BE904293A - Procede de fabrication de la vincamine a partir de la tabersonine. - Google Patents
Procede de fabrication de la vincamine a partir de la tabersonine.Info
- Publication number
- BE904293A BE904293A BE0/216321A BE216321A BE904293A BE 904293 A BE904293 A BE 904293A BE 0/216321 A BE0/216321 A BE 0/216321A BE 216321 A BE216321 A BE 216321A BE 904293 A BE904293 A BE 904293A
- Authority
- BE
- Belgium
- Prior art keywords
- vincamine
- acid
- tabersonin
- vincadifformin
- salified
- Prior art date
Links
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 title abstract 6
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 title abstract 3
- FNGGIPWAZSFKCN-ACRUOGEOSA-N tabersonine Chemical compound N1C2=CC=CC=C2[C@]2([C@H]34)C1=C(C(=O)OC)C[C@]3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-ACRUOGEOSA-N 0.000 title abstract 3
- 229960002726 vincamine Drugs 0.000 title abstract 3
- FNGGIPWAZSFKCN-UHFFFAOYSA-N xi-tabersonine Natural products N1C2=CC=CC=C2C2(C34)C1=C(C(=O)OC)CC3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- JSLDLCGKZDUQSH-RTBUJCADSA-N 19-epivindolinine Natural products O=C(OC)[C@H]1[C@@]23[C@H](C)[C@]4([C@@H]5N(CC=C4)CC[C@]25c2c(N3)cccc2)C1 JSLDLCGKZDUQSH-RTBUJCADSA-N 0.000 title 1
- KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- GIGFIWJRTMBSRP-UHFFFAOYSA-N DL-Vincadifformin Natural products C1C(C(=O)OC)=C2NC3=CC=CC=C3C22CCN3CCCC1(CC)C23 GIGFIWJRTMBSRP-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- KQRZXSFABBICGL-UHFFFAOYSA-N Tabersonin Natural products COC(=O)C1=C2Nc3ccccc3C24CCN5CC=CC(C1)C45 KQRZXSFABBICGL-UHFFFAOYSA-N 0.000 abstract 2
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Ce pocédé de semi-synthèse de la vincamine à partir de tabersonine, comprend les étapes suivantes : on hydrogène la tabersonine en solution par le nickel de Rayney anhydre en vincadifformine; on salifie cette dernière par un acide, on oxyde la vincadifformine salifiée par un mélange anhydre, solide à température ambiante, d'acide maléique et d'acide permaléique à 40-50% du peracide; on transpose le composé oxydé par chauffage entre 30 et 50 degré C pendant 2-4 en obtenant la vincamine; et enfin, on isole cette dernière pour précipitation par l'ammoniaque.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH905/85A CH664153A5 (it) | 1985-02-28 | 1985-02-28 | Procedimento per la preparazione della vincamina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE904293A true BE904293A (fr) | 1986-06-16 |
Family
ID=4197907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/216321A BE904293A (fr) | 1985-02-28 | 1986-02-26 | Procede de fabrication de la vincamine a partir de la tabersonine. |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE904293A (fr) |
| CH (1) | CH664153A5 (fr) |
| DE (1) | DE3606665A1 (fr) |
| ES (1) | ES8705435A1 (fr) |
| FR (1) | FR2577926B3 (fr) |
| IT (1) | IT1191553B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276599B (zh) * | 2011-08-18 | 2012-10-17 | 张家口市格瑞高新技术有限公司 | 半合成法长春胺的制备工艺 |
| CN104788447B (zh) * | 2015-04-21 | 2016-08-31 | 张家港威胜生物医药有限公司 | 一种半合成法制备长春胺的生产工艺 |
-
1985
- 1985-02-28 CH CH905/85A patent/CH664153A5/it not_active IP Right Cessation
-
1986
- 1986-02-26 BE BE0/216321A patent/BE904293A/fr not_active IP Right Cessation
- 1986-02-28 IT IT83605/86A patent/IT1191553B/it active
- 1986-02-28 FR FR8602845A patent/FR2577926B3/fr not_active Expired
- 1986-02-28 ES ES552560A patent/ES8705435A1/es not_active Expired
- 1986-02-28 DE DE19863606665 patent/DE3606665A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES552560A0 (es) | 1987-05-01 |
| DE3606665A1 (de) | 1986-09-04 |
| IT8683605A0 (it) | 1986-02-28 |
| CH664153A5 (it) | 1988-02-15 |
| IT1191553B (it) | 1988-03-23 |
| FR2577926B3 (fr) | 1987-08-07 |
| FR2577926A1 (fr) | 1986-08-29 |
| ES8705435A1 (es) | 1987-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: ARYSEARCH ARYLAN A.G. Effective date: 19880228 |