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KR840002354A - 시스, 엔도-2-아자비사이클로-[3.3.0]-옥탄-3-카복실산 유도체의 제조방법 - Google Patents

시스, 엔도-2-아자비사이클로-[3.3.0]-옥탄-3-카복실산 유도체의 제조방법 Download PDF

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KR840002354A
KR840002354A KR1019820004953A KR820004953A KR840002354A KR 840002354 A KR840002354 A KR 840002354A KR 1019820004953 A KR1019820004953 A KR 1019820004953A KR 820004953 A KR820004953 A KR 820004953A KR 840002354 A KR840002354 A KR 840002354A
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KR890000007B1 (ko
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데츠 볼커
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하인리히 벡커, 베른하르트 벡크
휙스트 아크티엔 게젤샤프트
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

내용 없음.

Description

시스, 엔도－2－아자비사이클로－[3,3,0]－옥탄－3－카복실산 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (3)

  1. 다음 일반식(Ⅱ)의 화합물을 다음 일반식(Ⅲa) 또는 (Ⅲb)의 화합물과 반응시킨후 생성물을 수소첨가시키거나 또는 산 또는 염기로 처리함을 특징으로 하는, 다음 일반식(Ⅰ)의 화합물 및 이의 생리적으로 허용되는 염의 제조방법.
    상기식에서, 1 및 5번 브리지－헤드 탄소원자상의 수소원자는 서로에 대해 시스－배위이며 3번 탄소 원자상의 카복실그룹은 2환성 환계에 대해 엔도－위치로 배향하고, R1은 수소, 알릴, 비닐 또는 보호된 천연 α－아미노산 R1－CH(NH2)－COOH의 측쇄이며, R2는 수소, (탄소수 1내지 6의)－알킬, (탄소수 2내지 6의)알케일 또는 아릴－(탄소수 1내지 4의)－알킬이고(단 일반식(Ⅱ)에서는 수소를 제외한다).
    Y는 수소 또는 하이드록실이며, Z는 수소이거나, 또는 Y 및 Z는 함께 산소이고, X는(탄소수 1내지 6의)－알킬, (탄소수 2내지 6의)－알케닐 또는(탄소수 5내지 9의)－사이클로알킬, 또는(탄소수 1내지 4의)－알킬, (탄소수 1내지 4의)－알콕시, 하이드록실, 할로겐, 니트로, 아미노, (탄소수 1내지 4의)－알킬아미노, 디－(탄소수 1내지 4의(－알킬아미노 또는 메틸렌디옥시로 모노－, 디－또는 트리－치환된(탄소수 6내지 12)의－아릴 또는 인돌－3－일이며, W는 카복실－에스네르화그룹이다.
  2. 다음 일반식(Ⅵ)의 엔아민 또는 다음 일반식(Ⅶ)의 기를 다음 일반식(Ⅷ)의 N－아실화된 β－할로게노－α－아미노－카복실산 에스테르 또는 다음 일반식(Ⅸ)의 아크릴산 에스테르와 반응시켜 다음 일반식(Ⅹ)의 화합물을 생성시킨후, 이 화합물을 강산의 첨가, 아실 아미드 및 에스테르 분비로써 폐환하여 다음 일반식(XIa) 또는 (IXb)의 화합물을 생성시키고, 이화합물을 전이 금속 촉매 존재하에 촉매적 수소첨가로써 또는 저급 알콜중 보란－아민 착화합물 또는 착붕소 수소화물로 환원시킴으로써 W가 수소인 다음 일반식(Ⅲa) 또는 (Ⅲb)의 화합물로 전환시키며, 임의로 이생성물을 에스테르화하여 W가 탄소수 1내지 6의 알킬 또는 탄소수 7내지 8의 아르알킬인 다음 일반식(Ⅲa) 또는(Ⅲb)의 화합물을 생성시킴을 특징으로 하는, 다음 일반식(Ⅲa) 또는 (Ⅲb)의 화합물 및 이의 산(W가 수소인 경우) 또는 염기와의 염의 제조방법.
    상기 일반식(Ⅲa) 도는 (Ⅲb)에서 W는 수소, 탄소수 1내지 6의 알킬 또는 탄소수 7내지 8의 아르알킬이며, 상기 일반식(Ⅵ)에서, X1은 탄소수 2내지 10의 디알킬아미노이고, 상기 일반식(Ⅶ)에서 m 및 0은 1내지 3의 정수이며, m 및 0의 총합은 3이상이고, A는 CH2, NH, O 또는 S이며,상기 일반식(Ⅷ)에서, X2는 뉴클레오퓨직 그룹이고, Y1은 탄소수 1내지 5의 알카노일, 탄소수 7내지 9의 아르오일 또는 펩타이드 화학에서 통상적이고 산조건하에서 분리되는 기타 보호그룹이며, R2는 탄소수 1내지 5의 알킬 또는 탄소수 7내지 9의 아르알킬이고, 상기 일반식(Ⅸ)에서 Y1및 R2는 전술한 바와 같으며, 상기 일반식(Ⅹ)에서 R2및 Y1은 전술한 바와 같다.
  3. a) X가 아릴이면, 아릴메틸 케톤 X－CO－CH3을 글리옥실산 에스테르 CHO－CO2R2및 α－아미노산 에스데르 H2N－CHR1－CO2W(여기서 W′는 염기성 또는 산성 가수분해로써 분리되는 기이고, 만일 W′가 벤질이면 R2는 벤질 또는 니트로벤질이 아니다)와 반응시켜 다음 일반식(Ⅳ)의 화합물을 생성시키거나, 또는 b) 케토－아크릴산 에스테르 X－CO_CH=CH=CO2R2를 α－아미노산 에스테르 H2N－CHCR1)－CO2W′와 반응시켜 다음 일반식(Ⅳ)의 화합물을 생성시키고, 적절하다면 a) 또는 b)에 따라 수득한 이화합물을, W′가 산성 또는 염기성 조건하에서 제거될수 있는 기이면, 산성 또는 염기성 에스테르 분리시키거나, 또는 W′가 벤질 또는 니트로벤질이면(R2=벤질 또는 니트로벤질)이화합물을 가수소분해로써 카복실산으로 전환시키고 이 생성물을 수소첨가시켜 X,R1및 R2가 전술한 바와같고 Y가 수소 또는 하이드록실이며 Z가 수소인, 다음 일반식(Ⅱ)의 화합물 또는 적절하다면 산－촉매적으로 에스테르 분리시키는 이의 저급알킬 에스테르를 생성시킴을 특징으로 하는, 다음 일반식(Ⅱ)의 화합물의 제조방법.
    상기식에서, x,R1,R2및 W′는 전술한 바와같고, Y는 수소 또는 하이드록실이며, Z는 수소이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8204953A 1981-11-05 1982-11-03 시스, 엔도-2-아자비사이클로-[3.3.0]-옥탄-3-카복실산 유도체의 제조방법 KR890000007B1 (ko)

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Application Number Priority Date Filing Date Title
DEP3143946.2 1981-11-05
DE3143946 1981-11-05
DE3143946.2 1981-11-05
DE19823226768 DE3226768A1 (de) 1981-11-05 1982-07-17 Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
DEP3226768.1 1982-07-17

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KR840002354A true KR840002354A (ko) 1984-06-25
KR890000007B1 KR890000007B1 (ko) 1989-03-02

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EP0079022A3 (en) 1983-10-05
IE822636L (en) 1983-05-05
GR77381B (ko) 1984-09-11
DK114492D0 (da) 1992-09-17
DE3226768A1 (de) 1983-05-26
LU88260I2 (ko) 1994-02-03
US4727160A (en) 1988-02-23
DD203047A5 (de) 1983-10-12
DK166624C (da) 1993-11-08
US4879403A (en) 1989-11-07
AU585429B2 (en) 1989-06-15
AU9014582A (en) 1983-05-12
AR240675A1 (es) 1990-08-31
EP0150263B1 (de) 1990-06-20
NL930039I2 (nl) 1993-09-16
ES8308542A1 (es) 1983-09-01
DE3280196D1 (de) 1990-07-26
SU1277895A3 (ru) 1986-12-15

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