KR850001229A - 4'-탈메틸-4-에피포도필로톡신 유도체의 제조방법 - Google Patents

4'-탈메틸-4-에피포도필로톡신 유도체의 제조방법 Download PDF

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KR850001229A
KR850001229A KR1019840004453A KR840004453A KR850001229A KR 850001229 A KR850001229 A KR 850001229A KR 1019840004453 A KR1019840004453 A KR 1019840004453A KR 840004453 A KR840004453 A KR 840004453A KR 850001229 A KR850001229 A KR 850001229A
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group
general formula
compound
acetaldehyde
following general
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KR1019840004453A
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KR900006215B1 (ko
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하마오(외 6) 우메자와
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이찌가와 도꾸지
자이단호오진 비세이부쓰 가가꾸 껭꾸우가이
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

내용 없음

Description

4'-탈메틸-4-에피포도필로톡신 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 다음 일반식(V)으로 표시되는 화합물을 다음 일반식(VI)로 표시되는 알데히드 또는 이의 아세틸 화합물과 반응시키고 또 이어 X1", X2" 또는 OY1중에 보호기가 함유된 경우에는 이를 제거하여 다음 일반식(I)으로 표시되는 신규의 4'-탈메틸-4-에피포도필로톡신 또는 그 염을 제조하는 방법.
    상기 일반식(I), (V) 및 (VI)에서, R은 저급알킬기이고, 또, X1및 X2는 독립하여 하이드록시기 또는 아미노기로서1, 개가 아미노기일 경우 다른 하나는 하이드록시기이며, X1" 및 X2" 중 하나는 하이드록시기 또는 보호된 하이드록시기이고, 또 다른 하나는 아미노기 또는 보호된 아미노기이며, 또 Y1은 수소 또는 보호기이다.
  2. 제1항에 있어서, 일반식(V)화합물과 일반식(VI)화합물의 반응이 설폰산, 양이온교환수지 또는 루이스산 존재하에서 행해지는 제조방법.
  3. 제1항에 있어서, R이 메틸기, 에틸기 또는 프로필기인 제조방법.
  4. 제1항에 있어서, 일반식(VI)화합물/일반식(V)화합물의 몰비율이 0.5내지 100인 제조방법.
  5. 제1항에 있어서, 반응이 불활성 용매중에서 행해지는 제조방법.
  6. 제1항에 있어서, 반응이 0내지 30℃로 행해지는 제조방법.
  7. 제1항에 있어서, 일반식(VI)의 화합물이 아세트알데히드, 프로피온알데히드, 아세트알데히드 디메틸아세탈, 아세트알데히드 디에틸아세탈 또는 아세트알데히드 디프로필아세탈인 제조방법.
  8. 제2항에 있어서, 설폰산이 아릴설폰산인 제조방법.
  9. 제8항에 있어서, 아릴설폰산이 P-톨루엔설폰산인 제조방법.
  10. 다음 일반식(VIII)으로 표시되는 4-0-(2-아미노-2-탈옥시-β-D-글루코피라노실)-4'-탈메틸-4-에피포도필토톡신(2위치의 아미노기, 3위치의 하이드록시기 및 4'-위치의 하이드록시는 보호될수도 있다)을 설폰산 존재하에서 아세트알데히드 또는 이의 아세탈과 반응시키고 또 이어 반응생성물에 보호기가 존재하는 경우 이를 제거하여 다음 일반식(VII)으로 표시되는 4-0-(2-아미노-2-탈옥시-4,6-0-에틸리덴-β-D-글루코피타노실)-4'-탈메틸-4-에피포도필토톡신 또는 그 염을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840004453A 1983-07-29 1984-07-26 4'-탈메틸-4-에피포도필로톡신 유도체의 제조방법 KR900006215B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP83-1376876 1983-07-29
JP83-137687 1983-07-29
JP58137687A JPS6032799A (ja) 1983-07-29 1983-07-29 新規４′−デメチル−４−エピポドフィロトキシン誘導体

Publications (2)

Publication Number Publication Date
KR850001229A true KR850001229A (ko) 1985-03-16
KR900006215B1 KR900006215B1 (ko) 1990-08-25

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KR1019840004453A KR900006215B1 (ko) 1983-07-29 1984-07-26 4'-탈메틸-4-에피포도필로톡신 유도체의 제조방법

Country Status (9)

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US (1) US4547567A (ko)
EP (1) EP0141057B1 (ko)
JP (1) JPS6032799A (ko)
KR (1) KR900006215B1 (ko)
AT (1) ATE36859T1 (ko)
AU (1) AU565168B2 (ko)
CA (1) CA1216287A (ko)
DE (1) DE3473763D1 (ko)
ES (1) ES8602022A1 (ko)

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JPS61189230A (ja) * 1985-02-19 1986-08-22 Nippon Kayaku Co Ltd エトポシド製剤
JPS61227590A (ja) * 1985-04-02 1986-10-09 Microbial Chem Res Found 新規４′−デメチル−４−エピポドフイロトキシン誘導体
IL77334A (en) * 1985-12-16 1991-04-15 Univ Bar Ilan Synthesis of 9-epipodophyllotoxin glucoside derivatives and some novel intermediates therefor
US4772589A (en) * 1986-10-29 1988-09-20 Bristol-Myers Etoposide solution in NMP
US4916217A (en) * 1987-01-08 1990-04-10 Bristol-Myers Company Phosphorus containing derivatives of epipodophyllotoxin
US4853467A (en) * 1987-05-19 1989-08-01 Bristol-Myers Company Nitrogen containing derivatives of epipodophyllotoxin glucosides
US4874851A (en) * 1987-07-01 1989-10-17 Bristol-Meyers Company 3',4'-dinitrogen substituted epipodophyllotoxin glucoside derivatives
US4868291A (en) * 1987-08-20 1989-09-19 Bristol-Myers Company 4'-deshydroxyepipodophyllotoxin glucosides: synthesis and use
US4888419A (en) * 1987-08-31 1989-12-19 Bristol-Myers Company 3'-demethoxyepipodophyllotoxin glucoside derivatives
US4912204A (en) * 1988-09-06 1990-03-27 Bristol-Myers Company Fluoro-substituted epipodophyllotoxin glucosides
EP0366122A3 (en) * 1988-10-26 1991-03-20 Warner-Lambert Company Demethylepipodophyllotoxin derivatives
US5061791A (en) * 1988-12-21 1991-10-29 Warner-Lambert Company 4-bromo-4'-demethylepipodophyllotoxin derivatives
DE3913327A1 (de) * 1989-04-22 1990-10-25 Behringwerke Ag Verfahren zur herstellung von glucosaminyl-epi-podo-phyllotoxin-derivaten
US5066645A (en) * 1989-09-01 1991-11-19 Bristol-Myers Company Epipodophyllotoxin altroside derivatives
US6610299B1 (en) 1989-10-19 2003-08-26 Aventis Pharma Deutschland Gmbh Glycosyl-etoposide prodrugs, a process for preparation thereof and the use thereof in combination with functionalized tumor-specific enzyme conjugates
US7241595B2 (en) * 1989-10-20 2007-07-10 Sanofi-Aventis Pharma Deutschland Gmbh Glycosyl-etoposide prodrugs, a process for preparation thereof and the use thereof in combination with functionalized tumor-specific enzyme conjugates
US6475486B1 (en) 1990-10-18 2002-11-05 Aventis Pharma Deutschland Gmbh Glycosyl-etoposide prodrugs, a process for preparation thereof and the use thereof in combination with functionalized tumor-specific enzyme conjugates
US5081234A (en) * 1990-04-30 1992-01-14 Bristol-Myers Squibb Co. 4'-demethylepipodophyllotoxin glycosides
CN1025918C (zh) * 1990-06-07 1994-09-14 国家医药管理局上海医药工业研究院 抗肿瘤药表鬼臼毒吡喃糖甙的合成新工艺
TW260671B (ko) * 1991-04-29 1995-10-21 Bristol Myers Squibb Co
US5463040A (en) * 1994-06-28 1995-10-31 Teva Pharmaceutical Industries, Ltd. Method of preparing etoposide
AU3265195A (en) * 1994-08-26 1996-03-22 Institute Of Materia Medica Chinese Academy Of Medical Sciences Novel taxol derivative
FR2739857B1 (fr) * 1995-10-12 1998-01-02 Pf Medicament Nouveaux derives amines de 2",3"-didesoxyglycosides d'epipodophyllotoxine, leur procede de preparation, leur utilisation comme medicament et leur utilisation destinee aux traitements anticancereux
US6207673B1 (en) 1997-03-12 2001-03-27 The University Of North Carolina At Chapel Hill Covalent conjugates of topoisomerase I and topoisomerase II inhibitors
AU775373B2 (en) 1999-10-01 2004-07-29 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
KR100418183B1 (ko) * 2000-01-03 2004-02-11 한국화학연구원 4-Ｏ-[2-(Ｎ,Ｎ-디알킬아미노)-2-데옥시-4,6-Ｏ,Ｏ-(알케닐리덴 또는알키닐리덴)-β-Ｄ-글루코실]-4'-Ｏ-데메틸-에피-포도필로톡신 화합물, 이의 제조방법 및 이를 포함하는 항암제 조성물

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US3060169A (en) * 1955-05-13 1962-10-23 Saul & Co Condensation products of glucosides with carbonyl compounds
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EP0141057A1 (en) 1985-05-15
DE3473763D1 (en) 1988-10-06
CA1216287A (en) 1987-01-06
EP0141057B1 (en) 1988-08-31
ATE36859T1 (de) 1988-09-15
AU3122484A (en) 1985-01-31
ES534698A0 (es) 1985-11-01
JPS6032799A (ja) 1985-02-19
KR900006215B1 (ko) 1990-08-25
AU565168B2 (en) 1987-09-10
US4547567A (en) 1985-10-15
JPH0212478B2 (ko) 1990-03-20
ES8602022A1 (es) 1985-11-01

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