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WO1998015557A1 - Procede de fabrication de biotine (+) - Google Patents

Procede de fabrication de biotine (+) Download PDF

Info

Publication number
WO1998015557A1
WO1998015557A1 PCT/EP1997/005482 EP9705482W WO9815557A1 WO 1998015557 A1 WO1998015557 A1 WO 1998015557A1 EP 9705482 W EP9705482 W EP 9705482W WO 9815557 A1 WO9815557 A1 WO 9815557A1
Authority
WO
WIPO (PCT)
Prior art keywords
thienoimidazole
general formula
stage
acid
derivative
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/EP1997/005482
Other languages
German (de)
English (en)
Inventor
Walter Brieden
John Mcgarrity
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.)
Lonza AG
Original Assignee
Lonza AG
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 Lonza AG filed Critical Lonza AG
Priority to AU49443/97A priority Critical patent/AU4944397A/en
Publication of WO1998015557A1 publication Critical patent/WO1998015557A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • an acyl group is introduced in the N-3 position of the furoimidazole derivative.
  • the acylating reagents customary in the art such as, for example, the aliphatic or aromatic acid halides such as acetyl chloride, propionyl chloride or benzoyl chloride, the aliphatic or aromatic Carboxylic acid anhydrides such as acetic anhydride, the halogen formic acid esters such as chloroformic acid ethyl ester or ketene.
  • the acetic acid anhydiide which can act both as a reactant and as a solvent, has proven to be particularly suitable.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention a pour objet un nouveau procédé de fabrication de biotine (+) de formule (I), caractérisé en ce qu'un dérivé furo-imidazole de formule générale (II) est acylé en position 3 de N, le composé acylé est transformé, au moyen d'un donneur S, en un thiéno-imidazole, le groupe acyle est enlevé en position 3 de N, la chaîne latérale est introduite au moyen d'un réactif de Grignard et, après élimination du groupe hydroxy, hydrogénation du composé insaturé obtenu et séparation des groupes protecteurs en position 1 de N, on obtient le produit final biotine (+). La biotine (+) est une vitamine essentielle et est utilisée notamment dans le secteur pharmaceutique.
PCT/EP1997/005482 1996-10-09 1997-10-06 Procede de fabrication de biotine (+) Ceased WO1998015557A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU49443/97A AU4944397A (en) 1996-10-09 1997-10-06 Method for the manufacture of biotine (+)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH2451/96 1996-10-09
CH245196 1996-10-09

Publications (1)

Publication Number Publication Date
WO1998015557A1 true WO1998015557A1 (fr) 1998-04-16

Family

ID=4234132

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/005482 Ceased WO1998015557A1 (fr) 1996-10-09 1997-10-06 Procede de fabrication de biotine (+)

Country Status (2)

Country Link
AU (1) AU4944397A (fr)
WO (1) WO1998015557A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1167373A1 (fr) * 2000-06-22 2002-01-02 E-Sung Chemicals Co., Ltd. Composés de ferrocenyldiphosphine-ruthenium et procédé d'hydrogénation de double liaison exocyclique de d-thiophene à d-thiophane
JP2022067673A (ja) * 2020-10-21 2022-05-09 株式会社トクヤマ チオラクトン化合物の製造方法
CN116239604A (zh) * 2022-12-06 2023-06-09 江西天新药业股份有限公司 生物素前体的精制方法以及制得的生物素前体晶体

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273270A1 (fr) * 1986-12-18 1988-07-06 Lonza Ag Procédé pour la préparation de la (+)-biotine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273270A1 (fr) * 1986-12-18 1988-07-06 Lonza Ag Procédé pour la préparation de la (+)-biotine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1167373A1 (fr) * 2000-06-22 2002-01-02 E-Sung Chemicals Co., Ltd. Composés de ferrocenyldiphosphine-ruthenium et procédé d'hydrogénation de double liaison exocyclique de d-thiophene à d-thiophane
JP2022067673A (ja) * 2020-10-21 2022-05-09 株式会社トクヤマ チオラクトン化合物の製造方法
CN116239604A (zh) * 2022-12-06 2023-06-09 江西天新药业股份有限公司 生物素前体的精制方法以及制得的生物素前体晶体

Also Published As

Publication number Publication date
AU4944397A (en) 1998-05-05

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