CH593283A5 - Vincamine derivs for treating behaviour disorders - by ring closure of indoloquinolizine deriv - Google Patents
Vincamine derivs for treating behaviour disorders - by ring closure of indoloquinolizine derivInfo
- Publication number
- CH593283A5 CH593283A5 CH176574A CH176574A CH593283A5 CH 593283 A5 CH593283 A5 CH 593283A5 CH 176574 A CH176574 A CH 176574A CH 176574 A CH176574 A CH 176574A CH 593283 A5 CH593283 A5 CH 593283A5
- Authority
- CH
- Switzerland
- Prior art keywords
- vincamine
- indoloquinolizine
- derivs
- deriv
- treating
- 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 claims description 8
- 229960002726 vincamine Drugs 0.000 title claims description 7
- 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 claims description 4
- 206010000117 Abnormal behaviour Diseases 0.000 title abstract 2
- DBVVQINTNHWWGH-UHFFFAOYSA-N indolo[3,2-a]quinolizine Chemical compound C1=CC=CC2=C3C4=CC=CC=C4N=C3C=CN21 DBVVQINTNHWWGH-UHFFFAOYSA-N 0.000 title 1
- CMLQXZNMSSZRCH-UHFFFAOYSA-N indoloquinolizine Natural products C1=CC=CC2=C3N=C(C=CC=C4)C4=C3C=CN21 CMLQXZNMSSZRCH-UHFFFAOYSA-N 0.000 title 1
- 238000006798 ring closing metathesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 4
- 241000124008 Mammalia Species 0.000 abstract description 2
- 230000003970 cerebral vascular damage Effects 0.000 abstract description 2
- 208000009999 tuberous sclerosis Diseases 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000006378 damage Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- WYIJGAVIVKPUGJ-GIVPXCGWSA-N brovincamine Chemical compound BrC1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 WYIJGAVIVKPUGJ-GIVPXCGWSA-N 0.000 description 3
- 229950002641 brovincamine Drugs 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Heterocyclic cpds. of formula (I) are new: (where R1 = Br, F, Cl, OH, 1-4C alkyl, 1-4C alkoxy) also their acid addn. salts. (I) may be in its optically active form or a racemate. (I) are used to treat behaviour disorders, caused by cerebral vascular damage and cerebral sclerosis, in genatrics and disturbance of consciousness resulting from cranial injuries. The daily dose for larger mammal is 1-500 mg.
Description
Die Erfindung betrifft 11 -Brom-vineamin (Formel 1, siehe Formelblatt), seinen Antpoden (Spiegelbild der Formel I) oder das Gemisch der beiden Antipoden.
Erfindungsgem'ss gelangt man zu der neuen Verbindung der Formel I, seinen Antipoden (Spiegelbild der Formel I) oder dem Gemisch der beiden Antipoden, indem man Vincamin in seinen optisch aktiven Formen oder in Form seines Racemates bromiert. Die Bromierung erfolgt nach an sich bekannten Methoden, indem die Einführung von Brom in den Benzolkern durch Eisen(III)chlond oder -bromid, Bortribromid, Zink(II)chlorid, Aluminiumchlorid oder Jod unterstützt wird.
Die Reaktion kann beispielsweise so erfolgen, dass man optisch aktives bzw. racemisches Vincamin in einem unter den Reaktionsbedingungen inerten Lösungsmittel, wie Chloroform, Chlorbenzol, Methylenchlorid, unter Zugabe einer der oben angeführten Katalysatoren suspendiert und hierauf bei Temperaturen von -20 bis A20 eine Lösung von Brom in einem der oben angeführten inerten Lösungsmittel zutropfen lässt.
Die entstandenen Verbindungen können hierauf nach an sich bekannter Weise aus dem Reaktionsgemisch isoliert und gereinigt werden.
Das erfindungsgemässe Verfahren kann sowohl zur Herstellung der optisch aktiven Formen wie auch zur Herstellung des Racemates von 11-Brom-vincamin verwendet werden. Gegebenenfalls kann die racemische Verbindung durch an sich bekannte Verfahren in die optisch aktiven Produkte zerlegt werden.
ll-Brom-vincamin in seinen optisch aktiven Formen wie auch in Form seines Racemates zeichnet sich durch interessante pharmakologische Eigenschaften aus und kann als Heilmittel Verwendung finden.
Am Beobachtungstest an der Maus konnte eine Erregbarkeitssteigerung bei Dosen von 10 bis 100 mg/kg p.o. beob achtet werden. Die Schlafphasen im n Elektroenzephalo- gramm der Ratte zeigten eine Abnahme des Schlafes und eine Zunahme des Wachzustandes bei Dosen von 10 mg/kg bis 30 mg/kg i.p. oder p.o. Derartige Veränderungen sind Ausdruck einer Vigilanzerhöhung und Psychostimulation.
Aufgrund obiger Wirkungen sind die Verbindungen indiziert zur Behandlung von Störungen der Vigilanz, insbesondere zur Bekämpfung von Verhaltensstörungen aufgrund von zerebralen Gefässschädigungen und Zerebralsklerose in der Geriatrie, und bei Bewusstseinsstörungen infolge von Schädeltraumata.
Die zu verwendenden Dosen variieren naturgemäss je nach eingesetzter Substanz, Art der Administration und des zu behandelnden Zustandes. Im allgemeinen werden jedoch im Tierexperiment befriedigende Resultate erreicht mit einer Dosis von 10 bis 100 mg/kg Körpergewicht. Für grössere Säugetiere liegt die Tagesdosis bei etwa 1 bis 500 mg. Diese Dosen können nötigenfalls in 2 bis 3 Anteilen von 0,5 - 30 mg 1 1-Brom-vincamin neben festen oder flüssigen Trägersubstanzen oder Verdünnungsmitteln oder als Retard-Form verabreicht werden.
In dem nachfolgenden Beispiel, das die Erfindung näher erläutert, ihren Umfang aber in keiner Weise einschränken soll, erfolgen alle Temperaturangaben in Celsiusgraden und sind unkorrigiert.
Die Vorzeichen der Drehwerte beziehen sich bei allen optisch aktiven Verbindungen auf Messungen mit Chloroform als Lösungsmittel.
EMI1.1
Beispiel: (3S, 145, 16S)-1 1 -Brom- vincamin 14,19 g (3S, 14S, 16S)-Vincamin und 10,81 g Eisentrichlorid-hexahydrat wurden bei 0 in 80 ml Chloroform suspendiert und dazu unter Rühren 44 ml einer l-M Lösung von Brom in Chloroform getropft. Nach halbstündigem Weiterrühren bei 0 wurde mit 120 ml 2-N-Ammoniak versetzt, der rostbraune Niederschlag abfiltriert, die beiden Phasen des Filtrats getrennt, die Wasserphase mit 40 ml Methylenchlorid nachextrahiert, die organischen Phasen mit Wasser gewaschen, vereinigt, mit Natriumsulfat getrocknet und eingedampft.
Beim Aufnehmen des Rückstandes in 80 ml Isopropylalkohol erfolgte spontane Kristallisation. Diese rohen Kristal- le von 11 -Brom-vincamin wurden bei 0 isoliert.
Reines 11 -Brom-vincamin erhielt man beim Chromatographieren der rohen Kristalle auf Kieselgel mit Methylenchlorid: Methanol = 98 : 2 als Lösungsmittel und nachfolgendem Kristallisieren aus Isopropylalkohol.
Smp. 214 (Zers.); GalD20 = +8,7" (10/o, CHCI3) NMR-Spektrum (CDCI,, 100 MHz): 0,86 (T, 7 Hz / H3C(21) / 3 H); 1,18-3,49 (M /14H); darunter bei ca. 2,07 + 2,16 (AB, 15 Hz/ H2C(15) 3,80 (ca. S / HaCOOC(22) + HC(3) / 4H); 4,63 (S / HO-C(14), austauschbar / 1 H); 7,04-7,48 (M / HC(9 + 10 + 12) / 3 H);
Auf analoge Weise erhält man ausgehend von rac.-Vincamin rac.-ll-Brom-vincamin; Smp.: 2300 (Zers.).
The invention relates to 11-bromo-vineamine (formula 1, see formula sheet), its antipodes (mirror image of formula I) or the mixture of the two antipodes.
According to the invention, the new compound of the formula I, its antipodes (mirror image of the formula I) or the mixture of the two antipodes is obtained by brominating vincamine in its optically active forms or in the form of its racemate. The bromination takes place according to methods known per se, in that the introduction of bromine into the benzene nucleus is supported by iron (III) chloride or bromide, boron tribromide, zinc (II) chloride, aluminum chloride or iodine.
The reaction can be carried out, for example, by suspending optically active or racemic vincamine in a solvent which is inert under the reaction conditions, such as chloroform, chlorobenzene, methylene chloride, with the addition of one of the catalysts listed above, and then a solution of at temperatures from -20 to A20 Bromine can be added dropwise in one of the inert solvents listed above.
The compounds formed can then be isolated from the reaction mixture and purified in a manner known per se.
The process according to the invention can be used both for the preparation of the optically active forms and for the preparation of the racemate of 11-bromovincamine. Optionally, the racemic compound can be broken down into the optically active products by processes known per se.
ll-bromovincamine in its optically active forms as well as in the form of its racemate is characterized by interesting pharmacological properties and can be used as a medicinal product.
In the observation test on the mouse, an increase in excitability could be seen at doses of 10 to 100 mg / kg p.o. to be observed. The sleep phases in the n electroencephalogram of the rat showed a decrease in sleep and an increase in the waking state at doses of 10 mg / kg to 30 mg / kg i.p. or p.o. Such changes are an expression of an increase in vigilance and psychostimulation.
On the basis of the above effects, the compounds are indicated for the treatment of disorders of vigilance, in particular for combating behavioral disorders due to cerebral vascular damage and cerebral sclerosis in geriatrics, and for disorders of consciousness due to head trauma.
The doses to be used naturally vary depending on the substance used, the type of administration and the condition to be treated. In general, however, satisfactory results are achieved in animal experiments with a dose of 10 to 100 mg / kg body weight. For larger mammals, the daily dose is around 1 to 500 mg. If necessary, these doses can be administered in 2 to 3 proportions of 0.5-30 mg 1 1-bromovincamine in addition to solid or liquid carriers or diluents or as a sustained-release form.
In the following example, which explains the invention in more detail but is not intended to limit its scope in any way, all temperatures are given in degrees Celsius and are uncorrected.
The signs of the rotation values for all optically active compounds relate to measurements with chloroform as solvent.
EMI1.1
Example: (3S, 145, 16S) -1 1 -bromovincamine 14.19 g (3S, 14S, 16S) -vincamine and 10.81 g iron trichloride hexahydrate were suspended at 0 in 80 ml chloroform and 44 added with stirring ml of a 1M solution of bromine in chloroform was added dropwise. After stirring at 0 for half an hour, 120 ml of 2N ammonia were added, the rust-brown precipitate was filtered off, the two phases of the filtrate were separated, the aqueous phase was re-extracted with 40 ml of methylene chloride, the organic phases were washed with water, combined, dried with sodium sulfate and evaporated .
When the residue was taken up in 80 ml of isopropyl alcohol, spontaneous crystallization occurred. These crude crystals of 11-bromo-vincamine were isolated at 0.
Pure 11-bromovincamine was obtained when the crude crystals were chromatographed on silica gel using methylene chloride: methanol = 98: 2 as solvent and subsequent crystallization from isopropyl alcohol.
M.p. 214 (dec.); GalD20 = +8.7 "(10 / o, CHCl3) NMR spectrum (CDCl ,, 100 MHz): 0.86 (T, 7 Hz / H3C (21) / 3H); 1.18-3.49 (M / 14H); below that at approx. 2.07 + 2.16 (AB, 15 Hz / H2C (15) 3.80 (approx. S / HaCOOC (22) + HC (3) / 4H); 4, 63 (S / HO-C (14), exchangeable / 1H); 7.04-7.48 (M / HC (9 + 10 + 12) / 3H);
In an analogous manner, starting from rac.-vincamine, rac.-II-bromo-vincamine is obtained; M.p .: 2300 (dec.).
Claims (1)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH176574A CH593283A5 (en) | 1974-02-08 | 1974-02-08 | Vincamine derivs for treating behaviour disorders - by ring closure of indoloquinolizine deriv |
| DK639774AA DK139358B (en) | 1973-12-18 | 1974-12-09 | Analogous process for the preparation of vincamine derivatives or acid addition salts thereof. |
| SE7415416A SE422798B (en) | 1973-12-18 | 1974-12-09 | ANALOGY PROCEDURE FOR PREPARING VINCAMIN DERIVATIVES |
| DE19742458164 DE2458164A1 (en) | 1973-12-18 | 1974-12-09 | METHOD FOR PRODUCING NEW HETEROCYCLIC COMPOUNDS |
| NO744456A NO744456L (en) | 1973-12-18 | 1974-12-10 | |
| FI3552/74A FI59096C (en) | 1973-12-18 | 1974-12-10 | FOERFARANDE FOER FRAMSTAELLNING AV NYA VINKAMINDERIVAT ANVAENDBARA SAOSOM PSYKOSTIMULANTER |
| NL7416237A NL7416237A (en) | 1973-12-18 | 1974-12-13 | NEW HETEROCYCLICAL COMPOUNDS AND METHOD FOR PREPARING THEM. |
| AU76483/74A AU492672B2 (en) | 1973-12-18 | 1974-12-16 | Vincamine derivatives |
| GB54159/74A GB1492579A (en) | 1973-12-18 | 1974-12-16 | Vincamine derivatives |
| IE2591/74A IE40791B1 (en) | 1973-12-18 | 1974-12-16 | Vincamine derivatives |
| PH16634A PH12927A (en) | 1973-12-18 | 1974-12-16 | Vingamine derivatives |
| IL4625374A IL46253A (en) | 1973-12-18 | 1974-12-16 | Vincamine derivatives their preparation and pharmaceutical compositions containing them |
| ES432952A ES432952A1 (en) | 1973-12-18 | 1974-12-16 | Vincamine derivatives |
| CA216,230A CA1051899A (en) | 1973-12-18 | 1974-12-17 | Vincamine compounds |
| DD183107A DD116043A5 (en) | 1973-12-18 | 1974-12-17 | |
| JP49144170A JPS5817474B2 (en) | 1973-12-18 | 1974-12-17 | Yuukikagoubutsuni Cansurukairiyou |
| FR7441717A FR2254342B1 (en) | 1973-12-18 | 1974-12-18 | |
| ES450740A ES450740A1 (en) | 1973-12-18 | 1976-08-16 | Vincamine derivatives |
| ES450741A ES450741A1 (en) | 1973-12-18 | 1976-08-16 | Vincamine derivatives |
| AT652577A AT358191B (en) | 1974-02-08 | 1977-09-12 | METHOD FOR PRODUCING THE NEW 11- -BROMVINCAMINE |
| US05/857,019 US4146643A (en) | 1973-12-18 | 1977-12-02 | Increasing vigilance or treating cerebral insufficiency with substituted vincamines |
| HK539/80A HK53980A (en) | 1973-12-18 | 1980-09-25 | Vincamine derivatives |
| MY186/81A MY8100186A (en) | 1973-12-18 | 1981-12-30 | Vincamine de |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH176574A CH593283A5 (en) | 1974-02-08 | 1974-02-08 | Vincamine derivs for treating behaviour disorders - by ring closure of indoloquinolizine deriv |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH593283A5 true CH593283A5 (en) | 1977-11-30 |
Family
ID=4218044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176574A CH593283A5 (en) | 1973-12-18 | 1974-02-08 | Vincamine derivs for treating behaviour disorders - by ring closure of indoloquinolizine deriv |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH593283A5 (en) |
-
1974
- 1974-02-08 CH CH176574A patent/CH593283A5/en not_active IP Right Cessation
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |