Patent GB-1070816-A (GB)
Title: Amides of unsaturated fatty acids and process for their production
IPC: C07D213/80
Filed: 1965-07-30
Abstract: Novel compounds of formula <FORM:1070816/C2/1> wherein R1CO- represents the acyl radical of a fatty acid having 18-20 carbon atoms and containing 2-4 non-cumulated C-C double bonds, R2 is halogen, C1-C4 alkyl, an alkoxy, alkenyloxy, alkylthio, or alkenylthio radical having up to 6 carbon atoms, C1-C5 hydroxyalkyl, alkanoyloxyalkyl having at most 4 carbon atoms, oxoalkyl having at most 10 carbon atoms, hydroxy, mercapto, sulpho, sulphamoyl, nitro, cyano, or amino, or a mono-or di-alkylamino group having at most 4 carbon atoms, an alkanoylamino group having at most carbon atoms, a mono- or di-chloroanilino group, an alkoxycarbonyl group having at most 3 carbon atoms, a carbamoyl group, or a mono-or di-alkyl carbamoyl group of at most 5 carbon atoms, R3 is hydrogen, halogen or a C1-C4 alkyl radical, and R4 is hydrogen or a C1-C4 alkyl radical, and urea adducts thereof, and the acid addition salts of those compounds containing an amino, alkylamino or dialkylamino substituent, are prepared by reacting an acid of formula R1COOH, or a reactive functional derivative thereof, with an amine of formula III <FORM:1070816/C2/2> or with an isocyanate, isothiocyanate, N-chrlorocarbonyl derivative, or sulphurous acid mono-alkyl ester-amide, phosphoric acid-o-phenylene diester amide, or an N-trimethylsilyl or N,N1 - dipyridyl - carbodiimide derivative thereof, or by reacting the saturated bromine addition product of the acid or a reactive functional derivative thereof with an amine of Formula III or a derivative thereof as defined above, and debrominating the product, and, in either case, if desired, converting the product into a urea adduct.  Compounds of Formula I or the corresponding polybromine fatty acids amides containing a nitro substituent may be reduced to the corresponding amino compounds. Similarly, an oxoalkyl radical may be reduced to a hydroxyalkyl radical, or a hydroxyalkyl or amino group can be acylated to the corresponding alkanoyloxyalkyl or alkanoylamino group.  Linoleic acid p-nitrophenyl ester is prepared by reacting linoleic acid and p-nitrophenol in the presence of N,N1-dicyclohexylcarbodiimide. Octadeca - 7,9 - dienoyl chloride is produced by bromination of oleic acid, dehydrobromination of the addition product and conversion into the acid chloride using oxalyl chloride.  Therapeutic compositions having anti-viral and tumour-inhibiting activity, which may be administered orally, rectally, topically or parenterally, contain as active ingredient a novel compound as described above. ALSO:N-trimethyl silyl derivatives of amides of Formula I <FORM:1070816/C3/1> wherein R1-CO- represents the acyl radical of a fatty acid having 18-20 carbon atoms and 2-4 non-cumulated C-C double bonds, R2 is halogen, C1-C4 alkyl, an alkoxy, alkenyloxy, alkylthio or alkenylthio radical having up to 6 carbon atoms, C1-C5 hydroxyalkyl, alkanoyloxyalkyl of at most 4 carbon atoms, oxoalkyl of at most 10 carbon atoms, hydroxyl, mercapto, sulpho, sulphamoyl, nitro, cyano, amino, or a mono- or di-alkylamino group having at most 4 carbon atoms, an alkanoylamino group of at most 2 carbon atoms, mono- or di-chloroaniline, an alkoxycarbonyl group having at most 3 carbon atoms, carbamoyl, or mono- or di-alkyl carbamoyl having at most 5 carbon atoms, R3 is hydrogen, halogen, or C1-C4 alkyl, and R4 is hydrogen or C1-C4 alkyl, may be prepared by reacting amines of Formula III <FORM:1070816/C3/2> with trimethylsilyl chloride in an inert, anhydrous organic solvent, and reacting the N-trimethylsilyl derivatives with an acid R1COOH or a reactive functional derivative thereof, in an inert organic solvent.