WO2004063203A1 - Procede de preparation de cefotaxime sodique - Google Patents

Procede de preparation de cefotaxime sodique Download PDF

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Publication number
WO2004063203A1
WO2004063203A1 PCT/IB2003/006196 IB0306196W WO2004063203A1 WO 2004063203 A1 WO2004063203 A1 WO 2004063203A1 IB 0306196 W IB0306196 W IB 0306196W WO 2004063203 A1 WO2004063203 A1 WO 2004063203A1
Authority
WO
WIPO (PCT)
Prior art keywords
sodium
formula
cefotaxime
acetate
polar solvent
Prior art date
Application number
PCT/IB2003/006196
Other languages
English (en)
Inventor
Gautam Kumar Das
Pramod Narayan Deshpande
Shanmugam Srinivasan
Original Assignee
Orchid Chemicals & Pharmaceuticals 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 Orchid Chemicals & Pharmaceuticals Ltd filed Critical Orchid Chemicals & Pharmaceuticals Ltd
Priority to AU2003288635A priority Critical patent/AU2003288635A1/en
Publication of WO2004063203A1 publication Critical patent/WO2004063203A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Definitions

  • the present invention relates to a process for the preparation of active cephalosporin antibiotic derivative.
  • the present invention more particularly relates to an improved process for the preparation of sterile cefotaxime sodium of formula (I).
  • Cefotaxime is a broad spectrum third generation cephalosporin antibiotic and having activity against wide range of gram-positive and gram-negative microorganisms.
  • Cefotaxime sodium is physiologically acceptable non-toxic salt of cefotaxime and may be administered to human.
  • the preparation involves the condensation of 7-ACA with MAEM to yield cefotaxime, followed by converting the cefotaxime into its sodium salt.
  • US patent 4,152,432 discloses the process for the preparation of cefotaxime sodium of formula (I), which involves treating the cefotaxime acid in aqueous solvent such as methanol, ethanol or acetone in the presence of base and sodium ions to give cefotaxime sodium.
  • aqueous solvent such as methanol, ethanol or acetone
  • US patent 5,831,086 describes the process for the preparation of sodium cefotaxime. The process described in this patent involves the usage acetone/water.
  • the main objective of the present invention is to provide a process for the preparation of sterile cefotaxime sodium of formula (I), which has better quality such as color and solubility.
  • Another objective of the present invention is to provide direct manufacturing process for the preparation of crystalline sterile cefotaxime sodium of formula (I), from cefotaxime acid.
  • Still another objective of the present invention is to provide a process for the preparation of cefotaxime sodium of formula (I), in good yield, high purity and with desirable particle size.
  • the present invention provides an improved process for the preparation of sterile cefotaxime sodium of formula (I),
  • the polar solvent used in step (i) is selected from methanol, ethanol, or acetone.
  • the less polar solvent used in step (i) is selected from ethyl acetate, methyl acetate or n-butyl acetate.
  • the sodium salt of carboxylic acid used in step (iii) is selected from sodium lactate, sodium acetate, sodium 2-ethyl hexonate, sodium diethylacetate and the like or mixtures thereof.
  • the base employed in step (i) is selected from triethyl amine, diethyl amine, n-butyl amine and preferably triethyl amine.
  • the compound of formula (I) was isolated from reaction mass by adding suitable organic solvent such as ethyl acetate, methyl acetate, n-butyl acetate and preferably ethyl acetate.
  • suitable organic solvent such as ethyl acetate, methyl acetate, n-butyl acetate and preferably ethyl acetate.
  • the compound of formula (II) was prepared in good yield and with high purity by the procedure described in the co-pending application No. PCT/IB03/04628 filed on October 21, 2003.
  • Example 1 The present invention is exemplified by the following example, which is provided for illustration only and should not be construed to limit the scope of the invention.
  • Example 1

Landscapes

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

Abstract

L'invention concerne un procédé amélioré de préparation de céfotaxime sodique stérile représenté par la formule (I), à partir du composé représenté par la formule (II).
PCT/IB2003/006196 2003-01-10 2003-12-24 Procede de preparation de cefotaxime sodique WO2004063203A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003288635A AU2003288635A1 (en) 2003-01-10 2003-12-24 Process for the preparation of cefotaxime sodium

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN23/MAS/2003 2003-01-10
IN23CH2003 2003-01-10

Publications (1)

Publication Number Publication Date
WO2004063203A1 true WO2004063203A1 (fr) 2004-07-29

Family

ID=32697212

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2003/006196 WO2004063203A1 (fr) 2003-01-10 2003-12-24 Procede de preparation de cefotaxime sodique

Country Status (1)

Country Link
WO (1) WO2004063203A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102584854A (zh) * 2012-02-02 2012-07-18 瑞阳制药有限公司 头孢噻肟钠无水结晶的制备工艺
CN103275101A (zh) * 2013-05-17 2013-09-04 天津大学 制备头孢噻肟钠晶体的方法
CN103319504A (zh) * 2013-06-28 2013-09-25 华北制药河北华民药业有限责任公司 一种头孢噻肟钠的结晶方法
CN104086569A (zh) * 2014-07-29 2014-10-08 石药集团中诺药业（石家庄）有限公司 一种头孢噻肟钠的制备方法
CN104892636A (zh) * 2015-05-21 2015-09-09 天津大学 一种制备头孢噻肟钠晶体的方法
CN113024580A (zh) * 2021-03-10 2021-06-25 苏州东瑞制药有限公司 一种头孢噻肟钠的制备方法
CN114028336A (zh) * 2021-10-20 2022-02-11 华北制药河北华民药业有限责任公司 一种注射用头孢噻肟钠的制备方法
CN109678669B (zh) * 2019-02-26 2024-01-09 广西科伦制药有限公司 一种将头孢噻肟钠生产母液中的乙酸乙酯与甲醇分离的装置

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2708439B1 (de) * 1977-02-26 1978-07-13 Hoechst Ag Verfahren zur Herstellung von sterilem Natriumsalz der 7-([2-(2-Amino-thiazol-4-yl)-2-syn-methoximino]-acetamido)-cephalosporansaeure
EP0001024A1 (fr) * 1977-08-17 1979-03-07 Roussel-Uclaf Forme cristalline du sel de sodium d'un dérivé oximiné de l'acide 7-amino thiazolyl acétamido céphalosporanique, son procédé de préparation et les compositions pharmaceutiques la renfermant
US4152432A (en) * 1976-01-23 1979-05-01 Roussel Uclaf 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
WO1996020198A1 (fr) * 1994-12-23 1996-07-04 Biochemie Gesellschaft Mbh Production de cefotaxime et de nouveaux sels de sodium
US5574154A (en) * 1994-09-29 1996-11-12 Alnejma Bulk Pharmaceutical Co. A.B.P.C. Process for the preparation of cephalosporanic compounds
US5945532A (en) * 1995-12-26 1999-08-31 Lupin Laboratories Limited Method for manufacture of cephalosporin and intermediates thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4152432A (en) * 1976-01-23 1979-05-01 Roussel Uclaf 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
DE2708439B1 (de) * 1977-02-26 1978-07-13 Hoechst Ag Verfahren zur Herstellung von sterilem Natriumsalz der 7-([2-(2-Amino-thiazol-4-yl)-2-syn-methoximino]-acetamido)-cephalosporansaeure
EP0001024A1 (fr) * 1977-08-17 1979-03-07 Roussel-Uclaf Forme cristalline du sel de sodium d'un dérivé oximiné de l'acide 7-amino thiazolyl acétamido céphalosporanique, son procédé de préparation et les compositions pharmaceutiques la renfermant
US5574154A (en) * 1994-09-29 1996-11-12 Alnejma Bulk Pharmaceutical Co. A.B.P.C. Process for the preparation of cephalosporanic compounds
WO1996020198A1 (fr) * 1994-12-23 1996-07-04 Biochemie Gesellschaft Mbh Production de cefotaxime et de nouveaux sels de sodium
US5945532A (en) * 1995-12-26 1999-08-31 Lupin Laboratories Limited Method for manufacture of cephalosporin and intermediates thereof

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102584854A (zh) * 2012-02-02 2012-07-18 瑞阳制药有限公司 头孢噻肟钠无水结晶的制备工艺
CN103275101A (zh) * 2013-05-17 2013-09-04 天津大学 制备头孢噻肟钠晶体的方法
CN103275101B (zh) * 2013-05-17 2015-08-05 天津大学 制备头孢噻肟钠晶体的方法
CN103319504A (zh) * 2013-06-28 2013-09-25 华北制药河北华民药业有限责任公司 一种头孢噻肟钠的结晶方法
CN104086569A (zh) * 2014-07-29 2014-10-08 石药集团中诺药业（石家庄）有限公司 一种头孢噻肟钠的制备方法
CN104892636A (zh) * 2015-05-21 2015-09-09 天津大学 一种制备头孢噻肟钠晶体的方法
CN109678669B (zh) * 2019-02-26 2024-01-09 广西科伦制药有限公司 一种将头孢噻肟钠生产母液中的乙酸乙酯与甲醇分离的装置
CN113024580A (zh) * 2021-03-10 2021-06-25 苏州东瑞制药有限公司 一种头孢噻肟钠的制备方法
CN114028336A (zh) * 2021-10-20 2022-02-11 华北制药河北华民药业有限责任公司 一种注射用头孢噻肟钠的制备方法

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