Pyruvate derivatives
View Patent ↗Certain known and novel pyruvate derivatives are particularly active in restoring or preserving metabolic integrity in oxidatively competent cells that have been subjected to oxygen deprivation. These pyruvate-derived compounds include, but are not limited to oximes, amides, pyruvate analogues, modified pyruvate analogues, esters of pyruvate (e.g., polyol-pyruvate esters, pyruvate thioesters, glycerol-pyruvate esters and dihydroxyacetone-pyruvate esters). Such pyruvate derivatives (including single tautomers, single stereoisomers and mixtures of tautomers and/or stereoisomers, and the pharmaceutically acceptable salts thereof) are useful in the manufacture of pharmaceutical compositions for treating a number of conditions characterized by oxidative stress.
1. The compound selected from:
3-(5-chloro-benzothiazol-2-ylsulfanyl)-2-hydroxyimino-propionic acid ethyl ester,
2-hydroxyimino-3-(5-methoxy-1H-benzoimidazol-2-ylsulfanyl)-propionic acid ethyl ester, and
3-(1H-benzoimidazol-2-ylsulfanyl)-2-hydroxyimino-propionic acid ethyl ester,
or a single tautomer, single stereoisomer, a mixture of tautomers and/or stereoisomers, or a pharmaceutically acceptable salt thereof.
2. A pharmaceutical formulation comprising a compound of claim 1 and a pharmaceutically acceptable excipient.
3. The compound selected from:
3-(1H-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid,
2-oxo-3-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanyl)-propionic acid ethyl ester,
3-(benzoselenazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester,
3-(1H-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester,
3-(5-chloro-benzothiazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester,
3-(5-methoxy-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester, and
3-(4,5-dihydro-thiazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester,
or a single tautomer, single stercoisomer, a mixture of tautomers and/or stereoisomers, or a pharmaceutically acceptable salt thereof.
4. A pharmaceutical formulation comprising a compound of claim 3 and a pharmaceutically acceptable excipient.