FI69628C - Nytt foerfarande foer framstaellning av apovinkaminsyraestrar - Google Patents
Nytt foerfarande foer framstaellning av apovinkaminsyraestrar Download PDFInfo
- Publication number
- FI69628C FI69628C FI812785A FI812785A FI69628C FI 69628 C FI69628 C FI 69628C FI 812785 A FI812785 A FI 812785A FI 812785 A FI812785 A FI 812785A FI 69628 C FI69628 C FI 69628C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- process according
- formula
- reaction
- organic solvent
- Prior art date
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- ZFCQLDAGNBFMJQ-QUCCMNQESA-N apovincaminic acid Chemical class C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(O)=O)N5C2=C1 ZFCQLDAGNBFMJQ-QUCCMNQESA-N 0.000 description 6
- 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 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 description 5
- -1 methylenemalonic acid diesters Chemical class 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 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 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960002726 vincamine Drugs 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229950006936 apovincamine Drugs 0.000 description 2
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- DDNCQMVWWZOMLN-RBBKRZOGSA-N (-)-ethyl apovincaminate Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-RBBKRZOGSA-N 0.000 description 1
- IDVYOLJGJUDVNL-UHFFFAOYSA-N 1,2,3,4,6,7-hexahydroindolo[3,2-a]quinolizine Chemical class C1=CC=C2C3=C4CCCCN4CCC3=NC2=C1 IDVYOLJGJUDVNL-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802208A HU183207B (en) | 1980-09-10 | 1980-09-10 | Process for preparing apovincaminic acid esters |
| HU220880 | 1980-09-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI812785L FI812785L (fi) | 1982-03-11 |
| FI69628B FI69628B (fi) | 1985-11-29 |
| FI69628C true FI69628C (fi) | 1986-03-10 |
Family
ID=10958296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI812785A FI69628C (fi) | 1980-09-10 | 1981-09-08 | Nytt foerfarande foer framstaellning av apovinkaminsyraestrar |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5780384A (en, 2012) |
| AT (1) | AT382616B (en, 2012) |
| AU (1) | AU544436B2 (en, 2012) |
| BE (1) | BE890274A (en, 2012) |
| CA (1) | CA1162543A (en, 2012) |
| CH (1) | CH646167A5 (en, 2012) |
| DD (1) | DD201680A5 (en, 2012) |
| DE (1) | DE3135728C2 (en, 2012) |
| DK (1) | DK151020C (en, 2012) |
| ES (1) | ES8206522A1 (en, 2012) |
| FI (1) | FI69628C (en, 2012) |
| FR (1) | FR2489824B1 (en, 2012) |
| GB (1) | GB2086886B (en, 2012) |
| GR (1) | GR75030B (en, 2012) |
| HU (1) | HU183207B (en, 2012) |
| IL (1) | IL63720A0 (en, 2012) |
| IT (1) | IT1146707B (en, 2012) |
| NL (1) | NL8104044A (en, 2012) |
| NO (1) | NO813067L (en, 2012) |
| NZ (1) | NZ198318A (en, 2012) |
| PT (1) | PT73644B (en, 2012) |
| SE (1) | SE443141B (en, 2012) |
| SU (1) | SU1114336A3 (en, 2012) |
| YU (1) | YU41987B (en, 2012) |
| ZA (1) | ZA816100B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2052449B1 (es) * | 1992-12-22 | 1995-02-16 | Covex Sa | Nuevo procedimiento para la preparacion del apovincaminato de etilo. |
| EP1369344B1 (en) | 2001-03-15 | 2009-09-16 | Honda Access Corporation | Structure for mounting a saddle bag on a motorcycle |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2389625B1 (en, 2012) * | 1977-05-06 | 1980-04-18 | Roussel Uclaf | |
| HU179292B (en) * | 1978-12-01 | 1982-09-28 | Richter Gedeon Vegyeszet | Process for preparing ester derivatives of apovincaminic acid |
| HU181495B (en) * | 1979-05-31 | 1983-07-28 | Richter Gedeon Vegyeszet | Process for producing hydroxy-imino-eburnane derivatives |
-
1980
- 1980-09-10 HU HU802208A patent/HU183207B/hu not_active IP Right Cessation
-
1981
- 1981-08-31 AT AT0376081A patent/AT382616B/de not_active IP Right Cessation
- 1981-09-01 NL NL8104044A patent/NL8104044A/nl not_active Application Discontinuation
- 1981-09-02 ZA ZA816100A patent/ZA816100B/xx unknown
- 1981-09-02 IL IL63720A patent/IL63720A0/xx not_active IP Right Cessation
- 1981-09-04 IT IT68172/81A patent/IT1146707B/it active
- 1981-09-07 DD DD81233097A patent/DD201680A5/de not_active IP Right Cessation
- 1981-09-08 FI FI812785A patent/FI69628C/fi not_active IP Right Cessation
- 1981-09-08 GR GR65987A patent/GR75030B/el unknown
- 1981-09-08 SE SE8105338A patent/SE443141B/sv not_active IP Right Cessation
- 1981-09-08 BE BE0/205907A patent/BE890274A/fr not_active IP Right Cessation
- 1981-09-08 DK DK396881A patent/DK151020C/da not_active IP Right Cessation
- 1981-09-08 CH CH579581A patent/CH646167A5/de not_active IP Right Cessation
- 1981-09-09 ES ES505325A patent/ES8206522A1/es not_active Expired
- 1981-09-09 GB GB8127201A patent/GB2086886B/en not_active Expired
- 1981-09-09 CA CA000385471A patent/CA1162543A/en not_active Expired
- 1981-09-09 DE DE3135728A patent/DE3135728C2/de not_active Expired - Fee Related
- 1981-09-09 SU SU813333370A patent/SU1114336A3/ru active
- 1981-09-09 NZ NZ198318A patent/NZ198318A/xx unknown
- 1981-09-09 PT PT73644A patent/PT73644B/pt not_active IP Right Cessation
- 1981-09-09 FR FR8117112A patent/FR2489824B1/fr not_active Expired
- 1981-09-09 JP JP56141112A patent/JPS5780384A/ja active Granted
- 1981-09-09 NO NO813067A patent/NO813067L/no unknown
- 1981-09-09 AU AU75092/81A patent/AU544436B2/en not_active Ceased
- 1981-09-10 YU YU2181/81A patent/YU41987B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYéSZETI GYAR R.T. |