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KR840005453A - 펜엠 유도체의 제조방법 - Google Patents

펜엠 유도체의 제조방법 Download PDF

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KR840005453A
KR840005453A KR1019830003078A KR830003078A KR840005453A KR 840005453 A KR840005453 A KR 840005453A KR 1019830003078 A KR1019830003078 A KR 1019830003078A KR 830003078 A KR830003078 A KR 830003078A KR 840005453 A KR840005453 A KR 840005453A
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KR900007181B1 (ko
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데비드 쿠케(외 1) 미카엘
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원본미기재
훽스트 유케이 리미티드
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D499/88—Compounds with a double bond between positions 2 and 3 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

내용 없음

Description

펜엠 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 다음 일반식(Ⅱ)화합물을 다음 그룹 R2를 함유하는 아실화제와 반응시키고 바람직하다면 하나 또는 그 이상의 다음(a) 내지 (h)공정을 바람직한 순서로 수행함을 특징으로 하는 다음 일반식(I)화합물 또는 이의 염의 제조방법.
  2. (a) 일반식(I)의 에스테르를 상응하는 유리산으로 전환시킴, (b) 일반식(I)의 유리산을 이의 에스테르로 전환시킴, (c) 일반식(I)화합물을 트란스 에스테르화시킴, (d) 일반식(I)의 유리산 또는 에스테르를 염으로 전환시킴, (e) 그룹 R을 에스테르화시키는 것 이외에 존재하는 보호그룹을 제거시킴, (f) 그룹 R2를 다른 그룹 R2로 전환시킴, (g) 그룹 R1치환체를 R1의 다른 치환체로 전환시킴, 및 (h) 그룹 R2치환체를 이의 다른 치환체로 전환시킴.
  4. 상기식에서, R은 수소원자 또는 카복실 에스테르 그룹이며, R1은 펜엠환 구조 2-위치에 부착된 산소원자에 대해 환탄소원자에 결합하는 페닐, 나프틸, 티에닐, 피리딜, 퀴놀릴 또는 이소퀴놀릴 그룹이고 R1은 비치환 또는 할로겐원자 및
  6. 그룹으로부터 채택한 같거나 또는 다를 수 있는 1,2또는 3치환체에 의해 치환될 수 있고(여기에서 R3, R3' 및 R3"는 각기 1 내지 4개의 탄소원자를 함유하는 알킬그룹이며, R3, R3' 및 R3"는 같거나 또는 다를 수 있다), R2는 (i) 수소원자, 또는 (ii) 비치환 또는 다음 (a) 내지 (h)로 부터 채택한 같거나 또는 다를 수 있는 하나 또는 그 이상의 치환체에 의해 치환된 1 내지 15개의 탄소원자를 함유하는 직쇄 또는 측쇄 알킬 그룹 : (a) 4이하의 탄소원자를 함유하는 알킬, 알케닐 및 알키닐 그룹; (b) 3 내지 7개의 탄소원자를 함유하는 사이클로 알킬 및 사이클로알케닐 그룹; (c) 비치환 또는 4이상의 탄소원자를 함유하는 알킬, 알킬티오 및 알콕시 그룹; 할로겐원자; 트리플루오로메틸그룹; 시아노그룹; 카복실그룹; R4가 4이하의 탄소원자를 함유하는 알킬 그룹인 일반식 -COOR4그룹; 아미도 및 설폰아미도 그룹; R5및 R6는 같거나 또는 다를 수 있는데 각기 수소원자 또는 R4가 상술한 바와 같은 -COR4, -SO2R4또는 R4그룹인 일반식의 그룹으로부터 채택한 같거나 또는 다를 수 있는 하나 또는 그 이상의 치환체에 의해 치환될 수 있는 아릴그룹; (d) 트리플루오로메틸 및 2,2,2-트리플루오로에틸그룹; (e) 할로겐원자; (f) 하이드록시그룹, 4이하의 탄소원자를 함유하는 알콕시그룹, 및 아릴잔기가 (c)항에서 상술한 바대로 치환될 수 있는 아릴옥시그룹, R2가 상술한 바와 같은 일반식 R2CO2-의 아실옥시 그룹 및 일반식 R2CO-의 아실그룹; (g) 시아노 및 아지도 그룹; 및 (h) 아미노 그룹 및 R5및 R6가 (c)항에서 상술한 바와 같은 일반식의 그룹; 또는 (iii) 비치환 또는 알킬그룹 R2에 대해 상술한 바대로 치환될 수 있고 3내지 7개의 탄소원자를 함유하는 또는 사이클로알킬그룹; (iv) 비치환 또는 (c)항에서 상술한 바대로 치환될 수 있는 아릴그룹을 나타낸다.
  7. 제1항에 있어서, 다음 일반식(Ⅲ) 화합물과 염기와 반응시킴을 특징으로 하는 제1항의 일반식(Ⅱ) 화합물의 제조방법.
  9. 상기식에서 R 및 R1은 상술한 바와 같고, R9는 1 내지 4의 탄소원자를 함유하는 알킬그룹 또는 페닐그룹이며, R10은 염소 또는 브롬원자이다.
  10. 제2항에 있어서, 다음 일반식(Ⅳ) 화합물을 할로겐화시킴을 특징으로 하는 제2항의 일반식(Ⅲ)화합물의 제조방법.
  12. 상기식에서, R, R1, R9는 상술한 바와 같고, R8은 1 내지 8, 바람직하게는 1 내지 4의 탄소원자를 함유하는 알킬그룹, 4이하의 탄소원자를 함유하는 알케닐그룹, 또는 페닐 그룹이다.
  13. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019830003078A 1982-07-08 1983-07-06 펜엠 유도체의 제조방법 KR900007181B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB8219745 1982-07-08
GB19745 1982-07-08
GB8219745 1982-07-08

Publications (2)

Publication Number Publication Date
KR840005453A true KR840005453A (ko) 1984-11-12
KR900007181B1 KR900007181B1 (ko) 1990-09-29

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KR1019830003078A KR900007181B1 (ko) 1982-07-08 1983-07-06 펜엠 유도체의 제조방법

Country Status (22)

Country Link
US (1) US4738959A (ko)
EP (1) EP0099059B1 (ko)
JP (1) JPS5921693A (ko)
KR (1) KR900007181B1 (ko)
AT (1) ATE35270T1 (ko)
AU (1) AU567103B2 (ko)
CA (1) CA1227194A (ko)
DE (1) DE3377132D1 (ko)
DK (1) DK314483A (ko)
ES (3) ES523890A0 (ko)
FI (1) FI77662C (ko)
GB (2) GB2122619B (ko)
GR (1) GR78890B (ko)
HU (3) HU193460B (ko)
IE (1) IE55581B1 (ko)
IL (1) IL69174A0 (ko)
MA (1) MA19842A1 (ko)
NO (3) NO832487L (ko)
NZ (1) NZ204829A (ko)
PH (1) PH23148A (ko)
PT (1) PT76996B (ko)
ZA (1) ZA834955B (ko)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE28648T1 (de) * 1982-03-26 1987-08-15 Hoechst Uk Ltd 7-oxo-4-thia-1-azabicyclo(3,2,0)heptan-derivate
GB8416565D0 (en) * 1984-06-29 1984-08-01 Hoechst Uk Ltd Antibacterial derivatives
GB2197864B (en) * 1984-06-29 1989-05-17 Hoechst Uk Ltd Antibacterial 7-oxo-4-thia-1-azabicyclo(3.2.0)-hept-2-ene derivatives
GB2197865B (en) * 1984-06-29 1989-05-17 Hoechst Uk Ltd Azetidinone derivatives
GB2164334B (en) * 1984-09-10 1988-08-03 Hoechst Uk Ltd Antibacterial 7-oxo-4-thia-1-azabicyclo 3,2,0 hept-2-ene derivativess
JPS61236785A (ja) * 1985-04-15 1986-10-22 Sankyo Co Ltd アゼチジノン誘導体
US4868296A (en) * 1985-10-29 1989-09-19 Pfizer Inc. 6-(1-carbamoyl-1-hydroxymethyl) penicillanic acid derivatives
US4797394A (en) * 1985-10-29 1989-01-10 Pfizer Inc. 6-(1-carbamoyl-1-hydroxymethyl)penicillanic acid derivatives
JPS62179860A (ja) * 1986-01-31 1987-08-07 Sintokogio Ltd 低圧鋳造装置

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4168314A (en) * 1977-11-17 1979-09-18 Merck & Co., Inc. 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
US4301074A (en) * 1977-11-17 1981-11-17 Merck & Co., Inc. 6-(1'-Hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid
EP0003960B1 (de) * 1978-02-02 1983-06-29 Ciba-Geigy Ag 6-Substituierte Thia-Azaverbindungen, ihre Herstellung und diese enthaltende pharmazeutische Präparate
JPS5625110A (en) * 1978-12-18 1981-03-10 Bristol Myers Co Antibacterial
JPS56115788A (en) * 1980-02-19 1981-09-11 Sankyo Co Ltd Azetidinone derivative and its preparation
US4395418A (en) * 1980-06-06 1983-07-26 Sankyo Company Limited Penem-3-carboxylic acid derivatives
GB2083462B (en) * 1980-08-16 1984-05-02 Beecham Group Ltd 2-thiopenem derivatives
US4347183A (en) * 1981-02-02 1982-08-31 Schering Corporation Process for the synthesis of penems and carbapenems
US4431658A (en) * 1981-02-02 1984-02-14 Schering Corporation Aza penem compounds
ES8305366A1 (es) * 1981-07-08 1983-04-01 Hoechst Uk Ltd "procedimiento para la preparacion de derivados de penem".
EP0069378B1 (en) * 1981-07-08 1987-01-07 Hoechst Uk Limited Antibacterial penem derivatives

Also Published As

Publication number Publication date
HU193460B (en) 1987-10-28
GB2160865A (en) 1986-01-02
ZA834955B (en) 1984-03-28
GR78890B (ko) 1984-10-02
PT76996B (en) 1986-03-12
ES8602013A1 (es) 1985-11-01
EP0099059B1 (en) 1988-06-22
FI77662C (fi) 1989-04-10
DK314483A (da) 1984-01-09
KR900007181B1 (ko) 1990-09-29
GB2122619B (en) 1986-01-08
US4738959A (en) 1988-04-19
ATE35270T1 (de) 1988-07-15
AU567103B2 (en) 1987-11-12
GB8515248D0 (en) 1985-07-17
ES539161A0 (es) 1985-11-01
FI77662B (fi) 1988-12-30
NO842960L (no) 1984-01-09
PT76996A (en) 1983-08-01
FI832479A0 (fi) 1983-07-06
FI832479L (fi) 1984-01-09
AU1665383A (en) 1984-01-12
IE831592L (en) 1984-01-08
HU193459B (en) 1987-10-28
HU192819B (en) 1987-07-28
IL69174A0 (en) 1983-11-30
DE3377132D1 (en) 1988-07-28
CA1227194A (en) 1987-09-22
GB2122619A (en) 1984-01-18
GB8318513D0 (en) 1983-08-10
GB2160865B (en) 1986-11-26
ES539160A0 (es) 1985-11-01
JPS5921693A (ja) 1984-02-03
NO832487L (no) 1984-01-09
IE55581B1 (en) 1990-11-07
NO841108L (no) 1984-01-09
ES8504203A1 (es) 1985-04-01
DK314483D0 (da) 1983-07-07
ES523890A0 (es) 1985-04-01
HUT40622A (en) 1987-01-28
ES8601875A1 (es) 1985-11-01
MA19842A1 (fr) 1984-04-01
EP0099059A1 (en) 1984-01-25
PH23148A (en) 1989-05-11
NZ204829A (en) 1986-07-11

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