DE2703920A1 - (14,15)-Dihydro-eburnamenine derivs. - (14,15)-Dihydro-eburnamenine derivs. - Google Patents
(14,15)-Dihydro-eburnamenine derivs. - (14,15)-Dihydro-eburnamenine derivs.Info
- Publication number
- DE2703920A1 DE2703920A1 DE19772703920 DE2703920A DE2703920A1 DE 2703920 A1 DE2703920 A1 DE 2703920A1 DE 19772703920 DE19772703920 DE 19772703920 DE 2703920 A DE2703920 A DE 2703920A DE 2703920 A1 DE2703920 A1 DE 2703920A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- eburnamenine
- derivs
- compounds
- dihydro
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- -1 formamido Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 2
- 230000036571 hydration Effects 0.000 abstract description 2
- 238000006703 hydration reaction Methods 0.000 abstract description 2
- 229910000510 noble metal Inorganic materials 0.000 abstract description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract description 2
- 229910003446 platinum oxide Inorganic materials 0.000 abstract description 2
- 208000000044 Amnesia Diseases 0.000 abstract 1
- VYXFLLCQSGSEMS-UHFFFAOYSA-N Dihydroeburnamenine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CCN5C2=C1 VYXFLLCQSGSEMS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 231100000863 loss of memory Toxicity 0.000 abstract 1
- 239000003368 psychostimulant agent Substances 0.000 abstract 1
- VKTOXAGUZWAECL-UHFFFAOYSA-N trans-eburnamenine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-UHFFFAOYSA-N 0.000 abstract 1
- 208000009999 tuberous sclerosis Diseases 0.000 abstract 1
- 208000019553 vascular disease Diseases 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 206010019196 Head injury Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002582 psychostimulating effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003966 vascular damage Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Neue organische Verbindungeh, ihre HerstellungNew organic compounds, their production
und Verwendung Gegenstand der Erfindung sind Verbindunggen der Formel I, worin R Wasserstoff in 10- oder 11-Stellung ständiges Fluor, Chlor, Brom oder Jod, eine in ll-Stellung ständige Gruppe der Reihe Amino oder Formamido oder eine ll-Alkanoylaminogruppe mit 2 bis 5 Kohlenstoffatomen bedeutet, in Form der Basen oder von Säureadditionssalzen, R steht insbesondere für Wasserstoff, 10-Fluor, 10-Brom und ll-Brom.and Use The invention relates to compounds of the formula I, wherein R is hydrogen in the 10- or 11-position fluorine, chlorine, bromine or Iodine, a group in the II-position of the series amino or formamido or a II-alkanoylamino group with 2 to 5 carbon atoms means in the form of bases or of acid addition salts, R is in particular hydrogen, 10-fluorine, 10-bromine and ll-bromine.
Erfindungsgemäss gelangt man zu den Verbindungen der Formel I. indem man Verbindungen der Formel II, worin R obige Bedeutung besitzt, in 14,15-Stellung hydriert.According to the invention, the compounds of the formula I are obtained by one compounds of the formula II, where R has the above meaning, hydrogenated in the 14,15 position.
Das erfindungsgemässe Verfahren kann analog zu bekannten Methoden durchgeführt werden.The method according to the invention can be carried out analogously to known methods be performed.
Man hydriert zweckmässig in Gegenwart eines Edelmetallkatalysators wie Palladium, Raney-Nickel oder Platin.It is expedient to hydrogenate in the presence of a noble metal catalyst such as palladium, Raney nickel or platinum.
Die jlydrierung kann bei Raumtemperatur durchgeführt werden.The hydration can be carried out at room temperature.
Die nach dem erfindungsgemässen Verfahren erhältlichen Verbindungen der Formel I können in freier Form als Base, oder in Form ihrer Additionssalze mit Säuren vorliegen.The compounds obtainable by the process according to the invention of the formula I can be used in free form as a base, or in the form of their addition salts with Acids are present.
Aus den frcien Basen lassen sich in bekannter Weise Säureadditionssalze herstellen und umgekehrt.Acid addition salts can be prepared from the French bases in a known manner manufacture and vice versa.
Zur Salzbildung können z.B. folcjende Säuren verwendet werden: Chlorwassrstoff-, Schwefel-, Phosphor-, Wein-, Malein- und Methansulfonäure.Folic acids, for example, can be used to form salts: Hydrogen chloride, Sulfuric, phosphoric, tartaric, maleic and methanesulfonic acids.
Die Ausgangsprodukte sind bekannt oder analog zu bekannten Methoden, beispielsweise wie im experimentellen Teil beschrieben, herstellbar.The starting products are known or analogous to known methods, for example, as described in the experimental part, can be produced.
Die Verbindungen der Formel I in freier Form oder in From von Additienssaizen mit physiologisch verträglichen Säuren (erfindungsgemässe Verbindungen) zeichnen sich durch interessante pharmakologische Eigenschaften aus und können daher als Heilmittel Verwendung finden.The compounds of the formula I in free form or in the form of additives draw with physiologically compatible acids (compounds according to the invention) are characterized by interesting pharmacological properties and can therefore be used as Find remedies use.
So sind sie nützlich, da sie vigilanzwrhöhende und psychostimulierende Eigenschaften besitzen.So they are useful as they are vigilance-increasing and psychostimulating Possess properties.
Die crifindungsgemässen Verbindungen sind deshalb indiziert bei zerebralen Gefässchädigungen, bei der Zerebralskelerose, bei Zerebralinsuffizienz oder ei Bewusstseinsverlusten aufgrund von Schädeltraumata.The connections according to the invention are therefore indicated for cerebral ones Vascular damage, in cerebral kerosis, in cerebral insufficiency or a loss of consciousness due to head trauma.
Die Erfindung betrifft auch Heilmittel, die eine Verbindung der Formel I in freier Form oder in Form ihrer physiologisch verträglichen Additionssalze mit Säuren enthalten. Diese ileilmittel, beispielsweise eine Lösung oder eine Tablette, können nach bekannten Methoden, unter Verwendung der üblichen Hilfs- und Trägerstoffe, hergestellt werden.The invention also relates to medicaments containing a compound of the formula I in free form or in the form of their physiologically acceptable addition salts with Contain acids. These drugs, such as a solution or tablet, can by known methods, using the usual auxiliaries and carriers, getting produced.
Alle Temperaturagaben erfolgen in Celsiusgraden. All temperatures are given in degrees Celsius.
Beispiel: (3s, 16s)-14,15-Dihydroeburnamenin 200 mg Platinoxid wurden in 5 ml Essigsäure vorhydriert, dazu eine Lösung von 2,78 g (10 mol) (3s,16s)-Eburnamenin in 5 ml Essigsäure gegeben und das Gemisch 2 Tage bei 740 Torr und Zimmertemperatur hydriert.Example: (3s, 16s) -14,15-Dihydroeburnamenin 200 mg of platinum oxide were Pre-hydrogenated in 5 ml of acetic acid, plus a solution of 2.78 g (10 mol) (3s, 16s) -Eburnamenin in 5 ml of acetic acid and the mixture for 2 days at 740 torr and room temperature hydrogenated.
Nach Filtration durch Celite, Abdampfen des Lösungsmittels im Vakuum, Verteilen des Rückstandes zwischen 20 ml 2N Ammoniak und 20 ml Methylenchlorid und Eindampfen der organischen Phase verblieb öliges (3s, 16s)-14,15-Dihydroeburnamenin, welches nach der Bildung von Kristallkeimen aus 2-Propanol bei 0° kristallisiert werden konnte.After filtration through Celite, evaporation of the solvent in vacuo, Distribute the residue between 20 ml of 2N ammonia and 20 ml of methylene chloride and Evaporation of the organic phase remained oily (3s, 16s) -14,15-dihydroeburnamenine, which crystallizes after the formation of crystal nuclei from 2-propanol at 0 ° could be.
Sinn. 820.Sense. 820.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH140876 | 1976-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2703920A1 true DE2703920A1 (en) | 1977-08-11 |
Family
ID=4209745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772703920 Withdrawn DE2703920A1 (en) | 1976-02-05 | 1977-01-31 | (14,15)-Dihydro-eburnamenine derivs. - (14,15)-Dihydro-eburnamenine derivs. |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2703920A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356305A (en) * | 1979-08-13 | 1982-10-26 | Richter Gedeon Vegyeszeti Gyar Rt. | Process for the preparation of halovincamone derivatives |
| EP0115920A3 (en) * | 1983-01-26 | 1986-02-05 | American Home Products Corporation | Pyrazino(2',3'-3,4)pyrido(1,2-a) indole derivatives |
| US4839362A (en) * | 1985-04-19 | 1989-06-13 | Richter Gedeon Vegyeszeti Gyar Rt. | Eburnamenine derivatives, pharmaceutical compositions and methods employing them and processes for their preparation |
| US4883876A (en) * | 1987-09-07 | 1989-11-28 | Taisho Pharmaceutical Co., Ltd. | Acylated vincaminic acid derivatives |
| US5093337A (en) * | 1987-11-19 | 1992-03-03 | Roussel Uclaf | Substituted derivatives of 20,21-dinoreburnamenine, their use as medicaments and the pharmaceutical compositions containing them |
-
1977
- 1977-01-31 DE DE19772703920 patent/DE2703920A1/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356305A (en) * | 1979-08-13 | 1982-10-26 | Richter Gedeon Vegyeszeti Gyar Rt. | Process for the preparation of halovincamone derivatives |
| EP0115920A3 (en) * | 1983-01-26 | 1986-02-05 | American Home Products Corporation | Pyrazino(2',3'-3,4)pyrido(1,2-a) indole derivatives |
| US4839362A (en) * | 1985-04-19 | 1989-06-13 | Richter Gedeon Vegyeszeti Gyar Rt. | Eburnamenine derivatives, pharmaceutical compositions and methods employing them and processes for their preparation |
| US4883876A (en) * | 1987-09-07 | 1989-11-28 | Taisho Pharmaceutical Co., Ltd. | Acylated vincaminic acid derivatives |
| EP0307167A3 (en) * | 1987-09-07 | 1990-01-24 | Taisho Pharmaceutical Co. Ltd | Vincaminic acid derivatives |
| US5093337A (en) * | 1987-11-19 | 1992-03-03 | Roussel Uclaf | Substituted derivatives of 20,21-dinoreburnamenine, their use as medicaments and the pharmaceutical compositions containing them |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |