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WO2013041999A4 - An improved process for cefpodoxime acid - Google Patents

An improved process for cefpodoxime acid Download PDF

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Publication number
WO2013041999A4
WO2013041999A4 PCT/IB2012/054602 IB2012054602W WO2013041999A4 WO 2013041999 A4 WO2013041999 A4 WO 2013041999A4 IB 2012054602 W IB2012054602 W IB 2012054602W WO 2013041999 A4 WO2013041999 A4 WO 2013041999A4
Authority
WO
WIPO (PCT)
Prior art keywords
acid
organic base
cefpodoxime
amino
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.)
Ceased
Application number
PCT/IB2012/054602
Other languages
French (fr)
Other versions
WO2013041999A1 (en
Inventor
Sandeep Singh
Alok Srivastava
Manish Dhanuka
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.)
Dhanuka Laboratories Ltd
Original Assignee
Dhanuka 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 Dhanuka Laboratories Ltd filed Critical Dhanuka Laboratories Ltd
Priority to EP12784684.8A priority Critical patent/EP2758407A1/en
Publication of WO2013041999A1 publication Critical patent/WO2013041999A1/en
Publication of WO2013041999A4 publication Critical patent/WO2013041999A4/en
Anticipated expiration legal-status Critical
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
    • C07D501/28—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by an aliphatic carboxylic acid, which is substituted by hetero atoms
    • 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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • C07D501/06—Acylation of 7-aminocephalosporanic acid

Landscapes

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

Abstract

The present invention relates to an improved process for the preparation of cefpodoxime acid from 7-Amino cephalosporanic acid. Further the preparation of cefpodoxime proxetil from cefpodoxime acid is also described.

Claims

AMENDED CLAIMS received by the International Bureau on 14.03.2013 We Claim:
1 . An improved process for the preparation of Cefpodoxime acid, said process comprisingsteps of:
a) reacting 7-amino-cephalosporanic acid with methane sulphonic acid or methane sulphonic acid/ trimethyl borate or Borontrifluoride Sulpholane complex in a protic solvent,
b) quenching the reaction mixture of step (a) by adding to chilled methanol, c) treating the solution of step (b) with first organic base to adjust the pH to a value of around 0,5, filtering the solid and obtaining clear filtrate,
d) treating the clear filtrate of step (C) with second organic base to adjust the pH between 3.3 to 3.5,
e) filtering the precipitated solid of step (d) to yield 7-amino-3-methoxymethyl-3- cephem carboxylic acid,
f) reacting 7-amino 3-methoxy methyl-3-cephem carboxylic acid with benzothiazole 2-yl-(z)-2-methoxy imino-2-(2-aminothiazole-4-yl) thioacetate in presence of organic based to obtained cefpodoxime acid.
2. The process of claim 1 , wherein in step(c) the first organic base used is ammonia inmethanol.
3. The process of claim 1 , wherein in step (d) the second organic base used is selectedfrom a group consisting of triethylamine, diethylamine, diisopropyl amine andtetramethyl guanidine.
4. A process for the preparation of Cefpodoxime proxetil comprising acylating cefpodoximeacid stated in claim 1(f) characterized in that the compoundCefpodoxime acid is producedby a process according to claiml .
PCT/IB2012/054602 2011-09-20 2012-09-06 An improved process for cefpodoxime acid Ceased WO2013041999A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12784684.8A EP2758407A1 (en) 2011-09-20 2012-09-06 An improved process for cefpodoxime acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2718DE2011 2011-09-20
IN2718/DEL/2011 2011-09-20

Publications (2)

Publication Number Publication Date
WO2013041999A1 WO2013041999A1 (en) 2013-03-28
WO2013041999A4 true WO2013041999A4 (en) 2013-06-13

Family

ID=47178227

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2012/054602 Ceased WO2013041999A1 (en) 2011-09-20 2012-09-06 An improved process for cefpodoxime acid

Country Status (2)

Country Link
EP (1) EP2758407A1 (en)
WO (1) WO2013041999A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN106478666B (en) * 2016-09-22 2018-07-31 湖北凌晟药业有限公司 The preparation method of 7- amino -3- methoxyl methyl -3- cephem -4- carboxylic acids
CN112480144A (en) * 2020-12-07 2021-03-12 湖北凌晟药业有限公司 Preparation method of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4409215A (en) 1979-11-19 1983-10-11 Fujisawa Pharmaceutical Co., Ltd. 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof
US4486425A (en) 1980-09-30 1984-12-04 Sankyo Company Limited 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylates
JPS57192392A (en) 1981-05-19 1982-11-26 Sankyo Co Ltd Production of 3-alkoxymethylcephalosporin
JPS5896091A (en) 1981-12-01 1983-06-07 Sankyo Co Ltd Preparation of 3-alkoxymethylcephalosporins
JPS59163387A (en) 1983-03-07 1984-09-14 Sankyo Co Ltd Preparation of 3-alkoxymethylcephalosporin
AT384222B (en) 1985-06-03 1987-10-12 Biochemie Gmbh METHOD FOR PRODUCING 7-AMINO-3ALKOXYMETHYL-3-CEPHEM-4-CARBONIC ACIDS
EP0262744B1 (en) 1986-10-02 1994-03-23 Asahi Kasei Kogyo Kabushiki Kaisha A process for preparing 3-alkoxymethylcephalosphorins
JPS63115887A (en) 1986-11-04 1988-05-20 Asahi Chem Ind Co Ltd Method for producing 7-amino-3-alkoxymethylcephalosporins
JP2612493B2 (en) 1988-05-24 1997-05-21 旭化成工業株式会社 Method for producing 3-substituted methyl-3-cephem-4-carboxylic acids
ATE123286T1 (en) * 1990-11-07 1995-06-15 Sankyo Co METHOD FOR PRODUCING 3-ALKOXYMETHYL CEPHALOSPORINE DERIVATIVES.
AU2003303657A1 (en) * 2003-01-06 2004-07-29 Lupin Limited A process for the manufacture of cefpodoxime proxetil
WO2011077217A1 (en) * 2009-12-21 2011-06-30 Nectar Lifesciences Ltd. An improved process for the preparation of cefpodoxime acid

Also Published As

Publication number Publication date
EP2758407A1 (en) 2014-07-30
WO2013041999A1 (en) 2013-03-28

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