CH204760A - Process for the preparation of a new therapeutically effective amidine. - Google Patents

Process for the preparation of a new therapeutically effective amidine.

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Publication number
CH204760A
CH204760A CH204760DA CH204760A CH 204760 A CH204760 A CH 204760A CH 204760D A CH204760D A CH 204760DA CH 204760 A CH204760 A CH 204760A
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CH
Switzerland
Prior art keywords
isopropyl
methyl
reaction
process according
amidine
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH204760A publication Critical patent/CH204760A/en

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Description

  

  Verfahren zur Herstellung eines neuen therapeutisch     wirksamen        Amidines.       Es wurde     .gefunden,    dass man zu     einem     neuen therapeutisch wirksamen     Amidin    ge  langen kann, wenn man einen     31Vlethyl-6-          isopropyl-phenogyacetimidoäther    mit Ammo  niak umsetzt.  



  Das so     gewonnene        3-Methyl-6-isopropyl-          phenoayäthenylamidin    :der Formel  
EMI0001.0011     
    bildet ein Hydrachlorid vom F. 182 bis     183',          das        sich,    in     Wasser    löst.  



  Die neue     Verbindung    soll     therapeutische          Verwendung    finden.  



  <I>Beispiel:</I>  Man leitet     @Salzsäuregas    in :ein     ,gekühltes     Gemisch     äquimolarer    Mengen von     Alkohol     und     3-Methyl-6-isopropyl-phenogyacetonitril            (Kp.        0,4        114    bis     1-18-,    hergestellt zum Bei  spiel durch     Umsetzung    von     Chloracetonitril     mit     Thymol    in     Gegenwart    von säurebinden  den Mitteln)     ein    und     verreibt        das,

      entstan  dene     3@Methyl-6-iisopropyl-phenogyacetimido-          äthyläther=hydrochlorid    mit :einem indiffe  renten     Lösungsmittel    wie     Petroläther,    Äther  oder Benzol.

   Man erhält     es    so in Farm     eines     farblosen,     feuchtigkeitsempfindlichen        Kri-          stallpulvers.    27 Teile     3-1Vlethyl-6-isopropyl-          phenogy    -     acetimddoäthyläther    -     hydrochlorid,     aus dem sich während der     Umsetzung        3-          Methyl    - 6 -     isopropyl    -     phenogyacetimidoäthyl-          äther    bildet,

   werden mit einer     alkoholischen          Lösung    von 3 Teilen     Ammoniak    bis. .zum       Verschwinden    des     zunächst    entstehenden       Ammonchlorids        geschüttelt.    Sodann wird :der  Alkohol     abdestilliert        und    :der Rückstand aus       Aceton        umkristallisiert.    Man :erhält :so :

  das       ä    -     Methyl    - 6 -     isopropyl    -     phenogyäthenyl-        ami-          din.-hydrochlorid    als     farbloses        Kristallpulver,          aus    dem sich     mittels    Alkalien die freie     Base          gewinnen:        lässt.     



  Statt von 3-Methyl=6-isopropyl-phenogy-           acetimidoä,thyläther    kann man ebensogut  auch von einem andern Äther, wie z. B. vom       Methyl-,        Propyl-    oder     Butyläther,        ausgehen.     



  An Stelle des     salzsauren    Salzes des     3-          Methyl    - 6 -     isopropyl    -     phenoxya.e        etimi        doäthyl-          äthers    kann auch die freie Base selbst oder  ein anderes Salz, wie z. B. das     Hydrobromid     oder das schwefelsaure Salz     Verwendung    fin  den.



  Process for the production of a new therapeutically active amidine. It was found that a new therapeutically active amidine can be obtained by reacting a 31Vlethyl-6-isopropyl-phenogyacetimidoether with ammonia.



  The 3-methyl-6-isopropylphenoayäthenylamidin thus obtained: the formula
EMI0001.0011
    forms a hydrachloride from F. 182 to 183 ', which dissolves in water.



  The new compound should find therapeutic use.



  <I> Example: </I> @ Hydrochloric acid gas is passed into: a cooled mixture of equimolar amounts of alcohol and 3-methyl-6-isopropyl-phenogyacetonitrile (boiling point 0.4 114 to 1-18-, produced for example by reacting chloroacetonitrile with thymol in the presence of acid-binding agents) and triturates

      3 @ methyl-6-isopropyl-phenogyacetimidoethylether = hydrochloride was formed with: an inert solvent such as petroleum ether, ether or benzene.

   It is obtained in this way in the form of a colorless, moisture-sensitive crystal powder. 27 parts of 3-1Vlethyl-6-isopropyl-phenogy-acetimddoäthyläther hydrochloride, from which 3-methyl-6-isopropyl-phenogyacetimidoethylether is formed during the reaction,

   be with an alcoholic solution of 3 parts ammonia up. . Shaken for the disappearance of the ammonium chloride initially formed. Then: the alcohol is distilled off and: the residue is recrystallized from acetone. One: receives: so:

  the ä - methyl - 6 - isopropyl - phenogyäthenyl ami- din.-hydrochloride as a colorless crystal powder, from which the free base can be obtained by means of alkalis:.



  Instead of 3-methyl = 6-isopropyl-phenogy-acetimidoä, ethyl ether one can just as well also from another ether, such as z. B. from the methyl, propyl or butyl ether, start.



  Instead of the hydrochloric acid salt of 3-methyl-6-isopropyl-phenoxya.e etimi doäthyl- äthers, the free base itself or another salt, such as. B. the hydrobromide or the sulfuric acid salt use fin the.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen therapeutisch wirksamen Amidines, dadurch gekennzeichnet, dass man einen 3-112ethyl-6- isopropyl-phenoxyacetimidoätlier mit Ammo- niak. umsetzt. Das so gewonnene 3-l@lethyl-6-isopropy 1- phenoxyäthenyl-amidin der Formel EMI0002.0026 bildet ein Hydrochlorid vom F. 18? bis 183'# das sich in Wasser löst. PATENT CLAIM: Process for the production of a new therapeutically effective amidine, characterized in that a 3-112ethyl-6-isopropyl-phenoxyacetimido etlier is mixed with ammonia. implements. The 3-l @ lethyl-6-isopropy 1-phenoxyethenyl-amidine of the formula obtained in this way EMI0002.0026 forms a hydrochloride of F. 18? to 183 '# that dissolves in water. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRÜCFIE 1. Verfahren nah Patentanspruch, dadurch gekennzeichnet, da.ss man zur Umsetzung <B>3</B> - Methyl - G - i.sopropyl- phenoxyacetimido- äthyläther verwendet. The new compound should find therapeutic use. SUBSTANTIVE CLAIM 1. Method according to claim, characterized in that one uses <B> 3 </B> - methyl - G - i.sopropyl phenoxyacetimido ethyl ether for the reaction. ?. Verfahren nach Patentan.spru,ch, dadurch gekennzeichnet, da.ss man zur Umsetzung einen 3 - Methyl- 6 -isopropyl - phen.oxya.cet-- imido < itlier verwendet, der aus einem Salz desselben erhalten wurde. 3. ?. Process according to patent claim, characterized in that a 3-methyl-6-isopropyl-phen.oxya.cet-imido <itlier obtained from a salt thereof is used for the reaction. 3. Verfahren nach Patentanspruch und Un- teranspruch 2, dadurch gekennzeichnet, dass man zur Umsetzung einen 3-Methyl- 6 - isopropyl - phenoxyacetimidoätlier ver wendet. der aus einem Hydrohalogenid des.;elben erhalten wurde. 1. Process according to patent claim and dependent claim 2, characterized in that a 3-methyl-6-isopropyl-phenoxyacetimido ether is used for the reaction. obtained from a hydrohalide of the same. 1. Verfahren nach Patentanspruch und den Unteranspriichen 2 und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 3 - 3Zel liy 1- 6 - isopropyl-plienoxyaeet- imidoäther verwendet, der aus dem Ilvdro- clilorid.desselben erhalten wurde. y 5. Process according to patent claim and dependent claims 2 and 3, characterized in that a 3 - 3 cell lithium 1-6 - isopropyl-plienoxyaeet imido ether obtained from Ilvdro-clilorid.d the same is used for the reaction. y 5. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis d, dadurch ge kennzeichnet, dass man zur Umsetzung 3 - Methyl - f> - isopropyl - phenoxy acetimido- ä.thyläther verwendet, der aus dem Hydro- chlorid desselben erhalten wurde. Process according to claim and dependent claims 1 to d, characterized in that 3 - methyl - f> - isopropyl - phenoxy acetimido Ä.thyläther is used for the reaction, which was obtained from the hydrochloride of the same.
CH204760D 1935-06-21 1935-06-21 Process for the preparation of a new therapeutically effective amidine. CH204760A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204760T 1935-06-21
CH200478T 1938-10-15

Publications (1)

Publication Number Publication Date
CH204760A true CH204760A (en) 1939-05-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH204760D CH204760A (en) 1935-06-21 1935-06-21 Process for the preparation of a new therapeutically effective amidine.

Country Status (1)

Country Link
CH (1) CH204760A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2517468A (en) * 1948-05-28 1950-08-01 Ciba Pharm Prod Inc Phenoxyacetamidines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2517468A (en) * 1948-05-28 1950-08-01 Ciba Pharm Prod Inc Phenoxyacetamidines

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