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1. WO2007138928 - PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-2 -HYDROXYPROPIONIC CYCLOPROPYLAMIDE DERIVATIVES AND SALTS THEREOF

Publication Number WO/2007/138928
Publication Date 06.12.2007
International Application No. PCT/JP2007/060435
International Filing Date 22.05.2007
IPC
C07D 263/16 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
263Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
02not condensed with other rings
08having one double bond between ring members or between a ring member and a non-ring member
16with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
C07C 67/31 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
30by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
31by introduction of functional groups containing oxygen only in singly bound form
C07C 69/675 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
69Esters of carboxylic acids; Esters of carbonic or haloformic acids
66Esters of carboxylic acids having esterified carboxyl groups bound to acyclic carbon atoms and having any of the groups OH, O-metal, -CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
67of saturated acids
675of saturated hydroxy-carboxylic acids
C07C 231/12 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
231Preparation of carboxylic acid amides
12by reactions not involving the formation of carboxamide groups
C07C 231/16 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
231Preparation of carboxylic acid amides
16Preparation of optical isomers
C07C 237/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
237Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
02having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
04the carbon skeleton being acyclic and saturated
CPC
C07B 2200/07
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
07Optical isomers
C07B 53/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
53Asymmetric syntheses
C07C 231/18
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
231Preparation of carboxylic acid amides
16Preparation of optical isomers
18by stereospecific synthesis
C07C 237/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
237Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
02having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
04the carbon skeleton being acyclic and saturated
C07C 237/22
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
237Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
02having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
22having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
C07C 2601/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
2601Systems containing only non-condensed rings
02with a three-membered ring
Applicants
  • 株式会社カネカ KANEKA CORPORATION [JP]/[JP] (AllExceptUS)
  • 森 耕平 MORI, Kohei [JP]/[JP] (UsOnly)
  • 西山 章 NISHIYAMA, Akira [JP]/[JP] (UsOnly)
  • 田岡 直明 TAOKA, Naoaki [JP]/[JP] (UsOnly)
  • 森山 大輔 MORIYAMA, Daisuke [JP]/[JP] (UsOnly)
  • 長嶋 伸夫 NAGASHIMA, Nobuo [JP]/[JP] (UsOnly)
Inventors
  • 森 耕平 MORI, Kohei
  • 西山 章 NISHIYAMA, Akira
  • 田岡 直明 TAOKA, Naoaki
  • 森山 大輔 MORIYAMA, Daisuke
  • 長嶋 伸夫 NAGASHIMA, Nobuo
Common Representative
  • 株式会社カネカ KANEKA CORPORATION
Priority Data
2006-14674526.05.2006JP
Publication Language Japanese (JA)
Filing Language Japanese (JA)
Designated States
Title
(EN) PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-2 -HYDROXYPROPIONIC CYCLOPROPYLAMIDE DERIVATIVES AND SALTS THEREOF
(FR) PROCÉDÉ DE PRODUCTION DE DÉRIVÉS OPTIQUEMENT ACTIFS DE CYCLOPROPYLAMIDE D'ACIDE 3-AMINO-2-HYDROXYPROPIONIQUE ET DE LEURS SELS
(JA) 光学活性3-アミノ-2-ヒドロキシプロピオン酸シクロプロピルアミド誘導体およびその塩の製造方法
Abstract
(EN)
The invention aims at providing an industrially practical process by which optically active 3-amino-2-hydroxypropionic cyclopropylamide derivatives useful as intermediates of drugs or salts thereof can be easily produced from inexpensive and easily available raw materials; and these useful intermediates. This aim can be attained by a process which comprises subjecting an easily available 2-halo-3-oxopropionic acid derivative to asymmetric reduction and epoxidation successively to form an optically active epoxycarboxylic acid derivative, reacting the epoxycarboxylic acid derivative with cyclopropylamine to form an optically active epoxyamide derivative, reacting the epoxyamide derivative with nitrile to form an optically active oxazoline-amide derivative, and subjecting the oxazoline-amide derivative to selective acidic solvolysis of oxazoline skeleton to form an optically active 3-amino-2-hydroxypropionic cyclopropylamide derivative or a salt thereof.
(FR)
La présente invention a pour objet un procédé d'utilité industrielle de production simple de dérivés optiquement actifs de cyclopropylamide d'acide 3-amino-2-hydroxypropionique, qui peuvent être employés en tant qu'intermédiaires de médicaments, ou de leurs sels, à partir de composants peu onéreux et largement disponibles. La présente invention a également pour objet lesdits intermédiaires. Ledit objet peut être atteint par un procédé qui comprend les étapes consitant à soumettre un dérivé d'acide 2-halogéno-3-oxopropionique largement disponible à une réduction asymétrique et une époxydation successives pour former un dérivé d'acide époxycarboxylique optiquement actif, à faire réagir ledit dérivé d'acide époxycarboxylique avec la cyclopropylamine pour former un dérivé d'époxamide optiquement actif, à faire réagir le dérivé d'époxamide avec un nitrile pour former un dérivé d'oxazoline-amide optiquement actif, et à soumettre ledit dérivé d'oxazoline-amide à une solvolyse acide sélective du squelette oxazoline pour former un dérivé optiquement actif de cyclopropylamide d'acide 3-amino-2-hydroxypropionique ou l'un de ses sels.
(JA)
 本願は、医薬品中間体として有用な光学活性3-アミノ-2-ヒドロキシプロピオン酸シクロプロピルアミド誘導体またはその塩を安価で入手容易な原料から簡便に製造でき、工業的生産に対して実用的な方法並びにこれらの有用中間体を提供することを課題とする。この課題は以下の方法により解決される。まず、入手容易な2-ハロ-3-オキソプロピオン酸誘導体を不斉還元した後に、これをエポキシ化して光学活性エポキシカルボン酸誘導体を製造する。次に、シクロプロピルアミンと反応させて光学活性エポキシアミド誘導体に変換した後、ニトリルと反応させて光学活性オキサゾリンアミド誘導体を製造する。続いて、オキサゾリン骨格の選択的な酸加溶媒分解により、光学活性3-アミノ-2-ヒドロキシプロピオン酸シクロプロピルアミド誘導体またはその塩を製造する。                                                                               
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