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US 4,443,619 AGranted
Chlorocitric acids
AssigneeHoffmann-La Roche Inc.
InventorsRobert W. Guthrie, Richard W. Kierstead, Francis A. Mennona, Ann C. Sullivan
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Abstract
The present invention relates to chlorocitric acids of the formula ##STR1## and stereoisomers, optical antipodes and pharmaceutically acceptable salts thereof, to methods of preparation thereof, including intermediates involved therein, and to their use as anorectic agents for the treatment of obesity in mammals.
Claims2
A process for the preparation of the mono-potassium dihydrogen salt of (.+-.)-threo-epoxyaconitic acid which comprises the steps of
- (a) contacting transaconitic acid of the formula ##STR38## with a sufficient amount of potassium hydroxide in water to neutralize said acid and thus to form the tri-potassium metal salt of transaconitic acid of the formula ##STR39## (b) contacting the reaction product of step (a) with an excess of chlorine gas so as to form a salt of (.+-.)-threo-chlorocitric acid, .beta.-lactone of the formula ##STR40## (c) reacting in situ the reaction product of step (b) with potassium hydroxide in an aqueous solvent at temperatures in the range of from about 0.degree. C. to about 40.degree. C. to form a potassium metal salt of (.+-.)-threo-epoxyaconitic acid of the formula ##STR41## (d) adjusting the pH to a value within the range of about 7.0 to about 7.5 and reacting the reaction product of step (c) with two molar equivalents of an acid to form the corresponding potassium metal dihydrogen salt of (.+-.)-threo-epoxyaconitic acid.
Dependencies are inferred from the claim text.