BE1003228A4 - Procede de synthese de la vinblastine et de la vincristine - Google Patents
Procede de synthese de la vinblastine et de la vincristine Download PDFInfo
- Publication number
- BE1003228A4 BE1003228A4 BE8800908A BE8800908A BE1003228A4 BE 1003228 A4 BE1003228 A4 BE 1003228A4 BE 8800908 A BE8800908 A BE 8800908A BE 8800908 A BE8800908 A BE 8800908A BE 1003228 A4 BE1003228 A4 BE 1003228A4
- Authority
- BE
- Belgium
- Prior art keywords
- vinblastine
- vincristine
- synthesis
- dihydro
- indole
- Prior art date
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)
Abstract
Procédé amélioré pour la préparation d'alcaloïdes dimères, en particulier de la vincristine et de la vinblastine, des composés connus pour leur activité antivirale et antileucémique ou anti-néoplasique, à partir d'un dérivé d'indole et d'un dérivé de dihydro-indole et réduction du composé iminium intermédiaire à l'aide de dérivés dihydro-1,4 pyridiniques déterminés, permettant une augmentation notable du rendement en énamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000543832A CA1341262C (fr) | 1987-08-06 | 1987-08-06 | Nouveau procede de synthese de 3',4'-anhydrovinblastine de la vinblastine et de la 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 (fr) |
| AU (1) | AU617342B2 (fr) |
| BE (1) | BE1003228A4 (fr) |
| CA (1) | CA1341262C (fr) |
| CH (1) | CH676711A5 (fr) |
| DE (1) | DE3826412A1 (fr) |
| GB (1) | GB2215331B (fr) |
| HU (1) | HU208829B (fr) |
| IT (1) | IT1227155B (fr) |
| NL (1) | NL8801966A (fr) |
| SE (1) | SE467875B (fr) |
| ZA (1) | ZA885765B (fr) |
Families Citing this family (6)
| 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 (fr) * | 1990-11-30 | 2002-01-01 | Hiroshi Ikawa | Derives de 1,4-dihydropyridine et methode de preparation |
| 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)
| 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)
| 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 (fr) * | 1987-01-22 | 2001-06-26 | James P. Kutney | Procede pour la synthese de 3',4'-anhydrovinblastine, de la vinblastine et de la vincristine |
-
1987
- 1987-08-06 CA CA000543832A patent/CA1341262C/fr 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)
| 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)
| 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 (fr) | 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 (fr) | 2001-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: THE UNIVERSITY OF BRITISH COLUMBIA Effective date: 19990831 |