BE550342A - - Google Patents

Info

Publication number
BE550342A
BE550342A BE550342DA BE550342A BE 550342 A BE550342 A BE 550342A BE 550342D A BE550342D A BE 550342DA BE 550342 A BE550342 A BE 550342A
Authority
BE
Belgium
Prior art keywords
emi
formula
anion
quaternaries
lower alkyl
Prior art date
Application number
Other languages
French (fr)
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.)
Publication of BE550342A publication Critical patent/BE550342A/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  La présente intention concerne un procédé

  
 <EMI ID=1.1>  
 <EMI ID=2.1> 
 <EMI ID=3.1> 

  

 <EMI ID=4.1> 


  
 <EMI ID=5.1>   <EMI ID=6.1> 

  
emploie notamment des esters réactifs d'alcools inférieurs., par exemple des halogénures d'alcoyles inférieurs comme le chlorure, le bromure ou l'iodure de méthyle, d'éthyle ou

  
de propyle, ou d'autre part des sulfates d'alcoyles inférieurs,  comme le sulfaté de diméthyle ou le sulfate de dlbutyle, des

  
 <EMI ID=7.1> 

  
élevée, en vase clos si c'est nécessaire.

  
Les sels d'ammonium quaternaires obtenus conformément au procédé peuvent être transformés de manière usuelle en leurs hydroxydes d'ammonium quaternaires par 

  
 <EMI ID=8.1> 

  
 <EMI ID=9.1> 

  
baryum ou en traitant les sels quaternaires par des &#65533;changeurs d'anions. A partir des bases ainsi obtenues, on peut, par réaction avec des acides , obtenir les sels quaternaires d'acides inorganiques ou organiques.!! tels ceux des acides

  
 <EMI ID=10.1> 

  
citrique ou benzoïque. On peut toutefois les préparer aussi directement à partir des halogénures d'ammonium quaternaires, par réaction sur les sels d'argent des acides organiques ou  <EMI ID=11.1> 

  
Les nouveaux composes obtenus selon la présente  <EMI ID=12.1> 

  
elles sont stérilisées et/ou renferment des substances

  
 <EMI ID=13.1> 

  
 <EMI ID=14.1>   <EMI ID=15.1> 

  
par dose 100 à 200 mg de substance active.

  
 <EMI ID=16.1> 

  
 <EMI ID=17.1> 

  
mise en ;oeuvre du procédé défini ci-dessus.

  
L'invention est décrite plus en détail dans l'exemple non limitatif qui suit. Dans cet exemple, les températures sont indiquées en degrés centigrades. 

  
Exemple

  
Tout en agitant fortement;, on fait bouillir

  
 <EMI ID=18.1> 

  
filtration la fraction cristalline précipitée-, lave ensuite

  
 <EMI ID=19.1> 

  
obtient ainsi, Ce composé fond à 213-214[deg.] en se décomposant. 

  
 <EMI ID=20.1> 

  
 <EMI ID=21.1> 

  
 <EMI ID=22.1> 

  
 <EMI ID=23.1> 

  
tenue comme suit: 

  
Tout en agitant bien, et en refroidissant, on

  
 <EMI ID=24.1> 

  
 <EMI ID=25.1> 

  
On met en suspension 7,66 parties en poids de

  
 <EMI ID=26.1> 

  
 <EMI ID=27.1> 

  
'dans la chambre cathodique d'une cellule électrolytique* Cette

  
 <EMI ID=28.1> 

  
 <EMI ID=29.1> 

  
 <EMI ID=30.1> 

  
de 0,0448 ampères par centimètre carrée l'imide étant totalement dissous au bout de 302 minutes. On arrête l'électrolyse

  
 <EMI ID=31.1> 

  
 <EMI ID=32.1> 

  
reprises avec de l'éther, /réunit les extraits éthérés, lave* . à l'eau, sèche sur du sulfate ;de sodium anhydre et évapore. On malaxe le résidu à fond avec du pentane, sépare par - <EMI ID=33.1> 



  The present intention relates to a process

  
 <EMI ID = 1.1>
 <EMI ID = 2.1>
 <EMI ID = 3.1>

  

 <EMI ID = 4.1>


  
 <EMI ID = 5.1> <EMI ID = 6.1>

  
employs in particular reactive esters of lower alcohols, for example lower alkyl halides such as methyl, ethyl or methyl chloride, bromide or iodide or

  
propyl, or on the other hand lower alkyl sulfates, such as dimethyl sulfate or dlbutyl sulfate,

  
 <EMI ID = 7.1>

  
high, in isolation if necessary.

  
The quaternary ammonium salts obtained in accordance with the process can be converted in the usual manner into their quaternary ammonium hydroxides by

  
 <EMI ID = 8.1>

  
 <EMI ID = 9.1>

  
barium or by treating quaternary salts with & anion changers. From the bases thus obtained, it is possible, by reaction with acids, to obtain the quaternary salts of inorganic or organic acids. such as acids

  
 <EMI ID = 10.1>

  
citric or benzoic. However, they can also be prepared directly from quaternary ammonium halides, by reaction with the silver salts of organic acids or <EMI ID = 11.1>

  
The new compounds obtained according to this <EMI ID = 12.1>

  
they are sterilized and / or contain substances

  
 <EMI ID = 13.1>

  
 <EMI ID = 14.1> <EMI ID = 15.1>

  
per dose 100 to 200 mg of active substance.

  
 <EMI ID = 16.1>

  
 <EMI ID = 17.1>

  
implementation of the method defined above.

  
The invention is described in more detail in the non-limiting example which follows. In this example, temperatures are shown in degrees centigrade.

  
Example

  
While stirring strongly ;, we boil

  
 <EMI ID = 18.1>

  
filtration of the precipitated crystalline fraction, then washed

  
 <EMI ID = 19.1>

  
thus obtained, This compound melts at 213-214 [deg.] on decomposition.

  
 <EMI ID = 20.1>

  
 <EMI ID = 21.1>

  
 <EMI ID = 22.1>

  
 <EMI ID = 23.1>

  
held as follows:

  
While stirring well, and cooling, we

  
 <EMI ID = 24.1>

  
 <EMI ID = 25.1>

  
7.66 parts by weight of

  
 <EMI ID = 26.1>

  
 <EMI ID = 27.1>

  
'in the cathode chamber of an electrolytic cell * This

  
 <EMI ID = 28.1>

  
 <EMI ID = 29.1>

  
 <EMI ID = 30.1>

  
of 0.0448 amperes per square centimeter, the imide being completely dissolved after 302 minutes. We stop electrolysis

  
 <EMI ID = 31.1>

  
 <EMI ID = 32.1>

  
taken up with ether, / combines the ethereal extracts, washing *. with water, dried over anhydrous sodium sulfate and evaporated. The residue is mixed thoroughly with pentane, separated by - <EMI ID = 33.1>


    

Claims (1)

<EMI ID=34.1> <EMI ID = 34.1> <EMI ID=35.1> <EMI ID = 35.1> <EMI ID=36.1> <EMI ID = 36.1> <EMI ID=37.1> <EMI ID = 37.1> <EMI ID=38.1> <EMI ID = 38.1> <EMI ID=39.1> <EMI ID = 39.1> un anion thérapeutiquement utilisable, ledit procédé étant caractérisé par -le fait qu'on traite un composé de formulés a therapeutically usable anion, said method being characterized in that a compound of formulated <EMI ID=40.1> <EMI ID = 40.1> <EMI ID=41.1> <EMI ID = 41.1> <EMI ID=42.1> <EMI ID = 42.1> <EMI ID=43.1> <EMI ID = 43.1> un reste alcoylique Inférieur et;, si on le désire, qu'on a Lower alkyl residue and ;, if desired, that échange dans les composés obtenus un anion contre un autre exchange in the compounds obtained one anion against another anion . anion. Le présent procédé peut encore être caractérise par les points suivants: The present process can be further characterized by the following points: <EMI ID=44.1> <EMI ID = 44.1> ae formuLë! ae formuLë! <EMI ID=45.1> <EMI ID = 45.1> <EMI ID=46.1> <EMI ID = 46.1> <EMI ID=47.1> <EMI ID = 47.1> <EMI ID=48.1> <EMI ID = 48.1> <EMI ID=49.1> <EMI ID = 49.1> <EMI ID=50.1> <EMI ID = 50.1> <EMI ID=51.1> <EMI ID=52.1> <EMI ID = 51.1> <EMI ID = 52.1> quaternaires de formule : quaternaries of formula: <EMI ID=53.1> <EMI ID = 53.1> <EMI ID=54.1> <EMI ID = 54.1> sous 6). under 6). <EMI ID=55.1> <EMI ID = 55.1> quaternaires de formule quaternaries of formula <EMI ID=56.1> <EMI ID = 56.1> <EMI ID=57.1> <EMI ID = 57.1> <EMI ID=58.1> <EMI ID = 58.1> <EMI ID=59.1> <EMI ID = 59.1> <EMI ID=60.1> <EMI ID = 60.1> <EMI ID=61.1> <EMI ID = 61.1> <EMI ID=62.1> <EMI ID=63.1> <EMI ID = 62.1> <EMI ID = 63.1> formule formula <EMI ID=64.1> <EMI ID = 64.1> <EMI ID=65.1> <EMI ID = 65.1> <EMI ID=66.1> <EMI ID = 66.1> <EMI ID=67.1> <EMI ID = 67.1> <EMI ID=68.1> <EMI ID = 68.1>
BE550342D 1955-08-15 BE550342A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US1173166XA 1955-08-15 1955-08-15

Publications (1)

Publication Number Publication Date
BE550342A true BE550342A (en)

Family

ID=22372204

Family Applications (1)

Application Number Title Priority Date Filing Date
BE550342D BE550342A (en) 1955-08-15

Country Status (2)

Country Link
BE (1) BE550342A (en)
FR (1) FR1173166A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10501812A (en) * 1994-06-20 1998-02-17 スミスクライン・ビーチャム・コーポレイション Endothelin receptor antagonist
US5929106A (en) * 1997-10-27 1999-07-27 Smithkline Beecham Corporation Endothelin receptor antagonists

Also Published As

Publication number Publication date
FR1173166A (en) 1959-02-20

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