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KR920700208A - 탁솔유도체 화합물과 그의 제조방법 - Google Patents

탁솔유도체 화합물과 그의 제조방법

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Publication number
KR920700208A
KR920700208A KR1019900702418A KR900702418A KR920700208A KR 920700208 A KR920700208 A KR 920700208A KR 1019900702418 A KR1019900702418 A KR 1019900702418A KR 900702418 A KR900702418 A KR 900702418A KR 920700208 A KR920700208 A KR 920700208A
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South Korea
Prior art keywords
compound
taxol
formula
group
structural formula
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KR1019900702418A
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English (en)
Inventor
제이. 스텔라 발렌티노
이. 메쑤 아브라함
Original Assignee
프란세스 디겐 호로비츠
유니버시티 오브 켄사스
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Publication of KR920700208A publication Critical patent/KR920700208A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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

Abstract

내용 없음

Description

탁솔유도체 화합물과 그의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (26)

  1. 다음 구조식(Ⅱ)로 표시되는 것임을 특징으로 하는 화합물과 그의 산부가염.
    상기식에서, R 및 R1는 각각 수소원자 또는 알라닌, 루신, 이소루신, 살린, 페닐알라닌, 프로린, 리신 및 아르기닌으로 이루어진 그룹 또는 다음 구조식(Ⅲ)으로 표시되는 그룹에서 선택되는 아미노산의 잔류물이다.
    상기식에서, n은 1 내지 3의 정수이고, R2및 R3는 각각 1 내지 3개의 탄소원자를 갖는 알킬라디칼에 있는 수소이며, 이들이 달라 붙은 질소원자와 함께 R 및 R1중의 적어도 하나는 수소원자가 아니라는 것을 조건부로 4 내지 5개의 탄소원자를 갖는 포화된 히테로고리를 형성할 수 있다.
  2. 제1항에 있어서, 적어도 R 및 R1중의 하나는 L－알라닌, L－이소루신, L－발린, L－페닐알라닌, L－프로린, L－리신 및 L－아르기닌으로 이루어진 그룹에서 선택된 것임을 특징으로 하는 탁솔유도체 화합물.
  3. 제1항에 있어서, 적어도 R 및 R1중의 하나가 다음 구조식(Ⅲ)으로 표시되는 그룹임을 특징으로 하는 탁솔유도체 화합물.
    상기식에서, n은 1 내지 3의 정수이고, R2및 R3는 각각 1 내지 3개의 탄소원자를 갖는 알킬라디칼이다.
  4. 제1항에 있어서의 화합물은 2´－(N,N－디메틸글리실)탁솔 또는 그의 산부가염임을 특징으로 하는 탁솔유도체 화합물.
  5. 제1항에 있어서의 화합물은 2´－(N,N－디에틸아미노프로피오닐)탁솔 또는 그의 산부가염임을 특징으로 하는 탁솔유도체 화합물.
  6. 제1항에 있어서의화합물은 7－(N,N－디메틸글리실)탁솔 또는 그의 산부가염임을 특징으로 하는 탁속유도체 화합물.
  7. 제1항에 있어서의화합물은 2´, 7－(N,N－디메틸글리실)탁솔 또는 그의 산부가염임을 특징으로 하는 탁솔유도체 화합물.
  8. 제1항에 있어서의화합물은 7－(알라닐)탁솔 또는 그의 산부가염임을 특징으로 하는 탁솔유도체 화합물.
  9. 다음 구조식(Ⅱ)로 표시되는 유효한양의 함종양 화합물이 적어도 하나 또는 약제학적으로 허용가능한 그의 염 및 약제학적으로 허용가능한 단체, 희석재 또는 부형제로 포함하여서 이루어지는 것임을 특징으로 하는 약제학적 조성물.
    상기식에서, R 및 R1는 각각 수소원자 또는 알라닌, 루신, 이소루신, 살린, 페닐알라닌, 프로린, 리신 및 아르기닌으로 이루어진 그룹 또는 다음 구조식(Ⅲ)으로 표시되는 그룹에서 선택되는 아미노산의 잔류물이다.
    상기식에서, n은 1 내지 3의 정수이고, R2및 R3는 각각 1 내지 3개의 탄소원자를 갖는 알킬라디칼에 있는 수소이며, 이들이 달라 붙은 질소원자와 함께 R 및 R1중의 적어도 하나는 수소원자가 아니라는 것을 조건부로 4 내지 5개의 탄소원자를 갖는 포화된 히테로고리를 형성할 수 있다.
  10. 제9항에 있어서의 화합물중 적어도 하나는 2´－(N,N－디메틸글리실)탁솔임을 특징으로 하는 약제학적 조성물.
  11. 제10항에 있어서의 화합물중 적어도 하나는 2´－(N,N－디에틸아미노프로피오닐)탁솔임을 특징으로 하는 약제학적 조성물.
  12. 제1항에 따른 화합물 중 적어도 하나를 환자에게 항종양에 유효한 양만큼 투여하여서 되는 종양 치료방법.
  13. 제12항에 있어서, 안간의 폐종양, 흑색종, 백혈병, 유암 및 결장암에서 선택되는 종양치료를 포함하는 치료방법.
  14. 탁솔과 다음 구조식(Ⅳ)로 표시되는 화합물과 반응시켜서 되는 다음 구조식(Ⅱ)로 표시되는 화합물의 제조방법.
    상기식에서, R 및 R1는 각각 수소원자 또는 다음 구조식(Ⅲ)으로 표시되는 그룹이다.
    상기식에서, n은 1 내지 3의 정수이고, R2및 R3는 각각 1 내지 3개의 탄소원자를 갖는 알킬라디칼에 있는 수소원자이며, 이들이 달라 붙은 질소원자와 함께 R 및 R1중의 적어도 하나는 수소원자가 아니라는 것을 조건부로 4 내지 5개의 탄소원자를 갖는 포화된 히테로고리를 형성할 수 있다.
    상기식에서, n R2및 R3는 상기에서 나타낸 것과 같다.
  15. 제14항에 있어서, 상기 탁솔과 상기 구조식(Ⅳ)의 화합물은 1:1당량비로 반응시켜서 R이 상기 구조식(Ⅲ)의 그룹이며 R´는 수소원자인 상기 구조식(Ⅱ)로 표시되는 2´－치환된 화합물을 형성시키는 것임을 특징으로 하는 제조방법.
  16. 제14항에 있어서, 상기 구조식(Ⅳ)의 화합물은 2당량은 탁솔 1당량과 반응하여 R 및 R´가 각각 상기 구조식(Ⅲ)의 그룹인 상기구조식(Ⅱ)로 표시되는 2´,7－이(치환된) 화합물을 형성시키는 것임을 특징으로 하는 제조방법.
  17. 제16항에 있어서, 상기 2´,7－이(치환된) 화합물은 분해반응이고, 2´－치환이 분해하여 R이 수소원자이고 R´가 상기 구조식(Ⅲ)의 그룹인 상기 구조식(Ⅱ)로 표시되는 7－치환된 화합물을 형성시키는 것임을 특징으로 하는 방법.
  18. 제14항에 있어서, 상기 반응은 축합시약의 존재 및 촉매의 존재 또는 부존재하에서 수행되는 것임을 특징으로 하는 제조방법.
  19. 제17항에 있어서, 상기 분해반응은 같은 2´,7－이(치환된) 화합물이 pH가 7 내지 7.4가 되도록 하여 되는 것임을 특징으로 하는 제조방법.
  20. 탁솔과 N－보호된 아미노산을 반응시키고 계속해서 상기 아미노산을 비보호시켜서 되는 다음 구조식(Ⅱ)로 표시되는 화합물의 제조방법.
    상기식에서, R 및 R1는 각각 수소원자 또는 R 및 R1중의 적어도 하나는 수소원자가 아니라는 것을 조건부로 하는 아미노산의 잔류물이다.
  21. 제20항에 있어서, 상기 탁솔과 상기 N－보호된 아미노산은 1:1당량비로 반응시켜서 2´－치환된 탁솔유도체를 형성시키는 것임을 특징으로 하는 제조방법.
  22. 제20항에 있어서, 상기 탁솔과 상기 N－보호된 아미노산은 1:2당량비로 반응시켜서 2´7－이치환된 탁솔유도체를 형성시키는 것임을 특징으로 하는 제조방법.
  23. 제22항에 있어서, 상기 구조식(Ⅱ)의 화합물은 분해반응을 받고 2´－치환물 아미노산이 분해하여서 7－(아미노산)탁솔 유도체를 형성시키는 것임을 특징으로 하는 제조방법.
  24. 제20항에 있어서, 상기 비보호단계는 약산처리로 수행하는 것임을 특징으로 하는 제조방법.
  25. 탁솔과 히드록실 보호기 화합물을 반응시켜서 2´－(보호된)탁솔을 제조하고, 상기 2´－(보호된)탁솔과 알라닌, 루신, 이소루산, 발린, 페닐알라닌, 프로린, 리신, 아르기닌 또는 다음 구조식(Ⅳ)의 화합물을 반응시켜서 2´－(보호된),7－(치환된)탁솔을 제조한 다음 2－위치를 비보호시켜서 되는 다음 구조식(Ⅱ)로 표시되는 화합물의 제조방법.
    상기식에서, R은 알라닌, 루신, 이소루신, 살린, 페닐알라닌, 프로린, 리신 및 아르기닌으로 이루어진 그룹 또는 다음 구조식(Ⅲ)으로 표시되는 그룹에서 선택된 아미노산의 잔류물이다.
    상기식에서, R은 아랄닌, 루신, 이소루신, 살린, 페닐알라닌, 프로린, 리신 및 아르기닌으로 이루어진 그룹 또는 다음 구조식(Ⅲ)으로 표시되는 그룹에서 선택된 아미노산의 잔류물이다.
    상기식에서, n은 1 내지 3의 정수이고, R2및 R3는 각각 1 내지 3개의 탄소원자를 갖는 알킬라디칼에 있는 수소원자이며, 이들이 달라 붙은 질소원자와 함께 4 내지 5개의 탄소원자를 갖는 포화된 히테로고리를 형성할 수 있다.
    상기식에서, R2및 R3및 n은 상기에서 나타낸 것과 같다.
  26. 제25항에 있어서, 상기 비보호단계는 상기 2´－(보호된), 7－(치환된)탁솔과 아연과 초산의 혼합물을 반응시켜서 수행되는 것임을 특징으로 하는 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900702418A 1989-03-09 1990-03-09 탁솔유도체 화합물과 그의 제조방법 KR920700208A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/321,152 US4960790A (en) 1989-03-09 1989-03-09 Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof
PCT/US1990/001262 WO1990010443A1 (en) 1989-03-09 1990-03-09 Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof

Publications (1)

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KR920700208A true KR920700208A (ko) 1992-02-19

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Country Link
US (1) US4960790A (ko)
EP (1) EP0419653A4 (ko)
JP (1) JPH04504845A (ko)
KR (1) KR920700208A (ko)
CN (1) CN1058018A (ko)
AU (1) AU628161B2 (ko)
CA (1) CA2028096A1 (ko)
GR (1) GR1000684B (ko)
HU (1) HU206617B (ko)
OA (1) OA09458A (ko)
WO (1) WO1990010443A1 (ko)

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