WO2007105253A8 - PREPARATION OF (1-OXA- OR l-THIA-)3- CEPHEM DERIVATIVES - Google Patents

PREPARATION OF (1-OXA- OR l-THIA-)3- CEPHEM DERIVATIVES

Info

Publication number
WO2007105253A8
WO2007105253A8 PCT/IT2007/000185 IT2007000185W WO2007105253A8 WO 2007105253 A8 WO2007105253 A8 WO 2007105253A8 IT 2007000185 W IT2007000185 W IT 2007000185W WO 2007105253 A8 WO2007105253 A8 WO 2007105253A8
Authority
WO
WIPO (PCT)
Prior art keywords
oxa
thia
cephem
tetrazol
alkyl
Prior art date
Application number
PCT/IT2007/000185
Other languages
French (fr)
Other versions
WO2007105253A3 (en
WO2007105253A2 (en
WO2007105253B1 (en
Inventor
Asta Leone Dall
Original Assignee
Carthesia S A S Di Emanuela Mi
Asta Leone Dall
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
Priority claimed from ITMI20060466 external-priority patent/ITMI20060466A1/en
Priority claimed from ITMI20061096 external-priority patent/ITMI20061096A1/en
Application filed by Carthesia S A S Di Emanuela Mi, Asta Leone Dall filed Critical Carthesia S A S Di Emanuela Mi
Priority to JP2009500008A priority Critical patent/JP2009530268A/en
Priority to EP07736690A priority patent/EP1996595A2/en
Publication of WO2007105253A2 publication Critical patent/WO2007105253A2/en
Publication of WO2007105253A3 publication Critical patent/WO2007105253A3/en
Publication of WO2007105253B1 publication Critical patent/WO2007105253B1/en
Publication of WO2007105253A8 publication Critical patent/WO2007105253A8/en

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
    • C07D501/02—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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D503/02—Preparation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D503/10—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D505/02—Preparation
    • C07D505/06—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D505/10—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D505/12—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 substituted in position 7
    • C07D505/14—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 substituted in position 7 with hetero atoms directly attached in position 7
    • C07D505/16—Nitrogen atoms

Abstract

There is described a process for the preparation of carboxy-protected 7β-amino-7α-methoxy-(l-oxa- or l-thia-)3-(l-substituted-lH-tetrazol-5-yl)thiomethyl-3- cephem-4-carboxylic acid. Said process comprises (a) reacting a carboxy- protected 7-amino-3-chloromethyl-(l-oxa- or 1-thia-) 3-cephem-4-carboxylate with an alkyl- or aryl-sulfenyl chloride; (b) reacting the corresponding 7-alkyl- or aryl-thioimino derivative with a l-(alkyl- o ω-hydroxyalkyl-)lH-tetrazol-5- ylthiol; and (c) reacting the corresponding 7-(alkyl- or aryl-)thioimino-3-(l- substituted-lH-tetrazol-5-yl)Momethyl- (1-oxa- or l-thia-)3-cephem with methanol in the presence of triphenylphosphine and aluminum chloride neutralized with a base. The reaction of the obtained carboxy-protected 7β-amino- 7α-methoxy-(1-oxa- or 1 -thia-)3 -(1-substituted- 1H-tetrazol-5 -yl)thiomethyl-3 - cephem-4-carboxylic acid with activated 2-(cyanomethylthio)acetic or 2- (difiuoromethyl thio)acetic acid affords, after final removal of the protecting ester group, cefmetazole and fiomoxef, respectively. The 7-(alkyl- or aryl)thioimino-3- (1-substituted-1H-tetrazol-5-yl)thiomethyl-1-dethia-1-oxa-3-cephem intermediates are new compounds.
PCT/IT2007/000185 2006-03-15 2007-03-14 PREPARATION OF (1-OXA- OR l-THIA-)3- CEPHEM DERIVATIVES WO2007105253A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2009500008A JP2009530268A (en) 2006-03-15 2007-03-14 Process for the preparation of (1-oxa- or 1-thia-) 3-cephem derivatives and related intermediates
EP07736690A EP1996595A2 (en) 2006-03-15 2007-03-14 PROCESS FOR THE PREPARATION OF (1-OXA- OR l-THIA-)3- CEPHEM DERIVATIVES AND RELATED INTERMEDIATES

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
ITMI2006A000466 2006-03-15
ITMI20060466 ITMI20060466A1 (en) 2006-03-15 2006-03-15 PROCEDURE FOR THE PREPARATION OF 1-OXA-O 1-TIA-3-CEFEN DERIVATIVES AND RELATED INTERMEDIATES
ITMI2006A001096 2006-06-06
ITMI20061096 ITMI20061096A1 (en) 2006-06-06 2006-06-06 PROCEDURE FOR THE PREPARATION OF (1-TIA-) 3-CEFEM DERIVATIVES

Publications (4)

Publication Number Publication Date
WO2007105253A2 WO2007105253A2 (en) 2007-09-20
WO2007105253A3 WO2007105253A3 (en) 2007-11-01
WO2007105253B1 WO2007105253B1 (en) 2007-12-06
WO2007105253A8 true WO2007105253A8 (en) 2008-10-30

Family

ID=38255802

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IT2007/000185 WO2007105253A2 (en) 2006-03-15 2007-03-14 PREPARATION OF (1-OXA- OR l-THIA-)3- CEPHEM DERIVATIVES

Country Status (4)

Country Link
EP (1) EP1996595A2 (en)
JP (1) JP2009530268A (en)
KR (1) KR20080111062A (en)
WO (1) WO2007105253A2 (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101787040B (en) * 2010-03-02 2011-09-07 哈药集团制药总厂 Method for preparing cefmetazole sodium
CN101792455B (en) * 2010-03-17 2012-07-04 河北九派制药有限公司 Preparation method of high-purity 7-alpha-amino-7-methoxy-3-methyltetrazole thiomethyl cephalosporin benzyl ester
CN101792454B (en) * 2010-03-17 2011-12-07 河北九派制药有限公司 Preparation method of 7-alpha amino 7-methoxyl-3-methly tetrazole sulfur methyl cafe-benzyl alkanoic acid
CN102675342A (en) * 2011-03-15 2012-09-19 四平市精细化学品有限公司 Preparation method of 7 beta-amino-7 alpha-methoxy-3-((1-methyl-1H-tetrazole-5-group) sulfomethyl)-3-cephem-4-diphenylmethyl carboxylate
CN102391291B (en) * 2011-09-21 2014-06-04 河北九派制药有限公司 Cefmetazole acid preparation method
JP2015524426A (en) * 2012-07-25 2015-08-24 ジェ イル ファルマシューティカル シーオー．， エルティーディー．Ｊｅ Ｉｌ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． Novel production method of 1-oxacephalosporin derivative
CN102850379B (en) * 2012-08-30 2015-08-12 三峡大学 The synthetic method of methoxy cephalosporin intermediate 7-MAC
CN102952149B (en) * 2012-11-09 2015-06-24 浙江新和成股份有限公司 One-pot synthesis method of flomoxef intermediate
CN104151324B (en) * 2014-09-03 2016-08-24 齐鲁天和惠世制药有限公司 A kind of solvent crystallization prepares the method for ampicillin
CN104327100B (en) * 2014-09-30 2016-09-28 华北制药河北华民药业有限责任公司 High-purity 6315-S preparation technology
CN104557978B (en) * 2014-12-31 2017-07-18 重庆福安药业(集团)股份有限公司 A kind of preparation method of cefmetazole sodium
CN105037393B (en) * 2015-06-24 2017-11-10 浙江永宁药业股份有限公司 A kind of preparation method of Flomoxef Sodium
CN105399755B (en) * 2015-11-03 2018-05-11 浙江永宁药业股份有限公司 A kind of synthetic method of Flomoxef acid
KR102115644B1 (en) * 2017-09-13 2020-05-27 주식회사 동도물산 Method of manufacturing 7α-alkoxy oxacephem intermediate compound
CN107722041B (en) * 2017-11-12 2020-05-05 广州维奥康药业科技有限公司 Preparation method of cefmetazole acid
CN109608478A (en) * 2018-11-15 2019-04-12 山东晶辉生物技术有限公司 A kind of synthetic method of Flomoxef acid
CN109970766A (en) * 2019-04-22 2019-07-05 山西千岫制药有限公司 A kind of preparation method of Flomoxef acid
CN110003241A (en) * 2019-04-23 2019-07-12 山西千岫制药有限公司 A kind of preparation method of latamoxef parent nucleus
CN110804635B (en) * 2019-11-11 2021-08-17 济南康和医药科技有限公司 Synthesis method of latamoxef sodium
CN114292283A (en) * 2022-01-24 2022-04-08 广州维奥康药业科技有限公司 Preparation method of cefmetazole sodium impurity for injection

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5417755B2 (en) * 1973-11-26 1979-07-02
US4109084A (en) * 1976-12-08 1978-08-22 E. R. Squibb & Sons, Inc. Thiooxime cephalosporin derivatives
JPS59139385A (en) * 1982-12-23 1984-08-10 Shionogi & Co Ltd Fluoromethylthiooxacephalosporin
JPS6348286A (en) * 1986-08-15 1988-02-29 Shionogi & Co Ltd Imino compound and production thereof
KR20000073152A (en) * 1999-05-07 2000-12-05 조생현 A Process for preparing 7-alpha-methoxy-cephalosporanic acid derivatives

Also Published As

Publication number Publication date
EP1996595A2 (en) 2008-12-03
KR20080111062A (en) 2008-12-22
JP2009530268A (en) 2009-08-27
WO2007105253A3 (en) 2007-11-01
WO2007105253A2 (en) 2007-09-20
WO2007105253B1 (en) 2007-12-06

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