C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 401/12 (2006.01) A61K 31/4439 (2006.01) A61P 1/04 (2006.01)
Patent
CA 2553877
The present invention relates to an improved method for the synthesis of the (S)- or (R)- enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5- dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5- dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)- enantiomer of omeprazole.
L'invention se rapporte à un procédé amélioré de synthèse de (S)- ou (R)- énantiomère d'oméprazole, caractérisé par le fait que 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole ou 2-[[(4-X-3,5-dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole, X étant un nucléofuge, est oxydé dans le sulphoxyde correspondant qui est obtenu en tant que composé cristallin. La recristallisation du sulphoxyde ainsi obtenue permet de produire un composé à pureté chimique ou optique améliorée, qui est par la suite transformé en (S)- ou (R)- énantiomère d'oméprazole.
Fregler Christina
von Unge Sverker
Astrazeneca Ab
Fetherstonhaugh & Co.
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