GB1140833A - Lincomycin derivatives - Google Patents

Abstract

1,140,833. Halo-lincomycins derivatives. UPJOHN CO. 7 Feb., 1966 [20 Oct., 1965], No. 5298/66. Heading C2C. The invention comprises (a) a process for preparing a compound of formula wherein Halo is chlorine or bromine, R is a C 1-20 alkyl, C 3-8 cycloalkyl, C 4-8 cycloalkylalkyl or C 7-12 aralkyl group and Ac is hydrogen or the acyl radical of an acid of one of the formulµ wherein R 1 and R 2 are C 1-20 alkylidene, C 3-8 cycloalkylidene, C 4-8 cycloalkyl-alkylidene or C 7-12 aralkylidene groups, R 3 is hydrogen or a group HR 2 and Z is a protective hydrocarbonyloxy-or substituted hydrocarbonyloxy-group removable by hydrogenolysis or a trityl, diphenyl (p-methoxyphenyl) methyl, bis-(p-methoxyphenyl) phenyl-methyl, benzyl or p-nitrobenzyl group, by reaction of a corresponding hydroxy compound with a Rydon reagent of one of the formulµ obtained by the addition of a halogen to triphenyl phosphine or triphenyl phosphite or of an alkyl halide to triphenyl phosphite, the reaction being optionally preceded or followed by interconversion of the group AcNH; and (b) the products obtained when Halo is bromine. The products may be obtained as acid addition salts. The close analogues of lincomycin have antibiotic activity, and various other of the products have buffering or antacid properties, react with isocyanates to form urethanes or modify polyurethane resins, or have surface active properties. The thiocyanic acid addition salt when condensed with formaldehyde forms a pickling inhibitor, the fluosilicic acid addition salt has moth-proofing properties and the hexafluoroarsenic acid and hexafluorophosphoric acid addition salts have parasitic activity.