KR850001167A - 2-아자비시클로[3.1.0] 헥산-3-카복실산 유도체의 제조방법 - Google Patents

2-아자비시클로[3.1.0] 헥산-3-카복실산 유도체의 제조방법 Download PDF

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KR850001167A
KR850001167A KR1019840003851A KR840003851A KR850001167A KR 850001167 A KR850001167 A KR 850001167A KR 1019840003851 A KR1019840003851 A KR 1019840003851A KR 840003851 A KR840003851 A KR 840003851A KR 850001167 A KR850001167 A KR 850001167A
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compound
formula
alkyl
azabicyclo
hexane
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KR910007884B1 (ko
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우르바흐 한스외르그 (외 2)
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하인리히 벡커,베른하르트 베크
훽스트 아크티엔 게젤샤프트
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

내용 없음

Description

2-아자비시클로[3.1.0] 헥산-3-카복실산 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. a) 일반식(II)의 화합물을 일반식(IIIa) 또는 (IIIb)의 화합물 또는 이의 입체성이성체 혼합물과 반응시킨 다음, 그 생성물을 수소화시키거나 산 또는 염기로 처리하거나, b) Y와 Z가 함께 산소인 일반식(I)의 화합물을 제조하기 위해, b1) 일반식(IV)의 화합물을 일반식(V)의 화합물과 반응시키고, 경우에 따라서, 유리 카복실기를 생성시키면서 W 및/또는 R2를 분리시키거나, b2) 일반식(IV)의 화합물을 일반식(VI)의 화합물 및 일반식(VII)의 화합물과 반응시키고, 경우에 따라서, 유리카복실기를 생성시키면서 W 및/또는 R2를 분리시키거나, c) Y 및 Z가 각각 수소인 일반식(I)의 화합물을 제조하기 위해서, 일반식(IV)의 화합물을 일반식(VIII)의 화합물과 반응시키고, 생성된 쉬프(Schiff's) 염기를 환원시킨 후, 경우에 따라서, 유리카복실기를 생성시키면서 W 및/또는 R2를 분리시키거나, d) Y는 히드록실이고 Z가 수소인 일반식(I)의 화합물을 제조하기 위해, Y와 Z가 함께 산소인 일반식(I)의 화합물을 복합 보로네이트 또는 보란-아민 복합물로써 환원시키고; 경우에 따라서, 상기 a) 내지 d)에 따라서 수득한 R이 수소인 일반식(I)의 화합물을 R이(C1내지 C6)-알킬 또는 (C7내지 C9)-아르알킬인 일반식(I)의 에스테르로 전환시키고, 경우에 따라서, 일반식(I)의 화합물을 생리학적으로 허용되는 이의 염으로 전환시킴을 특징으로하여, 일반식(I)의 화합물 및 생리학적으로 허용되는 이의 염을 제조하는 방법.
    상기 식에서, n은 0 또는 1이고, R는 수소, (C1내지 C6)-알킬, (C2내지 C6)-알케닐 또는 (C6내지 C12)-아릴-(C1내지 C4)-알킬이고, R1은 수소; 아미노(C1내지 C6)-아실아미노 또는 벤조일아미노에 의해 임의로 치환될 수 있는(C1내지 C6)-알킬; (C1내지 C4)-알킬, (C1내지 C2)-알콕시 또는 할로겐에 의해 각각 치환될 수 있는 (C2내지 C6)-알케닐; (C5내지 C9)-시클로알킬, (C5내지 C9)-시클로알케닐, (C5내지 C7)-시클로알킬-(C1내지 C4)-알킬, (C6내지 C12)-아릴 또는 부분적으로 수소화된(C6내지 C12)-아릴; 상기 정의한 바와 같이 알릴라디칼부위에 치환될 수 있는(C6내지 C12)-아릴-(C1내지 C4)-알킬 또는 (C7내지 C13)-아로일-(C1내지 C2)-알킬; 각각 5 내지 7 또는 8 내지 10개의 고리원자(이중 1 또는 2개의 고리원자는 황 또는 산소이고/이거나 1 내지 4개의 고리원자는 질소원자이다)를 가지는 일환식 또는 이환식 헤테로사이클릭라디칼; 또는 천연 α-아미노산 R1-CH(NH2)-COOH의 임의 보호된 측쇄이고, R2는 수소, (C1내지 C6)-알킬, (C2내지 C6)-알케닐 또는 (C6내지 C12)-아릴-(C1내지 C4)-알킬이고, 단, 일반식(II)에서 R2는 수소는 아니며, Y는 수소 또는 히드록실이고, Z는 수소이거나, Y와 Z는 함께 산소이며, X는 (C1내지 C4)-알킬, (C1내지 C4)-알콕시, 히드록실, 할로겐, 니트로, 아미노, 아실아미노, (C1내지 C4)-알킬아미노, 디-(C1내지 C4)-알킬아미노 및/또는 메틸렌 디옥시에 의해 각각 일치환, 이치환 또는 삼치환 될 수 있는 (C1내지 C6)-알킬, (C2내지 C6)-알케닐, (C5내지 C8)-시클로알킬, (C6내지 C12)-아릴; 또는 3-인돌일이고, W는 카복실을 에스테르화시키는 기이다.
  2. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐 프로필)-S-알라닐-시스-2-아자비시클로[3.1.0] 헥산-엔도-3-S-카복실산을 제조하는 방법.
  3. 제1항에 있어서, N-(1-S-카복시-3-페닐 프로필)-S-알라닐-시스-2-아자비시클로[3.1.0] 헥산-엔도-3-S-카복실산을 제조하는 방법.
  4. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐프로필)-S-리실-시스-2-아자비시클로[3.1.0] 헥산-엔도-3-S-카복실산을 제조하는 방법.
  5. 제1항에 있어서, N-(1-S-카복시-3-페닐프로필)-S-리실-시스-2-아자비시클로[3.1.0] 헥산-엔도-3-S-카복실산을 제조하는 방법.
  6. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐 프로필)-0-에틸-S-티로실-시스-2-아자비시클로[3.1.0] 헥산-엔도-3-S-카복실산을 제조하는 방법.
  7. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐 프로필)-0-메틸-S-티로실-시스-2-아자비시클로[3.1.0] 헥산-엔도-3-S-카복실산을 제조하는 방법.
  8. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐 프로필)-S-알라닐-시스-2-아자비시클로[3.1.0] 헥산-엑소-3-S-카복실산을 제조하는 방법.
  9. 제1항에 있어서, N-(1-S-카복시-3-페닐 프로필)-S-알라닐-시스-2-아자비시클로[3.1.0] 헥산-엑소-3-S-카복실산을 제조하는 방법.
  10. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐프로필)-S-리실-시스-2-아자비시클로[3.1.0] 헥산-엑소-3-S-카복실산을 제조하는 방법.
  11. 제1항에 있어서, N-(1-S-카복시-3-페닐프로필)-S-리실-시스-2-아자비시클로[3.1.0] 헥산-엑소-3-S-카복실산을 제조하는 방법.
  12. 제1항에 있어서, N-(1-S-카복시에톡시-3-페닐프로필)-0-에틸-S-티로실-시스-2-아자비시클로[3.1.0] 헥산-엑소-3-S-카복실산을 제조하는 방법.
  13. 제1항에 있어서, N-(1-S-카보에톡시-3-페닐프로필)-0-메틸-S-티로실-시스-2-아자비시클로[3.1.0] 헥산-엑소-3-S-카복실산을 제조하는 방법.
  14. 일반식(XI)의 화합물을 염기의 존재하에서 전위 반응시키고, 경우에 따라서 생성된 W가 수소인 일반식(IIIa) 또는 (IIIb)의 화합물을 에스테르화시킴을 특징으로 하여, 일반식(IIIa) 또는 (IIIb)의 화합물 및 이의 입체이성체 혼합물을 제조하는 방법.
    상기식에서, W는 수소 또는 카복실을 에스테르화시키는 기이고, Hal은 할로겐이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840003851A 1983-07-06 1984-07-04 2-아자비시클로[3.1.0]헥산-3-카복실산 유도체의 제조방법 KR910007884B1 (ko)

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DE19833324263 DE3324263A1 (de) 1983-07-06 1983-07-06 Derivate der 2-azabicyclo(3.1.0)hexan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie 2-azabicyclo(3.1.0)hexan-derivate als zwischenprodukte und verfahren zu deren herstellung
DEP3324263.1 1983-07-06

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KR850001167A true KR850001167A (ko) 1985-03-16
KR910007884B1 KR910007884B1 (ko) 1991-10-04

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US (1) US4591598A (ko)
EP (1) EP0131226B1 (ko)
JP (1) JPH0710879B2 (ko)
KR (1) KR910007884B1 (ko)
AT (1) ATE53203T1 (ko)
AU (1) AU573227B2 (ko)
CA (1) CA1263000A1 (ko)
DE (2) DE3324263A1 (ko)
DK (1) DK330284A (ko)
ES (3) ES534001A0 (ko)
FI (1) FI842691A (ko)
GR (1) GR82242B (ko)
HU (2) HU209413B (ko)
PT (1) PT78848B (ko)
ZA (1) ZA845160B (ko)

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CA1263000A1 (en) 1989-11-14
FI842691A0 (fi) 1984-07-04
EP0131226B1 (de) 1990-05-30
US4591598A (en) 1986-05-27
JPS6051199A (ja) 1985-03-22
ES8504705A1 (es) 1985-04-16
EP0131226A3 (en) 1987-08-26
GR82242B (ko) 1984-12-13
HUT39160A (en) 1986-08-28
DE3482385D1 (de) 1990-07-05
HUT37803A (en) 1986-02-28
AU3029884A (en) 1985-01-10
DE3324263A1 (de) 1985-01-17
ZA845160B (en) 1985-02-27
ES535452A0 (es) 1985-05-16
KR910007884B1 (ko) 1991-10-04
EP0131226A2 (de) 1985-01-16
DK330284A (da) 1985-01-07
PT78848B (de) 1986-07-22
ES534001A0 (es) 1985-04-16
HU209413B (en) 1994-05-30
ES8505341A1 (es) 1985-05-16
DK330284D0 (da) 1984-07-05
FI842691A (fi) 1985-01-07
ATE53203T1 (de) 1990-06-15
HU194827B (en) 1988-03-28
PT78848A (de) 1984-08-01
ES8505342A1 (es) 1985-05-16
JPH0710879B2 (ja) 1995-02-08
ES535453A0 (es) 1985-05-16
CA1267902C (ko) 1990-04-17
AU573227B2 (en) 1988-06-02

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