KR970042558A - β-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법 - Google Patents

β-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법 Download PDF

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KR970042558A
KR970042558A KR1019950046454A KR19950046454A KR970042558A KR 970042558 A KR970042558 A KR 970042558A KR 1019950046454 A KR1019950046454 A KR 1019950046454A KR 19950046454 A KR19950046454 A KR 19950046454A KR 970042558 A KR970042558 A KR 970042558A
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South Korea
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methyl
carbapenem
compound
carboxylate
general formula
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KR1019950046454A
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KR0183541B1 (ko
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이철해
김경숙
김재학
김영숙
배은미
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강박광
재단법인 한국화학연구소
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Priority to KR1019950046454A priority Critical patent/KR0183541B1/ko
Priority to US08/760,431 priority patent/US5869477A/en
Priority to JP9521177A priority patent/JP3048646B2/ja
Priority to EP96940727A priority patent/EP1019405A1/en
Priority to PCT/KR1996/000232 priority patent/WO1997020844A1/en
Publication of KR970042558A publication Critical patent/KR970042558A/ko
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Publication of KR0183541B1 publication Critical patent/KR0183541B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/14—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

본 발명은 하기 일반식(1)의 β-메틸 카르바페넴 카르복시에스테르 유도체, 이의 제조방법 및 이를 포함하는 항균제 조성물에 관한 것으로, 하기 일반식(2)의 β-메틸 카르바페넴 화합물을 하기 일반식(3)의 할라이드 또는 술포네이트 화합물과 반응시켜 제조되는 일반식(1)의 화합물은 녹농균을 제외한 그람양성균 및 그람음성균에 대하여 우수한 항균 활성을 나타내며 경구 투여시 높은 흡수율을 나타낸다.

Description

β-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (6)

  1. 하기 일반식(1)의 β-메틸 카르바페넴 카르복시에스테르 유도체 화합물
    상기식에서 R1은 C1-C6의 저급 알킬, 알케닐, 시클로알킬, 페닐 또는 헤테로아릴기를 나타내며, R2는 피발로일옥시알킬, 저급 알콕시 카르보닐옥시알킬 또는 알킬 디옥솔렌온알킬이다.
  2. 제1항에 있어서, R2는 5-메틸디옥솔렌온메틸, 피발로일옥시메틸 또는 시클로헥실옥시카르보닐옥시에틸인 것을 특징으로 하는 화합물
  3. 제1항에 있어서, 하기 화합물 중 어느 하나인 것을 특징으로 하는 화합물
    (1S,5R,6S)-3-[(5-메틸-2-옥소-1,3-디옥솔렌-4-일)메틸]-2-[(1'R)-1'-시클로프로필히드록시메틸]-6-[(1'R)-1'-히드록시에틸]-1-메틸-2-카르바페넴-3-카르복실레이트;
    (1S,5R,6S)-3-[(5-메틸-2-옥소-1,3-디옥솔렌-4-일)메틸]-2-[(1'R)-1'-시클로펜틸히드록시메틸]-6-[(1'R)-1'-히드록시에틸]-1-메틸-2-카르바페넴-3-카르복실레이트;
    (1S,5R,6S)-3-[(5-메틸-2-옥소-1,3-디옥솔렌-4-일)메틸]-2-[(1'R)-1'-이소프로필히드록시메틸]-6-[(1'R)-1'-히드록시에틸]-1-메틸-2-카르바페넴-3-카르복실레이트;
    (1S,5R,6S)-3-(시클로헥실옥시카르보닐옥시-1-메틸)-2-[(1'R)-1'-이소프로필히드록시메틸]-6-[(1'R)-1'-히드록시에틸]-1-메틸-2-카르바페넴-3-카르복실레이트;
    (1S,5R,6S)-3-[(1-메틸)에톡시카르보닐옥시-1-메틸]-2-[(1'R)-1'-이소프로필히드록시메틸]-6-[(1'R)-1'-히드록시에틸]-1-메틸-2-카르바페넴-3-카르복실레이트;
    (1S,5R,6S)-3-(피발로일옥시메틸)-2-[(1'R)-1'-이소프로필히드록시메틸]-6-[(1'R)-1'-히드록시에틸]-1-메틸-2-카르바페넴-3-카르복실레이트;
  4. 하기 일반식(2)의 β-메틸 카르바페넴 화합물을 하기 일반식(3)의 할라이드 또는 술포네이트 화합물과 반응시켜 상기 일반식(1)의 β-메틸 카르바페넴 카르복시에스테르 화합물을 제조하는 방법
  5. 일반식(1)의 화합물과 생리학적으로 허용되는 담체 또는 부형제를 포함하는 항균제 조성물
    상기식에서 R1및 R2는 일반식(1)에서 정의한 것과 같고, X는 할로겐 원자 또는 술포네이트기를 나타내고, R은 수소 원자이거나 무기 또는 유기 염기로부터 유도된 양이온을 나타낸다.
  6. 일반식(1)의 화합물과 생리학적으로 허용되는 담체 또는 부형제를 포함하는 항균제 조성물
KR1019950046454A 1995-12-04 1995-12-04 베타-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법 KR0183541B1 (ko)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1019950046454A KR0183541B1 (ko) 1995-12-04 1995-12-04 베타-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법
US08/760,431 US5869477A (en) 1995-12-04 1996-12-04 β-methylcarbapenem derivatives, process for the preparation thereof and pharmaceutical composition comprising same
JP9521177A JP3048646B2 (ja) 1995-12-04 1996-12-04 β―メチルカルバペネム誘導体、その製造方法およびそれを含む医薬組成物
EP96940727A EP1019405A1 (en) 1995-12-04 1996-12-04 Beta-methylcarbapenem derivatives, process for the preparation thereof and pharmaceutical composition comprising same
PCT/KR1996/000232 WO1997020844A1 (en) 1995-12-04 1996-12-04 β-METHYLCARBAPENEM DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019950046454A KR0183541B1 (ko) 1995-12-04 1995-12-04 베타-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법

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KR970042558A true KR970042558A (ko) 1997-07-24
KR0183541B1 KR0183541B1 (ko) 1999-05-01

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KR1019950046454A KR0183541B1 (ko) 1995-12-04 1995-12-04 베타-메틸 카르바페넴 카르복시 에스테르 유도체 및 이의 제조방법

Country Status (5)

Country Link
US (1) US5869477A (ko)
EP (1) EP1019405A1 (ko)
JP (1) JP3048646B2 (ko)
KR (1) KR0183541B1 (ko)
WO (1) WO1997020844A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1612211A4 (en) * 2003-04-08 2008-07-02 Dainippon Sumitomo Pharma Co NEW CARBAPENEM COMPOUNDS
JP2012224973A (ja) * 2011-04-05 2012-11-15 Rumi Kondo 下丹田用サポーター

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4260627A (en) * 1978-10-24 1981-04-07 Merck & Co., Inc. 1-, 6- And 2-substituted-1-carba-2-penem-3-carboxylic acids
US4429128A (en) * 1981-02-09 1984-01-31 Pfizer Inc. Carbapenams and carbapen-2-ems and process therefor
US4479947A (en) * 1981-07-13 1984-10-30 Merck & Co., Inc. Oral absorption enhancement of carboxylic acid pharmaceuticals using (5-alkyl-2-oxo-1,3-dioxolen-4-yl)methyl ester group
EP0292191A1 (en) * 1987-05-21 1988-11-23 Merck & Co. Inc. 2-(Substituted methyl)-1-alkylcarbapenem derivatives
JPH03120280A (ja) * 1989-10-03 1991-05-22 Shionogi & Co Ltd ハロメチルカルバペネム化合物の製法
EP0430037A3 (en) * 1989-11-21 1992-05-27 Banyu Pharmaceutical Co., Ltd. Process for producing 2-carbon-substituted carbapenem derivatives

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JPH11500750A (ja) 1999-01-19
EP1019405A1 (en) 2000-07-19
US5869477A (en) 1999-02-09
KR0183541B1 (ko) 1999-05-01
WO1997020844A1 (en) 1997-06-12
JP3048646B2 (ja) 2000-06-05

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