EP1178992A2 - Preparation d'acide de cefpodoxime - Google Patents

Preparation d'acide de cefpodoxime

Info

Publication number
EP1178992A2
EP1178992A2 EP00969048A EP00969048A EP1178992A2 EP 1178992 A2 EP1178992 A2 EP 1178992A2 EP 00969048 A EP00969048 A EP 00969048A EP 00969048 A EP00969048 A EP 00969048A EP 1178992 A2 EP1178992 A2 EP 1178992A2
Authority
EP
European Patent Office
Prior art keywords
formula
acid
cefpodoxime
organic solvent
preparation
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.)
Withdrawn
Application number
EP00969048A
Other languages
German (de)
English (en)
Inventor
Yatendra Kumar
Rakesh Kumar Arora
Kaptan Singh
Hashim Nizar
Shantanu De
Jag Mohan Khanna
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.)
Ranbaxy Laboratories Ltd
Original Assignee
Ranbaxy Laboratories Ltd
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 Ranbaxy Laboratories Ltd filed Critical Ranbaxy Laboratories Ltd
Publication of EP1178992A2 publication Critical patent/EP1178992A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to a new process for the preparation of cefpodoxime acid, an antibiotic belonging to cephalosporin class of compounds. More specifically, the present invention relates to the preparation of cefpodoxime acid of high purity and yield.
  • cefpodoxime acid prepared according to the process of the present invention can be converted into its prodrug, cefpodoxime proxetil, by methods known in the art.
  • Cefpodoxime proxetil is chemically an isopropyloxy carbonyl oxyethyl (proxetil) ester of cefpodoxime. It is a potent antibiotic and is of great therapeutic interest in the treatment of acute bronchitis, exacerbations, pneumonia, sinusitis, recurrence of chronic tonsillitis, pharyngitis, and acute otitis media.
  • the present invention provides a process for the preparation of Cefpodoxime acid having the Formula I
  • MAEM 3-methoxymethyl-7-aminocephalosporanic acid
  • 7AMCA in the presence of an organic solvent and an organic base as herein described and optionally in the presence of water, washing with a water-immiscible solvent as herein described, precipitating the product by adjusting the pH to an acidic pH, isolating and drying the product having the Formula I.
  • the reaction between MAEM and 7AMCA is carried out at a temperature ranging from -5°C to about ambient temperature for about 2 to 12 hours.
  • the organic solvent used is selected from tetrahydrofuran, N, N-dimethylaceta- mide, N,N-dimethylformamide, chlorinated hydrocarbons, ketones or a mixture thereof.
  • the reaction is carried out in tetrahydrofuran in the presence of water.
  • the reaction is carried out in the presence of organic bases such as triethylamine, N-methylpiperidine, pyridine, 1 ,8-diazabicycloundecene, 4-dimeth- ylaminopyridine, or a mixture thereof.
  • the water-immiscible solvent used is chlorinated hydrocarbon, aromatic hydrocarbon or ketones.
  • cefpodoxime acid having the Formula I prepared according to the process of the present invention is a syn-isomer of this compound.
  • the present invention provides a method by which the syn-isomer of cefpodoxime acid is obtained in high purity and good yields without the necessity for protecting the amino group of acylating agent.
  • Aqueous layer was separated and washed with methylene chloride.
  • the aqueous layer was acidified to pH 2.75 with aqueous hydrochloric acid and the separated product was filtered. It was washed with water and dried under reduced pressure to yield 6.65gm (76%) of Cefpodoxime acid of 95.7% purity (HPLC).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

L'invention concerne un nouveau procédé permettant la préparation d'acide de cefpodoxime, lequel peut ensuite être converti en cefpodoxime proxetil par des procédés connus des spécialistes.
EP00969048A 1999-05-07 2000-05-05 Preparation d'acide de cefpodoxime Withdrawn EP1178992A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30701099A 1999-05-07 1999-05-07
US307010 1999-05-07
PCT/IB2000/000585 WO2000068234A2 (fr) 1999-05-07 2000-05-05 Preparation d'acide de cefpodoxime

Publications (1)

Publication Number Publication Date
EP1178992A2 true EP1178992A2 (fr) 2002-02-13

Family

ID=23187851

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00969048A Withdrawn EP1178992A2 (fr) 1999-05-07 2000-05-05 Preparation d'acide de cefpodoxime

Country Status (4)

Country Link
EP (1) EP1178992A2 (fr)
AU (1) AU7224300A (fr)
HK (1) HK1044761A1 (fr)
WO (1) WO2000068234A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037833A1 (fr) * 2002-10-24 2004-05-06 Orchid Chemicals & Pharmaceuticals Ltd Procede de preparation d'antibiotiques cephalosporines
WO2011077217A1 (fr) * 2009-12-21 2011-06-30 Nectar Lifesciences Ltd. Procédé amélioré de préparation d'acide de cefpodoxime
CN106046024B (zh) * 2016-06-30 2019-01-15 齐鲁动物保健品有限公司 一种头孢泊肟酯的制备方法
CN111320514A (zh) * 2020-04-03 2020-06-23 南京昊绿生物科技有限公司 一种头孢泊肟d3的合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0037380A2 (fr) 1980-03-28 1981-10-07 BIOCHEMIE Gesellschaft m.b.H. Procédé pour la production d'antibiotiques du type céphalosporine, intermédiaires pour utilisation dans ce procédé et leur production
WO1998031685A1 (fr) 1997-01-16 1998-07-23 Biochemie Gesellschaft Mbh Procede de purification

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2476087A1 (fr) * 1980-02-18 1981-08-21 Roussel Uclaf Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
JPS60260583A (ja) * 1985-05-14 1985-12-23 Sankyo Co Ltd セフアロスポリン誘導体の製法
JPS60260584A (ja) * 1985-05-14 1985-12-23 Sankyo Co Ltd セフアロスポリン誘導体
DK0531875T3 (da) * 1991-09-07 2004-06-21 Aventis Pharma Gmbh Diastereomer af 3-cephem-4-carboxylsyre-1-(-isopropoxycarbonyloxy)-ethylester og fremgangsmåde til dens fremstilling

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0037380A2 (fr) 1980-03-28 1981-10-07 BIOCHEMIE Gesellschaft m.b.H. Procédé pour la production d'antibiotiques du type céphalosporine, intermédiaires pour utilisation dans ce procédé et leur production
WO1998031685A1 (fr) 1997-01-16 1998-07-23 Biochemie Gesellschaft Mbh Procede de purification

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0068234A3

Also Published As

Publication number Publication date
WO2000068234A2 (fr) 2000-11-16
AU7224300A (en) 2000-11-21
WO2000068234A3 (fr) 2001-02-08
HK1044761A1 (zh) 2002-11-01

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