GB942452A - Unsaturated fatty acids and salts thereof and a process for their preparation - Google Patents

Abstract

The invention comprises compounds of the general formula: CH3(CH2)x-CH2-C­C-(CH2)7-COOR (wherein x is 1, 3, 5 or 7 and R represents hydrogen or one equivalent of another physiologically harmless cation, e.g. a physiologically harmless metal such as an alkali metal, calcium, magnesium or aluminium, ammonium or the cation of an organic base, e.g. an ethanolamine, ethylene-diamine, procaine, piperidine, pyrrolidine, morpholine, streptomycin, dihydrostreptomycin or isonicotinic acid hydrazide), and the preparation thereof by (a) condensing a compound of the general formula: CH3-(CH2)x1-C­C-R1 (wherein x1 is 2, 4, 6 or 8 and R1 represents a metal or a Grignard reagent residue) with a compound of the general formula: Hal-(CH2)7-R2 (wherein Hal represents a halogen atom and R2 represents -COOR or a radical convertible thereto), or (b) reacting a compound of the general formula: R1-C­-C(CH2)7-R2 with a compound of the general formula: Hal-CH2-(CH2)x-CH3, or (c) eliminating a substituent capable of elimination from the heptamethylene chain of a compound of the general formula: CH3(CH2)x-CH2-C­C-(CH2) 7-R2 (if necessary after protection of the triple bond), and in all cases, if necessary, converting R2 to -COOR, and, if desired, converting a resulting acid into a salt with a physiologically harmless base or a resulting salt into the free acid. Pharmaceutical preparations.-The foregoing compounds have inflammation- and edemainhibiting activity, for which purpose they may be injected, e.g. intravenously or intraninsularly, in the form of physiological isotonic solutions of the appropriate salts, or suspensions of sparingly soluble salts or of the free acids. 1-Chlorohexadecyne-(8) is prepared by reacting nonyne- (1) with 1-chloro-7-iodoheptane in the presence of sodamide or lithium amide, or by reacting 9-chlorononyne-(1) with heptyl iodide in the presence of lithium amide. Analogous compounds are obtained by replacing nonyne-(1) by pentyne-(1), heptyne-(1) or undecyne-(1) in the first process. 9-Chlorononyne-(1) is prepared by reacting 1-chloro-7-iodoheptane with sodium acetylide. Organometallic compounds of the second general formula above are prepared by reacting pentyne-(1), heptyne-(1), nonyne-(1) or undecyne-(1), or their mercury compounds, in a boiling inert solvent, with the salt-forming metal or metal compound added in finely divided form, e.g. finely divided lithium, magnesium, lithium amide, sodium oxide, ethyl magnesium bromide or phenyl lithium.