EP1178992A2 - Process for the preparation of cefpodoxime acid - Google Patents
Process for the preparation of cefpodoxime acidInfo
- 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- Withdrawn
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
Description
Claims
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 (en) | 1999-05-07 | 2000-05-05 | Process for the preparation of cefpodoxime acid |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1178992A2 true EP1178992A2 (en) | 2002-02-13 |
Family
ID=23187851
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00969048A Withdrawn EP1178992A2 (en) | 1999-05-07 | 2000-05-05 | Process for the preparation of cefpodoxime acid |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1178992A2 (en) |
AU (1) | AU7224300A (en) |
HK (1) | HK1044761A1 (en) |
WO (1) | WO2000068234A2 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004037833A1 (en) * | 2002-10-24 | 2004-05-06 | Orchid Chemicals & Pharmaceuticals Ltd | Process for the preparation of cephalosporin antibiotics |
WO2011077217A1 (en) * | 2009-12-21 | 2011-06-30 | Nectar Lifesciences Ltd. | An improved process for the preparation of cefpodoxime acid |
CN106046024B (en) * | 2016-06-30 | 2019-01-15 | 齐鲁动物保健品有限公司 | A kind of preparation method of Cefpodoxime Proxetil |
CN111320514A (en) * | 2020-04-03 | 2020-06-23 | 南京昊绿生物科技有限公司 | Synthesis method of cefpodoxime D3 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0037380A2 (en) | 1980-03-28 | 1981-10-07 | BIOCHEMIE Gesellschaft m.b.H. | New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production |
WO1998031685A1 (en) | 1997-01-16 | 1998-07-23 | Biochemie Gesellschaft Mbh | Purification process |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2476087A1 (en) * | 1980-02-18 | 1981-08-21 | Roussel Uclaf | NOVEL OXIMES DERIVED FROM 3-ALKYLOXY OR 3-ALKYL-THIOMETHYL 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS |
JPS60260584A (en) * | 1985-05-14 | 1985-12-23 | Sankyo Co Ltd | Cephalosporin derivative and its preparation |
JPS60260583A (en) * | 1985-05-14 | 1985-12-23 | Sankyo Co Ltd | Preparation of cephalosporin derivative |
DK0531875T3 (en) * | 1991-09-07 | 2004-06-21 | Aventis Pharma Gmbh | Diastereomer of 3-cephem-4-carboxylic acid 1- (- isopropoxycarbonyloxy) ethyl ester and process for its preparation |
-
2000
- 2000-05-05 AU AU72243/00A patent/AU7224300A/en not_active Abandoned
- 2000-05-05 EP EP00969048A patent/EP1178992A2/en not_active Withdrawn
- 2000-05-05 WO PCT/IB2000/000585 patent/WO2000068234A2/en not_active Application Discontinuation
-
2002
- 2002-08-12 HK HK02105883.7A patent/HK1044761A1/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0037380A2 (en) | 1980-03-28 | 1981-10-07 | BIOCHEMIE Gesellschaft m.b.H. | New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production |
WO1998031685A1 (en) | 1997-01-16 | 1998-07-23 | Biochemie Gesellschaft Mbh | Purification process |
Non-Patent Citations (1)
Title |
---|
See also references of WO0068234A3 |
Also Published As
Publication number | Publication date |
---|---|
WO2000068234A3 (en) | 2001-02-08 |
HK1044761A1 (en) | 2002-11-01 |
AU7224300A (en) | 2000-11-21 |
WO2000068234A2 (en) | 2000-11-16 |
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