KR860004064A - 결정성 아미노메틸 화합물의 제조방법 - Google Patents

결정성 아미노메틸 화합물의 제조방법 Download PDF

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KR860004064A
KR860004064A KR1019850008172A KR850008172A KR860004064A KR 860004064 A KR860004064 A KR 860004064A KR 1019850008172 A KR1019850008172 A KR 1019850008172A KR 850008172 A KR850008172 A KR 850008172A KR 860004064 A KR860004064 A KR 860004064A
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organic solvent
phenem
carboxylic acid
water
substituted
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KR1019850008172A
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KR890001009B1 (ko
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슈나이더 페터
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아놀드 자일러·에른스트 알테르
시바-가이기 에이지
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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
    • 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
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/568—Four-membered rings

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

Abstract

내용 없음

Description

결정성 아미노메틸 화합물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (18)

  1. (5R,6S)-2-아미노메틸-6-[(1R)-1-히드록시에틸]-2-펜엠-3-카복실산을 함수 유기용매중의 과포화 용액으로 부터 결정화시킨 다음 생성물을 수집하고 건조시킴을 특징으로하여, 결정성(5R,6S)-아미노메틸-6-[(1R)-1-히드록시에틸]-2-펜엠-3-카복실산을 제조하는 방법.
  2. 제1항에 있어서, 함수 유기용매가 탄소수 1 내지 4의 저급 알칸올, 탄소수 1 내지 4의 글리콜 및 이들의 모노-및 디-(C1-C2)-알킬에테르 중에서 선택된 수-상용성 유기용매와 물의 혼합물 임을 특징으로 하는 방법.
  3. 제2항에 있어서, 함수 유기 용매가, 함수량이 2 내지 20%이며 언급된 수-상용성 유기 용매중의 하나와 물로 이루어진 혼합물임을 특징으로 하는 방법.
  4. 제2항에 있어서, 함수 유기 용매가, 함수량이 2 내지 20%이며 탄소수 1 내지 4의 저급알칸올과 물로 이루어진 혼합물임을 특징으로 하는 방법.
  5. 제2항에 있어서, 함수 유기 용매가, 함수량이 2 내지 10%이며 탄소수 1 내지 4의 저급알칸올과 물로 이루어진 혼합물임을 특징으로 하는 방법.
  6. 제2항에 있어서, 유기용매가 에탄올, n-프로판올 및 2-부탄올중에서 선택됨을 특징으로 하는 방법.
  7. 제2항에 있어서, 함수 유기용매가 96% 에탄올임을 특징으로 하는 방법.
  8. 제1항에 있어서, (5R,6S)-2-아미노메틸-6-[(1R)-1-히드록시에틸]-2-펜엠-3-카복실산을 실온에서 또는 50℃까지의 상승된 온도에서 함수 유기용매중에 용해시키고 용액을 0℃ 내지 20℃까지 냉각시킴으로써 용액의 과포화를 수행함을 특징으로 하는 방법.
  9. 제1항에 있어서, (5R,6S)-2-아미노-메틸-6-[(1R)-1-히드록시 에틸]-2-펜엠-3-카복실산을 , 2 내지 10%의 함수량을 갖는 제2항에 언급된 유기 용매중 하나의 용매중에서 교반시키면서 숙성(digesting)시킴을 특징으로 하는 방법.
  10. 제9항에 있어서, (5R,6S)-2-아미노메틸-6-[(1R)-1-하이드록시에틸]-2-펜엠-3-카복실산, 96% 에탄올중에서 교반시키면서 숙성시킴을 특징으로 하는 방법.
  11. 제1항에 있어서, 결정체를 상온 또는 약간 상승된 온도에서 건조시킴을 특징으로 하는 방법.
  12. 제1항에 있어서, 결정체를 감압하에 건조시킴을 특징으로 하는 방법.
  13. 제1항에 있어서, 하기와 같은 격자간격(d-값) 및 그것의 X-선 분말 패턴의 상대선 강도(Guinier)에 의한 카메라, 방사선원; 구리-kα1)를 특징으로 하는 결정성(5R,6S)-2-아미노 메틸-6-[(1R)-2히드록시에틸]-2-펜엠-3-카복실산을 제조하는 방법.
  14. 제1항에 있어서, 결정체를 위해 사용된 (5R,6S)-2-아미노 메틸-6-[(1R)-2히드록시에틸]-2-펜엠-3-카복실산을 하기 일반식(I)의 화합물 중의 보호된 관능기를 유리관능기로 전환시켜 제조함을 특징으로 하는 방법.
    상기식에서, R1은 보호된 히드록시기이고, R2는 보호된 아미노기이며, R3는 보호된 카복시기이다.
  15. 제14항에 있어서, 일반식(I)의 출발화합물에서, R1이 트리-(C1-C4)-알킬실리옥시, 할로-(C1-C4)-알콕시카보닐옥시 또는 임의로 할로-치환된(C1-C4)-저급 알케닐옥시카보닐옥시이고, R2가 아지도, 프탈리미도, 임의로 할로-치환된(C1-C4)-저급 알케닐옥시카보닐 아미노 또는 임의로 니트로-치환된 벤조일옥시카보닐아미노이며 R8가 임의로 니트로-치환된 벤질옥시카보닐, 임의로 할로-치환된(C1-C4)-저급알케닐옥시카보닐, 또는 시아노 또는 트리(C1-C4)-저급알킬실릴에 의해 2-위치에 치환된 에톡시카보닐임을 특징으로 하는 방법.
  16. 제14항에 있어서, R1이 알릴옥시카보닐옥시이고, R2가 알릴옥시카보닐 아미노이며, R8가 알릴옥시카보닐인 일반식(I)의 화합물을 출발물질로서 사용함을 특징으로 하는 방법.
  17. 제16항에 있어서, 모든 보호기를 동시에 제거하면서, 일반식(I)의 화합물을 테트라키스-트리페닐포스핀-팔라듐의 존재하에 그리고 임의로 트리페닐포스핀의 존재하에 알릴기 수용체와 반응시킴을 특징으로 하는 방법.
  18. 하기 일반식(I)의 화합물중의 보호된 관능기를 유리 관능기로 전환시키고 그 생성물을 결정형태로 분리시킴을 특징으로 하여, 결정성 (5R,6S)-2-아미노 메틸-6-[(1R)-1-히드록시-에틸]-2-펜엠-3-카복실산을 제조하는 방법.
    상기식에서, R1은 보호된 히드록시기이고, R2는 보호된 아미노기이며, R3는 보호된 카복시기이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850008172A 1984-11-02 1985-11-02 결정성 아미노메틸 화합물의 제조방법 KR890001009B1 (ko)

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CH5266/84-8 1984-11-02
CH05266/84-8 1984-11-02
CH526684 1984-11-02

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KR860004064A true KR860004064A (ko) 1986-06-16
KR890001009B1 KR890001009B1 (ko) 1989-04-18

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US (1) US4761408A (ko)
EP (1) EP0181571A1 (ko)
JP (1) JPS61165390A (ko)
KR (1) KR890001009B1 (ko)
AU (1) AU580636B2 (ko)
DD (1) DD242408A5 (ko)
DK (1) DK505485A (ko)
ES (1) ES8701765A1 (ko)
FI (1) FI854268A (ko)
GR (1) GR852625B (ko)
HU (1) HUT39184A (ko)
IL (1) IL76897A (ko)
NO (1) NO854364L (ko)
NZ (1) NZ214046A (ko)
PH (1) PH23259A (ko)
PT (1) PT81411B (ko)
ZA (1) ZA858402B (ko)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI871835A (fi) * 1986-04-29 1987-10-30 Ciba Geigy Ag Kristallint hydrat.
IE60588B1 (en) * 1986-07-30 1994-07-27 Sumitomo Pharma Carbapenem compound in crystalline form, and its production and use
GB8818789D0 (en) * 1988-08-08 1988-09-07 Erba Carlo Spa Crystalline(5r 6s)-2-carbamoyloxymethyl-6-((1r)-hydroxyethyl)-2-penem-carboxylic acid & pharmaceutical formulation
DE60008497T2 (de) * 1999-10-12 2004-12-02 Daiichi Suntory Pharma Co., Ltd. Arzneimittel zur oralen verabreichung
US20040202714A1 (en) * 1999-10-12 2004-10-14 Daiichi Suntory Pharma Co., Ltd. Oral pharmaceutical composition

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0042026B1 (de) * 1978-02-02 1986-01-08 Ciba-Geigy Ag 3,4-Disubstituierte Azetidin-2-onverbindungen und Verfahren zu ihrer Herstellung
US4272437A (en) * 1978-12-18 1981-06-09 Bristol-Myers Company Antibacterial agents, and 4-thio azetidinone intermediates
IL59081A0 (en) * 1979-01-10 1980-05-30 Schering Corp 2-penem compounds and a method for preparing them
AT368506B (de) * 1979-02-24 1982-10-25 Erba Farmitalia Verfahren zur herstellung von neuen penemcarbonsaeuren und deren salzen
US4386030A (en) * 1979-12-31 1983-05-31 Merck & Co., Inc. Process for preparing 6-(1'-hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid
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
EP0180252B1 (en) * 1981-07-15 1989-04-26 Sumitomo Pharmaceuticals Company, Limited Process of preparing azetidinone compounds
US4540580A (en) * 1982-11-16 1985-09-10 Schering Corporation 2-[(1'R)-1'-Aminoalkyl]penems
EP0125208A1 (de) * 1983-05-06 1984-11-14 Ciba-Geigy Ag Aminoniederalkyl-penem-Verbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verwendung von letzteren
EP0132101A1 (en) * 1983-07-14 1985-01-23 Pfizer Inc. 2-Heterocycloalkylthiopenem derivatives
US4656165A (en) * 1983-09-02 1987-04-07 Ciba-Geigy Corporation Aminomethyl penem compounds
US4634556A (en) * 1985-05-10 1987-01-06 Schering Corporation Crystalline sodium (5R, 6S, 8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxylate and process for making same

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IL76897A (en) 1989-10-31
HUT39184A (en) 1986-08-28
FI854268A (fi) 1986-05-03
FI854268A0 (fi) 1985-10-30
ES8701765A1 (es) 1986-12-01
GR852625B (ko) 1986-03-03
EP0181571A1 (de) 1986-05-21
IL76897A0 (en) 1986-02-28
DK505485D0 (da) 1985-11-01
AU4930685A (en) 1986-05-08
PT81411A (en) 1985-11-01
NO854364L (no) 1986-05-05
PT81411B (en) 1987-08-04
ZA858402B (en) 1986-06-25
NZ214046A (en) 1988-09-29
PH23259A (en) 1989-06-16
ES548435A0 (es) 1986-12-01
DK505485A (da) 1986-05-03
AU580636B2 (en) 1989-01-19
JPS61165390A (ja) 1986-07-26
KR890001009B1 (ko) 1989-04-18
US4761408A (en) 1988-08-02
DD242408A5 (de) 1987-01-28

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