# US 10,370,328 B2 · Oxindole compounds and pharmaceutical compositions thereof

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- Number: US 10,370,328 B2
- Document ID: US10370328B2
- Status: Granted
- Kind: B2
- Application number: 15/565,820
- Filed: 2016-04-28
- Published: 2018-05-17
- Granted: 2019-08-06
- Earliest claimed: 2015-04-30
- Assignees: MUSC Foundation for Research Development
- Applicants: Musc Foundation for Research Development; U.S. Department of Veterans Affairs
- Inventors: Craig C. Beeson; Christopher C. Lindsey; Baerbel Rohrer; Yuri Karl Peterson
- Web page: https://patentgrep.com/patent/US10370328B2

## CPC

- C07D 209/38: in positions 2 and 3, e.g. isatin
- A61P 27/02: Ophthalmic agents
- C07D 209/34: in position 2
- C07D 209/36: in position 3, e.g. adrenochrome
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 403/14: containing three or more hetero rings
- C07D 405/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 498/04: Ortho-condensed systems
- C07F 9/5728: {condensed with carbocyclic rings or carbocyclic ring systems}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

A pharmaceutical composition, comprising a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.