- 1-propyl-3-(pyridazin-3-ylmethyl)indolin-2-one;
- N-(5-chloro-2-oxo-1-propyl-3-(pyridazin-3-ylmethyl)indolin-3-yl)nicotinamide;
- 3-((1H-benzo[d]imidazol-2-yl)methylene)-5-chloro-1-ethylindolin-2-one;
- 5-chloro-3-hydroxy-1-propyl-3-(pyrazin-2-ylmethyl)indolin-2-one;
- 5-chloro-3-hydroxy-1-methyl-3-(pyridin-4-ylmethyl)indolin-2-one;
- 5-chloro-3-hydroxy-1-propyl-3-(pyridazin-4-ylmethyl)indolin-2-one;
- 3-hydroxy-1-methyl-3-(pyridin-4-ylmethyl)indolin-2-one;
- (E)-3-((11H-benzo[d]imidazol-2-yl)methylene)-5-chloro-1-methylindolin-2-one;
- N-(3-((1H-benzo[d]imidazol-2-yl)methyl)-1-methyl-2-oxoindolin-3-yl)nicotinamide;
- 1-ethyl-3-hydroxy-3-(pyridazin-3-ylmethyl)indolin-2-one;
- 1-ethyl-5-methyl-3,3-bis(pyridazin-4-ylmethyl)indolin-2-one;
- 1-propyl-3,3-bis(pyridazin-4-ylmethyl)indolin-2-one;
- 1-ethyl-3-hydroxy-5-methyl-3-(pyridazin-3-ylmethyl)indolin-2-one;
- N-(3-((1H-benzo[d]imidazol-2-yl)methyl)-5-chloro-1-ethyl-2-oxoindolin-3-yl)isonicotinamide;
- 3-(benzo[d]oxazol-2-ylmethylene)-5-chloro-1-methylindolin-2-one;
- N-(3-((1H-benzo[d]imidazol-2-yl)methyl)-5-chloro-2-oxo-1-propylindolin-3-yl)benzamide;
- 1-methyl-3-(oxazolo[4,5-b]pyridin-2-ylmethylene)indolin-2-one;
- 5-chloro-2-oxo-1-(2-(piperidin-1-yl)ethyl)-3-(pyridin-2-ylmethyl)indolin-3-yl dimethylcarbamate;
- N-(3-((3-methoxypyridin-2-yl)methyl)-2-oxo-1-propylindolin-3-yl)benzamide;
- N-(5-chloro-1-ethyl-2-oxo-3-(pyridin-2-ylmethyl)indolin-3-yl)-4-methylbenzenesulfonamide;
- 3-(1-ethyl-5-methyl-3-((1-methyl-1H-indazol-4-yl)methyl)-2-oxoindolin-3-yl)-1,1-dimethylurea;
- 1,1-dimethyl-3-(3-((1-methyl-1H-indazol-4-yl)methyl)-2-oxo-1-propylindolin-3-yl)urea;
- 3-(3-(benzo[d][1,3]dioxol-4-ylmethyl)-2-oxo-1-propylindolin-3-yl)-1,1-dimethylurea;
- 3-(3-(benzo[d][1,3]dioxol-4-ylmethyl)-5-chloro-1-methyl-2-oxoindolin-3-yl)-1,1-dimethylurea;
- 3-(3-(benzo[d][1,3]dioxol-4-ylmethyl)-5-chloro-2-oxo-1-propylindolin-3-yl)-1,1-dimethylurea;
- 3-(1,5-dimethyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl)-1,1-dimethylurea;
- 3-(1-ethyl-2-oxo-3-(3,4,5-tri methoxybenzyl)indolin-3-yl)-1,1-dimethylurea;
- 3-(3-((1-benzoyl-1H-indol-3-yl)methyl)-1-ethyl-2-oxoindolin-3-yl)-1,1-dimethylurea;
- 3-(3-((1-benzoyl-1H-indol-3-yl)methyl)-1-methyl-2-oxoindolin-3-yl)-1,1-dimethylurea;
- 3-(3-((1-benzoyl-1H-indol-3-yl)methyl)-2-oxo-1-propylindolin-3-yl)-1,1-dimethylurea;
- 3-(3-((1-benzoyl-1H-indol-3-yl)methyl)-5-methyl-2-oxo-1-propylindolin-3-yl)-1,1-dimethylurea;
- or
- 2-((5-chloro-1-ethyl-3-hydroxy-2-oxoindolin-3-yl)methyl)-6-methoxyphenyl dimethylsulfamate.
60 more elements
Dependencies are inferred from the claim text.