2r,4s,r,s- and 2s,4r,r,s-hydroxyitraconazole- and...

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 405/14 (2006.01) A61K 31/495 (2006.01) C07D 249/12 (2006.01) C07D 521/00 (2006.01) C07F 9/6558 (2006.01)

Patent

CA 2269617

A substantially pure single enantiomer of a compound of formula (1), wherein X1 and X2 are independently chlorine or fluorine and R is hydrogen, -P(O)(OH)2 or -SO3H, or a salt thereof. A method of preparation of optically pure isomers of hydroxyitraconazole, in particular the two cis dioxolane diastereomers of the sec-butyl (R,S)-isomer, and to phosphate and sulfate derivatives thereof is disclosed. Pharmaceutical compositions containing these compounds and their use for the treatment of fungal infection are also disclosed.

L'invention concerne un énantiomère individuel sensiblement pur d'un composé de formule (A) dans laquelle X?1¿ et X?2¿ représentent indépendamment du chlore et du fluor et R représente hydrogène, -P(O)(OH)¿2? ou SO¿3?H, ou un sel dudit composé. L'invention concerne également un procédé pour préparer des isomères optiquement purs d'hydroxyitraconazole, en particulier les deux diastéréomères de cis dioxolanne de l'isomère sec-butyle (R,S), et pour réaliser la phosphatation et la sulfatation des dérivés desdits isomères. L'invention concerne également des compositions pharmaceutiques renfermant ces composés, et leur utilisation dans le traitement d'infections fongiques.

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