CH276619A - Process for the preparation of a new derivative of p-amino-salicylic acid. - Google Patents

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

Info

Publication number
CH276619A
CH276619A CH276619DA CH276619A CH 276619 A CH276619 A CH 276619A CH 276619D A CH276619D A CH 276619DA CH 276619 A CH276619 A CH 276619A
Authority
CH
Switzerland
Prior art keywords
amino
preparation
salicylic acid
new derivative
iodizing agent
Prior art date
Application number
Other languages
German (de)
Inventor
Hans Dr Suter
Zutter Hans
Widler Hans
Original Assignee
Cilag 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 Cilag Ag filed Critical Cilag Ag
Publication of CH276619A publication Critical patent/CH276619A/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren zur Herstellung eines neuen Derivates der     p-Amino-salicylsäure.       Die Erfindung betrifft ein Verfahren zur  Herstellung des     2-Oxy-J-amino-3,5-dijod-ben-          zoesäure-äthylesters    von der Formel  
EMI0001.0004     
    Es wurde gefunden, dass diese Verbindung  eine überraschend gute     Wirksamkeit    gegen  Mikroorganismen, insbesondere gegen säure  feste Bakterien, entfaltet. Die neue Verbin  dung soll zu therapeutischen Zwecken, ferner  auch als     Zwisehenproduht    Verwendung fin  den.  



  Das erfindungsgemässe Verfahren ist da  durch     gekennzeiehnet,        dass    man auf     J-Amino-          2-oxy-benzoesäure-äthylester    ein jodierendes  Mittel einwirken lässt. Das     Jodierungsmittel     kann in Gegenwart von Jodüberträgern ein  wirken gelassen werden. Als     Jodüberträger     eignen sieh zum Beispiel     N-Chlorverbindun-          gen,    wie Chloramin T,     N-Chlor-        resp.     



       Diehlor-harnstoff,    und     Alkali-        resp.    Erdalkali  hypoehlorite. Als     Jodierungsmittel    hat sich  u. a. Jodchlorid als geeignet. erwiesen.  



  Die     Jodierung    wird     zweekmässig    in Gegen  wart eines Lösungsmittels, das sieh nach dem  zu verwendenden     Jodierungsmittel    richtet,    z. B. in Eisessig,     Chloroform,        Schwefelkohlen-          stoff    oder     izi    wässeriger     mineralsaurer        resp.     alkalischer Lösung, vorgenommen.  



  Das     Verfahrensprodukt,    der     2-Oxy        -J-          amino-3,5-dijod-benzoesäure-äthylester,    bildet  ein hellgelbes Kristallpulver, das bei 164 bis  1650 schmilzt.  



  Er ist in Äther,     Äthanol,    Aceton, Benzol  und Chloroform leichtlöslich und schwerlös  lich in Wasser, verdünnten Mineralsäuren und       Petroläther.     



       Beispiel:          ?\?    g     2-Oa-y-J-amino-benzoesäure-äthylester     werden in 200     cm3    Eisessig gelöst und dieser  Lösung unter     Turbinieren    bei 10 bis 200  460     em3    einer     Jodchloridlösung    in Eisessig zu  getropft, die 7,5 g Jod pro 100     cm3    enthält.

    Das Reaktionsgemisch wird eine Stunde     wei-          tcrturbiniert,    dann in Wasser gegossen und  der ausfallende     2-Oxy-3,5-dijod-J-amino-ben-          zoesäure-äthy        lester    aus     Aceton-Wasser    umge  fällt. Man erhält 46,6 g, entsprechend 88,6 %  der Theorie, eines hellgelben Kristallpulvers,  das bei 164 bis 1650 schmilzt. Die neue Ver  bindung löst. sieh leicht. in Äthanol,     Aeeton,     Äther, Benzol und Chloroform, schwer in  Wasser, verdünnten Mineralsäuren und     Pe-          troläther.  



  Process for the preparation of a new derivative of p-amino-salicylic acid. The invention relates to a process for the preparation of the 2-oxy-J-amino-3,5-diiodo-benzoic acid ethyl ester of the formula
EMI0001.0004
    It has been found that this compound has a surprisingly good activity against microorganisms, in particular against acid-resistant bacteria. The new compound is intended to be used for therapeutic purposes and also as an intermediate product.



  The method according to the invention is characterized by the fact that an iodizing agent is allowed to act on ethyl J-amino-2-oxy-benzoate. The iodizing agent can be allowed to act in the presence of iodine carriers. Examples of suitable iodine carriers are N-chlorine compounds, such as chloramine T, N-chlorine, or



       Diehlor urea, and alkali resp. Alkaline earth hypoehlorite. As an iodizing agent has u. a. Iodine chloride as suitable. proven.



  The iodination is two-way in the presence of a solvent that depends on the iodizing agent to be used, z. B. in glacial acetic acid, chloroform, carbon disulfide or izi aqueous mineral acid, respectively. alkaline solution.



  The process product, ethyl 2-oxy-I-amino-3,5-diiodo-benzoate, forms a light yellow crystal powder that melts at 164 to 1650.



  It is easily soluble in ether, ethanol, acetone, benzene and chloroform and hardly soluble in water, diluted mineral acids and petroleum ether.



       Example:? \? g of 2-Oa-y-I-amino-benzoic acid ethyl ester are dissolved in 200 cm3 of glacial acetic acid and this solution is added dropwise to this solution with turbines at 10 to 200,460 cm3 of an iodine chloride solution in glacial acetic acid which contains 7.5 g of iodine per 100 cm3.

    The reaction mixture is turbinated for a further hour, then poured into water and the 2-oxy-3,5-diiodo-I-amino-benzoic acid-ethyl ester which precipitates is converted from acetone-water. 46.6 g, corresponding to 88.6% of theory, of a light yellow crystal powder which melts at 164 to 1650 are obtained. The new connection loosens. see easily. in ethanol, aeeton, ether, benzene and chloroform, difficult in water, dilute mineral acids and petroleum ether.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen Derivates der p-Amino-salicylsäure, dadurch gekennzeichnet, dass man auf -1-Amino-2-oxy- benzoesäure-äthylester ein jodierendes Mittel einwirken lässt. Der so erhaltene 2-Ox@--4- amino-3,5-dijod-benzoesäure-äthylester bildet ein hellgelbes Kristallpulver, das bei 164 bis 7.650 schmilzt. PATENT CLAIM Process for the preparation of a new derivative of p-amino-salicylic acid, characterized in that an iodizing agent is allowed to act on ethyl -1-amino-2-oxybenzoate. The thus obtained 2-Ox @ -4-amino-3,5-diiodobenzoic acid ethyl ester forms a light yellow crystal powder which melts at 164 to 7,650. Er ist in Äther, Äthanol, Ace ton, Benzol und Chloroform leichtlöslich und sehwerlöslieh in Wasser, verdünnten -Mineral säuren und Petroläther. UNTERANSPRUCH Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als jodieren- des Mittel Jodchlorid verwendet. It is easily soluble in ether, ethanol, acetone, benzene and chloroform and visually soluble in water, diluted mineral acids and petroleum ether. SUBSTANTIAL CLAIM Process according to patent claim, characterized in that iodine chloride is used as the iodizing agent.
CH276619D 1949-02-14 1949-02-14 Process for the preparation of a new derivative of p-amino-salicylic acid. CH276619A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH276619T 1949-02-14
CH273250T 1949-02-14

Publications (1)

Publication Number Publication Date
CH276619A true CH276619A (en) 1951-07-15

Family

ID=25731439

Family Applications (1)

Application Number Title Priority Date Filing Date
CH276619D CH276619A (en) 1949-02-14 1949-02-14 Process for the preparation of a new derivative of p-amino-salicylic acid.

Country Status (1)

Country Link
CH (1) CH276619A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218349A (en) * 1958-05-12 1965-11-16 Glaxo Lab Ltd Esters of tetraiodoanthranilic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218349A (en) * 1958-05-12 1965-11-16 Glaxo Lab Ltd Esters of tetraiodoanthranilic acid

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