CH281041A - Process for the preparation of a derivative of p-amino-salicylic acid. - Google Patents

Process for the preparation of a derivative of p-amino-salicylic acid.

Info

Publication number
CH281041A
CH281041A CH281041DA CH281041A CH 281041 A CH281041 A CH 281041A CH 281041D A CH281041D A CH 281041DA CH 281041 A CH281041 A CH 281041A
Authority
CH
Switzerland
Prior art keywords
amino
salicylic acid
preparation
derivative
acid
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft V Siegfried
Original Assignee
Vormals B Siegfried Ag
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 Vormals B Siegfried Ag filed Critical Vormals B Siegfried Ag
Publication of CH281041A publication Critical patent/CH281041A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren zur Herstellung eines Derivates der     p-Amino-salicylsäure.       Es wurde gefunden, dass man zu Substanzen  mit wertvollen therapeutischen Eigenschaften  gelangt., wenn man p-     Amino-salicylsäure    oder  deren Salze oder Ester mit     acylierenden    Mit  teln behandelt, die eine     Cyclopentenyl-    oder       Cyclopentylgruppe    enthalten.

   Dieses Resultat  war um so überraschender, als in der Literatur  darauf hingewiesen wird,     da.ss    bei Substitu  tion in der     4-Aminogruppe    zum Beispiel durch       aliphatische    Säuren die     bakteriostatische    Wir  kung vermindert wird     (The        Lancet    1946,  Seite 15).  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     Chaulmo-          ogrylamino-2-oxy-l-benzoesäure,    welches da  durch gekennzeichnet ist, dass man auf     p-          Amino-salicylsäure    ein     Chaulmoograsäurehalo-          genid    einwirken lässt. Das Produkt soll als  Arzneimittel verwendet werden.

      <I>Beispiel:</I>  Zu 85 g     p-Amino-salicylsäure    in 1000     ems     Äther und 150 g     Dimethylanilin    gibt man un  ter Kühlung 166 g     Chaulmoograsäurechlorid,     extrahiert nach beendeter Reaktion mit Soda  lösung und fällt durch Zugabe von Salzsäure  das Reaktionsprodukt aus. Nach     Abnutschen,     Trocknen im Vakuum und     Umkristallisieren     aus Alkohol schmilzt die     4-Chaulmoogryl-          amino-2-oxy-l-benzoesäure    bei 217 bis 219  C  (unter Zersetzung).



  Process for the preparation of a derivative of p-amino-salicylic acid. It has been found that substances with valuable therapeutic properties are obtained if p-amino-salicylic acid or its salts or esters are treated with acylating agents which contain a cyclopentenyl or cyclopentyl group.

   This result was all the more surprising as it is pointed out in the literature that the bacteriostatic effect is reduced if the 4-amino group is substituted, for example by aliphatic acids (The Lancet 1946, page 15).



  The subject of the present patent is a process for the preparation of chaulmo- ogrylamino-2-oxy-1-benzoic acid, which is characterized in that a chaulmoogric acid halide is allowed to act on p-amino-salicylic acid. The product is intended to be used as a medicinal product.

      <I> Example: </I> To 85 g of p-aminosalicylic acid in 1000 ems of ether and 150 g of dimethylaniline, 166 g of chaulmoogravic acid chloride are added under cooling, extracted after the reaction with soda solution and the reaction product is precipitated by adding hydrochloric acid . After filtering off with suction, drying in vacuo and recrystallization from alcohol, the 4-Chaulmoogryl-amino-2-oxy-1-benzoic acid melts at 217 to 219 ° C. (with decomposition).

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 4-Chaulmo- ogrylamino-2-oxy-l-benzoesäure, dadurch ge kennzeichnet, dass man auf p-Amino-salicyl- säure ein Chaulmoograsäurehalogenid einwir ken lässt. Das so erhaltene kristalline Erzeug nis schmilzt bei 217 bis 219 C unter Zerset zung. PATENT CLAIM: Process for the production of 4-chaulmo- ogrylamino-2-oxy-1-benzoic acid, characterized in that a chaulmoogric acid halide is allowed to act on p-amino-salicylic acid. The resulting crystalline product melts at 217 to 219 C with decomposition.
CH281041D 1949-07-06 1949-07-06 Process for the preparation of a derivative of p-amino-salicylic acid. CH281041A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH281041T 1949-07-06
CH278408T 1949-07-06

Publications (1)

Publication Number Publication Date
CH281041A true CH281041A (en) 1952-02-15

Family

ID=25731829

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281041D CH281041A (en) 1949-07-06 1949-07-06 Process for the preparation of a derivative of p-amino-salicylic acid.

Country Status (1)

Country Link
CH (1) CH281041A (en)

Similar Documents

Publication Publication Date Title
CH420120A (en) Process for the preparation of metal salts of α-hydroxy-γ-methyl mercaptobutyric acid
CH281041A (en) Process for the preparation of a derivative of p-amino-salicylic acid.
AT210064B (en) X-ray contrast media
DE719026C (en) Process for the production of preparations containing the circulatory hormone kallikrein
DE619348C (en) Process for the production of pure diacetyl from wood vinegar or other mixtures containing diacetyl
AT231420B (en) Process for the preparation of metal salts of α-hydroxy-γ-methyl mercaptobutyric acid
DE1155786B (en) Process for the preparation of 1,4-diaminoanthraquinone-2-sulfonic acid or its sodium salt
AT219204B (en) Process for the preparation of 3-alkoxy-19-nor-δ &lt;2,5 (10)&gt; -androstadien-17-one
AT155799B (en) Process for the preparation of l-ascorbic acid.
DE2045750C3 (en) Process for the separation of chlorine from aqueous electrolysis solutions
DE944790C (en) Process for the preparation of thioether dicarboxylic acids or their salts
DE573034C (en) Process for the production of water-soluble preparations from diphenolisatin and its substitution products
CH401940A (en) Process for the preparation of 1,1,1-trifluoro-2-bromo-2-chloroethane
CH233730A (en) Process for the preparation of an aromatic carboxamide.
CH150525A (en) Process for producing a cellulose ester.
CH281042A (en) Process for the preparation of a derivative of p-amino-salicylic acid.
CH301585A (en) Process for the preparation of a new thioketopiperidine.
CH278408A (en) Process for the preparation of a derivative of p-amino-salicylic acid.
DE1135910B (en) Process for the preparation of 2,5-bis-methylaethyleneimino-hydroquinone
DE1136703B (en) Process for the preparation of choleretically active phenyl-ethylcarbinol-carboxylic acid esters
CH338462A (en) Process for the preparation of a water-soluble theophylline derivative
CH178944A (en) Process for the preparation of 2-oxydiphenyl ether-5-carboxylic acid.
CH408914A (en) Process for the preparation of pyridoxine
CH125887A (en) Process for the preparation of 2,4-dioxy-5.B-phenylethylbenzoic acid.
CH341485A (en) Process for the production of lactose-phosphoric acid esters