Methods utilizing aryl thioimines in synthesis of...

C - Chemistry – Metallurgy – 07 – H

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C07H 17/08 (2006.01) A61K 31/7048 (2006.01) A61P 31/04 (2006.01)

Patent

CA 2430734

An efficient deoximation technique for use in synthesis of erythromycin derivatives, involving aryl thioimine intermediates is disclosed. The aryl thioimine intermediates can be utilized in a method for protecting a ketone of a ketone-containing erythromycin derivative as a thioimine; a method for deoximating an oxime-containing erythromycin derivative, or a method for preparing a 6-O-alkyl erythromycin derivative. Presently preferred erythromycin derivatives have a C-9 oxime or a C-9 ketone.

L'invention concerne une technique efficace de désoximation, destinée à être utilisée dans la synthèse de dérivés d'érythromycine, impliquant des intermédiaires d'aryle thioimine. Ces intermédiaires d'aryle thioimine peuvent être utilisés dans un procédé de protection d'une cétone d'un dérivé d'érythromycine contenant une cétone, sous la forme d'une thioimine ; dans un procédé de désoximation d'un dérivé d'érythromycine contenant un oxime, ou dans un procédé de préparation d'un dérivé d'érythromycine 6-O-alkyle. Les dérivés d'érythromycine actuellement préférés contiennent un oxime C-9 ou une cétone C-9.

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