Processes for the preparation of tricyclic amino alcohol...

C - Chemistry – Metallurgy – 07 – D

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C07D 209/88 (2006.01) C07C 45/63 (2006.01) C07C 49/80 (2006.01) C07C 205/26 (2006.01) C07C 205/45 (2006.01) C07D 301/26 (2006.01) C07D 303/08 (2006.01) C07D 307/91 (2006.01) C07D 333/76 (2006.01)

Patent

CA 2383757

A process for the preparation of tricyclic amino alcohol derivatives including 2-[N-[2-(9H-carbazol-2-yloxy)ethyl]]-amino-1-[(3- methylsulfonylamino)phenyl]ethanol useful in the treatment of diabetes, obesity, hyperlipemia and so on; and intermediates therefor as represented by general formula (5) or (6) or the like wherein R11 is hydrogen or the like; B is chloro or the like; and *1 represents an asymmetric carbon atom. 2-Halo-1- (3-nitrophenyl)ethanone derivatives and 1-(3- nitrophenyl)oxirane derivatives, which are intermediates for the preparation of tricyclic amino alcohol derivatives, are easy of purification, and particularly optically active 1-(3- nitrophenyl)oxirane derivatives are effective in enhancing the optical purities of the final products.

L'invention porte sur un procédé de préparation: de dérivés d'amino alcool tricyclique dont le 2-[N-[2-(9H-carbazol-yloxy) éthyl]]-amino-1-[(3-méthylsulfonylamino)phényle]éthanol, qu'on utilise dans le traitement du diabète, de l'obésité, de l'hyperlipémie, etc.; et de ses intermédiaires de formule générale (5) ou (6) (dans lesquelles: R?11¿ est H ou analogue; B est chloro ou analogue, et *1 est un atome asymétrique de carbone). Les dérivés du 2-halo-1-(3-nitrophényle)éthanone et du 1-(3-nitrophényle)oxyrane, intermédiaires de préparation de dérivés d'amino alcool tricyclique, sont faciles à purifier, en particulier les dérivés optiquement actifs du 1-(3-nitrophényle)oxyrane s'avèrent efficaces pour améliorer la pureté optique des produits finaux.

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