BE1003228A4 - Procede de synthese de la vinblastine et de la vincristine - Google Patents

Procede de synthese de la vinblastine et de la vincristine Download PDF

Info

Publication number: BE1003228A4
Authority: BE; Belgium
Prior art keywords: vinblastine; vincristine; synthesis; dihydro; indole
Prior art date: 1987-08-06

Application number

BE8800908A

Other languages

English (en)

French (fr)

Inventor

P Kutney James

S L Choi Lewis

Nakano Jun

Tsukamoto Hiroki

A Boulet Camille

Mchugh Michael

Original Assignee

Univ 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.)

1987-08-06

Filing date

1988-08-05

Publication date

1992-02-04

1988-08-05 Application filed by Univ British Columbia filed Critical Univ British Columbia

1992-02-04 Application granted granted Critical

1992-02-04 Publication of BE1003228A4 publication Critical patent/BE1003228A4/fr

Links

JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 title abstract 2
238000000034 method Methods 0.000 title abstract 2
229960003048 vinblastine Drugs 0.000 title abstract 2
229960004528 vincristine Drugs 0.000 title abstract 2
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 title abstract 2
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 title abstract 2
230000015572 biosynthetic process Effects 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract 2
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 abstract 1
229930013930 alkaloid Natural products 0.000 abstract 1
230000000719 anti-leukaemic effect Effects 0.000 abstract 1
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
230000000840 anti-viral effect Effects 0.000 abstract 1
150000002081 enamines Chemical class 0.000 abstract 1
150000002475 indoles Chemical class 0.000 abstract 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 abstract 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BE8800908A 1987-08-06 1988-08-05 Procede de synthese de la vinblastine et de la vincristine BE1003228A4 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000543832A CA1341262C (en)	1987-08-06	1987-08-06	A new process of the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine

Publications (1)

Publication Number	Publication Date
BE1003228A4 true BE1003228A4 (fr)	1992-02-04

Family

ID=4136214

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE8800908A BE1003228A4 (fr)	1987-08-06	1988-08-05	Procede de synthese de la vinblastine et de la vincristine

Country Status (12)

Country	Link
JP (1)	JPH0613532B2 (da)
AU (1)	AU617342B2 (da)
BE (1)	BE1003228A4 (da)
CA (1)	CA1341262C (da)
CH (1)	CH676711A5 (da)
DE (1)	DE3826412A1 (da)
GB (1)	GB2215331B (da)
HU (1)	HU208829B (da)
IT (1)	IT1227155B (da)
NL (1)	NL8801966A (da)
SE (1)	SE467875B (da)
ZA (1)	ZA885765B (da)

Families Citing this family (6)

* 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
USRE37449E1 (en)	1987-02-06	2001-11-13	University Of British Columbia	Process of synthesis of 3′,4′-anhydrovinblastine, vinblastine and vincristine
US5432279A (en) *	1989-03-04	1995-07-11	Mitsui Petrochemical Industries, Inc.	Process for the preparation of binary indole alkaloids
CA2056799C (en) *	1990-11-30	2002-01-01	Hiroshi Ikawa	1,4-dihydropyridine derivatives and methods of producing the same
JP3010151U (ja) *	1994-04-26	1995-04-25	スミ子片山	切込みのついた筒形食器収納ケース。
FR2779146B1 (fr) *	1998-06-02	2002-01-18	Roowin	Nouveaux derives de vinca-alcaloides et procedes de preparation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4144237A (en) *	1975-05-30	1979-03-13	The United States Of America As Represented By The Department Of Health, Education And Welfare	Synthetic vinblastine and vincristine derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU195513B (en) *	1984-10-16	1988-05-30	Richter Gedeon Vegyeszet	Process for producing stable solutions of alkaloides with bis-indole skeleton
AU590873B2 (en) *	1985-03-12	1989-11-23	University Of Vermont And State Agricultural College, The	Synthesis of vinblastine and vincristine type compounds
CA1341261C (en) *	1987-01-22	2001-06-26	James P. Kutney	Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine

1987
- 1987-08-06 CA CA000543832A patent/CA1341262C/en not_active Expired - Fee Related
1988
- 1988-08-03 SE SE8802813A patent/SE467875B/sv not_active IP Right Cessation
- 1988-08-03 DE DE3826412A patent/DE3826412A1/de not_active Ceased
- 1988-08-05 CH CH2974/88A patent/CH676711A5/de not_active IP Right Cessation
- 1988-08-05 IT IT8821678A patent/IT1227155B/it active
- 1988-08-05 BE BE8800908A patent/BE1003228A4/fr not_active IP Right Cessation
- 1988-08-05 NL NL8801966A patent/NL8801966A/nl not_active Application Discontinuation
- 1988-08-05 ZA ZA885765A patent/ZA885765B/xx unknown
- 1988-08-05 AU AU20512/88A patent/AU617342B2/en not_active Ceased
- 1988-08-06 JP JP63196999A patent/JPH0613532B2/ja not_active Expired - Lifetime
- 1988-08-08 GB GB8818765A patent/GB2215331B/en not_active Expired - Lifetime
- 1988-08-08 HU HU884126A patent/HU208829B/hu not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4144237A (en) *	1975-05-30	1979-03-13	The United States Of America As Represented By The Department Of Health, Education And Welfare	Synthetic vinblastine and vincristine derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMISTRY AND INDUSTRY, 2 avril 1977, pages 277-278; T. MAKINO et al.: "Asymmetric reduction of aplha,beta-unsaturated iminium salt with N-glucopyranosyl-1,4-dihydronicotinamides" *

Also Published As

Publication number	Publication date
CH676711A5 (da)	1991-02-28
GB8818765D0 (en)	1988-09-07
NL8801966A (nl)	1989-03-01
AU2051288A (en)	1989-02-09
HU208829B (en)	1994-01-28
IT1227155B (it)	1991-03-19
SE8802813D0 (sv)	1988-08-03
JPH0613532B2 (ja)	1994-02-23
HUT50351A (en)	1990-01-29
GB2215331B (en)	1992-01-02
SE8802813L (sv)	1989-02-07
ZA885765B (en)	1989-09-27
IT8821678A0 (it)	1988-08-05
JPH01151590A (ja)	1989-06-14
DE3826412A1 (de)	1989-02-16
GB2215331A (en)	1989-09-20
SE467875B (sv)	1992-09-28
AU617342B2 (en)	1991-11-28
CA1341262C (en)	2001-06-26

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Legal Events

Date

Code

Title

Description

2000-02-29

RE

Patent lapsed

Owner name: THE UNIVERSITY OF BRITISH COLUMBIA

Effective date: 19990831