WO1998056762A3 - Procede de preparation de composes de phenyloxyrane actifs sur le plan optique - Google Patents

Procede de preparation de composes de phenyloxyrane actifs sur le plan optique Download PDF

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Publication number
WO1998056762A3
WO1998056762A3 PCT/JP1998/002521 JP9802521W WO9856762A3 WO 1998056762 A3 WO1998056762 A3 WO 1998056762A3 JP 9802521 W JP9802521 W JP 9802521W WO 9856762 A3 WO9856762 A3 WO 9856762A3
Authority
WO
WIPO (PCT)
Prior art keywords
optically active
represented
compounds
ring
compound
Prior art date
Application number
PCT/JP1998/002521
Other languages
English (en)
Other versions
WO1998056762A2 (fr
Inventor
Tomiki Hashiyama
Naoyuki Harada
Hiroaki Arakawa
Mari Kusama
Yasuhiko Ozaki
Tooru Kuroda
Masahiko Seki
Original Assignee
Tanabe Seiyaku Co
Tomiki Hashiyama
Naoyuki Harada
Hiroaki Arakawa
Mari Kusama
Yasuhiko Ozaki
Tooru Kuroda
Masahiko Seki
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 Tanabe Seiyaku Co, Tomiki Hashiyama, Naoyuki Harada, Hiroaki Arakawa, Mari Kusama, Yasuhiko Ozaki, Tooru Kuroda, Masahiko Seki filed Critical Tanabe Seiyaku Co
Priority to EP98923162A priority Critical patent/EP0988297A2/fr
Priority to CA002293404A priority patent/CA2293404A1/fr
Priority to AU75519/98A priority patent/AU7551998A/en
Priority to IL13309598A priority patent/IL133095A0/xx
Publication of WO1998056762A2 publication Critical patent/WO1998056762A2/fr
Publication of WO1998056762A3 publication Critical patent/WO1998056762A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Landscapes

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

Abstract

Cette invention concerne un procédé de préparation d'un composé de phényloxyrane actif sur le plan optique, lequel composé correspond à la formule (II) où l'anneau A représente un anneau de benzène substitué ou non. R représente un groupe -CO2Rq ou un groupe pouvant être transformé en un groupe -CO¿2R?q, étant entendu que Rq représente un résidu d'ester. Le symbole * représente enfin un atome de carbone asymétrique. Ce procédé fait appel à un dérivé de styrène correspondant à la formule (I) où l'anneau A et R sont tels que définis précédemment. Ce procédé consiste à traiter le dérivé de styrène à l'aide d'un agent d'oxydation asymétrique qui se compose d'un composé de cétone chiral et d'un agent oxydant ou, encore, d'un composé de dioxyrane chiral.
PCT/JP1998/002521 1997-06-11 1998-06-05 Procede de preparation de composes de phenyloxyrane actifs sur le plan optique WO1998056762A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP98923162A EP0988297A2 (fr) 1997-06-11 1998-06-05 Procede de preparation de composes de phenyloxyrane actifs sur le plan optique
CA002293404A CA2293404A1 (fr) 1997-06-11 1998-06-05 Procede de preparation de composes de phenyloxyrane actifs sur le plan optique
AU75519/98A AU7551998A (en) 1997-06-11 1998-06-05 Process for preparing optically active phenyloxirane compounds
IL13309598A IL133095A0 (en) 1997-06-11 1998-06-05 Process for preparing optically active phenyloxirane compounds

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP17104297 1997-06-11
JP9/171042 1997-06-11
JP35554697 1997-12-24
JP9/355546 1997-12-24

Publications (2)

Publication Number Publication Date
WO1998056762A2 WO1998056762A2 (fr) 1998-12-17
WO1998056762A3 true WO1998056762A3 (fr) 1999-03-25

Family

ID=26493875

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1998/002521 WO1998056762A2 (fr) 1997-06-11 1998-06-05 Procede de preparation de composes de phenyloxyrane actifs sur le plan optique

Country Status (7)

Country Link
EP (1) EP0988297A2 (fr)
KR (1) KR20010013668A (fr)
CN (1) CN1266430A (fr)
AU (1) AU7551998A (fr)
CA (1) CA2293404A1 (fr)
IL (1) IL133095A0 (fr)
WO (1) WO1998056762A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999046257A1 (fr) * 1998-03-11 1999-09-16 Tanabe Seiyaku Co., Ltd. Production de biaryldicarboxylate d'oxoalkylene
AU2960099A (en) * 1998-04-08 1999-11-01 Tanabe Seiyaku Co., Ltd. Process for producing hydroxylactone compound

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59196881A (ja) * 1983-04-21 1984-11-08 Shionogi & Co Ltd 新規なエポキシド誘導体
GB2139620A (en) * 1983-04-21 1984-11-14 Shionogi & Co Process for production of diltiazem hydrochloride
JPS6013776A (ja) * 1983-07-05 1985-01-24 Sawai Seiyaku Kk 光学活性３−（ｐ−アルコキシフエニル）グリシツド酸誘導体の製造法
EP0342903A1 (fr) * 1988-05-18 1989-11-23 MARION LABORATORIES, INC. (a Delaware corporation) Résolution optique de l'acide 3-(4-méthoxyphényl)-glycidique avec conversion in-situ en esters alkyliques
EP0343714A1 (fr) * 1988-05-20 1989-11-29 Dsm N.V. Stéréoisomères de phénylglycidate, produits de conversion de ceux-ci avec 2-nitrothiophénol et préparation de diltiazème
EP0362556A1 (fr) * 1988-09-02 1990-04-11 Tanabe Seiyaku Co., Ltd. Procédé de préparation d'esters de l'acide 3-phénylglycidique optiquement actifs
FR2662178A1 (fr) * 1990-05-17 1991-11-22 Zambon Spa Procede de preparation d'intermediaires utiles dans la synthese de benzothiazepines.
EP0498706A1 (fr) * 1991-02-08 1992-08-12 Synthelabo Procédé de préparation du (-)-(2R,3S)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle
JPH0678B2 (ja) * 1988-09-02 1994-01-05 田辺製薬株式会社 光学活性３―フェニルグリシッド酸エステル類化合物の製法
JPH0678790A (ja) * 1992-09-03 1994-03-22 Tanabe Seiyaku Co Ltd 光学活性３−（４−メトキシフェニル）グリシッド酸エステル類化合物の製法
JPH06279398A (ja) * 1993-01-27 1994-10-04 Shionogi & Co Ltd ベンゾチアゼピン誘導体の製造法

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59196881A (ja) * 1983-04-21 1984-11-08 Shionogi & Co Ltd 新規なエポキシド誘導体
GB2139620A (en) * 1983-04-21 1984-11-14 Shionogi & Co Process for production of diltiazem hydrochloride
JPS6013776A (ja) * 1983-07-05 1985-01-24 Sawai Seiyaku Kk 光学活性３−（ｐ−アルコキシフエニル）グリシツド酸誘導体の製造法
JPH02231480A (ja) * 1988-05-18 1990-09-13 Marion Lab Inc その場でアルキルエステルに転化する３‐（４‐メトキシフェニル）グリシド酸の改良分割
EP0342903A1 (fr) * 1988-05-18 1989-11-23 MARION LABORATORIES, INC. (a Delaware corporation) Résolution optique de l'acide 3-(4-méthoxyphényl)-glycidique avec conversion in-situ en esters alkyliques
EP0343714A1 (fr) * 1988-05-20 1989-11-29 Dsm N.V. Stéréoisomères de phénylglycidate, produits de conversion de ceux-ci avec 2-nitrothiophénol et préparation de diltiazème
JPH07121231B2 (ja) * 1988-05-20 1995-12-25 デーエスエム ナムローゼ フェンノートシャップ 立体異性体的に純粋なフエニルグリシド酸エステルの製造方法および（２ｓ，３ｓ）‐２‐（４′‐メトキシフエニル）‐３‐アセトキシ‐５‐〔２‐（ジメチルアミノ）エチル〕‐２，３‐ジヒドロ‐１，５‐ベンゾチアゼピン‐４（５ｈ）‐オンの製造方法
EP0362556A1 (fr) * 1988-09-02 1990-04-11 Tanabe Seiyaku Co., Ltd. Procédé de préparation d'esters de l'acide 3-phénylglycidique optiquement actifs
JPH0678B2 (ja) * 1988-09-02 1994-01-05 田辺製薬株式会社 光学活性３―フェニルグリシッド酸エステル類化合物の製法
FR2662178A1 (fr) * 1990-05-17 1991-11-22 Zambon Spa Procede de preparation d'intermediaires utiles dans la synthese de benzothiazepines.
JPH04228095A (ja) * 1990-05-17 1992-08-18 Zambon Group Spa （２ｒ，３ｓ）−３−（４−メトキシ−フェニル）−グリシド酸エステルの製造方法
EP0498706A1 (fr) * 1991-02-08 1992-08-12 Synthelabo Procédé de préparation du (-)-(2R,3S)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle
JPH0576389A (ja) * 1991-02-08 1993-03-30 Synthelabo Sa （−）−（２ｒ，３ｓ）−２，３−エポキシ−３−（４−メトキシフエニル）プロピオン酸メチルの製造方法
JPH0678790A (ja) * 1992-09-03 1994-03-22 Tanabe Seiyaku Co Ltd 光学活性３−（４−メトキシフェニル）グリシッド酸エステル類化合物の製法
JPH06279398A (ja) * 1993-01-27 1994-10-04 Shionogi & Co Ltd ベンゾチアゼピン誘導体の製造法

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
A. ARMSTRONG ET AL., CHEMICAL COMMUNICATIONS, no. 5, 1998, pages 621 - 2, XP002076049 *
DAN YANG ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 118, 1996, pages 11311 - 2, XP002076047 *
PATENT ABSTRACTS OF JAPAN vol. 18, no. 334 (C - 1216) 24 June 1994 (1994-06-24) *
PATENT ABSTRACTS OF JAPAN vol. 9, no. 125 (C - 283) 30 May 1985 (1985-05-30) *
PATENT ABSTRACTS OF JAPAN vol. 95, no. 1 28 February 1995 (1995-02-28) *
R. W. MURRAY, CHEMICAL REVIEWS, vol. 89, 1989, pages 1187 - 1201, XP002076048 *
S. MIYANO ET AL., BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 57, 1984, pages 1943 - 7, XP002076050 *

Also Published As

Publication number Publication date
AU7551998A (en) 1998-12-30
CN1266430A (zh) 2000-09-13
WO1998056762A2 (fr) 1998-12-17
EP0988297A2 (fr) 2000-03-29
KR20010013668A (ko) 2001-02-26
IL133095A0 (en) 2001-03-19
CA2293404A1 (fr) 1998-12-17

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