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1. WO2008125577 - A METHOD FOR THE PREPARATION OF AN ENANTIOMERICALLY PURE BENZAZEPINE

Publication Number WO/2008/125577
Publication Date 23.10.2008
International Application No. PCT/EP2008/054315
International Filing Date 10.04.2008
IPC
C07D 471/04 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
471Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/-C07D463/251
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
C07D 471/14 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
471Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/-C07D463/251
12in which the condensed system contains three hetero rings
14Ortho-condensed systems
CPC
C07D 471/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
471Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
C07D 471/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
471Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
12in which the condensed system contains three hetero rings
14Ortho-condensed systems
Applicants
  • N.V. ORGANON [NL]/[NL] (AllExceptUS)
  • KEMPERMAN, Gerardus Johannes [NL]/[NL] (UsOnly)
  • SEERDEN, Johannes Paulus Gerardus [NL]/[NL] (UsOnly)
Inventors
  • KEMPERMAN, Gerardus Johannes
  • SEERDEN, Johannes Paulus Gerardus
Agents
  • BROEKKAMP, Chris L.E.
Priority Data
07105979.411.04.2007EP
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) A METHOD FOR THE PREPARATION OF AN ENANTIOMERICALLY PURE BENZAZEPINE
(FR) PROCÉDÉ DE PRÉPARATION D'UNE BENZAZÉPINE ÉNANTIOMÉRIQUEMENT PURE
Abstract
(EN) The invention relates to a method for the preparation of a cyclic compound according to formula (III) comprising reacting a compound according to Formula (I) and a compound according to formula (II), wherein in Formula (I), R1, R2, R3 and R4 may be hydrogen or substituent groups comprising one or more carbon atoms and/or hetero-atoms, wherein R1, R2, R3 and R4 can be combined in aromatic or aliphatic ring structures, -Y is a ring element comprising 1-3 substituted or unsubstituted carbon atoms and/or heteroatoms in the ring and -R5 is hydrogen or a hydrocarbon substituent group comprising one or more carbon atoms and optionally one or more hetero atoms, and wherein in Formula (II), Z1 and Z2 are, leaving groups, X is a reactive functional hydrocarbon group for subsequent ring closure, comprising one or more carbon atoms and a reactive functional group and having a chain of between 1 to 6 atoms between the carbon atom attached to the central carbon atom of formula (II) and the reactive functional group and R8 is hydrogen or a hydrocarbon substituent different from X making the central carbon atom of formula II a chiral centre in Formula (III) and wherein reactive functional group X can be or can be extended to be compound of formula (IV) which can be ring closed to produce the polycyclic component of formula (V). More in particular, the invention relates to the preparation of mirtazapine precursors and mirtazapine preferably having a substantial enantiomeric excess.
(FR) L'invention concerne un procédé de préparation d'un composé cyclique de formule (III), ce procédé consistant à mettre à réagir un composé de formule (I) et un composé de formule (II). Dans la formule (I), R1, R2, R3 and R4 peuvent être combinés sous forme de structures de noyaux aromatiques ou aliphatiques, -Y est un élément de noyau comprenant 1 à 3 atomes de carbone substitués ou non substitués et/ou des hétéroatomes dans le noyau et -R5 représente hydrogène ou un groupe substituant d'hydrocarbone comprenant un ou plusieurs atomes de carbone et éventuellement un ou plusieurs hétéroatomes. Dans la formule (II), Z1 and Z2 sont des groupes labiles; X représente un groupe d'hydrocarbones fonctionnels réactifs pour la fermeture du noyau ultérieure et comprendun ou plusieurs atomes de carbone et un groupe fonctionnel réactif et ayant une chaîne de un à six atomes compris entre l'atome de carbone attaché à l'atome de carbone central de formule (II) et le groupe fonctionnel réactif, et R8 représente hydrogène ou un substituant d'hydrocarbone différent de X faisant de l'atome de carbone central de formule (II) un centre chiral de formule (III). Le groupe fonctionnel réactif X peut être un composé ou peut être allongé pour être un composé de formule (IV) qui peut être un noyau fermé pour produire le composant polycyclique de formule (V). Plus particulièrement, l'invention concerne la préparation de précurseurs de la mirtazapine et la mirtazapine ayant de préférence un excès énantiomère substantiel.
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