WO2005076694A3 - Improved process for the production of cefotaxime sodium - Google Patents

Improved process for the production of cefotaxime sodium Download PDF

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Publication number
WO2005076694A3
WO2005076694A3 PCT/IB2004/000090 IB2004000090W WO2005076694A3 WO 2005076694 A3 WO2005076694 A3 WO 2005076694A3 IB 2004000090 W IB2004000090 W IB 2004000090W WO 2005076694 A3 WO2005076694 A3 WO 2005076694A3
Authority
WO
WIPO (PCT)
Prior art keywords
syn
production
amino
cephem
acetoxymethyl
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/IB2004/000090
Other languages
French (fr)
Other versions
WO2005076694A2 (en
Inventor
Mukarram Siddiqui Moham Jaweed
Rashid Abdul Rehman Khan
Ram Prasad Yadav
Mohammed Younus Khan
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.)
Wockhardt Ltd
Original Assignee
Wockhardt 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 Wockhardt Ltd filed Critical Wockhardt Ltd
Priority to EP04702760A priority Critical patent/EP1704153A2/en
Priority to PCT/IB2004/000090 priority patent/WO2005076694A2/en
Publication of WO2005076694A2 publication Critical patent/WO2005076694A2/en
Publication of WO2005076694A3 publication Critical patent/WO2005076694A3/en
Anticipated expiration legal-status Critical
Priority to US11/487,959 priority patent/US20070004916A1/en
Ceased legal-status Critical Current

Links

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
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

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

Abstract

A process for the production of 7-[2-(2-amino-4-thiazolyl)-2-syn-methoxyimino-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (Cefotaxime) in aqueous isopropyl alcohol is discussed. The synthesis is effected by condensing 7-aminocephalosporanic acid (7-ACA) with 2-(2-chloroacetamidothiazol-4-yl)-2-syn-methoxyiminoacetyl chloride followed by deblocking amino function by thiourea in basic medium. Finally, 7-[2-(2-amino-4-thiazolyl)-2- syn- methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid is converted into sodium salt with sodium-2-ethylhexanoate in solvent mixture of ethyl acetate and methanol in presence of triethylamine in more than 99 % HPLC purity.
PCT/IB2004/000090 2004-01-16 2004-01-16 Improved process for the production of cefotaxime sodium Ceased WO2005076694A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP04702760A EP1704153A2 (en) 2004-01-16 2004-01-16 Improved process for the production of cefotaxime sodium
PCT/IB2004/000090 WO2005076694A2 (en) 2004-01-16 2004-01-16 Improved process for the production of cefotaxime sodium
US11/487,959 US20070004916A1 (en) 2004-01-16 2006-07-17 Process for the production of cefotaxime sodium

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2004/000090 WO2005076694A2 (en) 2004-01-16 2004-01-16 Improved process for the production of cefotaxime sodium

Publications (2)

Publication Number Publication Date
WO2005076694A2 WO2005076694A2 (en) 2005-08-25
WO2005076694A3 true WO2005076694A3 (en) 2005-12-01

Family

ID=34856828

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2004/000090 Ceased WO2005076694A2 (en) 2004-01-16 2004-01-16 Improved process for the production of cefotaxime sodium

Country Status (3)

Country Link
US (1) US20070004916A1 (en)
EP (1) EP1704153A2 (en)
WO (1) WO2005076694A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011117421A1 (en) 2011-11-02 2013-05-02 Hans-Peter Gabel Pharmaceutical composition useful for treating Lyme disease, comprises mixture of active substances including ceftriaxone and cefotaxime
CN102584854A (en) * 2012-02-02 2012-07-18 瑞阳制药有限公司 Preparation technology of anhydrous crystal of cefotaxime sodium
CN109081847A (en) * 2017-06-14 2018-12-25 郝志艳 A kind of 1/2 water cefotaxime sodium compound
CN114028336B (en) * 2021-10-20 2023-04-04 华北制药河北华民药业有限责任公司 Preparation method of cefotaxime sodium for injection
CN116617234A (en) * 2023-04-24 2023-08-22 南京恩泰医药科技有限公司 Preparation process of cefotaxime sodium powder for injection

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278671A (en) * 1976-04-14 1981-07-14 Takeda Chemical Industries, Ltd. 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido] cephalosporins
US4616081A (en) * 1982-07-07 1986-10-07 Asahi Kasei Kogyo Kabushiki Kaisha Cephalosporin compounds

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK154939C (en) * 1974-12-19 1989-06-12 Takeda Chemical Industries Ltd METHOD OF ANALOGUE FOR THE PREPARATION OF THIAZOLYLACETAMIDO-CEPHEM COMPOUNDS OR PHARMACEUTICAL ACCEPTABLE SALTS OR ESTERS THEREOF
DE2760123C2 (en) * 1976-01-23 1986-04-30 Roussel-Uclaf, Paris 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporanic acids, their preparation and pharmaceutical compositions containing them
CY1365A (en) * 1980-03-28 1987-08-07 Biochemie Gmbh New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production
ES2006988A6 (en) * 1988-06-20 1989-05-16 Gema Sa Process for preparing cephalosporins and intermediates therefor.
IT1234385B (en) * 1989-05-23 1992-05-18 Sbd Synthetic And Biolog Devel IMPROVED PROCEDURE FOR THE PRODUCTION OF AN ANTIBIOTIC SUBSTANCE BELONGING TO THE CEPHALOSPORINE GROUP
KR950014571B1 (en) * 1991-11-18 1995-12-08 제일제당주식회사 Method for producing cefem derivatives
GB9216759D0 (en) * 1992-08-07 1992-09-23 Finpael Spa Process for the production of 7-amino thiazolyl cephalosporins

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278671A (en) * 1976-04-14 1981-07-14 Takeda Chemical Industries, Ltd. 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido] cephalosporins
US4616081A (en) * 1982-07-07 1986-10-07 Asahi Kasei Kogyo Kabushiki Kaisha Cephalosporin compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
OCHIAI M. ET AL: "Synthesis and structure-activity relationships of 7-beta-[2-(2-aminothiazol-4-yl)acetamido]cephalosporin derivatives: V.Synthesis and antibacterial activity of 7-beta[2-aminothiazol-4-yl2-methoxyiminoacetamido]-cephalosporin Derivatives and related Compounds", J. ANTIBIOTICS, vol. 34, no. 2, February 1981 (1981-02-01), pages 171 - 185, XP009007625 *

Also Published As

Publication number Publication date
EP1704153A2 (en) 2006-09-27
US20070004916A1 (en) 2007-01-04
WO2005076694A2 (en) 2005-08-25

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