DE379319C - Process for the preparation of double salts of yohimbine and methylhydrastimide - Google Patents

Process for the preparation of double salts of yohimbine and methylhydrastimide

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Publication number
DE379319C
DE379319C DEF52658D DEF0052658D DE379319C DE 379319 C DE379319 C DE 379319C DE F52658 D DEF52658 D DE F52658D DE F0052658 D DEF0052658 D DE F0052658D DE 379319 C DE379319 C DE 379319C
Authority
DE
Germany
Prior art keywords
yohimbine
methylhydrastimide
preparation
double salts
parts
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.)
Expired
Application number
DEF52658D
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KARL FLEISCHER DR
OTTO HIRSCH TABOR DR
Original Assignee
KARL FLEISCHER DR
OTTO HIRSCH TABOR DR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by KARL FLEISCHER DR, OTTO HIRSCH TABOR DR filed Critical KARL FLEISCHER DR
Priority to DEF52658D priority Critical patent/DE379319C/en
Application granted granted Critical
Publication of DE379319C publication Critical patent/DE379319C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D459/00—Heterocyclic compounds containing benz [g] indolo [2, 3-a] quinolizine ring systems, e.g. yohimbine; 16, 18-lactones thereof, e.g. reserpic acid lactone

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

Verfahren zur Darstellung von Doppelsalzen des Vohimbins und lWethylhydrastimids. Es ist bekannt, daß sowohl dem Y ohimbin wie auch dem Methylhydrastimid (vgl. Therap. Monatsh. igog, S. 581) eine gefäßerweiternde Wirkung zukommt. Es schien daher die Darstellung von Verbindungen wertvoll, in denen die therapeutische Wirkung beider Stoffe vereinigt ist. Versuche haben nun dargetan, daß es mit Hilfe zwei- oder mehrbasischer aliphatischer Carbonsäuren gelingt, in Wasser leichtlösliche Doppelsalze des Yohimbins und Methylhydrastimids nach den üblichen Salzbildungsmethoden herzustellen. Dabei wurde weiter gefunden, daß es nicht erforderlich ist, das als Ausgangsstoff dienende Methylhydrastamid in die Imidbase überzuführen; dieser Übergang erfolgt vielmehr gleichzeitig mit der Bildung des Doppelsalzes. Die Anwendung mehr als zweibasischer Säuren ermöglicht es ferner, die beiden Basen in verschiedenen Molekularverhältnissen zur Vereinigung zu bringen und so die Wirkung der entstehenden Salze zu beeinflussen.Process for the preparation of double salts of vohimbine and l-methylhydrastimide. It is known that both yohimbine and methylhydrastimide (see Therap. Monthly igog, p. 581) has a vasodilating effect. It therefore seemed the Representation of compounds valuable in which the therapeutic effects of both Substances is united. Experiments have now shown that it is with the help of di- or polybasic Aliphatic carboxylic acids succeed in producing double salts of yohimbine which are readily soluble in water and to prepare methylhydrastimide by the usual salt formation methods. Included it was also found that it is not necessary to use the starting material Converting methylhydrastamide into the imide base; rather, this transition occurs simultaneously with the formation of the double salt. The application more than dibasic Acids also make it possible to have the two bases in different molecular ratios to unite and thus to influence the effect of the resulting salts.

Die entstandenen gelbgefärbten Verbindungen zeichnen sich dem Yohimbin gegenüber durch eine starke Verringerung der Giftigkeit aus. Sie sollentherapeutische Verwendungfinden. Beispiel I. Eine Mischung von 368 Teilen Yohimbin, 414 Teilen Methylhydrastamid und 168 Teilen Weinsäure wird durch Erwärmen mit wenig Wasser in Lösung gebracht. Aus der gelben Lösung erhält man beim Eindunsten im Vakuum ein gelbes Pulver, das sich unter vorheriger Dunkelfärbung bei etwa 207° unter Aufschäumen zersetzt.The resulting yellow-colored compounds are characterized by yohimbine compared with a strong reduction in toxicity. You should be therapeutic Find use. Example I. A mixture of 368 parts of yohimbine, 414 parts Methylhydrastamide and 168 parts of tartaric acid are made by heating with a little water brought into solution. A vacuum is obtained from the yellow solution when it evaporates yellow powder which has previously darkened at about 207 ° with foaming decomposed.

Beispiel 1I. 368 Teile Yohimbin, 89,8 Teile Methylhydrastamid und 2io Teile Zitronensäure (gegebenenfalls ein kleiner Überschuß) werden in der in. Beispiel I angegebenen Weise zur Lösung gebracht und aufgearbeitet. Das erhaltene Doppelsalz bildet ein gelbes Pulver, das unter vorheriger Veränderung sich bei etwa 145' unter Aufschäumen zersetzt.Example 1I. 368 parts of yohimbine, 89.8 parts of methylhydrastamide and 2io parts of citric acid (if necessary a small excess) are dissolved in the manner indicated in Example I and worked up. The double salt obtained forms a yellow powder which, previously changing, decomposes at about 145 'with foaming.

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung von Doppelsalzen des Yohimbins und Methylhydrastimids, dadurch gekennzeichnet, daß man die Basen mit mehrbasischen aliphatischen Carbonsäuren nach einer der üblichen Methoden zur Umsetzung bringt.PATENT CLAIM Process for the preparation of double salts of yohimbine and methylhydrastimide, characterized in that the bases with polybasic brings aliphatic carboxylic acids to implementation by one of the customary methods.
DEF52658D 1922-09-30 1922-09-30 Process for the preparation of double salts of yohimbine and methylhydrastimide Expired DE379319C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF52658D DE379319C (en) 1922-09-30 1922-09-30 Process for the preparation of double salts of yohimbine and methylhydrastimide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF52658D DE379319C (en) 1922-09-30 1922-09-30 Process for the preparation of double salts of yohimbine and methylhydrastimide

Publications (1)

Publication Number Publication Date
DE379319C true DE379319C (en) 1923-08-20

Family

ID=7105626

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF52658D Expired DE379319C (en) 1922-09-30 1922-09-30 Process for the preparation of double salts of yohimbine and methylhydrastimide

Country Status (1)

Country Link
DE (1) DE379319C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1020342B (en) * 1953-05-08 1957-12-05 Lilly Co Eli Process for the preparation of a protoveratrine and oxyprotoveratrine salt

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1020342B (en) * 1953-05-08 1957-12-05 Lilly Co Eli Process for the preparation of a protoveratrine and oxyprotoveratrine salt

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