Method for high enantiomer selection preparation of (S)-Omeprazole

An enantioselective, enantiomeric technology, applied in pharmaceutical formulations, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problem of large usage of chiral ligands, increased cost and operational complexity, Waste of omeprazole raw materials and other issues
CN1810803BActive Publication Date: 2010-11-17JIANGSU AOSAIKANG PHARMA CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
JIANGSU AOSAIKANG PHARMA CO LTD
Publication Date
2010-11-17

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Abstract

The present invention relates to antimer selective catalytic oxidation process for preparing optical active antimer or optically pure antimer (S)-omeprazole. In the presence of the titanium containing catalyst in-situ created with metal titanium reagent and chiral glycol ligand and the oxidant, omeprazole sulfide is catalytically oxidized with antimer. Compared with the process utilizing tetraisopropanol titanium-diethyl tartrate system, the process of the present invention has the advantages of cheap material, high antimer selectivity and high yield. The present invention also relates to thepreparation of (S)-omeprazole in neutralized state, partial crystallized state or completely crystallized state.
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Description

technical field

[0001] The invention relates to a method for preparing (S)-omeprazole with high enantioselectivity. Background technique

[0002] Compound 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]-sulfinyl]-1H-benzimidazole (commonly known as azulene Meprazole) and pharmaceutically acceptable salts thereof are described in EP 5129. Particular alkali metal salts of omeprazole are described in EP 124495 . Omeprazole is a proton pump inhibitor, which can effectively inhibit gastric acid secretion and is used as an antiulcer agent. From a more general point of view, omeprazole can be used to prevent and treat diseases related to stomach acid in mammals, especially humans.

[0003] In asymmetrically substituted sulfoxide compounds, the sulfur atom is chiral. The chirality of omeprazole is shown on the sulfur atom of sulfoxide. In fact, omeprazole also has a pair of enantiomers, and (S)-(-)-enantiomer corresponds to (S)-omeprazole.

[0004] Sodium, magnesium, l...

Claims

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