Process for synthesis of substituted sulphoxides

Details Process for synthesis of substituted sulphoxides Process for synthesis of substituted sulphoxides

C - Chemistry, Metallurgy

07

D

C07D 401/12 (2006.01) C07D 235/28 (2006.01) C07D 413/00 (2006.01) C07D 471/04 (2006.01) C07D 495/04 (2006.01)

Patent

CA 2193994

A novel process for enantioselective synthesis of single enantiomers of omeprazole or its alkaline salts, of other optically pure substituted 2-(2-pyridinylmethyl-sulphinyl)-1H-benzimidazoles as well as of other structurally related sulphoxides or their alkaline salts. The claimed process is an asymmetric oxidation of a pro-chiral sulphide to the single enantiomers or an enantiomerically enriched form of the corresponding sulphoxide. The application also claims the enantiomeric sulphoxide products produced by the process and their use in medicine. The invention also provides one of the single enantiomers of 2(((4-(3-methoxypropoxy)-3-methyl-2- pyridinyl)methyl)sulphinyl)-1H-benzimidazole or 2(2-(N- isobutyl-N-methylamino)-benzylsulphinyl)benzimidazole or pharmaceutically acceptable salts thereof; and one of the single enantiomers of the more or less lipophilic diastereomer of 2((4-methoxy-6,7,8,9-tetrahydro-5H-cyclohepta(b)pyridin-9- yl)-sulphinyl)-1H-benzimidazole or a pharmaceutically acceptable salt thereof.

La présente invention concerne un nouveau procédé de synthèse énantiosélective d'énantiomères simples d'oméprazole ou de ses sels alcalins, d'autres 2-(2-pyridinylméthyl-sulfinyl)-1H-benzimidazoles substitués, optiquement purs, ainsi que d'autres sulfoxydes structurellement apparentés ou de leurs sels alcalins. Le procédé de la présente invention consiste en une oxydation asymétrique de sulfures pro-chiraux donnant des énantiomères simples ou une forme énantiomériquement enrichie du sulfoxyde correspondant. L'invention concerne également des sulfoxydes énantiomères produits grâce à ce nouveau procédé et leur utilisation en médecine.

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