KR870002111A - 글루타콘산 유도체의 제조방법 - Google Patents

글루타콘산 유도체의 제조방법 Download PDF

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KR870002111A
KR870002111A KR1019850005992A KR850005992A KR870002111A KR 870002111 A KR870002111 A KR 870002111A KR 1019850005992 A KR1019850005992 A KR 1019850005992A KR 850005992 A KR850005992 A KR 850005992A KR 870002111 A KR870002111 A KR 870002111A
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South Korea
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acid derivative
base
alkoxy
acetic acid
alkyl
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KR1019850005992A
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KR920003897B1 (ko
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히로시 오노우에
히로미 다까하시
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요시또시 가즈오
시오오니세이야꾸 가부시끼가이샤
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음

Description

글루타콘산 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 염기의 존재하에서 티아졸 아세트산 유도체(I)와 알콕시아크릴산 유도체(Ⅱ)를 미카엘형 축합반응(Michael type condensation)시킴을 특징으로 하는 글루타콘산 유도체(Ⅱ)의 제조방법.
    (식중, R는 아미노 또는 보호 아미노이고; R1는 에스테르 형성기이고; R2는 수소, 시아노 또는 에스테르화 카르복시이고; R3는 수소, 시아노 또는 에스테르화 카르복시이고; 및, R4는 저급 알킬 또는 아르알킬이다)
  2. 제 1 항에 있어서, 보호 아미노 R의 보호기가 1C∼5C 알카노일, 할로-(1C∼5C)-알카노일, 2C∼6C알콕시포르밀, 8C-15C 아르알콕시포르밀, 또는 3C∼8C 알킬리덴 또는 아르알킬리덴인 방법.
  3. 제 1 항에 있어서, 에스테르 형성기 R1및 에스테르화 카르복시 R2및 R3의 보호기가 각각 1C∼8C알킬, 할로겐에 의해 치환된 1C∼5C 알킬, 1C∼5C 알콕시 또는 2C∼5C 설포닐, 7C∼15C 알케닐, 또는 7C∼15C 아르알킬인 방법.
  4. 제 1 항에 있어서, R4가 1C∼5C 알킬 또는 7C∼15C 아르알킬인 방법.
  5. 제 1 항에 있어서, 티아졸아세트산 유도체(I)를 염기와 반응시켜 활성 메틸렌을 카르보아니온(Ia)으로 전환시키고, 이 카르보아니온을 알콕시아크릴산 유도체(Ⅱ)와 미카엘(Michael)형 부가반응시켜 알콕시글루타르산 유도체(Ib)를 수득하고, 후자로 부터 알코올 R4OH를 이탈시킴으로써 글루타콘산 유도체(Ⅲ)를 수득함을 특징으로 하는 방법.
    (식중 R,R1,R2,R3및 R4는 제 1 항에서 정의한 바와 동일하다.)
  6. 제 1 항에 있어서, 티아졸아세트산 유도체, 알콕시 아크릴산 유도체 및 염기를 혼합함으로써 글루타콘산 유도체를 수득하는 방법.
  7. 제 6 항에 있어서, R3이 수소인 방법.
  8. 제 1 항에 있어서, 염기가 알칼리금속의 수소화물 또는 알콕시화물인 방법.
  9. 제 1 항에 있어서, 반응을 탄화수소, 에테르, 니트릴, 설폭시드, 아미드 또는 에스테르 용매 또는 이들의 혼합물중에서 선택된 용매내에서 수행하는 방법.
  10. 제 1 항에 있어서, -20∼70℃에서 5분∼10시간 동안 2∼5몰당량의 염기가 존재하는 3∼20중량부의 용매내에서 1∼3당량의 알콕시아크릴산 유도체(Ⅱ)를 티아졸아세트산 유도체(I)로 처리하는 방법.
  11. 제 10 항에 있어서, 알콕시-아크릴산 유도체를 반응용매로서 사용하는 방법.
  12. 제 1 항에 있어서, 생성물을 가수분해함으로써, 하기 일반식의 글루타콘산 유도체를 수득하는 방법.
    (식중 R는 제 1 항에서 정의한 바와 동일하다).
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850005992A 1984-08-24 1985-08-20 글루타콘산 유도체의 제조방법 KR920003897B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP176954 1984-08-24
JP59176954A JPS6153272A (ja) 1984-08-24 1984-08-24 グルタル酸誘導体の製法

Publications (2)

Publication Number Publication Date
KR870002111A true KR870002111A (ko) 1987-03-30
KR920003897B1 KR920003897B1 (ko) 1992-05-18

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Application Number Title Priority Date Filing Date
KR1019850005992A KR920003897B1 (ko) 1984-08-24 1985-08-20 글루타콘산 유도체의 제조방법

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US (1) US4713461A (ko)
EP (1) EP0172463B1 (ko)
JP (1) JPS6153272A (ko)
KR (1) KR920003897B1 (ko)
DE (1) DE3577555D1 (ko)
GB (1) GB2163431B (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6124580A (ja) * 1984-07-12 1986-02-03 Shionogi & Co Ltd アミノチアゾリルグルタル酸誘導体の製造方法
JPH0867676A (ja) * 1994-03-30 1996-03-12 Eisai Kagaku Kk 保護アミノチアゾリル酢酸誘導体

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3037997A1 (de) * 1980-10-08 1982-05-13 Bayer Ag (beta) -lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel
DE3037912A1 (de) * 1980-10-08 1982-05-27 Agfa-Gevaert Ag, 5090 Leverkusen Lichtempfindliches fotografisches silberhalogenid-aufzeichnungsmaterial
DE3145727A1 (de) * 1981-11-19 1983-05-26 Bayer Ag, 5090 Leverkusen Zwischenprodukte, verfahren zu deren herstellung und verfahren zur herstellung von cephalosporinen
JPS6034957A (ja) * 1983-08-05 1985-02-22 Meiji Seika Kaisha Ltd ２−置換メチレン−２−（２−アミノチアゾ−ル−４−イル）酢酸誘導体及びその製造方法
AU575854B2 (en) * 1983-10-04 1988-08-11 Shionogi & Co., Ltd. 7beta-(carboxyalkenamido) cephalosporins
JPS6124580A (ja) * 1984-07-12 1986-02-03 Shionogi & Co Ltd アミノチアゾリルグルタル酸誘導体の製造方法

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Publication number Publication date
EP0172463B1 (en) 1990-05-09
US4713461A (en) 1987-12-15
EP0172463A1 (en) 1986-02-26
DE3577555D1 (de) 1990-06-13
JPH0577670B2 (ko) 1993-10-27
GB8521035D0 (en) 1985-09-25
JPS6153272A (ja) 1986-03-17
GB2163431A (en) 1986-02-26
GB2163431B (en) 1988-06-29
KR920003897B1 (ko) 1992-05-18

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