BE638844A - - Google Patents

Info

Publication number
BE638844A
BE638844A BE638844DA BE638844A BE 638844 A BE638844 A BE 638844A BE 638844D A BE638844D A BE 638844DA BE 638844 A BE638844 A BE 638844A
Authority
BE
Belgium
Prior art keywords
emi
general formula
new
penicillins
inorganic
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 BE638844A publication Critical patent/BE638844A/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D499/00Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

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

Description

       

   <EMI ID=1.1> 

  
formule générale 1

  

 <EMI ID=2.1> 


  
 <EMI ID=3.1>   <EMI ID=4.1> 

  
cation d'une base azotée soit organique, soit inorganique avant tout d'aminé ou de diamine nuit aliphatique., soit

  
 <EMI ID=5.1> 

  
On vient de trouver que le* nouvelles pénicillines ayant la formule générale 1 font leur preuve non seulement-

  
 <EMI ID=6.1> 

  
celles des pénicillines déjà connues - contre les Staphy-

  
 <EMI ID=7.1> 

  
manifeste même pour Ion grandes dilutions.

  
Voici comment on prépare Ion nouvelles pénicillines

  
 <EMI ID=8.1> 

  
 <EMI ID=9.1> 

  

 <EMI ID=10.1> 


  
colt non dérivé - tel que par exemple l'halogénure (chlorure)

  
 <EMI ID=11.1> 

  
On peut facilement préparer les acides ayant la 

  
 <EMI ID=12.1>   <EMI ID=13.1> 

  
On peut procéder/de la façon suivantes on prépare d'abord l'anhydride mixte par réaction d'acide ayant la formule

  
 <EMI ID=14.1> 

  
On isole les nouvelles pénicillines ayant la formule

  
 <EMI ID=15.1> 

  
bres, soit en forme de leurs sels formés avec bases appropriées - soit organiques, soit inorganiques.

  
On a vérifié la constitution des nouvelles pénicillines^ par spectre infra-rouge; on a vérifié leur contenu par la 

  
 <EMI ID=16.1> 

  
de cette efficacité avec celle des pénicillines déjà connues, 

  
 <EMI ID=17.1>   <EMI ID=18.1> 

  
tion saturé* d'acétate de potassium dans l'alcool n-buty-

  
 <EMI ID=19.1> 

  
une poudre blanche, cristalline qui est facilement soluble dune l'eau*

  
 <EMI ID=20.1> 

  
On obtient la solution du sel sodique de la nouvelle pénicilline en partant d'un gramme d'acide 2-formyle-4,6dichlorphénoxy-acétique, de la dicyclohéxyle-carbodiimide et du sel sodique d'acide 6-aminopénicillanique - tout en procédant de la façon décrite à l'Exemple 1. On isole de la solution obtenue ainsi une substance en forme de poudre blanche, qui est facilement soluble dans l'eau - en séparant 

  
 <EMI ID=21.1> 

  
par lyophilisation. La nouvelle pénicilline est très stable dans le milieu acide.

  
 <EMI ID=22.1> 

  
On obtient le sel potassique de la nouvelle pénicilline en forme d'une substance blanche, cristalline en partent



   <EMI ID = 1.1>

  
general formula 1

  

 <EMI ID = 2.1>


  
 <EMI ID = 3.1> <EMI ID = 4.1>

  
cation of a nitrogenous base either organic or inorganic, above all amine or aliphatic overnight diamine., or

  
 <EMI ID = 5.1>

  
We have just found that the * new penicillins having the general formula 1 prove their worth not only-

  
 <EMI ID = 6.1>

  
those of the already known penicillins - against Staphy-

  
 <EMI ID = 7.1>

  
manifest even for large dilutions.

  
Here's how to prepare Ion new penicillins

  
 <EMI ID = 8.1>

  
 <EMI ID = 9.1>

  

 <EMI ID = 10.1>


  
non-derivative colt - such as for example halide (chloride)

  
 <EMI ID = 11.1>

  
Acids having the

  
 <EMI ID = 12.1> <EMI ID = 13.1>

  
It is possible to proceed in the following manner: the mixed anhydride is first prepared by reaction of an acid having the formula

  
 <EMI ID = 14.1>

  
The new penicillins having the formula

  
 <EMI ID = 15.1>

  
bres, either in the form of their salts formed with suitable bases - either organic or inorganic.

  
The constitution of the new penicillins has been verified by infra-red spectrum; we checked their content by

  
 <EMI ID = 16.1>

  
of this effectiveness with that of the already known penicillins,

  
 <EMI ID = 17.1> <EMI ID = 18.1>

  
saturated * ration of potassium acetate in n-butyl alcohol

  
 <EMI ID = 19.1>

  
a white, crystalline powder which is easily soluble in water *

  
 <EMI ID = 20.1>

  
The sodium salt solution of the new penicillin is obtained by starting from one gram of 2-formyl-4,6dichlorphenoxy-acetic acid, dicyclohexyl-carbodiimide and sodium salt of 6-aminopenicillanic acid - while proceeding from as described in Example 1. From the solution thus obtained, a substance in the form of a white powder, which is easily soluble in water, is isolated by separating

  
 <EMI ID = 21.1>

  
by freeze-drying. The new penicillin is very stable in the acidic environment.

  
 <EMI ID = 22.1>

  
The potassium salt of the new penicillin is obtained in the form of a white, crystalline substance.


    

Claims (1)

<EMI ID=23.1> <EMI ID = 23.1> <EMI ID=24.1> <EMI ID = 24.1> <EMI ID=25.1> <EMI ID = 25.1> drogène, soit de l'alcoyle possédant 1-4 atome. de carbone, drogen, or alkyl having 1-4 atoms. of carbon, <EMI ID=26.1> <EMI ID = 26.1> coxyle possédant 1-4 atomes de carbone, soit de l'oxhydryle, <EMI ID=27.1> coxyl having 1-4 carbon atoms, or oxhydryl, <EMI ID = 27.1> forment ensemble un autre cercle aromatique résultant de la condensation; Z signifie dans cette formule générale soit un atome d'hydrogène, soit un cation d'une base azotée soit organique, soit inorganique - avant tout d'amine. ou together form another aromatic circle resulting from condensation; Z signifies in this general formula either a hydrogen atom, or a cation of a nitrogenous base, either organic or inorganic - above all amine. or <EMI ID=28.1> <EMI ID = 28.1> procédé est caractérisé en ce que l'on condense soit un ocide ayant la formule générale II process is characterized in that one condenses either an ocide having the general formula II <EMI ID=29.1> <EMI ID = 29.1> <EMI ID=30.1> <EMI ID = 30.1>
BE638844D 1963-10-19 BE638844A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR951194A FR1377635A (en) 1963-10-19 1963-10-19 Process for the preparation of new semi-synthetic penicillins and products conforming to those obtained by the present process or similar process

Publications (1)

Publication Number Publication Date
BE638844A true BE638844A (en)

Family

ID=8814778

Family Applications (1)

Application Number Title Priority Date Filing Date
BE638844D BE638844A (en) 1963-10-19

Country Status (2)

Country Link
BE (1) BE638844A (en)
FR (1) FR1377635A (en)

Also Published As

Publication number Publication date
FR1377635A (en) 1964-11-06

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