ES8705435A1 - Process for the preparation of vincamine - Google Patents
Process for the preparation of vincamineInfo
- Publication number
- ES8705435A1 ES8705435A1 ES552560A ES552560A ES8705435A1 ES 8705435 A1 ES8705435 A1 ES 8705435A1 ES 552560 A ES552560 A ES 552560A ES 552560 A ES552560 A ES 552560A ES 8705435 A1 ES8705435 A1 ES 8705435A1
- Authority
- ES
- Spain
- Prior art keywords
- vincamine
- preparation
- vincadifformine
- acid
- tabersonine
- 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
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 8
- 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 4
- 229960002726 vincamine Drugs 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- GIGFIWJRTMBSRP-ACRUOGEOSA-N (-)-vincadifformine Chemical compound C1C(C(=O)OC)=C2NC3=CC=CC=C3[C@@]22CCN3CCC[C@]1(CC)[C@@H]23 GIGFIWJRTMBSRP-ACRUOGEOSA-N 0.000 abstract 4
- 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 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 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 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
- GIGFIWJRTMBSRP-UHFFFAOYSA-N DL-Vincadifformin Natural products C1C(C(=O)OC)=C2NC3=CC=CC=C3C22CCN3CCCC1(CC)C23 GIGFIWJRTMBSRP-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 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
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000002955 isolation 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
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 239000007787 solid Substances 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
- NAMSIRMSFVGAKD-UHFFFAOYSA-N vincadifformine Natural products CCC12CCCN3CCC4(C13)C(Nc1cc(OC)ccc41)=C(C2)C(=O)OC NAMSIRMSFVGAKD-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
The invention relates to a semisynthetic process for the preparation of vincamine, starting from tabersonine, which includes the following stages: hydrogenation of tabersonine in solution with anhydrous Raney nickel to give vincadifformine, preparation of the vincadifformine salt with an acid, oxidation of the vincadifformine salt with an anhydrous mixture, which is solid at room temperature, of maleic acid and permaleic acid having a peracid content of 40 to 50 %, rearrangement of the oxidised compound by heating for 2 to 4 hours at 30 to 50 DEG C to give vincamine, and isolation of the vincamine by precipitation with ammonia.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH905/85A CH664153A5 (en) | 1985-02-28 | 1985-02-28 | PROCEDURE FOR THE PREPARATION OF THE VINCAMINA. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES552560A0 ES552560A0 (en) | 1987-05-01 |
| ES8705435A1 true ES8705435A1 (en) | 1987-05-01 |
Family
ID=4197907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES552560A Expired ES8705435A1 (en) | 1985-02-28 | 1986-02-28 | Process for the preparation of vincamine |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE904293A (en) |
| CH (1) | CH664153A5 (en) |
| DE (1) | DE3606665A1 (en) |
| ES (1) | ES8705435A1 (en) |
| FR (1) | FR2577926B3 (en) |
| IT (1) | IT1191553B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276599B (en) * | 2011-08-18 | 2012-10-17 | 张家口市格瑞高新技术有限公司 | Process for preparing vincamine by semisynthetic method |
| CN104788447B (en) * | 2015-04-21 | 2016-08-31 | 张家港威胜生物医药有限公司 | A kind of semi-synthesis method prepares the production technology of vincamine |
-
1985
- 1985-02-28 CH CH905/85A patent/CH664153A5/en not_active IP Right Cessation
-
1986
- 1986-02-26 BE BE0/216321A patent/BE904293A/en not_active IP Right Cessation
- 1986-02-28 FR FR8602845A patent/FR2577926B3/en not_active Expired
- 1986-02-28 ES ES552560A patent/ES8705435A1/en not_active Expired
- 1986-02-28 IT IT83605/86A patent/IT1191553B/en active
- 1986-02-28 DE DE19863606665 patent/DE3606665A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT8683605A0 (en) | 1986-02-28 |
| CH664153A5 (en) | 1988-02-15 |
| FR2577926A1 (en) | 1986-08-29 |
| ES552560A0 (en) | 1987-05-01 |
| IT1191553B (en) | 1988-03-23 |
| FR2577926B3 (en) | 1987-08-07 |
| DE3606665A1 (en) | 1986-09-04 |
| BE904293A (en) | 1986-06-16 |
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