C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 489/08 (2006.01) C07D 489/02 (2006.01) C07D 489/12 (2006.01)
Patent
CA 2758231
The present application describes processes for the synthesis of morphinane and morphinone compounds, useful as pharmaceutical agents. Also included are novel intermediates useful in the preparation of these compounds. The process comprises quaternization of oripavine to provide a mixture of the R- and S-isomeric (at the nitrogen) quaternary salts. The R-isomer is readily isolated and converted to various N-(R)-morphinane and N-(S)- morphinone compounds. The R-isomer, S-isomer or a mixture of R- and S-isomers may be demethylated and converted to various morphinane and morphinone compounds.
La présente demande porte sur des procédés pour la synthèse de composés de morphinane et de morphinone, utiles comme agents pharmaceutiques. L'invention porte également sur de nouveaux intermédiaires utiles dans la préparation de ces composés. Le procédé comprend la quaternisation de l'oripavine pour fournir un mélange des isomères R et S (au niveau de l'azote) des sels quaternaires. L'isomère R est aisément isolé et converti en divers composés de N-(R)-morphinane et N-(S)-morphinone. L'isomère R, l'isomère S ou un mélange des isomères R et S peuvent être déméthylés et convertis en divers composés de morphinane et de morphinone.
Adams David Ryad
Carroll Robert
Hudlicky Tomas
Leisch Hannes
Machara Ales
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Brock University
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