DE1137021B - Process for the preparation of the morpholine salt of ª ‡ -acetylamino-isocaproic acid - Google Patents
Process for the preparation of the morpholine salt of ª ‡ -acetylamino-isocaproic acidInfo
- Publication number
- DE1137021B DE1137021B DES66725A DES0066725A DE1137021B DE 1137021 B DE1137021 B DE 1137021B DE S66725 A DES66725 A DE S66725A DE S0066725 A DES0066725 A DE S0066725A DE 1137021 B DE1137021 B DE 1137021B
- Authority
- DE
- Germany
- Prior art keywords
- acetylamino
- isocaproic acid
- morpholine
- preparation
- salt
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
S66725IVd/12pS66725IVd / 12p
ANMELDETAG: 4. APRIL 1957 REGISTRATION DATE: APRIL 4, 1957
BEKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHRIFT: 27. SEPTEMBER 1962 NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: SEPTEMBER 27, 1962
Die Erfindung betrifft die Herstellung des Morpholinsalzes der a-Acetylamino-isocapronsäure.The invention relates to the production of the morpholine salt of a-acetylamino-isocaproic acid.
Es wurde schon verschiedentlich die Herstellung von Salzen des Morpholins mit verschiedenen organischen Carbonsäuren beschrieben (vgl. insbesondere die deutsche Patentschrift 812 670), das Salz des Morpholins mit der α-Acetylamino-isocapronsäure ist jedoch bisher noch nicht beschrieben worden.The production of salts of morpholine with various organic ones has already been mentioned on various occasions Carboxylic acids described (cf. in particular German patent 812 670), the salt of Morpholine with the α-acetylamino-isocaproic acid is however, it has not yet been described.
Erfindungsgemäß wird dieses Salz nach an sich üblichen Methoden durch Umsetzung der ct-Acetylamino-isocapronsäure mit der Morpholinbase erhalten. Die Reaktion wird vorzugsweise bei gewöhnlicher Temperatur unter Verwendung von Wasser oder eines niedermolekularen Alkohols als Lösungsmittel ausgeführt. Man kann jedoch auch in anderen Lösungsmitteln und bei anderen Temperaturen, beispielsweise zwischen 0 und 100° C, arbeiten, doch sind diese Abänderungen unnötig, da beim Arbeiten unter den bevorzugten Bedingungen das erhaltene Produkt praktisch rein anfällt. Die a-Acetylamino-isocapronsäure kann in Form der freien Säure oder in Form von Salzen verwendet werden, wobei man selbstverständlich im letzteren Falle vorzugsweise auch das Morpholin in Form eines Salzes verwendet, das die Herstellung des Reaktionsproduktes durch doppelte Umsetzung ermöglicht.According to the invention, this salt is made by reacting ct-acetylamino-isocaproic acid by methods customary per se obtained with the morpholine base. The reaction is preferably carried out at ordinary temperature using water or a low molecular weight alcohol carried out as a solvent. However, you can also use other solvents and operate at other temperatures, e.g. between 0 and 100 ° C, but these are variations unnecessary, since when working under the preferred conditions the product obtained is practical purely accrues. The a-acetylamino-isocaproic acid can be in the form of the free acid or in the form of Salts can be used, in the latter case of course preferably also the morpholine used in the form of a salt, the preparation of the reaction product by double conversion enables.
Das neue Salz besitzt interessante pharmakologische Eigenschaften und ist ganz besonders gegen Schwindel (Vertigo) verschiedenen Ursprungs wirksam. Zu diesen Zwecken kann man es allein oder in Beimischung in festem Zustand oder in Form von Lösungen oder Suspensionen verwenden.The new salt has interesting pharmacological properties and is particularly against Dizziness (vertigo) of various origins is effective. For these purposes it can be used alone or in Use admixture in solid state or in the form of solutions or suspensions.
Es hat sich gezeigt, daß das erfindungsgemäß erhältliche Salz bei der vorbeugenden Behandlung des experimentellen Schwindels (Vertigo) bei der Maus bei täglichen Gaben von 50 mg/kg subkutan (angegeben ist die Menge a-Acetylamino-isocapronsäure in der täglichen Gabe) einen Schutz gegen Schwindel von 8% ab dem zweiten Behandlungstag, von 17°/o ab dem vierten Behandlungstag, von 18°/» ab dem sechsten Behandlungstag und 20 % nach dem achten Behandlungstag ergibt.It has been shown that the salt obtainable according to the invention in the preventive treatment of the experimental vertigo in the mouse with daily doses of 50 mg / kg subcutaneously (indicated is the amount of α-acetylamino-isocaproic acid in the daily dose) a protection against dizziness from 8% from the second day of treatment, from 17% from the fourth day of treatment, from 18% from the sixth day of treatment and 20% after the eighth Treatment day results.
Das folgende Beispiel erläutert die Erfindung. Der Schmelzpunkt wurde auf der Kofier-Bank bestimmt.The following example illustrates the invention. The melting point was determined on the Kofier bench.
Zu einer Lösung von 43,3 g DL-a-Acetylaminoisocapronsäure in 150 ecm Methanol gibt man 21,8 g Verfahren zur Herstellung des Morpholinsalzes der a-Acetylamino-isocapronsäureTo a solution of 43.3 g of DL-α-acetylaminoisocaproic acid 21.8 g of process for the preparation of the morpholine salt are added to 150 ecm of methanol of a-acetylamino-isocaproic acid
Anmelder:Applicant:
Societe des Usines Chimiques Rhone-Poulenc, ParisSociete des Usines Chimiques Rhone-Poulenc, Paris
Vertreter: Dr. F. Zumstein,Representative: Dr. F. Zumstein,
Dipl.-Chem. Dr. rer. nat. E. AssmannDipl.-Chem. Dr. rer. nat. E. Assmann
und Dipl.-Chem. Dr. R. Koenigsberger,and Dipl.-Chem. Dr. R. Koenigsberger,
Patentanwälte, München 2, Bräuhausstr. 4Patent Attorneys, Munich 2, Bräuhausstr. 4th
Beanspruchte Priorität:
Frankreich vom 7. April 1956 (Nr. 712 235)Claimed priority:
France of April 7 , 1956 (No. 712 235)
Paul Gailliot, Paris,Paul Gailliot, Paris,
Jean Baget, Ermont, Seine-et-Oise,Jean Baget, Ermont, Seine-et-Oise,
und Bernard Beas, Paris (Frankreich),and Bernard Beas, Paris (France),
sind als Erfinder genannt wordenhave been named as inventors
Morpholin in 25 ecm Methanol. Nach Eindampfen des Lösungsmittels im Vakuum erhält man 63,2 g des Morpholinsalzes der a-Acetylamino-isocapronsäure, das aus 600 ecm Acetonitril umkristallisiert wird. Man saugt ab, wäscht mit 20 ecm Acetonitril und trocknet im Vakuum unter 2 mm Hg 20 Stunden bei 20° C. Man erhält 52g des Morpholinsalzes vom F. = 125° C.Morpholine in 25 ecm methanol. After evaporating the solvent in vacuo, 63.2 g of des are obtained Morpholine salt of α-acetylamino-isocaproic acid, which is recrystallized from 600 ecm acetonitrile. Man sucks off, washed with 20 ecm acetonitrile and dried in a vacuum under 2 mm Hg for 20 hours at 20 ° C. 52g of the morpholine salt are obtained with a melting point of 125 ° C.
Claims (1)
Deutsche Patentschrift Nr. 812 670.Considered publications:
German patent specification No. 812 670.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1137021X | 1956-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1137021B true DE1137021B (en) | 1962-09-27 |
Family
ID=9640507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES66725A Pending DE1137021B (en) | 1956-04-07 | 1957-04-04 | Process for the preparation of the morpholine salt of ª ‡ -acetylamino-isocaproic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1137021B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE812670C (en) * | 1946-11-13 | 1951-09-03 | Egema Sarl | Process for the preparation of salts of salicylic acid with morpholine or its homologues |
-
1957
- 1957-04-04 DE DES66725A patent/DE1137021B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE812670C (en) * | 1946-11-13 | 1951-09-03 | Egema Sarl | Process for the preparation of salts of salicylic acid with morpholine or its homologues |
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