Brock University

Other

Ales Machara

Tomas Hudlicky

Lukas Werner

Mary Ann Endoma-Arias

Hannes Leisch

Robert James Carroll

Martina Wernerova

Ivan Snajdr

Brennan Augusta Murphy

Robert Carroll

David R Adams

The present application is directed to an efficient conversion of C-14 hydroxylated morphine alkaloids to various morphine analogs, such as naltrexone, naloxone and nalbuphone. One feature of this process is an intramolecular functional group transfer from the C-14 hydroxyl to the N-17 nitrogen atom following a palladium-catalyzed N-demethylation.

Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer

The present application relates to methods for the preparation of morphine derivatives. In particular, the present application relates to methods for the preparation of hydromorphone from oripavine and oripavine from thebaine.

Methods for the preparation of hydromorphone

The present invention provides a method for the N-demethylation and N-functionalization of an N-methylated heterocycle such as a morphine alkaloid or tropane alkaloid. The method comprises reacting the heterocycle with an functionalization agent in the presence of a transition metal catalyst in air or in the presence of an oxidant.

Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids

A high-yielding method for the N-demethylation of oxycodone- and oxymorphone-N-oxides by the reaction of these compounds with cyclodehydration reagents has been performed. This method has been utilized to improve the synthesis of various morphine analogs, such as naltrexone, nalbuphone and naloxone.

Processes and intermediates in the preparation of morphine analogs via N-demethylation of N-oxides using cyclodehydration reagents

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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.

Processes for the preparation of morphinane and morphinone compounds

The present application relates to processes for the preparation of intermediates useful in the manufacture of oseltamivir and the HPOsalt of oseltamivir, Tamiflu&#xae;. The application further relates to novel intermediate and compounds and oseltamivir analogs and to pharmaceutical compositions comprising said analog compounds. The application further relates to a method of using the novel analogs of oseltamivir to treat or prevent influenza.

Growing community of inventors

Brevnov, Czechia

Ales Machara