Process for the preparation of esomeprazole and salts thereof

Details Process for the preparation of esomeprazole and salts thereof Process for the preparation of esomeprazole and salts thereof

C - Chemistry, Metallurgy

07

D

C07D 401/12 (2006.01)

Patent

CA 2654427

A novel process for the preparation of omeprazole and its enantiomers, such as esomeprazole, as well as the preparation of related 2-(2-pyridinylmethyl-sulphinyl)-1H-benzimidazoles, including pantoprazole, lansoprazole and rabeprazole, as recemates or single enantiomers, and their alkali or alkaline salts has been developed. The novel process involves the surprising discovery that protection of the free-base benzimidazole sulfoxide (e.g. omeprazole or esomeprazole), by reaction with an alkyl, aryl or aralkyl chloroformate following oxidation of the corresponding sulfide, eliminates the need for its direct isolation. Subsequent removal of the protecting group with a solution of alkali or alkaline earth alkoxide in a C1-C4 alcohol directly provides the corresponding salt. By eliminating the need to handle the free-base benzimidazole sulfoxide, this advantageous procedure provides increased chemical yields over processes described in the art.

L'invention concerne un nouveau procédé de préparation de l'oméprazole et de ses énantiomères, par exemple l'ésoméprazole ; cette invention concerne également la préparation de 2-(2-pyridinylméthyl-sulfinyl)-1H-benzimidazoles apparentés, notamment le pantoprazole, le lansoprazole et le rabéprazole, sous la forme de mélanges racémiques ou d'énantiomères seuls, et de leurs sels alcalins ou alcalino-terreux. Ce nouveau procédé est fondé sur la découverte surprenante selon laquelle la protection du sulfoxyde de benzimidazole sous forme de base libre (par exemple d'oméprazole ou d'ésoméprazole), par réaction avec un chloroformiate d'alkyle, d'aryle ou d'aralkyle après oxydation du sulfure correspondant, évite de devoir l'isoler directement. L'élimination par la suite du groupe protecteur au moyen d'une solution d'un alkoxyde de métal alcalin ou alcalino-terreux dans un alcool en C1 à C4 permet d'obtenir directement le sel correspondant. Ce mode opératoire avantageux, qui élimine toute manipulation du sulfoxyde de benzimidazole sous forme de base libre, permet d'obtenir des rendements chimiques plus élevés par rapport aux procédés déjà connus dans la technique.

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