GB1205083A - Improvements in or relating to lineomycin derivatives and the manufacture thereof - Google Patents

Abstract

1,205,083. Lincomycin derivatives. UPJOHN CO. 17 April, 1968 [10 May, 1967], No. 18148/68. Heading C2C. Novel compounds of the Formula (I) are prepared by condensing compounds of the Formula (II) with appropriate aldehydes to give compounds of the Formula (III), acylating these to give compounds of the Formula (IV) and removing the acetal and, when necessary, the N-protecting groups. R 2 CO is an optionally substituted hydrocarbon carboxylic acyl radical of up to 18 carbon atoms or an alkoxycarbonyl group; X is Cl or Br; R and HR 1 are each C 1-20 alkyl, C 3-8 cycloalkyl or C 7-12 aralkyl; R 3 is H, C 1-20 alkyl, C 3-8 cycloalkyl or optionally substituted C 7-12 aralkyl; and Q is a protecting group, such as one removable by hydrogenolysis, e.g. hydrocarbonoxycarbonyl, benzyl or nitrobenzyl, or is R 3 other than H. Also claimed as novel are (IV), where Q is R 3 other than H or is hydrocarbonoxycarbonyl, (III) where Q is hydrocarbonoxycarbonyl, benzyl or nitrobenzyl and (I) where R 3 is additionally hydrocarbonoxycarbonyl. The lincomycin derivatives (I) have essentially the same antibacterial activity as lincomycin and can be made up into pharmaceutical compositions with suitable carriers. Thus, aqueous formulations can be used in pediatrics. Specifications 1,140,663 and 1,140,833 are referred to.