CH307808A - Process for the preparation of a new hydrazine compound. - Google Patents

Process for the preparation of a new hydrazine compound.

Info

Publication number
CH307808A
CH307808A CH307808DA CH307808A CH 307808 A CH307808 A CH 307808A CH 307808D A CH307808D A CH 307808DA CH 307808 A CH307808 A CH 307808A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
hydrazine compound
new
new hydrazine
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH307808A publication Critical patent/CH307808A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/20—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung einer neuen     Hydrazinverbindung.       Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur Herstellung von     3,6-Di-          liydra7ino-pyridazin    der Formel  
EMI0001.0004     
    Diese Verbindung besitzt wertvolle phar  makologische Eigenschaften. Sie zeichnet sich  insbesondere durch eine langandauernde und  sehr starke blutdrucksenkende Wirkung aus.  



  Die neue Verbindung wird erfindungsge  mäss dadurch erhalten,     da.ss    man     3,6-Dimer-          ecipto-pvridazin    mit     Hydrazin    umsetzt.  



  Die Reaktion wird zweckmässig in An  wesenheit von Verdünnungsmitteln, allenfalls  auch in Gegenwart von     Kondensationsmitteln,     und vorteilhaft bei erhöhter Temperatur       dureh-eführt.    Der     Ausgangsstoff    kann auch  in Form seiner Salze zur Anwendung gelan  gen.  



       .1e    nach der Arbeitsweise erhält man die  neue     1-lyclrazinverbindung    in Form der freien       Base    oder ihrer Salze. Aus     diesen    kann in       üblielier    Weise die freie Base gewonnen wer  den. Von letzterer lassen sieh     durch        _Umset-          zung    mit Säuren, die zur Bildung     t.herapeu-          liseli        verwendbarer    Salze geeignet sind, Salze  gewinnen, wie z.

   B. der Halogenwasserstoff-    Säuren, Schwefelsäure, Salpetersäure, Phos  phorsäure,     Rhodanwasserstoffsäure,    Essig  säure,     Propionsäure,        Oxalsäure,        Malonsäure,     Bernsteinsäure,     Äpfelsäure,        Methansulfon-          sättre,        Äthansulfonsäure,        Oxyäthansulfon-          -säure,        Benzol-    oder     Toluolsulfonsäure    oder  von selbsttherapeutisch wirksamen Säuren.  



  Im nachfolgenden Beispiel besteht zwi  schen Gewichtsteil und     Volumteil    die gleiche  Beziehung wie     zwischen    Gramm und Kubik  zentimeter. Die Temperaturen sind in Celsius  graden angegeben.  



  <I>Beispiel:</I>  2 Gewichtsteile     3,6-Dimercapto-pyridazin     werden in einem Gemisch von 10     Volumteilen     absolutem Äthylalkohol und 10     Volumteilen          Hydrazinhy        drat    6 Stunden am     Rückfluss    ge  kocht, wobei Schwefelwasserstoff entweicht.  Beim Stehen des Reaktionsgemisches über  Nacht bei 0  kristallisieren     1,5-Gewichtsteile          3,6-Dihydrazino-pyridazin    der Formel  
EMI0001.0045     
    aus. Einmal aus wenig     50o/oigem        Äthylalko-          hol    umkristallisiert., ist das Produkt rein.

    F. = 193-195  unter Zersetzung.      Das ans der Base mit 1 Äquivalent     2n-Sal-          petersäure    erhältliche Mononitrat schmilzt bei       191-7.92     unter Zersetzung und ist in Was  ser ziemlich leicht löslich.



  Process for the preparation of a new hydrazine compound. The present invention relates to a process for the preparation of 3,6-dihydra7ino-pyridazine of the formula
EMI0001.0004
    This compound has valuable pharmacological properties. It is characterized in particular by a long-lasting and very strong antihypertensive effect.



  According to the invention, the new compound is obtained by reacting 3,6-dimer-ecipto-pvridazine with hydrazine.



  The reaction is expediently carried out in the presence of diluents, possibly also in the presence of condensing agents, and advantageously at elevated temperature. The starting material can also be used in the form of its salts.



       .1e according to the procedure, the new 1-lyclrazine compound is obtained in the form of the free base or its salts. The free base can be obtained from these in a customary manner. By reacting with acids which are suitable for the formation of salts which can be used in therapy, salts can be obtained from the latter, e.g.

   B. the hydrohalic acids, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, malic acid, methanesulphonic acid, ethanesulphonic acid, oxyethanesulphonic acid, benzene or toluenesulphonic acid or even active.



  In the example below, the relationship between part by weight and part by volume is the same as that between grams and cubic centimeters. The temperatures are given in degrees Celsius.



  <I> Example: </I> 2 parts by weight of 3,6-dimercapto-pyridazine are refluxed for 6 hours in a mixture of 10 parts by volume of absolute ethyl alcohol and 10 parts by volume of hydrazine hydrate, with hydrogen sulfide escaping. When the reaction mixture is left to stand overnight at 0, 1.5 parts by weight of 3,6-dihydrazino-pyridazine of the formula crystallize
EMI0001.0045
    out. Once recrystallized from a little 50% ethyl alcohol, the product is pure.

    F. = 193-195 with decomposition. The mononitrate, which can be obtained from the base with 1 equivalent of 2N nitric acid, melts at 191-7.92 with decomposition and is fairly easily soluble in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Hydra zinverbindung, dadureh gekennzeichnet, dass man 3,6-Dimercapto-pyridazin mit Hydrazin umsetzt. Das so erhaltene 3,6-Dihydrazino-pyrid- azin schmilzt bei 193-195 und bildet ein Mononitrat vom F. = 191-192 . Es soll als Heilmittel Verwendung finden. PATENT CLAIM: Process for the production of a hydrazine compound, characterized in that 3,6-dimercapto-pyridazine is reacted with hydrazine. The 3,6-dihydrazino-pyridazine obtained in this way melts at 193-195 and forms a mononitrate with a m.p. = 191-192. It is said to be used as a remedy.
CH307808D 1952-08-20 1952-08-20 Process for the preparation of a new hydrazine compound. CH307808A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH307808T 1952-08-20

Publications (1)

Publication Number Publication Date
CH307808A true CH307808A (en) 1955-06-15

Family

ID=4493284

Family Applications (1)

Application Number Title Priority Date Filing Date
CH307808D CH307808A (en) 1952-08-20 1952-08-20 Process for the preparation of a new hydrazine compound.

Country Status (1)

Country Link
CH (1) CH307808A (en)

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