IT1153301B - Vincamine and 14,15-dehydro-vincamine prepn - Google Patents
Vincamine and 14,15-dehydro-vincamine prepnInfo
- Publication number
- IT1153301B IT1153301B IT23905/82A IT2390582A IT1153301B IT 1153301 B IT1153301 B IT 1153301B IT 23905/82 A IT23905/82 A IT 23905/82A IT 2390582 A IT2390582 A IT 2390582A IT 1153301 B IT1153301 B IT 1153301B
- Authority
- IT
- Italy
- Prior art keywords
- added
- vincamine
- copper salt
- peracid
- addn
- 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
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 title abstract 3
- 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
- 229960002726 vincamine Drugs 0.000 title abstract 3
- BQGJXFQCMYJENQ-GIVPXCGWSA-N 14,15-dehydrovincamine Chemical compound C12=CC=CC=C2N2[C@@](O)(C(=O)OC)C[C@@]3(CC)[C@H]4C2=C1CCN4CC=C3 BQGJXFQCMYJENQ-GIVPXCGWSA-N 0.000 title abstract 2
- BQGJXFQCMYJENQ-UHFFFAOYSA-N 14-epi-Delta17-vincamine Natural products C12=CC=CC=C2N2C(O)(C(=O)OC)CC3(CC)C4C2=C1CCN4CC=C3 BQGJXFQCMYJENQ-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001879 copper Chemical class 0.000 abstract 5
- 150000004965 peroxy acids Chemical class 0.000 abstract 4
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 230000008707 rearrangement Effects 0.000 abstract 3
- 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 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000002798 polar solvent Substances 0.000 abstract 2
- 239000003223 protective agent Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- 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 1
- OZDNDGXASTWERN-CTNGQTDRSA-N Apovincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-CTNGQTDRSA-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 abstract 1
- 229950006936 apovincamine Drugs 0.000 abstract 1
- 230000009920 chelation Effects 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 235000015424 sodium Nutrition 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 abstract 1
- 239000004296 sodium metabisulphite Substances 0.000 abstract 1
- 235000010262 sodium metabisulphite Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 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 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
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Process for the prepn. of vincamine (I) or 14,15-dehydro-vincamine (apovincamine) by oxidn. and then rearrangement of a soln. of vincadifformine or tabersonine respectively, is characterised in that a protecting agent is added to the starting soln., which is in a polar solvent at a temp. equal to or below 5 deg.C, then the oxidn. is effected with permaleic or peracetic acid, and when addn. of peracid is complete, the rearrangement is effected by heating the reaction mixt. at 20-50 deg.C. The protecting cpd. may be a copper salt, added in quantities such that the ratio of starting cpd. to copper salt is 1-10:1. The protecting agent may also be oxalic acid, which is added to the initial soln. at -5 deg.C, followed by addn. of the peracid at -2 deg.C. The polar solvent used is a lower aliphatic alcohol pref. methanol. The pH after addn. of the peracid is 6-2.5. Permaleic acid may be prepd. in situ from maleic anhydride and hydrogen peroxide. The peracid is added at -5 to 0 deg.C. At the end of the reaction the copper salt is sepd. When permaleic acid is used the precipitated copper salt is filtered off. When peracetic is used, the copper salt may be removed by chelation on a resin, such as a macroporous polystyrene polymer having amino-phosphonic, amino-diacetic or amino-oximic functional gps. The rearrangement is effected by heating at 30-50 deg.C, pref. 35-40 deg.C. Before or during this stage, a reducing agent, such as sodium metabisulphite, sulphur dioxide or sodium, may be added, which aids later purificn. Prepn. of vincamine used for the treatment of cerebrovascular troubles.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23905/82A IT1153301B (en) | 1982-10-25 | 1982-10-25 | Vincamine and 14,15-dehydro-vincamine prepn |
| CH572683A CH657617A5 (en) | 1982-10-25 | 1983-10-21 | PROCEDURE FOR THE PREPARATION OF VINCAMINA. |
| ES526749A ES526749A0 (en) | 1982-10-25 | 1983-10-25 | PROCEDURE FOR THE PREPARATION OF VINCAMINA |
| DE19833338705 DE3338705A1 (en) | 1982-10-25 | 1983-10-25 | Process for the preparation of vincamine |
| FR8316966A FR2534920A1 (en) | 1982-10-25 | 1983-10-25 | Vincamine and 14,15-dehydro-vincamine prepn |
| BE0/211767A BE898073A (en) | 1982-10-25 | 1983-10-25 | PROCESS FOR THE PREPARATION OF VINCAMINE. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23905/82A IT1153301B (en) | 1982-10-25 | 1982-10-25 | Vincamine and 14,15-dehydro-vincamine prepn |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IT8223905A0 IT8223905A0 (en) | 1982-10-25 |
| IT1153301B true IT1153301B (en) | 1987-01-14 |
Family
ID=11210783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT23905/82A IT1153301B (en) | 1982-10-25 | 1982-10-25 | Vincamine and 14,15-dehydro-vincamine prepn |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE898073A (en) |
| IT (1) | IT1153301B (en) |
-
1982
- 1982-10-25 IT IT23905/82A patent/IT1153301B/en active
-
1983
- 1983-10-25 BE BE0/211767A patent/BE898073A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE898073A (en) | 1984-02-15 |
| IT8223905A0 (en) | 1982-10-25 |
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