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US 6,387,945 B2Granted
Lipoic acid analogs
AssigneeThe Regents of the University of California
InventorsLester Packer, Oren Tirosh, Chandan K. Sen, Sashwati Roy
Life of this patent
Estimating the term…
Abstract
A compound is provided having the formula I: wherein the variables are defined in the specification. Methods of making the compounds, compositions including the compounds and methods of treatment of conditions involving reactive oxygen species are also provided.
Claims16
A compound having the formula I:
- wherein
- R1 and R2 independently denote a methylene, ethylene or unbranched or branched C3-16 alkylene, alkenylene or alkynylene group which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, wherein in said unbranched or branched C3-16 alkylene, alkenylene or alkynylene group an internal alkylene carbon atom in the carbon backbone thereof can be replaced by an oxygen atom,
- R3 and R4
- (i) independently denote
- (a) hydrogen,
- (b) a methyl, ethyl, vinyl or unbranched or branched C3-16 alkyl, alkenyl or alkynyl group which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, wherein in said unbranched or branched C3-16 alkyl, alkenyl or alkynyl group an internal alkylene carbon atom in the carbon backbone thereof can be replaced by an oxygen atom,
- (c) a cycloalkyl, alkylcycloalkyl, alkenylcycloalkyl or alkynylcycloalkyl group having 5 to 16 carbon atoms which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, or
- (d) an aryl, alkaryl, aralkyl, alkenylaryl, aralkenyl, alkynylaryl or aralkynyl group having 6 to 16 carbon atoms which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, or
- (ii) jointly with the nitrogen atom form a cyclic or aromatic amine which is unsubstituted or substituted with one or more alkyl, alkenyl, alkynyl, halogen, hydroxyl or amine groups,
- X denotes O, S, —NH— or —NR5—, and
- R5 denotes methyl, ethyl, or unbranched or branched C3-16 alkyl,
- or a pharmaceutically acceptable salt thereof.
9 more elements
A method of making a compound having the formula I
- wherein
- R1 and R2 independently denote a methylene, ethylene or unbranched or branched C3-16 alkylene, alkenylene or alkynylene group which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, wherein in said unbranched or branched C3-16 alkylene, alkenylene or alkynylene group an internal alkylene carbon atom in the carbon backbone thereof can be replaced by an oxygen atom,
- R3 and R4
- (i) independently denote
- (a) hydrogen,
- (b) a methyl, ethyl, vinyl or unbranched or branched C3-16 alkyl, alkenyl or alkynyl group which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, wherein in said unbranched or branched C3-16 alkyl, alkenyl or alkynyl group an internal alkylene carbon atom in the carbon backbone thereof can be replaced by an oxygen atom,
- (c) a cycloalkyl, alkylcycloalkyl, alkenylcycloalkyl or alkynylcycloalkyl group having 5 to 16 carbon atoms which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, or
- (d) an aryl, alkaryl, aralkyl, alkenylaryl, aralkenyl, alkynylaryl or aralkynyl group having 6 to 16 carbon atoms which is unsubstituted or substituted with one or more halogen, hydroxyl or amine groups, or
- (ii) jointly with the nitrogen atom form a cyclic or aromatic amine which is unsubstituted or substituted with one or more alkyl, alkenyl, alkynyl, halogen, hydroxyl or amine groups,
- X denotes O, S, —NH— or —NR5—, and
- R5 denotes methyl, ethyl, or unbranched or branched C3-16 alkyl,
- said method including the step of reacting a compound having the formula IV
- with a compound having the formula V
- R6—R2—NR3R4 V
- wherein
- R6 denotes OH, SH, NH2 or NHR5.
13 more elements
Dependencies are inferred from the claim text.