Preparation method of chiral sulfoxide medicament though catalysis of asymmetric oxidation of sulfides compound

A sulfoxide-based, asymmetric technology, applied in the field of catalytic asymmetric oxidation of prochiral sulfides to prepare chiral sulfoxide drugs, can solve the problem of increasing the complexity of the reaction system and operating costs, the use of large amounts of chiral ligands, Limit the industrial production of chiral sulfoxide drugs and other problems, and achieve the effects of high conversion rate, mild reaction conditions and easy availability of raw materials
CN104447692AActive Publication Date: 2015-03-25DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
Publication Date
2015-03-25

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Abstract

The invention provides a preparation method of a chiral sulfoxide medicament though catalysis of asymmetric oxidation of sulfides compounds. A chiral complex formed by quadridentate nitrogen organic ligand and metal manganese compound as a catalyst and hydrogen peroxide as an oxidant are used for asymmetric catalytic oxidation of prochiral thioether compound, so as to obtain the corresponding chiral sulfoxide medicament compounds including S-omeprazole, S-lansoprazole, S-pantoprazole, S-rabeprazole, R-Modafinil and R-sulindac. The reaction has the advantages of cleaness, mild reaction conditions, high conversion rate and antipodal selectivity, and shows industrial prospects.
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Description

technical field

[0001] The invention relates to a method for preparing chiral sulfoxide drugs by catalyzing asymmetric oxidation of prochiral sulfides. Background technique

[0002] The sulfoxide compound with pyridine-2-methylidene-1H-benzimidazole structure has the ability to inhibit H + / K + -ATPase (also known as proton pump) activity can effectively inhibit gastric acid secretion, and is widely used in the treatment of peptic ulcer-related diseases caused by excessive gastric acid secretion. The sulfoxide proton pump inhibitors currently on the market at home and abroad include 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl ]-1H-benzimidazole (Omeprazole, Omeprazole), 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl] Sulfinate]-1H-benzimidazole (Lansoprazole, Lansoprazole), 5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)methyl] Sulfinyl]-1H-benzimidazole (Pantoprazole, Pantoprazole), 2-[[[3-methyl-4-(3-methoxy-1-propoxy)-2-pyridyl] Methyl]s...

Claims

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