The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
SYNTHESIS AND ANTIMICROBIAL EVALUATION OF 20-DEOXO-20-(3, 5-DIMETHYLPIPERIDIN-l-YL)DESMYCOSIN (TILMICOSIN, EL-870) AND RELATED CYCLIC AMINO DERIVATIVES
MANUEL DEBONOKEVIN E. WILLARDHERBERT A. KIRSTJULIE A. WINDGARY D. CROUSEEDDIE V. TAOJEFFREY T. VICENZIFRED T. COUNTERJOHN L. OTTEARL E. OSESATOSHI OMURA
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1989 Volume 42 Issue 8 Pages 1253-1267

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Abstract

A series of 20-deoxo-20-cyclic (alkylamino) derivatives of tylosin, desmycosin, macrocin and lactenocin was prepared by reductive amination of the C-20 aldehyde group. The majority of the compounds were prepared using metal hydrides (sodium cyanoborohydride or sodium borohydride) as the reducing agents and a suitable cyclic alkylamine. Subsequently, a more convenient procedure was developed using formic acid as a reducing agent. The C-20 amino derivatives prepared from desmycosin exhibited good in vitro antimicrobial activity against Pasteurella haemolytica and Pasteurella multocida (MIC range of 0.78-6.25μg/ml) as well as Mycoplasma species (MIC range of 0.39 - 6.25 μg/ml). Several derivatives showed excellent oral efficacy against infections caused by P. multocida in chicks, One of these derivatives, 20-deoxo-20-(3, 5-dimethylpiperidin-1-yl)desmycosin (tilmicosin or EL-870) was selected for development as a therapeutic agent for pasteurellosis in calves and pigs.

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