HU209927B - Process for the preparation of ethyl apovincaminate - Google Patents
Process for the preparation of ethyl apovincaminate Download PDFInfo
- Publication number
- HU209927B HU209927B HU9301983A HU9301983A HU209927B HU 209927 B HU209927 B HU 209927B HU 9301983 A HU9301983 A HU 9301983A HU 9301983 A HU9301983 A HU 9301983A HU 209927 B HU209927 B HU 209927B
- Authority
- HU
- Hungary
- Prior art keywords
- ethanol
- ethyl
- ethyl apovincaminate
- formula
- apovincaminate
- Prior art date
Links
- DDNCQMVWWZOMLN-IRLDBZIGSA-N Vinpocetine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-IRLDBZIGSA-N 0.000 title claims description 14
- 229960000744 vinpocetine Drugs 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- ZFCQLDAGNBFMJQ-QUCCMNQESA-N apovincaminic acid Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(O)=O)N5C2=C1 ZFCQLDAGNBFMJQ-QUCCMNQESA-N 0.000 claims description 9
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical class FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- YXWJGZQOGXGSSC-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzonitrile Chemical group FC1=C(F)C(F)=C(C#N)C(F)=C1F YXWJGZQOGXGSSC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- -1 triethylamine Chemical class 0.000 claims description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000284 extract Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- HCCPWBWOSASKLG-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)-phenylmethanone Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(=O)C1=CC=CC=C1 HCCPWBWOSASKLG-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZRQUIRABLIQJRI-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-methoxybenzene Chemical compound COC1=C(F)C(F)=C(F)C(F)=C1F ZRQUIRABLIQJRI-UHFFFAOYSA-N 0.000 description 2
- INUOFQAJCYUOJR-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C(F)=C(F)C(F)=C1F INUOFQAJCYUOJR-UHFFFAOYSA-N 0.000 description 2
- FBGHCYZBCMDEOX-UHFFFAOYSA-N 1-(2,3,4,5,6-pentafluorophenyl)ethanone Chemical compound CC(=O)C1=C(F)C(F)=C(F)C(F)=C1F FBGHCYZBCMDEOX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- SXPRVMIZFRCAGC-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-methylbenzene Chemical compound CC1=C(F)C(F)=C(F)C(F)=C1F SXPRVMIZFRCAGC-UHFFFAOYSA-N 0.000 description 1
- XPARNGAWWCCOIM-UHFFFAOYSA-N 2-fluoro-1,3,5-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(F)C([N+]([O-])=O)=C1 XPARNGAWWCCOIM-UHFFFAOYSA-N 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9202595A ES2052449B1 (es) | 1992-12-22 | 1992-12-22 | Nuevo procedimiento para la preparacion del apovincaminato de etilo. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9301983D0 HU9301983D0 (en) | 1993-09-28 |
| HUT65826A HUT65826A (en) | 1994-07-28 |
| HU209927B true HU209927B (en) | 1994-12-28 |
Family
ID=8279195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9301983A HU209927B (en) | 1992-12-22 | 1993-07-09 | Process for the preparation of ethyl apovincaminate |
Country Status (7)
| Country | Link |
|---|---|
| BG (1) | BG61305B1 (cs) |
| CZ (1) | CZ138493A3 (cs) |
| ES (1) | ES2052449B1 (cs) |
| HU (1) | HU209927B (cs) |
| PL (1) | PL171090B1 (cs) |
| RO (1) | RO110500B1 (cs) |
| SK (1) | SK278851B6 (cs) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2459799A1 (fr) * | 1979-06-22 | 1981-01-16 | Synthelabo | Synthese de la ()-vincamine |
| HU180930B (en) * | 1979-12-28 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for producing ester-derivatives of halogenovincaminic acid |
| HU183207B (en) * | 1980-09-10 | 1984-04-28 | Richter Gedeon Vegyeszet | Process for preparing apovincaminic acid esters |
| ES8400746A1 (es) * | 1981-10-16 | 1983-11-01 | Elmu Sa | Procedimiento de obtencion de un ester del acido apovincami-nico |
| ES8604956A1 (es) * | 1985-11-20 | 1986-03-16 | Covex Sa | Procedimiento de obtencion del ester etilico del acido apo- vincaminico |
| CH676002A5 (en) * | 1986-05-23 | 1990-11-30 | Arysearch Arylan Ag | Ethyl apo:vincaminate prepn. - by esterification of vincamine with ethanol in presence of alkali metal followed by saponification |
-
1992
- 1992-12-22 ES ES9202595A patent/ES2052449B1/es not_active Expired - Lifetime
-
1993
- 1993-07-09 HU HU9301983A patent/HU209927B/hu not_active IP Right Cessation
- 1993-07-12 CZ CZ931384A patent/CZ138493A3/cs unknown
- 1993-07-15 PL PL29969293A patent/PL171090B1/pl unknown
- 1993-07-16 SK SK756-93A patent/SK278851B6/sk unknown
- 1993-07-16 RO RO9301002A patent/RO110500B1/ro unknown
- 1993-07-20 BG BG97969A patent/BG61305B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL299692A1 (en) | 1994-06-27 |
| HU9301983D0 (en) | 1993-09-28 |
| BG97969A (bg) | 1994-04-29 |
| ES2052449B1 (es) | 1995-02-16 |
| PL171090B1 (pl) | 1997-03-28 |
| BG61305B1 (bg) | 1997-05-30 |
| RO110500B1 (ro) | 1996-01-30 |
| SK278851B6 (sk) | 1998-04-08 |
| CZ279608B6 (cs) | 1995-05-17 |
| ES2052449A1 (es) | 1994-07-01 |
| CZ138493A3 (en) | 1995-05-17 |
| SK75693A3 (en) | 1994-11-09 |
| HUT65826A (en) | 1994-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |