CA1341261C - Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine - Google Patents

Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine Download PDF

Info

Publication number
CA1341261C
CA1341261C CA000527897A CA527897A CA1341261C CA 1341261 C CA1341261 C CA 1341261C CA 000527897 A CA000527897 A CA 000527897A CA 527897 A CA527897 A CA 527897A CA 1341261 C CA1341261 C CA 1341261C
Authority
CA
Canada
Prior art keywords
alkyl
group
alk
aryl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA000527897A
Other languages
English (en)
French (fr)
Inventor
James P. Kutney
Lewis S.L. Choi
Michael Mchugh
Camille A. Boulet
Hiroki Tsukamoto
Jun Nakano
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of British Columbia
Original Assignee
University of British Columbia
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of British Columbia filed Critical University of British Columbia
Priority to CA000527897A priority Critical patent/CA1341261C/en
Priority to DE3801450A priority patent/DE3801450C2/de
Priority to SE8800170A priority patent/SE467874B/sv
Priority to IT8819156A priority patent/IT1215751B/it
Priority to AU10668/88A priority patent/AU1066888A/en
Priority to NL8800134A priority patent/NL8800134A/nl
Priority to GB8801296A priority patent/GB2204036B/en
Priority to IL85154A priority patent/IL85154A/xx
Priority to CH206/88A priority patent/CH675724A5/de
Priority to ZA88408A priority patent/ZA88408B/xx
Priority to FR8800650A priority patent/FR2611202A1/fr
Priority to BE8800080A priority patent/BE1003068A4/fr
Priority to JP63013473A priority patent/JPH0613531B2/ja
Priority to US07/228,821 priority patent/US5047528A/en
Priority to FR888810637A priority patent/FR2622888B1/fr
Application granted granted Critical
Publication of CA1341261C publication Critical patent/CA1341261C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA000527897A 1987-01-22 1987-01-22 Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine Expired - Fee Related CA1341261C (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
CA000527897A CA1341261C (en) 1987-01-22 1987-01-22 Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine
SE8800170A SE467874B (sv) 1987-01-22 1988-01-20 Framstaellning av vinblastin och vinkristin
DE3801450A DE3801450C2 (de) 1987-01-22 1988-01-20 Verfahren für die Herstellung von Dimeralkaloidverbindungen, insbesondere von 3', 4'-Dihydrovinblastin, Vinblastin und Vincristin
FR8800650A FR2611202A1 (fr) 1987-01-22 1988-01-21 Procede de synthese de composes alcaloides dimeres
NL8800134A NL8800134A (nl) 1987-01-22 1988-01-21 Werkwijze voor de bereiding van vinblastine en vincristine.
GB8801296A GB2204036B (en) 1987-01-22 1988-01-21 Process for the synthesis of vinblastine and vincristine
IL85154A IL85154A (en) 1987-01-22 1988-01-21 Process for the synthesis of vinblastine and vincristine and related dimer alkaloid compounds
CH206/88A CH675724A5 (ja) 1987-01-22 1988-01-21
IT8819156A IT1215751B (it) 1987-01-22 1988-01-21 Procedimento di sintesi di vinblastina e vincristina.
AU10668/88A AU1066888A (en) 1987-01-22 1988-01-21 Process for the synthesis of vinblastine and vincristine
ZA88408A ZA88408B (en) 1987-01-22 1988-01-21 Process for the synthesis of vinblastine and vincristine
BE8800080A BE1003068A4 (fr) 1987-01-22 1988-01-22 Procede de synthese de composes alcaloides dimeres.
JP63013473A JPH0613531B2 (ja) 1987-01-22 1988-01-22 二量体の生成方法
US07/228,821 US5047528A (en) 1987-01-22 1988-08-02 Process of synthesis of vinblastine and vincristine
FR888810637A FR2622888B1 (fr) 1987-01-22 1988-08-05 Procede perfectionne de synthese de la vinblastine et de la vincristine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA000527897A CA1341261C (en) 1987-01-22 1987-01-22 Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine

Publications (1)

Publication Number Publication Date
CA1341261C true CA1341261C (en) 2001-06-26

Family

ID=4134803

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000527897A Expired - Fee Related CA1341261C (en) 1987-01-22 1987-01-22 Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine

Country Status (11)

Country Link
JP (1) JPH0613531B2 (ja)
CA (1) CA1341261C (ja)
CH (1) CH675724A5 (ja)
DE (1) DE3801450C2 (ja)
FR (1) FR2611202A1 (ja)
GB (1) GB2204036B (ja)
IL (1) IL85154A (ja)
IT (1) IT1215751B (ja)
NL (1) NL8800134A (ja)
SE (1) SE467874B (ja)
ZA (1) ZA88408B (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047528A (en) * 1987-01-22 1991-09-10 University Of Bristish Columbia Process of synthesis of vinblastine and vincristine
CA1341262C (en) * 1987-08-06 2001-06-26 Camille A. Boulet A new process of the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine
USRE37449E1 (en) 1987-02-06 2001-11-13 University Of British Columbia Process of synthesis of 3′,4′-anhydrovinblastine, vinblastine and vincristine
US5037977A (en) * 1988-08-11 1991-08-06 Mitsui Petrochemical Industries Ltd. Method for production of dimeric alkaloids
HU209687B (en) * 1989-03-04 1994-10-28 Mitsui Petrochemical Ind Process for producing bisz-indole-alkaloids
US5432279A (en) * 1989-03-04 1995-07-11 Mitsui Petrochemical Industries, Inc. Process for the preparation of binary indole alkaloids
FR2779146B1 (fr) * 1998-06-02 2002-01-18 Roowin Nouveaux derives de vinca-alcaloides et procedes de preparation
CN103936769B (zh) * 2014-04-30 2016-10-05 淮海工学院 一种制备高光学纯脱水长春碱的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2296418B1 (ja) * 1974-12-30 1978-07-21 Anvar
US4279817A (en) * 1975-05-30 1981-07-21 The United States Of America As Represented By The Department Of Health & Human Services Method for producing dimer alkaloids
GB1551054A (en) * 1976-03-04 1979-08-22 Atta Ur Rahman Syntheses of vinblastine vincristine and vinrosidine
FR2358412A1 (fr) * 1976-07-13 1978-02-10 Parcor Procede de preparation de la vincamine et d'alcaloides apparentes

Also Published As

Publication number Publication date
SE8800170D0 (sv) 1988-01-20
IT1215751B (it) 1990-02-22
FR2611202A1 (fr) 1988-08-26
JPH01131187A (ja) 1989-05-24
NL8800134A (nl) 1988-08-16
JPH0613531B2 (ja) 1994-02-23
IL85154A (en) 1992-08-18
SE467874B (sv) 1992-09-28
DE3801450C2 (de) 1999-02-25
SE8800170L (sv) 1988-07-23
CH675724A5 (ja) 1990-10-31
DE3801450A1 (de) 1988-08-18
GB8801296D0 (en) 1988-02-17
GB2204036A (en) 1988-11-02
IT8819156A0 (it) 1988-01-21
FR2611202B1 (ja) 1994-08-19
GB2204036B (en) 1991-03-27
ZA88408B (en) 1989-04-26
IL85154A0 (en) 1988-06-30

Similar Documents

Publication Publication Date Title
US4144237A (en) Synthetic vinblastine and vincristine derivatives
EP0021177B1 (en) Maytansinoids, their production and use
CA1341261C (en) Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine
Chang et al. Migratory aptitudes in pinacol rearrangement of vic‐dihydroxychlorins
US5047528A (en) Process of synthesis of vinblastine and vincristine
USRE37449E1 (en) Process of synthesis of 3′,4′-anhydrovinblastine, vinblastine and vincristine
US4145552A (en) Preparation of vincamine and related alkaloids
AU617342B2 (en) Process for the synthesis of dimer alkaloid compounds
US4866172A (en) Pristinamycin process
CA1100495A (en) Process for the preparation of alkaloids of the leurosine type
US3979395A (en) Process for the preparation of vincamine and other indole alkaloids
US4305875A (en) Process for the synthesis of vinblastine and leurosidine
EP0079785B1 (en) Method of preparing 1-formyl congeners of indole-dihydroindole dimers
US3894028A (en) Process for the preparation of optical antipode of vincamine and new indole derivatives
US4303584A (en) Method of preparing vincristine
US4322350A (en) Process for the synthesis of leurosine and of its derivatives
US4659816A (en) Process for the preparation of dimeric alkaloids
EP0440037B1 (en) Hydroxycarbonyl derivatives and process for making the same
IL87347A (en) Process for the synthesis of vinblastine and vincristine
BE1003068A4 (fr) Procede de synthese de composes alcaloides dimeres.
US4767855A (en) Process for the preparation of vincristine
KR850001919B1 (ko) 20'-하이드록시 빈블라스틴 및 유사화합물의 제조방법
MORI et al. Synthesis and biological activities of 2, 3-dimethyl-1, 4-benzoquinones having alkylthio and arylthio side chains
Matsumoto et al. HIGH PRESSURE ADDITION REACTIONS OF SOME 3a, 6a-DIAZAPENTALENES~
HU186266B (en) Process for producing novel 6,7-dihydro vinblastin-3,6 ether-derivatives

Legal Events

Date Code Title Description
MKLA Lapsed