WO2008111487A1 - ６－ヒドロキシエチルペナム化合物の製造方法 - Google Patents

６－ヒドロキシエチルペナム化合物の製造方法 Download PDF

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Publication number
WO2008111487A1
WO2008111487A1 PCT/JP2008/054057 JP2008054057W WO2008111487A1 WO 2008111487 A1 WO2008111487 A1 WO 2008111487A1 JP 2008054057 W JP2008054057 W JP 2008054057W WO 2008111487 A1 WO2008111487 A1 WO 2008111487A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
hydroxyethylpenam
producing
general formula
produced
Prior art date
Application number
PCT/JP2008/054057
Other languages
English (en)
French (fr)
Inventor
Hideo Tanaka
Manabu Kuroboshi
Syoichi Tateyama
Takae Yamada
Yutaka Kameyama
Original Assignee
National University Corporation Okayama University
Otsuka Chemical Co., 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 National University Corporation Okayama University, Otsuka Chemical Co., Ltd. filed Critical National University Corporation Okayama University
Priority to JP2009504010A priority Critical patent/JP5300713B2/ja
Priority to KR20097020983A priority patent/KR101491868B1/ko
Priority to ES08721477T priority patent/ES2398258T3/es
Priority to EP08721477A priority patent/EP2123657B1/en
Priority to US12/530,307 priority patent/US8293893B2/en
Priority to CN2008800072981A priority patent/CN101646680B/zh
Publication of WO2008111487A1 publication Critical patent/WO2008111487A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/04—Preparation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/86—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and 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
    • C07D499/861—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and 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 with a hydrocarbon radical or a substituted hydrocarbon radical, directly attached in position 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/897—Compounds with substituents other than a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, directly attached in position 2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

　本発明は、一般式（２）で表される６－ヒドロキシエチルペナム化合物を高い選択率で製造し得る方法を提供する。一般式（１） ［式中、Ｒは水素原子又はカルボン酸保護基を示す。Ｘ1及びＸ2は、各々ハロゲン原子を示す。］で表されるハロゲノペナム化合物にグリニャール試薬を反応させ、次いで生成する化合物にアミン化合物を反応させ、更に生成する化合物にアセトアルデヒドを反応させることにより、一般式（２） ［式中、Ｒ及びＸ2は前記に同じ。］で表される６－ヒドロキシエチルペナム化合物を、高い選択率で製造できる。
PCT/JP2008/054057 2007-03-09 2008-03-06 ６－ヒドロキシエチルペナム化合物の製造方法 WO2008111487A1 (ja)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2009504010A JP5300713B2 (ja) 2007-03-09 2008-03-06 ６−ヒドロキシエチルペナム化合物の製造方法
KR20097020983A KR101491868B1 (ko) 2007-03-09 2008-03-06 ６-히드록시에틸페남 화합물의 제조 방법
ES08721477T ES2398258T3 (es) 2007-03-09 2008-03-06 Procedimiento para producir un compuesto 6-hidroxieltil penam
EP08721477A EP2123657B1 (en) 2007-03-09 2008-03-06 Method for producing 6-hydroxyethylpenam compound
US12/530,307 US8293893B2 (en) 2007-03-09 2008-03-06 Method for producing 6-hydroxyethylpenam compound
CN2008800072981A CN101646680B (zh) 2007-03-09 2008-03-06 制备6-羟乙基青霉烷化合物的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007059496 2007-03-09
JP2007-059496 2007-03-09

Publications (1)

Publication Number Publication Date
WO2008111487A1 true WO2008111487A1 (ja) 2008-09-18

Family

ID=39759429

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/054057 WO2008111487A1 (ja) 2007-03-09 2008-03-06 ６－ヒドロキシエチルペナム化合物の製造方法

Country Status (7)

Country Link
US (1) US8293893B2 (ja)
EP (1) EP2123657B1 (ja)
JP (1) JP5300713B2 (ja)
KR (1) KR101491868B1 (ja)
CN (1) CN101646680B (ja)
ES (1) ES2398258T3 (ja)
WO (1) WO2008111487A1 (ja)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5665892A (en) * 1979-10-22 1981-06-03 Pfizer 6 betaahydroxyalkylpenicillaic acid derivative as betaalactamase inhibitor
JPS59112989A (ja) * 1982-12-08 1984-06-29 フア−ミタリア・カルロ・エルバ・ソシエタ・ペル・アツイオ−ニ （５ｒ）ペネム誘導体の製法
JPS61171485A (ja) * 1984-04-06 1986-08-02 ブリストル―マイアーズ　スクイブ　コムパニー カルバペネム及びペネム抗生物質の合成に有用な中間体、ならびにその製法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304779A (en) * 1979-05-09 1981-12-08 Schering Corporation 6-(Nitrogen-containing heterocyclic)hydroxymethylpenicillanic acids, compounds related thereto and processes for their preparation
FI77459C (fi) * 1982-12-08 1989-03-10 Erba Farmitalia Foerfarande foer framstaellning av (5r)-penemderivat.
US4762921A (en) * 1985-04-18 1988-08-09 Pfizer Inc. 6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
US4868296A (en) * 1985-10-29 1989-09-19 Pfizer Inc. 6-(1-carbamoyl-1-hydroxymethyl) penicillanic acid derivatives
US4782050A (en) * 1987-01-27 1988-11-01 Pfizer Inc. 6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives thereof
JPH0721746B2 (ja) 1988-07-14 1995-03-08 横河電機株式会社 データメモリ装置
MY112170A (en) * 1994-09-02 2001-04-30 Sec Dep For Defence Acting Through His Defence Evaluation And Research Agency United Kingdom Metalorganic compounds
CN101220050B (zh) * 2008-02-02 2010-06-09 河北工业大学 (3r,4r)-3-[(1r)叔丁基二甲基硅氧乙基]-4-乙酰氧基-2-氮杂环丁酮的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5665892A (en) * 1979-10-22 1981-06-03 Pfizer 6 betaahydroxyalkylpenicillaic acid derivative as betaalactamase inhibitor
JPS59112989A (ja) * 1982-12-08 1984-06-29 フア−ミタリア・カルロ・エルバ・ソシエタ・ペル・アツイオ−ニ （５ｒ）ペネム誘導体の製法
JPH0225914B2 (ja) 1982-12-08 1990-06-06 Erba Farmitalia
JPS61171485A (ja) * 1984-04-06 1986-08-02 ブリストル―マイアーズ　スクイブ　コムパニー カルバペネム及びペネム抗生物質の合成に有用な中間体、ならびにその製法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"Saishin Kouseizai Yoko", pages: 92
J. ORG. CHEM., vol. 42, 1977, pages 2960
KUROBOSHI M. ET AL.: "Diastereoselective synthesis of 6-bromo-6-(1-hydroxyethyl)penicillanate by cross-coupling of 6,6-dibromopenicillanate and acetaldehyde promoted with Grignard reagents: role of amine ligands", HETEROCYCLES, vol. 73, 17 August 2007 (2007-08-17), pages 877 - 882, XP008112525 *
See also references of EP2123657A4

Also Published As

Publication number Publication date
JP5300713B2 (ja) 2013-09-25
US20100113769A1 (en) 2010-05-06
KR101491868B1 (ko) 2015-02-09
EP2123657B1 (en) 2012-11-21
CN101646680B (zh) 2013-02-20
ES2398258T3 (es) 2013-03-14
EP2123657A1 (en) 2009-11-25
US8293893B2 (en) 2012-10-23
JPWO2008111487A1 (ja) 2010-06-24
EP2123657A4 (en) 2010-03-24
CN101646680A (zh) 2010-02-10
KR20090121377A (ko) 2009-11-25

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