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Title:
SYNTHESIS OF MORPHINE-6-GLUCURONIDE OR ONE OF THE DERIVATIVES THEREOF
Document Type and Number:
WIPO Patent Application WO/2010/067007
Kind Code:
A3
Abstract:
The invention relates to a method for preparing morphine-6-glucuronide or one of the derivatives thereof, comprising the following steps: (i) reacting a compound having formula (I), wherein R1 represents a carbonyl group, COR5CO or S02R6S02 with a glucuronic acid derivative having formula (II) wherein PG represents an acetyl, isobutyryl, benzoyl or pivaloyl group, X represents a trihalogenoacetamidate group and R4 represents a (C1-C4)alkylcarboxylate group, in the presence of an aromatic solvent and trifluoromethanesulfonyl of trimethylsilane; (ii) reacting the product obtained in step (i) with a strong basic agent; and, subsequently, (iii) recovering the product obtained in step (ii).

Inventors:
DLUBALA, Alain (Département Brevets174 avenue de France, Paris, F-75013, FR)
RIPOCHE, Isabelle (Ecole Nationale Supérieure de Clermont-Ferrand, Campus CezeauxBP 187, Aubiere Cedex, F-63174, FR)
TRECANT, Claire (16 rue de Copenhague, Strasbourg, F-67000, FR)
Application Number:
FR2009/052445
Publication Date:
July 07, 2011
Filing Date:
December 08, 2009
Export Citation:
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Assignee:
SANOFI (174 avenue de France, Paris, F-75013, FR)
DLUBALA, Alain (Département Brevets174 avenue de France, Paris, F-75013, FR)
RIPOCHE, Isabelle (Ecole Nationale Supérieure de Clermont-Ferrand, Campus CezeauxBP 187, Aubiere Cedex, F-63174, FR)
TRECANT, Claire (16 rue de Copenhague, Strasbourg, F-67000, FR)
International Classes:
C07D489/02; A61K31/485; A61K31/70; A61P25/04; A61P29/00; C07H15/24; C07H17/00; C07H17/04
Domestic Patent References:
WO1999064430A21999-12-16
WO1993003051A11993-02-18
WO2005063263A12005-07-14
Foreign References:
US3766188A1973-10-16
Other References:
HIDETOSHI YOSHIMURA ET AL: "METABOLISM OF DRUGS. LX.1). THE SYNTHESIS OF CODEINE AND MORPHINE GLUCURONIDES2)", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, TOKYO, JP, vol. 16, no. 11, 1 January 1968 (1968-01-01), pages 2114 - 2119, XP000614807, ISSN: 0009-2363
BERRANG B ET AL: "Synthesis of morphine-3,6-di-[beta]-D-glururonide", SYNTHESIS 199710 DE, no. 10, October 1997 (1997-10-01), pages 1165 - 1168, XP002544615, ISSN: 0039-7881
FRENSCH K ET AL: "OLIGO ETHYLENE GLYCOL ETHERS OF MORPHINE", LIEBIGS ANNALEN DER CHEMIE, no. 12, 1979, pages 2118 - 2120, XP002544616, ISSN: 0170-2041
AUTERHOFF H ET AL: "THE MARQUIS REACTION OF MORPHINE", ARCHIV DER PHARMAZIE (WEINHEIM), vol. 306, no. 11, 1973, pages 866 - 872, XP002544617, ISSN: 0365-6233
Attorney, Agent or Firm:
PIGASSE, Caroline (Département Brevets174 avenue de France, Paris, F-75013, FR)
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