Sanofi

Sanofi-aventis

Alain Dlubala

Claire Trecant

Isabelle Ripoche

Alain Medard

Gilles Oddon

Raphael Sole

Philippe Vayron

Marc Daumas

Jildaz Dhainaut

Ronan Guevel

Nicolas Raymond

Joel Turconi

Joël Turconi

Raphaël Sole

Provided is a new photochemical process for preparing artemisinin. Also provided are certain dihydroartemisinic acid derivatives useful for preparing artemisinin.

Photochemical process for producing artemisinin

The disclosure relates to derivatives of morphine-6-glucuronide of formula (I) wherein R1 is as defined in the disclosure, or an acid addition salt thereof, as well as in hydrate or solvate form. The disclosure also relates to the preparation method thereof and to the use of same in therapeutics.

Derivatives of morphine-6-glucuronide, preparation method thereof and use of same in therapeutics

The present invention relates to a method for the preparation of morphine compounds comprising a low content of &#x3b1;,&#x3b2;-unsaturated compounds, which comprises the steps of: (i) bringing the crude morphine compound into contact with a base, at a pH of greater than 13, under conditions which make possible the Michael addition reaction on the &#x3b1;,&#x3b2;-unsaturated compound(s) present; (ii) separating the morphine compound from the reaction mixture; and (iii) if appropriate, separating the addition product formed from the morphine compound. It also relates to a composition comprising at least 99% by dry weight of morphine compound or of a pharmaceutically acceptable salt thereof, and an &#x3b1;,&#x3b2;-unsaturated compound in a content of less than 100 ppm.

Method for the preparation of morphine compounds

The disclosure relates to compounds of formula (I): wherein R1, R2, and n are as defined in the disclosure, and addition salts solvates and hydrates thereof. The disclosure also relates to the preparation method of said compounds and to the use of the same in therapeutics.

Bicyclic derivatives of morphine-6-glucuronide, preparation method thereof and use of same in therapeutics

The invention discloses and claims N-Methylnaltrexone zwitterion, of formula (I), substantially in the anhydrous form or a hydrate thereof: 

N-methylnaltrexone zwitterion

The disclosure relates to a method for preparing morphine-6-glucuronide or one of the deritives thereof comprising reacting a compound of formula (I): wherein Ris as defined in the disclosure,with a glucuronic acid derivative of formula (II): wherein PG, X, and Rare as defined in the disclosure,in the presence of an aromatic solvent and trimethylsilyl trifluoromethanesulfonate;(ii) reacting the product obtained in step (i) with a strong basic agent; and then (iii) recovering the product obtained in step (ii).

Synthesis of morphine-6-glucuronide or one of the derivatives thereof

The invention relates to a novel process for preparing N-methylnaltrexone bromide, comprising at least the steps consisting in:

Processs for preparing N-alkylnaltrexone halides

A process for the preparation of for the preparation of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide and of its salts, wherein 1,5-dibromopentane is reacted with a compound of formula (IIIa) in the presence of NaCOin acetonitrile heated at reflux.

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Paris, France

Alain Dlubala