KR970061911A - 콜히친 유도체의 글리코사이드화 방법 및 그 제품 - Google Patents

콜히친 유도체의 글리코사이드화 방법 및 그 제품 Download PDF

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KR970061911A
KR970061911A KR1019970003702A KR19970003702A KR970061911A KR 970061911 A KR970061911 A KR 970061911A KR 1019970003702 A KR1019970003702 A KR 1019970003702A KR 19970003702 A KR19970003702 A KR 19970003702A KR 970061911 A KR970061911 A KR 970061911A
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hydrolyzed
target
protected
intermediate separation
glycoside product
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KR1019970003702A
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KR100206357B1 (ko
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봄바르델리 에지오
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다리오 보나꼬르시
인데나 에스피아
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    • 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
    • C07H17/06—Benzopyran radicals
    • C07H17/065—Benzo[b]pyrans
    • 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
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

본 발명은 콜히친 또는 티오콜히친글리코사이드류 또는 그들의 유도체의 제조방법에 관한 것이다.
콜히친(colchicine)은 통풍(gout)치료시 사용되는 슈도알칼로이드 화합물이다.

Description

콜히친 유도체의 글리코사이드화 방법 및 그 제품
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. 하기 구조식(Ⅰ)을 갖는 화합물의 제조방법으로,
    (Ⅰ)
    (여기에서, R은 메톡시 또는 티오메틸그룹이고; R1의 임의 보호된 β-D-글리코피라노실옥시 또는 6-데옥시갈락토피라노실옥시 잔기이며; R2는 C1∼C7알킬그룹, 바람직하기로는 메틸이다.
    적당히 보호된 1-후루오로글리코스 또는 1-후루오로후코스와 구조식(Ⅱ)의 화합물을 반응시키고,
    (Ⅱ)
    (여기에서, R과 R2는 전기와 같다) 임의로 글리사이드 잔기에 존재하는 보호그룹을 제거하는 것으로 구성된 구조식(Ⅰ)의 화합물 제조방법.
  2. 제1항에 있어서, R이 SCH3인 구조식(Ⅰ) 화합물의 제조방법.
  3. 제1항 또는 제2항에 있어서, 1-후루오글루코스 또는 후코스 유도체가 2,3,4,6-테트라-0-아세틸-a, D-글리코피라노실후루오라이드 또는 2,3,4-트리-0-아세틸-a, L-후코피라노실 후루오라이드인 방법.
  4. 제1항 또는 제2항에 있어서, 반응은 아세토니트릴, 니트로메탄, 할로겐화된 하이드로카본류로부터 선택된 용매중에서 수행하는 방법.
  5. 제3항에 있어서, 반응은 아세토니트릴, 니트로메탄, 할로겐화된 하이드로카본류로부터 선택된 용매중에서 수행하는 방법.
  6. 제4항에 있어서, 용매는 아세토니트릴인 방법.
  7. 제5항에 있어서, 용매는 아세토니트릴인 방법.
  8. 제1항 또는 제2항에 있어서, 보호된 글리코사이드 제품은 중간체 분리없이 가수분해시키고 목적물을 반응물로부터 직접 결정화시키는 방법.
  9. 제3항에 있어서, 보호된 글리코사이드 제품은 중간체 분리없이 가수분해시키고 목적물을 반응물로부터 직접 결정화시키는 방법.
  10. 제4항에 있어서, 보호된 글리코사이드 제품은 중간체 분리없이 가수분해시키고 목적물을 반응물로부터 직접 결정화시키는 방법.
  11. 제5항에 있어서, 보호된 글리코사이드 제품은 중간체 분리없이 가수분해시키고 목적물을 반응물로부터 직접 결정화시키는 방법.
  12. 제6항에 있어서, 보호된 글리코사이드 제품은 중간체 분리없이 가수분해시키고 목적물을 반응물로부터 직접 결정화시키는 방법.
  13. 제7항에 있어서, 보호된 글리코사이드 제품은 중간체 분리없이 가수분해시키고 목적물을 반응무로부터 직접 결정화시키는 방법.
  14. 3-(2',3',4'-트리-0-아세틸-L-후코피라노실)-3-데메틸티오콜히친.
  15. 3-L-루코피라노실-3-데메칠티오콜히친.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970003702A 1996-02-08 1997-02-06 콜히친 유도체의 글리코사이드화 방법 및 그 제품 KR100206357B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI96A000236 1996-02-08
IT96MI000236A IT1282584B1 (it) 1996-02-08 1996-02-08 Processo di glicosidazione di derivati colchicinici e prodotti ottenuti

Publications (2)

Publication Number Publication Date
KR970061911A true KR970061911A (ko) 1997-09-12
KR100206357B1 KR100206357B1 (ko) 1999-07-01

Family

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Country Status (13)

Country Link
US (1) US5777136A (ko)
EP (1) EP0789028B1 (ko)
JP (1) JP3029806B2 (ko)
KR (1) KR100206357B1 (ko)
AT (1) ATE217007T1 (ko)
AU (1) AU707718B2 (ko)
CA (1) CA2196932C (ko)
DE (1) DE69712240T2 (ko)
DK (1) DK0789028T3 (ko)
ES (1) ES2176533T3 (ko)
HK (1) HK1002362A1 (ko)
IT (1) IT1282584B1 (ko)
PT (1) PT789028E (ko)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2779147B1 (fr) * 1998-05-27 2000-06-30 Synthelabo Derive de thiocolchicoside sa preparation et son application en therapeutique
US6825236B2 (en) 2003-04-14 2004-11-30 California Pacific Medical Center Colchicine derivatives
ITMI20031144A1 (it) * 2003-06-06 2004-12-07 Indena Spa Analoghi del colchicoside.
SG165175A1 (en) * 2004-05-12 2010-10-28 Indena Spa Biotransformation of colchicinoid compounds
DE602008004113D1 (de) * 2008-05-28 2011-02-03 Indena Spa Verfahren zur Glycosidierung von Colchicin und Thiocolchicin
WO2010138670A2 (en) * 2009-05-27 2010-12-02 Mutual Pharmaceutical Company, Inc. Thiocolchicine derivatives, method of making and methods of use thereof
US20110178180A1 (en) * 2010-01-18 2011-07-21 Kurt Nielsen Deuterium-enriched colchicine, thiocolchicine, and derivatives thereof; methods of preparation; and use thereof
EP3086794B1 (en) 2013-12-23 2020-01-08 Alkaloids Corporation Process for the conversion of colchicinoids to their 3-glycosylated derivatives via their respective 3-demethyl analogues

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2112131A1 (en) * 1970-11-06 1972-06-16 Roussel Uclaf 2-and 3-glucose-2-yl-demethylthiololchicines - antimitotic agents,prepared from colchicine
FR2112710A5 (en) * 1970-11-06 1972-06-23 Roussel Uclaf Thiocolchicoside prepn - from thiocolchicine in high yield in three stages
US3816396A (en) * 1972-04-27 1974-06-11 Roussel Uclaf Thiocolchicine glucoside
US4692463A (en) * 1985-02-26 1987-09-08 The United States Of America As Represented By The Department Of Health And Human Services Antiinflammatory 2,3-didemethylcolchicine and additional derivatives
US5175342A (en) * 1988-08-24 1992-12-29 The United States Of America As Represented By The Department Of Health And Human Services Esters of 3-demethylthiocolchicine and n-acyl analogs

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Publication number Publication date
EP0789028A2 (en) 1997-08-13
ES2176533T3 (es) 2002-12-01
EP0789028A3 (en) 1998-01-28
EP0789028B1 (en) 2002-05-02
US5777136A (en) 1998-07-07
DE69712240D1 (de) 2002-06-06
CA2196932C (en) 2000-12-05
AU707718B2 (en) 1999-07-15
AU1253497A (en) 1997-08-14
DK0789028T3 (da) 2002-08-19
CA2196932A1 (en) 1997-08-09
JPH09309896A (ja) 1997-12-02
ITMI960236A0 (ko) 1996-02-08
ATE217007T1 (de) 2002-05-15
ITMI960236A1 (it) 1997-08-08
IT1282584B1 (it) 1998-03-31
DE69712240T2 (de) 2002-12-19
PT789028E (pt) 2002-09-30
JP3029806B2 (ja) 2000-04-10
HK1002362A1 (en) 1998-08-21
KR100206357B1 (ko) 1999-07-01

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