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US 9,796,668 B2Granted
Natural product analogs including an anti-inflammatory cyanoenone pharmacore and methods of use
AssigneeReata Pharmaceuticals, Inc.
InventorsEric Anderson, Gary L. Bolton, Deborah A. Ferguson, Xin Jiang, Robert M. Kral, Jr., Patrick M. O'Brien, Melean Visnick
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Abstract
This invention provides novel compounds comprising the following anti-inflammatory pharmacore: wherein X, R1 and R2 are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.
Claims7
A compound of the formula:
- wherein:
- R1 and R2 are each independently:
- hydrogen;
- or
- alkyl(C≦12), alkenyl(C≦12), alkynyl(C≦12), aryl(C≦12), aralkyl(C≦12), heteroaryl(C≦12), heteroaralkyl(C≦12), acyl(C≦12), alkoxy(C≦12), aryloxy(C≦12), aralkoxy(C≦12), heteroaryloxy(C≦12), heteroaralkoxy(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), arylamino(C≦12), aralkylamino(C≦12), hetero-arylamino(C≦12), heteroaralkylamino(C≦12), amido(C≦12), or a substituted version of any of these groups;
- or
- R1 and R2 are taken together and are alkanediyl(C≦12), alkenediyl(C≦12), alkanediyl(C≦12) or alkenediyl(C≦12);
- and
- R5 and R6 are each independently:
- hydrogen, hydroxy, halo, amino, hydroxyamino, nitro, cyano, azido, or mercapto;
- or
- alkyl(C≦12), alkenyl(C≦12), alkynyl(C≦12), aryl(C≦12), aralkyl(C≦12), heteroaryl(C≦12), heteroaralkyl(C≦12), acyl(C≦12), alkoxy(C≦12), alkenyloxy(C≦12), alkynyl-oxy(C≦12), aryloxy(C≦12), aralkoxy(C≦12), heteroaryloxy(C≦12), hetero-aralkoxy(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), alkoxy-amino(C≦12), alkenylamino(C≦12), alkynylamino(C≦12), arylamino(C≦12), aralkylamino(C≦12), heteroarylamino(C≦12), heteroaralkylamino(C≦12), amido(C≦12), alkylsilyl(C≦12), alkylsilyloxy(C≦12), or a substituted version of any of these groups;
- or pharmaceutically acceptable salts, esters, tautomers, acetals, ketals, or optical isomers thereof.
10 more elements
A compound of the formula:
- or pharmaceutically acceptable salts, tautomers, or optical isomers thereof.
A compound having the name:
- (S,E)-3-(4-hydroxystyryl)-3,5,5-trimethyl-6-oxocyclohex-1-enecarbonitrile.
A compound selected from the group consisting of:
- (S,E)-3-(4-hydroxystyryl)-3-methyl-6-oxocyclohex-1-enecarbonitrile, and
- (3S)-3-(4-hydroxystyryl)-3,5-dimethyl-6-oxocyclohex-1-enecarbonitrile.
Dependencies are inferred from the claim text.