Patent GB-1194238-A (GB)
Title: Therapeutically Active Substituted Saturated and Mono- and Polyunsaturated Alkyl-Glycerylethers
IPC: A61P31/04
Filed: 1967-12-15
Abstract: 1,194,238. Alkyl-α-glyceryl ethers. ASTRA NUTRITION A.B. 15 Dec., 1967 [16 Dec., 1966], No. 57149/67. Heading C2C. The invention comprises compounds of the Formula (I) where R<SP>1</SP> and R<SP>2</SP> are the same or different and represent hydrogen or aliphatic acyl groups of at most 24 carbon atoms, one of R<SP>3</SP> and R<SP>4</SP> is hydrogen and the other is an alkoxy or alkenyloxy group of at most 7 carbon atoms and R<SP>5</SP> represents a straight or branched, saturated or mono- or poly-unsaturated aliphatic group of 4 to 21 carbon atoms. They are extracted from naturally occurring lipid products containing α-glyceryl ethers, such as liver oils from Greenland shark, dog-fish, rat-fish, by distributing the lipid product, preferably after prepurification by removal of hydrocarbons and saponifiable constituents, between two media forming separate phases comprising an operation consisting of a preferably repeated extraction using two partially miscible liquids or chromatography of the lipid product in a solvent on a solid adsorbent such as silicic acid or deactivated aluminium oxide or treating the lipid product in a solvent with a substance capable of forming inclusion compounds with some part of the glyceryl ether mixture or by fractional crystallization from a polar solvent. Compounds of Formula (I) may be prepared by reacting a compound of the formula with a compound of the formula   wherein R<SP>3#1</SP>, R<SP>4#1</SP> and R<SP>5#1</SP> represent R<SP>3</SP>, R<SP>4</SP> or R<SP>5</SP> respectively or an atom or group capable of being transformed into R<SP>3</SP>, R<SP>4</SP> or R<SP>5</SP> respectively by methods known in the literature, R<SP>7</SP> represents an oxygen atom, a carbon-carbon bond or the group where R<SP>a</SP> represents hydrogen or alkyl, R<SP>b</SP> represents alkyl or aryl and R<SP>a</SP> and R<SP>b</SP> together may form a ring which may contain a hetero atom and X and Y are a pair representing the pairs of groups (a) hal, and -OM, (b) arylsulphonyl and -OM, (c) alkylsulphonyl and -OM, and (d) hydroxy and hydroxy, where that means halogen, preferably chlorine or bromine, and M is a positively charged atom or group, preferably K, Na or Li, to form a compound of the formula   whereafter if any of R<SP>3#1</SP> , R<SP>4#1</SP> and R<SP>5#1</SP> differ from R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> respectively, the differing groups are transformed into the predetermined group and whereafter the group is transformed to the group CH 2 OR<SP>1</SP>, CHOR<SP>2</SP>- by methods known in the literature. 2-Methoxy (or 2-ethoxy) hexadecyl p-toluenesulphonate is prepared by reacting p-toluenesulphonyl chloride with 2-methoxy (or 2- ethoxy) hexadecanol. 2 - Methoxy - hexadecanol - 1 is prepared by reducing with lithium aluminium hydride methyl 2-methoxy-hexadecanoate which is prepared by methylating 2-hydroxyhexadecanoic acid. 2 - Hydroxy - hexadecanoic acid is prepared by hydrolysing 2-bromohexadecanoic acid. 2 - Ethoxy - hexadecanol - 1 is prepared by reducing ethyl - 2 - ethoxy - hexadecanoate which is prepared from ethyl 2-bromohexadecanoate and sodium ethoxide. Pharmaceutical compositions comprising as active ingredient a compound of Formula (I) together with a pharmaceutically acceptable carrier are administered orally or parenterally and have anti-biotic and anti-carcinogenic activity.