Novel intermediates, process for preparing macrolide...

C - Chemistry – Metallurgy – 07 – H

Patent

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C07H 17/08 (2006.01)

Patent

CA 2352162

The present invention provides a process for preparing a high yield of purified clarithromycin having broad antimicrobial activity as a macrolide antibiotic agent by using 1,3-benzodithiol-2-ylium tetrafluoroborate (BDFT), which can easily be synthesized from anthranilic acid and used as a protecting group for oxime. In addition, the present invention also provides a process for preparing clarithromycin from 1,3-benzodithiol-2-sulfonic acid group that forms clarithromycin salt which precipitates into crystals in reaction solution thereof, and purifying clarithromycin including a significantly simplified purification step.

La présente invention concerne une méthode qui permet de préparer une grande quantité de clarithromycine purifiée ayant une activité antimicrobienne étendue en tant qu'agent antibiotique macrolide. Pour ce faire, on utilise le 1,3-benzodithiol-2-ylium tétrafluoroborate (BDFT), qui peut être synthétisé facilement à partir de l'acide anthranilique et utilisé comme groupe de protection pour l'oxime. L'invention concerne également une méthode de préparation de la clarithromycine à partir du groupe 1,3-benzodithiol-2-acide sulfonique, lequel forme un sel de clarithromycine pouvant être précipité en cristaux dans une solution de réaction dudit sel; elle concerne en outre une méthode de purification de la clarithromycine comprenant une étape de purification considérablement simplifiée.

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