CH234982A - Process for the preparation of a new therapeutically effective amidine. - Google Patents

Process for the preparation of a new therapeutically effective amidine.

Info

Publication number
CH234982A
CH234982A CH234982DA CH234982A CH 234982 A CH234982 A CH 234982A CH 234982D A CH234982D A CH 234982DA CH 234982 A CH234982 A CH 234982A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
therapeutically effective
imidazoline
new therapeutically
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 CH234982A publication Critical patent/CH234982A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Landscapes

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

Description

  

      Verfahren    zur Darstellung eines neuen therapeutisch wirksamen     Amidins..       Es     wurde    ,gefunden, dass man zu     einem          neuen    therapeutisch     wirksamen        Amidin    ge  langen kann,     wenn    man     einen    reaktionsfähi  gen, Ester des     2-Oxymethyl-imidazolins    mit       2.4-Dimethylanilvn    umsetzt. Gegebenenfalls  arbeitet man in Gegenwart     eines        Lösungs-          mittels.     



  Das so     gewonnene        2-[2'.4'-Dimerthyl-ph        e-          nylaminomethyll-imidazolin    ,der     Formel     
EMI0001.0020     
  
EMI0001.0021     
  
    bildet <SEP> ein <SEP> Hydrochlorid <SEP> vom <SEP> h". <SEP> 224-226 
<tb>  5 <SEP> unter <SEP> Zerseäung, <SEP> das <SEP> sich <SEP> in <SEP> Wasser <SEP> leicht
<tb>  löst.
<tb>  



  Die <SEP> neue <SEP> Verbindung <SEP> soll <SEP> therapeutische
<tb>  Verwendung <SEP> finden.
<tb>  



  <I>Beispiel:</I>
<tb>  15,4 <SEP> Teile <SEP> 2-Chlorrnethyl-imidazolin-lhy  drochlorid, <SEP> und <SEP> 24,2 <SEP> Teile <SEP> 2.4-Dimethylanilin
<tb>  werden <SEP> miteinander <SEP> auf <SEP> 100  <SEP> erhitzt.     
EMI0001.0022     
  
    Es <SEP> findet <SEP> bald <SEP> eine <SEP> lebhafte <SEP> Reaktion <SEP> mit
<tb>  Temperatursteigerung <SEP> statt. <SEP> Nach <SEP> erfolgter
<tb>  Reaktion <SEP> wird <SEP> abgekühlt <SEP> und <SEP> das <SEP> Reaktions  gemisch, <SEP> in <SEP> Wasser <SEP> aufgenommen. <SEP> Aus <SEP> der
<tb>  wässerigen <SEP> Lösung <SEP> fällt <SEP> man:

   <SEP> die <SEP> Base <SEP> mit
<tb>  Alkali. <SEP> Die <SEP> isolierte <SEP> Base <SEP> wird <SEP> im <SEP> Vakuum
<tb>  destilliert, <SEP> wobei <SEP> das <SEP> 2,- <SEP> [2'.4'-Dimethyl-phe  nylamiUamethyll-immdazodin <SEP> bei. <SEP> gp.o,8185
<tb>  bis <SEP> 187  <SEP> als <SEP> .gelbes, <SEP> zähflüssiges <SEP> 01 <SEP> übergeht.
<tb>  



  An <SEP> Stelle <SEP> von <SEP> 2-Chlorm@ethyl-imidazolin  hydrochlorkl <SEP> kann <SEP> man, <SEP> auch <SEP> von <SEP> einem <SEP> an  dern <SEP> .reaktionsföMgenEs:ter <SEP> ides! <SEP> 2-Oxymethyl  imidazolins, <SEP> wie <SEP> z. <SEP> B. <SEP> vom <SEP> Bromwasserstoff <SEP>   s'äure- <SEP> oder <SEP> vom <SEP> Toluolsulfonsäure-Ester, <SEP> aus  gellen.
<tb>  



  Ebenso. <SEP> kann <SEP> man <SEP> an <SEP> :Stelle <SEP> des <SEP> Hydro  chlorids <SEP> .die <SEP> freie <SEP> Base <SEP> oder <SEP> ein <SEP> anderes. <SEP> Salz
<tb>  verwenden.



      Process for the preparation of a new therapeutically active amidine .. It has been found that a new therapeutically active amidine can be obtained by reacting a reactive ester of 2-oxymethyl-imidazoline with 2,4-dimethylanilvn. If necessary, one works in the presence of a solvent.



  The 2- [2'.4'-dimerthyl-ph enylaminomethyll-imidazoline obtained in this way, of the formula
EMI0001.0020
  
EMI0001.0021
  
    <SEP> forms a <SEP> hydrochloride <SEP> from <SEP> h ". <SEP> 224-226
<tb> 5 <SEP> under <SEP> seeding, <SEP> the <SEP> <SEP> in <SEP> water <SEP> easily
<tb> solves.
<tb>



  The <SEP> new <SEP> connection <SEP> should <SEP> therapeutic
<tb> Find use <SEP>.
<tb>



  <I> Example: </I>
<tb> 15.4 <SEP> parts <SEP> 2-chloromethyl-imidazoline-hydrochloride, <SEP> and <SEP> 24.2 <SEP> parts <SEP> 2,4-dimethylaniline
<tb> <SEP> are heated together <SEP> to <SEP> 100 <SEP>.
EMI0001.0022
  
    <SEP> finds <SEP> soon <SEP> a <SEP> lively <SEP> reaction <SEP> with
<tb> Temperature increase <SEP> instead. <SEP> After <SEP> has taken place
<tb> Reaction <SEP>, <SEP> is cooled down <SEP> and <SEP> the <SEP> reaction mixture, <SEP> is absorbed in <SEP> water <SEP>. <SEP> From <SEP> the
<tb> aqueous <SEP> solution <SEP> drops <SEP> man:

   <SEP> the <SEP> Base <SEP> with
<tb> alkali. <SEP> The <SEP> isolated <SEP> Base <SEP> becomes <SEP> in the <SEP> vacuum
<tb> distilled, <SEP> where <SEP> is <SEP> 2, - <SEP> [2'.4'-Dimethyl-phe nylamiUamethyll-immdazodin <SEP>. <SEP> gp.o, 8185
<tb> to <SEP> 187 <SEP> changes to <SEP> .yellow, <SEP> viscous <SEP> 01 <SEP>.
<tb>



  At <SEP> place <SEP> of <SEP> 2-Chlorm @ ethyl-imidazolin hydrochloride <SEP> one can <SEP>, <SEP> also <SEP> from <SEP> one <SEP> to the other <SEP>. REACTIONS: ter <SEP> ides! <SEP> 2-oxymethyl imidazoline, <SEP> like <SEP> e.g. <SEP> B. <SEP> from <SEP> hydrogen bromide <SEP> acidic <SEP> or <SEP> from <SEP> toluenesulfonic acid ester, <SEP> gel.
<tb>



  As well. <SEP> can <SEP> one <SEP> at <SEP>: place <SEP> of the <SEP> hydrochloride <SEP>. The <SEP> free <SEP> base <SEP> or <SEP> a <SEP> other. <SEP> salt
Use <tb>.

Claims (1)

EMI0001.0023 PATENTANSPRUCH: <tb> Verfahren <SEP> zur <SEP> Darstellung <SEP> eines <SEP> neuen <tb> therapeutisch <SEP> wirksamen <SEP> A:midins; <SEP> dadurch <tb> gekennzeichnet, <SEP> @dass <SEP> man <SEP> einen <SEP> reaktionsfähi gen <SEP> Ester <SEP> des <SEP> 2-Oxymethyl-imidazolins: <SEP> mit <tb> 2.4-D,methyl@anilin <SEP> umsetzt. EMI0002.0001 Das <SEP> so <SEP> gewonnene <SEP> 2- <SEP> [ <SEP> 2'.4'-Dimethy <SEP> 1-phe nylamino@methyll-,imidaz,alin <SEP> der <SEP> Formel EMI0002.0002 bildet ein Hydrochlorid vom F.224-226 unter Zersetzung, das sich in Wasser leicht löst. Die neue Verbindung soll therapeutische Verwendung finden. EMI0001.0023 PATENT CLAIM: <tb> Method <SEP> for <SEP> display <SEP> of a <SEP> new one <tb> therapeutically <SEP> effective <SEP> A: midins; <SEP> thereby <tb> marked, <SEP> @that <SEP> you <SEP> a <SEP> reactive <SEP> ester <SEP> of <SEP> 2-oxymethyl-imidazoline: <SEP> with <tb> 2.4-D, methyl @ aniline <SEP> converts. EMI0002.0001 The <SEP> so <SEP> obtained <SEP> 2- <SEP> [<SEP> 2'.4'-Dimethy <SEP> 1-phe nylamino @ methyll-, imidaz, alin <SEP> of the <SEP> formula EMI0002.0002 Forms a hydrochloride of F.224-226 with decomposition, which dissolves easily in water. The new compound should find therapeutic use. EMI0002.0005 UlTE <SEP> R<B>A</B>N <SEP> SPRüCHE <tb> 1. <SEP> Verfahren <SEP> nach <SEP> Patentansprueh, <SEP> da durch <SEP> gekennzeichnet, <SEP> dass <SEP> man <SEP> zur <SEP> Umset zung <SEP> ein <SEP> ?-Halogen@niethyl-imi@dazolin <SEP> ver wendet. <tb> 2. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> da durch <SEP> bekennzeichnet. <SEP> da.ss <SEP> man <SEP> zur <SEP> Umset zung <SEP> 2-Chloritiethyl-imidazolin <SEP> verwendet. <tb> 3,. <SEP> Verfahren <SEP> naeh <SEP> Patentanspruch, <SEP> da dureb <SEP> gekerinzeieliiiet. <SEP> dass <SEP> man <SEP> in <SEP> Geigenwart <tb> eines <SEP> Lösung-mittels <SEP> a.rbcitet. EMI0002.0005 UlTE <SEP> R <B> A </B> N <SEP> SPEECH <tb> 1. <SEP> method <SEP> according to <SEP> patent claim, <SEP> as marked by <SEP>, <SEP> that <SEP> one <SEP> <SEP> for <SEP> implementation <SEP> < SEP>? -Halogen @ niethyl-imi @ dazolin <SEP> is used. <tb> 2. <SEP> method <SEP> according to <SEP> patent claim, <SEP> as denoted by <SEP>. <SEP> da.ss <SEP> one <SEP> is used for <SEP> implementation <SEP> 2-chloritiethyl-imidazoline <SEP>. <tb> 3 ,. <SEP> method <SEP> according to <SEP> patent claim, <SEP> because it is <SEP> kerinzeieliiiet. <SEP> that <SEP> man <SEP> in <SEP> Geigenwart <tb> of a <SEP> solution using <SEP> a.rbcitet.
CH234982D 1938-05-11 1938-05-11 Process for the preparation of a new therapeutically effective amidine. CH234982A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH234982T 1938-05-11
CH529054X 1938-05-11

Publications (1)

Publication Number Publication Date
CH234982A true CH234982A (en) 1944-10-31

Family

ID=25727954

Family Applications (1)

Application Number Title Priority Date Filing Date
CH234982D CH234982A (en) 1938-05-11 1938-05-11 Process for the preparation of a new therapeutically effective amidine.

Country Status (1)

Country Link
CH (1) CH234982A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2380733A1 (en) * 1976-11-16 1978-09-15 Ciba Geigy Ag PRODUCTS BASED ON (PHENYLAMINOMETHYL) -2 IMIDAZOLINES, USED TO FIGHT VARIOUS ECTOPARASITES AND MICRO-ORGANISMS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2380733A1 (en) * 1976-11-16 1978-09-15 Ciba Geigy Ag PRODUCTS BASED ON (PHENYLAMINOMETHYL) -2 IMIDAZOLINES, USED TO FIGHT VARIOUS ECTOPARASITES AND MICRO-ORGANISMS
FR2381030A1 (en) * 1976-11-16 1978-09-15 Ciba Geigy Ag 2-PHENYLAMINOMETHYL IMIDAZOLINES AND THEIR PREPARATION

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