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WO2008102671A1 - ４－ヒドロキシイソロイシンの精製方法 - Google Patents

４－ヒドロキシイソロイシンの精製方法 Download PDF

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Publication number
WO2008102671A1
WO2008102671A1 PCT/JP2008/052301 JP2008052301W WO2008102671A1 WO 2008102671 A1 WO2008102671 A1 WO 2008102671A1 JP 2008052301 W JP2008052301 W JP 2008052301W WO 2008102671 A1 WO2008102671 A1 WO 2008102671A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxyisoleucine
formula
compound represented
purifying
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2008/052301
Other languages
English (en)
French (fr)
Inventor
Munetaka Tokumasu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to CA002678990A priority Critical patent/CA2678990A1/en
Priority to EP08711159A priority patent/EP2123629A1/en
Priority to JP2009500149A priority patent/JPWO2008102671A1/ja
Publication of WO2008102671A1 publication Critical patent/WO2008102671A1/ja
Priority to US12/545,306 priority patent/US20100048947A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C07B63/02—Purification; Separation; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/34—Preparation of optical isomers by separation of optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

　本発明は、簡便、高純度、高収率で（２Ｓ，３Ｒ，４Ｓ）－４－ヒドロキシイソロイシンを単離精製及び分離除去する方法の提供を課題とする。具体的には、本発明は、以下の工程（ａ）、（ｂ）及び（ｃ）を含む、（２Ｓ，３Ｒ，４Ｓ）－４－ヒドロキシイソロイシン又はその化学的に許容しうる塩の精製方法を開示する： （ａ）混合物中の（２Ｓ，３Ｒ，４Ｓ）－４－ヒドロキシイソロイシン又はその化学的に許容しうる塩を、式Ｑ－ＣＨＯ［式中、Ｑは、それぞれ置換基を有してもよい、炭素数６～１４のアリール基、炭素数１～１０のアルキル基、炭素数３～１０のシクロアルキル基又は５～１０員のヘテロ環基を表す。］で表されるアルデヒド化合物又はその等価体と反応させて、式（１）で表される化合物 ［式中、Ｑは上記で定義したとおりである。］ 　に変換する工程、 （ｂ）有機溶媒を用いて式（１）で表される化合物を抽出する工程、及び （ｃ）式（１）で表される化合物を（２Ｓ，３Ｒ，４Ｓ）－４－ヒドロキシイソロイシン又はその化学的に許容しうる塩に変換する工程。
PCT/JP2008/052301 2007-02-22 2008-02-13 ４－ヒドロキシイソロイシンの精製方法 Ceased WO2008102671A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002678990A CA2678990A1 (en) 2007-02-22 2008-02-13 Method for purifying 4-hydroxyisoleucine
EP08711159A EP2123629A1 (en) 2007-02-22 2008-02-13 Method for purifying 4-hydroxyisoleucine
JP2009500149A JPWO2008102671A1 (ja) 2007-02-22 2008-02-13 ４−ヒドロキシイソロイシンの精製方法
US12/545,306 US20100048947A1 (en) 2007-02-22 2009-08-21 Purification method of 4-hydroxyisoleucine

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2007-042711 2007-02-22
JP2007042711 2007-02-22
JP2007144578 2007-05-31
JP2007-144578 2007-05-31

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/545,306 Continuation US20100048947A1 (en) 2007-02-22 2009-08-21 Purification method of 4-hydroxyisoleucine

Publications (1)

Publication Number Publication Date
WO2008102671A1 true WO2008102671A1 (ja) 2008-08-28

Family

ID=39709948

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/052301 Ceased WO2008102671A1 (ja) 2007-02-22 2008-02-13 ４－ヒドロキシイソロイシンの精製方法

Country Status (5)

Country Link
US (1) US20100048947A1 (ja)
EP (1) EP2123629A1 (ja)
JP (1) JPWO2008102671A1 (ja)
CA (1) CA2678990A1 (ja)
WO (1) WO2008102671A1 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4753864B2 (ja) * 2003-04-23 2011-08-24 フェリング ベスローテン フェンノートシャップ 薬効を有する医薬の含有割合が高いメサラジンサッシェ

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63250352A (ja) * 1987-03-11 1988-10-18 デグツサ・アクチエンゲゼルシヤフト （ｒ）‐４‐アミノ‐３‐ヒドロキシブタン酸の製法
EP0587476A1 (fr) 1992-09-07 1994-03-16 Société Civile JOUVENET Compositions renfermant des acide aminé mono ou polyhydroxylé pour le traitement du diabète non insulinodépendant
WO2001015689A1 (fr) 1999-08-27 2001-03-08 Centre National De La Recherche Scientifique (Cnrs) Utilisation d'acides amines pour la fabrication de medicaments destines au traitement des insulino-resistances
WO2004087091A2 (fr) 2003-03-28 2004-10-14 Societe D'extraction Des Principes Actifs (Vincience Sa) Composition cosmetique ou pharmaceutique comprenant des acides amines, utilisation et procede de traitement dermatologique
WO2004099120A1 (fr) 2003-05-07 2004-11-18 Centre National De La Recherche Scientifique (Cnrs) Procede de synthese de la 4-hydroxyisoleucine et de ses derives
WO2005021596A2 (en) 2003-08-28 2005-03-10 Technical Sourcing International, Inc. Compositions and methods for glycogen synthesis
WO2005039626A2 (en) 2003-10-27 2005-05-06 Innodia Inc. Use of hydroxylated amino acids for treating diabetes
WO2005084323A2 (en) 2004-03-02 2005-09-15 Technical Sourcing International, Inc. Compositions of bio-active compounds from fenugreek seed and methods for producing same
JP2006089449A (ja) 2004-09-22 2006-04-06 Tsi (China) Co Ltd 脂肪吸収抑制剤
WO2006051000A2 (en) 2004-11-10 2006-05-18 Centre National De La Recherche Scientifique (Cnrs) Method for preparing diastereoisomers of 4-hydroxy isoleucine
US20060223884A1 (en) 2005-03-22 2006-10-05 Nicolas Chapal Compounds and compositions for use in the prevention and treatment of obesity and related syndromes
JP2007042711A (ja) 2005-08-01 2007-02-15 Seiko Epson Corp 静電気保護部を備えるオペアンプ回路
JP2007144578A (ja) 2005-11-29 2007-06-14 Toshiba Mach Co Ltd 工作機械用アタッチメント式ヘッドおよび工作機械
WO2007105650A1 (ja) * 2006-03-10 2007-09-20 Ajinomoto Co., Inc. ４－ヒドロキシイソロイシン誘導体および同誘導体の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7338675B2 (en) * 2002-05-10 2008-03-04 Tsi Health Sciences, Inc. Fenugreek seed bio-active compositions and methods for extracting same
US7645466B2 (en) * 2004-03-02 2010-01-12 Tsi Group Limited Methods for deriving, isolating, and/or extracting amino acid compositions from Fenugreek seed

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63250352A (ja) * 1987-03-11 1988-10-18 デグツサ・アクチエンゲゼルシヤフト （ｒ）‐４‐アミノ‐３‐ヒドロキシブタン酸の製法
EP0587476A1 (fr) 1992-09-07 1994-03-16 Société Civile JOUVENET Compositions renfermant des acide aminé mono ou polyhydroxylé pour le traitement du diabète non insulinodépendant
JPH06157302A (ja) * 1992-09-07 1994-06-03 Lab Monal 非インスリン依存性糖尿病治療を目的としたインスリン分泌刺激組成物
US5470879A (en) 1992-09-07 1995-11-28 Laboratories Monal Treatment of non-insulin-dependent diabetes
WO2001015689A1 (fr) 1999-08-27 2001-03-08 Centre National De La Recherche Scientifique (Cnrs) Utilisation d'acides amines pour la fabrication de medicaments destines au traitement des insulino-resistances
WO2004087091A2 (fr) 2003-03-28 2004-10-14 Societe D'extraction Des Principes Actifs (Vincience Sa) Composition cosmetique ou pharmaceutique comprenant des acides amines, utilisation et procede de traitement dermatologique
WO2004099120A1 (fr) 2003-05-07 2004-11-18 Centre National De La Recherche Scientifique (Cnrs) Procede de synthese de la 4-hydroxyisoleucine et de ses derives
WO2005021596A2 (en) 2003-08-28 2005-03-10 Technical Sourcing International, Inc. Compositions and methods for glycogen synthesis
WO2005039626A2 (en) 2003-10-27 2005-05-06 Innodia Inc. Use of hydroxylated amino acids for treating diabetes
WO2005084323A2 (en) 2004-03-02 2005-09-15 Technical Sourcing International, Inc. Compositions of bio-active compounds from fenugreek seed and methods for producing same
JP2006089449A (ja) 2004-09-22 2006-04-06 Tsi (China) Co Ltd 脂肪吸収抑制剤
WO2006051000A2 (en) 2004-11-10 2006-05-18 Centre National De La Recherche Scientifique (Cnrs) Method for preparing diastereoisomers of 4-hydroxy isoleucine
US20060223884A1 (en) 2005-03-22 2006-10-05 Nicolas Chapal Compounds and compositions for use in the prevention and treatment of obesity and related syndromes
JP2007042711A (ja) 2005-08-01 2007-02-15 Seiko Epson Corp 静電気保護部を備えるオペアンプ回路
JP2007144578A (ja) 2005-11-29 2007-06-14 Toshiba Mach Co Ltd 工作機械用アタッチメント式ヘッドおよび工作機械
WO2007105650A1 (ja) * 2006-03-10 2007-09-20 Ajinomoto Co., Inc. ４－ヒドロキシイソロイシン誘導体および同誘導体の製造方法

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* Cited by examiner, † Cited by third party
Title
AMERICAN JOURNAL OF PHYSIOLOGY ENDOCRINOLOGY AND METABOLISM, vol. 287, 2004, pages E463 - E471
AMINO ACIDS, vol. 28, 2005, pages 71 - 76
DIABETES, vol. 47, no. 2, 1998, pages 206 - 210
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 5, 2002, pages 834 - 839
HARDING K.E. ET AL.: "Stereoselective synthesis of gamma-hydroxy alpha-amino acids via intramolecular amidomercuration", TETRAHEDRON, vol. 44, no. 17, 1988, pages 5605 - 5614, XP008116661 *
PHYTOCHEMISTRY, vol. 12, 1973, pages 1707 - 1711
PHYTOCHEMISTRY, vol. 15, 1976, pages 325
PHYTOCHEMISTRY, vol. 28, 1989, pages 1835 - 1841
WOLFE S. ET AL.: "Conversion of amino hydroxy acids to oxazolidine-4-carboxylic acids, oxazolidine-5-carboxylic acids and tetrahydrooxazine-4-carboxylic acids", TETRAHEDRON LETTERS, no. 41, 1979, pages 3913 - 3916, XP008116662 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4753864B2 (ja) * 2003-04-23 2011-08-24 フェリング ベスローテン フェンノートシャップ 薬効を有する医薬の含有割合が高いメサラジンサッシェ

Also Published As

Publication number Publication date
JPWO2008102671A1 (ja) 2010-05-27
US20100048947A1 (en) 2010-02-25
CA2678990A1 (en) 2008-08-28
EP2123629A1 (en) 2009-11-25

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