GB1140663A - Lincomycin derivatives - Google Patents

Abstract

1,140,663. Halo-lincomycin derivatives. UPJOHN CO. 7 Feb., 1966 [8 Feb., 1965; 1 Dec., 1965], No. 5299/66. Heading C2C. The invention comprises compounds of formula wherein R is a C 1-20 alkyl, C 3-8 cycloalkyl, C 4-8 cycloalkyl-alkyl, 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 an optionally substituted hydrocarbonyloxycarbonyl group or a trityl, diphenyl (p-methoxyphenyl) methyl, bis-(p-methoxyphenyl) phenyl-methyl, benzyl or p-nitrobenzyl group, and their preparation by reaction of the corresponding hydroxy compounds with thionyl chloride followed by heating, with if desired previous or subsequent interconversion of the group AcNH-. Inversion occurs in the reaction with thionyl chloride. Acid addition salts are also disclosed. The compounds of the invention closely analogous to lincomycin have antibiotic properties, and various products have buffer or antacid properties, react with isocyanates to form or modify polyurethanes or have surface active properties. The thiocyanic acid addition salts when condensed with formaldehyde form pickling inhibitors, the fluosilicic acid addition salt has mothproofing activity and the hexafluoroarsenic acid and hexafluorophosphoric acid addition salts have parasitic activity.