SE8800170L - Framstellning av vinblastin och vinkristin - Google Patents

Framstellning av vinblastin och vinkristin

Info

Publication number: SE8800170L
Authority: SE; Sweden
Prior art keywords: wine; iminium intermediate; vincristine; vinblastine; blast
Prior art date: 1987-01-22

Application number

SE8800170A

Other languages

English (en)

Other versions

SE8800170D0 (sv

SE467874B (sv

Inventor

J P Kutney

L S L Choi

J Nakano

H Tsukamoto

C A Boulet

M Mchugh

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.)

1987-01-22

Filing date

1988-01-20

Publication date

1988-07-23

1988-01-20 Application filed by Univ British Columbia filed Critical Univ British Columbia

1988-01-20 Publication of SE8800170D0 publication Critical patent/SE8800170D0/sv

1988-07-23 Publication of SE8800170L publication Critical patent/SE8800170L/sv

1992-09-28 Publication of SE467874B publication Critical patent/SE467874B/sv

Links

239000000543 intermediate Substances 0.000 abstract 4
238000000034 method Methods 0.000 abstract 3
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 abstract 2
GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 abstract 2
150000002081 enamines Chemical class 0.000 abstract 2
229960003048 vinblastine Drugs 0.000 abstract 2
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 2
229960004528 vincristine Drugs 0.000 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 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 abstract 2
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 abstract 1
WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 abstract 1
238000005273 aeration Methods 0.000 abstract 1
229910052783 alkali metal Inorganic materials 0.000 abstract 1
150000001340 alkali metals Chemical class 0.000 abstract 1
229930013930 alkaloid Natural products 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
CMKFQVZJOWHHDV-DYHNYNMBSA-N catharanthine Chemical compound C([C@@H]1C=C([C@@H]2[C@@]3(C1)C(=O)OC)CC)N2CCC1=C3NC2=CC=CC=C12 CMKFQVZJOWHHDV-DYHNYNMBSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 abstract 1
239000003153 chemical reaction reagent Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 abstract 1
125000001041 indolyl group Chemical group 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
238000005580 one pot reaction Methods 0.000 abstract 1
230000003647 oxidation Effects 0.000 abstract 1
238000007254 oxidation reaction Methods 0.000 abstract 1
230000001590 oxidative effect Effects 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 abstract 1
-1 vindoline Chemical compound 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
- 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)

SE8800170A 1987-01-22 1988-01-20 Framstaellning av vinblastin och vinkristin SE467874B (sv)

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 (3)

Publication Number	Publication Date
SE8800170D0 SE8800170D0 (sv)	1988-01-20
SE8800170L true SE8800170L (sv)	1988-07-23
SE467874B SE467874B (sv)	1992-09-28

Family

ID=4134803

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8800170A SE467874B (sv)	1987-01-22	1988-01-20	Framstaellning av vinblastin och vinkristin

Country Status (11)

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

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
CA2011389A1 (en) *	1989-03-04	1990-09-04	Naoya Sakamoto	Process for the preparation of binary 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 (sv) *	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

1987
- 1987-01-22 CA CA000527897A patent/CA1341261C/en not_active Expired - Fee Related
1988
- 1988-01-20 SE SE8800170A patent/SE467874B/sv not_active IP Right Cessation
- 1988-01-20 DE DE3801450A patent/DE3801450C2/de not_active Expired - Fee Related
- 1988-01-21 IT IT8819156A patent/IT1215751B/it active
- 1988-01-21 FR FR8800650A patent/FR2611202A1/fr active Granted
- 1988-01-21 NL NL8800134A patent/NL8800134A/nl not_active Application Discontinuation
- 1988-01-21 ZA ZA88408A patent/ZA88408B/xx unknown
- 1988-01-21 IL IL85154A patent/IL85154A/xx not_active IP Right Cessation
- 1988-01-21 CH CH206/88A patent/CH675724A5/de not_active IP Right Cessation
- 1988-01-21 GB GB8801296A patent/GB2204036B/en not_active Expired - Lifetime
- 1988-01-22 JP JP63013473A patent/JPH0613531B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE3801450A1 (de)	1988-08-18
FR2611202A1 (fr)	1988-08-26
IT8819156A0 (it)	1988-01-21
ZA88408B (en)	1989-04-26
IT1215751B (it)	1990-02-22
NL8800134A (nl)	1988-08-16
JPH01131187A (ja)	1989-05-24
CA1341261C (en)	2001-06-26
IL85154A (en)	1992-08-18
GB2204036A (en)	1988-11-02
CH675724A5 (sv)	1990-10-31
IL85154A0 (en)	1988-06-30
GB2204036B (en)	1991-03-27
JPH0613531B2 (ja)	1994-02-23
GB8801296D0 (en)	1988-02-17
SE8800170D0 (sv)	1988-01-20
SE467874B (sv)	1992-09-28
FR2611202B1 (sv)	1994-08-19
DE3801450C2 (de)	1999-02-25

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