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US 6,147,103 AGranted
Omeprazole process and compositions thereof
AssigneeMerck & Co., Inc.
InventorsNick Anousis, James W. McManus, Benjamin Newton Banks, Lingwen Zhou
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AssigneeMerck & Co., Inc.
InventorsNick Anousis, James W. McManus, Benjamin Newton Banks, Lingwen Zhou
Estimating the term…
The present invention describes an improved process for the preparation, isolation, and purification of the anti-ulcer agent omeprazole whereby the sulfide precursor pyrmetazole is reacted subsurfacely with exactly one molar equivalent of meta-chloroperoxybenzoic acid in methylene chloride or toluene solution; residual organic solvent is removed from the aqueous layer by vacuum distillation; crude product is obtained by reactive crystallization with an alkyl formate and seeding; and pure product is isolated by recrystallization in methanol-water containing aqueous NaOH by subsurface addition of aqueous acetic acid to pH 9.0, seeding, filtration, washing, and drying. Compositions of omeprazole containing no chromatographically detectable levels of residual non-alcoholic organic reaction solvent are also described.
A composition comprising 5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzi midazole (omeprazole) having less than three parts per million of residual aromatic hydrocarbon solvent and less than 20 p.p.m. of residual methanol relative to omeprazole.
A composition comprising 5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzi midazole (omeprazole) having less than three parts per million of residual chlorinated aliphatic hydrocarbon solvent and less than 20 p.p.m. of residual methanol relative to omeprazole.
A pharmaceutical composition comprising 5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzi midazole (omeprazole) having less than three parts per million of residual aromatic hydrocarbon solvent and less than 20 p.p.m. of residual methanol relative to omeprazole, and a pharmaceutically acceptable excipient.
A pharmaceutical composition comprising 5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzi midazole omeprazole) having less than three parts per million of residual chlorinated aliphatic hydrocarbon solvent and less than 20 p.p.m. of residual methanol relative to omeprazole, and a pharmaceutically acceptable excipient.
Dependencies are inferred from the claim text.