KR850001757A - 페넴화합물의 제조방법 - Google Patents

페넴화합물의 제조방법

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Publication number
KR850001757A
KR850001757A KR1019840004797A KR840004797A KR850001757A KR 850001757 A KR850001757 A KR 850001757A KR 1019840004797 A KR1019840004797 A KR 1019840004797A KR 840004797 A KR840004797 A KR 840004797A KR 850001757 A KR850001757 A KR 850001757A
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KR
South Korea
Prior art keywords
group
compound
iii
hydroxy
carbon atoms
Prior art date
Application number
KR1019840004797A
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English (en)
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KR910002098B1 (ko
Inventor
바티스티니(외3) 칼로
Original Assignee
죠지오 올란도
팜이탈리아 칼로 에르바 에스. 피. 에이.
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.)
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Publication of KR850001757A publication Critical patent/KR850001757A/ko
Application granted granted Critical
Publication of KR910002098B1 publication Critical patent/KR910002098B1/ko

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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
    • C07D499/04—Preparation
    • C07D499/06—Preparation by forming the ring or condensed ring systems
    • 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
    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음

Description

페넴화합물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 다음 일반식(Ⅱ)의 아제티디논유도체를 불활성 용매중 110 내지 150℃의 온도에서 2시간 내지 수일간 2몰 당량까지의 3가 유기인 화합물과 반응시킴을 특징으로 하여, 다음 일반식(Ⅰ)의 화합물을 제조하는 방법;
    상기 식에서 R1은 유기그룹이고, R2는 수소원자 또는 카복시보호그룹이며, X는 (ⅰ) 임의로 보호된 하이드록시 그룹, (ⅱ) 할로겐 원자, (ⅲ) 아지도 그룹, (ⅳ) 임의로 치환된 피리딜 그룹, (ⅴ) 포밀옥시그룹, 탄소수 2 내지 6의 비치환된 아실옥시그룹, 또는 탄소수 2 내지 6이고 하나 이상의 할로겐원자, 탄소수 2 내지 6의 아실그룹, 아미노, 하이드록시 또는 머르캅토그룹으로 치환된 아실옥시그룹(여기에서 아미년, 하이드록시 또는 머르캅토그룹은 유리형태이거나 보호된 형태이다), (ⅵ) 카바모일옥시 또는 N-알킬-카바모일옥시그룹, (ⅶ) 각각 탄소수 1 내지 12이고, 하나 이상의 할로겐원자, 포밀그룹, 탄소수 2 내지 6의 아실그룹, 아미노, 하이드록시 또는 머르캅토그룹(여기에서, 아미노, 머르캅토 또는 하이드록시 그룹은 유리형태이거나 보호된 형태이다)으로 치환되거나 비치환된 알콕시 또는 알킬티오그룹, (ⅷ) 트리아릴메틸티오그룹 또는 (ⅸ) 헤테로 시클릴티오 그룹이다.
  2. 제1항에 있어서, 반응을 약 140℃에서 5 내지 15시간동안 수행하는 방법.
  3. 제1항에 있어서, 상기의 불활성 용매가 톨루엔, 크실렌 및 디메틸포름아미드로 이루어진 그룹중에서 선택되는 방법.
  4. 제1항에 있어서, 상기의 유기인 화합물이 시클릭 또는 아시클륵 트리알킬포스파이트, 트리아릴 포스파이트, 혼합된 아릴포스파이트 및 포스포르아미드로 이루어진 그룹중에서 선택되는 방법.
  5. 제1항에 있어서, 상기의 불활성 용매가 크실렌이고, 상기의 유기인 화합물이 트리메틸포스파이트이며 상기의 반응을 약 140℃에서 5 내지 15시간동안 수행하는 방법.
  6. 제5항에 있어서, 상기의 아제티디논 유도체가 다음 일반식(Ⅱ')의 화합물이고, 이 화합물로부터 다음 일반식(Ⅰ')의 화합물을 제조하는 방법.
    상기식에서 R2는 제1항에 정의한 바와 같으며, R3는 수소원자 또는 하이드록시보호그룹이고, X'는 임의로 보호된 하이드록시 또는 카바모일 옥시그룹이다.
  7. 제6항에 있어서, 일반식(Ⅱ')의 아제티디논 유도체가 4β-t-부틸디 페닐 실릴글리콜로일티오-3-α-[1(R)-t-부틸디메틸실릴옥시에틸]-1-알릴옥시옥살릴-아제티딘-2-온이고, 이 유도체로부터 알릴(5R, 6S)-2-t- 부틸디페닐실릴옥시메틸-6-[1(R)-t-부틸디메틸실릴옥시에틸]-페넴-3-카복실레이트를 제조하는 방법.
  8. 제6항에 있어서, 일반식(Ⅱ')의 아제티디논 유도체가 4β-카바모일글리콜로일티오-3α-[1(R)-트리클로로에톡시카보닐옥시에틸]-1-(아세톡시메틸옥살릴)-아제티딘-2-온이고, 이 유도체로부터 아세톡시메틸(5R, 6S)-2-카바모일옥시-메틸-6-[1(R)-트리클로로에톡시카보닐옥시에틸]-페넴-3-카복실레이트를 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840004797A 1983-08-11 1984-08-10 페넴 화합물의 제조방법 KR910002098B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8321677 1983-08-11
GB838321677A GB8321677D0 (en) 1983-08-11 1983-08-11 Preparation of penems

Publications (2)

Publication Number Publication Date
KR850001757A true KR850001757A (ko) 1985-04-01
KR910002098B1 KR910002098B1 (ko) 1991-04-03

Family

ID=10547172

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019840004797A KR910002098B1 (ko) 1983-08-11 1984-08-10 페넴 화합물의 제조방법

Country Status (20)

Country Link
US (1) US4631150A (ko)
JP (1) JPS6058988A (ko)
KR (1) KR910002098B1 (ko)
AT (1) AT383808B (ko)
BE (1) BE900316A (ko)
CA (1) CA1279640C (ko)
CH (1) CH663024A5 (ko)
DE (1) DE3429102A1 (ko)
DK (1) DK167926B1 (ko)
ES (1) ES8600306A1 (ko)
FI (1) FI83521C (ko)
FR (1) FR2550533B1 (ko)
GB (2) GB8321677D0 (ko)
GR (1) GR80102B (ko)
HU (1) HU192415B (ko)
IL (1) IL72612A (ko)
IT (1) IT1209578B (ko)
NL (1) NL8402478A (ko)
PT (1) PT79065B (ko)
SE (1) SE463514B (ko)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8416651D0 (en) * 1984-06-29 1984-08-01 Erba Farmitalia Penem derivatives
DE3688960D1 (de) * 1985-09-11 1993-10-07 Ciba Geigy Synthese von Beta-Lactamverbindungen.
US5215997A (en) * 1985-09-11 1993-06-01 Ciba-Geigy Corporation Synthesis of beta-lactam compounds
ATE159021T1 (de) * 1986-01-17 1997-10-15 Beecham Group Plc Verfahren zur herstellung von penem derivaten und zwischenprodukte zu dieser herstellung
EP0233155A1 (de) * 1986-02-14 1987-08-19 Ciba-Geigy Ag Aminoacyloxymethyl-Verbindungen
US5215891A (en) * 1986-10-15 1993-06-01 Farmitalia Carlo Erba Process for preparing penems
US5312914A (en) * 1987-02-17 1994-05-17 Ciba-Geigy Corp Process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidinone
SG45180A1 (en) * 1987-02-17 1998-01-16 Ciba Geigy Ag A process for the manufacture of 4-acetoxy-3- hydroxy-ethyl-azetidinone
GB8713515D0 (en) * 1987-06-10 1987-07-15 Erba Farmitalia Methoxymethyl compounds
US5364768A (en) * 1987-07-07 1994-11-15 Farmitalia Carlo Erba S.R.L. Process for the preparation of penems
GB2206578B (en) * 1987-07-07 1991-07-03 Erba Carlo Spa Process for the preparation of penems
US4992543A (en) * 1988-10-19 1991-02-12 Pfizer Inc. Penem derivatives
US5191075A (en) * 1988-10-19 1993-03-02 Pfizer Inc Process for the preparation of penems
US5328908A (en) * 1988-10-24 1994-07-12 Procter & Gamble Pharmaceuticals, Inc. Antimicrobial quinolone thioureas
US5180719A (en) * 1988-10-24 1993-01-19 Norwich Eaton Pharmaceuticals, Inc. Antimicrobial quinolonyl lactam esters
US5491139A (en) * 1988-10-24 1996-02-13 The Procter & Gamble Company Antimicrobial quinolonyl lactams
US5273973A (en) * 1988-10-24 1993-12-28 Norwich Eaton Pharmaceuticals, Inc. Antimicrobial quinolonyl esters
EP0366189A3 (en) * 1988-10-24 1992-01-02 Norwich Eaton Pharmaceuticals, Inc. Novel antimicrobial lactam-quinolones
CA2001203C (en) * 1988-10-24 2001-02-13 Thomas P. Demuth, Jr. Novel antimicrobial dithiocarbamoyl quinolones
EP0399228A1 (de) * 1989-04-29 1990-11-28 Hoechst Aktiengesellschaft Verfahren zur Herstellung von Penemverbindungen
US5198544A (en) * 1989-04-29 1993-03-30 Hoechst Aktiengesellschaft Process for the preparation of penem compounds
DK0525057T3 (da) * 1990-04-18 2000-07-31 Procter & Gamble Pharma Antimikrobielle quinolonyllactamer
US5399679A (en) * 1992-06-16 1995-03-21 Farmitalia Carlo Erba S.R.L. (1'R,3S,4R)4-acylthio azetidinones
EP0597401A3 (en) * 1992-11-11 1995-07-26 Takeda Chemical Industries Ltd Preparation of penemes.
IT1286558B1 (it) * 1996-02-27 1998-07-15 Menarini Farma Ind Processo per la preparazione di 2-alogenometil-penems e loro uso per la preparazione di penems antibatterici
CN100417654C (zh) * 2004-01-09 2008-09-10 中国医学科学院医药生物技术研究所 2-苯羧酸酯青霉烯类化合物及其制备方法和应用

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4500457A (en) * 1977-05-09 1985-02-19 Ciba-Geigy Corporation Process for preparing thia-aza compounds with a beta-lactam ring
US4168314A (en) * 1977-11-17 1979-09-18 Merck & Co., Inc. 6-(1'-Hydroxyethyl)-2-aminoethylthio-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
EP0013067A1 (en) * 1978-12-22 1980-07-09 Beecham Group Plc Bicyclic beta-lactam antibacterial agents, their use in pharmaceutical compositions, processes for their preparation and intermediates for use in such processes
AU535080B2 (en) * 1979-02-24 1984-03-01 Farmitalia Carlo Erba S.R.L. Penicillins
US4269771A (en) * 1979-04-06 1981-05-26 Farmitalia Carlo Erba Total synthesis of 7-oxo-4-thia-1-azabicyclo-[3,2,0]-heptane-2-carboxyl derivatives useful as β-lactamase inhibitors and antibacterial agents
CH651037A5 (de) * 1980-06-06 1985-08-30 Sankyo Co Penem-3-carbonsaeurederivate und verfahren zu deren herstellung.
GB2079744A (en) * 1980-07-04 1982-01-27 Erba Farmitalia 6-Alkyl-2-functionalized penems
US4347183A (en) * 1981-02-02 1982-08-31 Schering Corporation Process for the synthesis of penems and carbapenems
JPS588084A (ja) * 1981-07-08 1983-01-18 Takeda Chem Ind Ltd （６ｒ）−置換−（５ｒ）−ペネム−３−カルボン酸誘導体およびその製造法
US4411906A (en) * 1981-11-25 1983-10-25 Schering Corporation (5R,6S,8R)-6-(1-Hydroxyethyl)-2-(2-fluoroethylthio)-penem-3-carboxylates
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US4443373A (en) * 1982-03-30 1984-04-17 Schering Corporation Process for the production of antibiotic penems
US4584133A (en) * 1983-11-07 1986-04-22 Schering Corporation Process for the production of penems

Also Published As

Publication number Publication date
DE3429102A1 (de) 1985-02-28
BE900316A (fr) 1985-02-08
PT79065B (en) 1986-11-14
KR910002098B1 (ko) 1991-04-03
FR2550533A1 (fr) 1985-02-15
NL8402478A (nl) 1985-03-01
ES534892A0 (es) 1985-09-16
GB8321677D0 (en) 1983-09-14
FI83521B (fi) 1991-04-15
PT79065A (en) 1984-09-01
SE463514B (sv) 1990-12-03
GB2144743B (en) 1987-01-28
ES8600306A1 (es) 1985-09-16
DK382084D0 (da) 1984-08-08
GR80102B (en) 1984-12-14
IT1209578B (it) 1989-08-30
GB2144743A (en) 1985-03-13
DK382084A (da) 1985-02-12
CH663024A5 (de) 1987-11-13
SE8404004D0 (sv) 1984-08-07
IT8422234A0 (it) 1984-08-06
FR2550533B1 (fr) 1987-01-30
IL72612A0 (en) 1984-11-30
AT383808B (de) 1987-08-25
FI83521C (fi) 1991-07-25
HU192415B (en) 1987-06-29
US4631150A (en) 1986-12-23
DK167926B1 (da) 1994-01-03
JPS6058988A (ja) 1985-04-05
FI843111A0 (fi) 1984-08-08
JPH037675B2 (ko) 1991-02-04
IL72612A (en) 1988-06-30
FI843111A (fi) 1985-02-12
CA1279640C (en) 1991-01-29
SE8404004L (sv) 1985-02-12
ATA255884A (de) 1987-01-15
GB8420236D0 (en) 1984-09-12
HUT34984A (en) 1985-05-28

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