CH183066A - Method for preparing a salicylic acid compound. - Google Patents

Method for preparing a salicylic acid compound.

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Publication number
CH183066A
CH183066A CH183066DA CH183066A CH 183066 A CH183066 A CH 183066A CH 183066D A CH183066D A CH 183066DA CH 183066 A CH183066 A CH 183066A
Authority
CH
Switzerland
Prior art keywords
salicylic acid
pyrazolone
isopropyl
dimethyl
phenyl
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH183066A publication Critical patent/CH183066A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring

Description

  

  Verfahren zur Darstellung einer     Salieylsänreverbindung.       Es wurde gefunden, dass     Salicylsäure     und     l.-Phenyl-2,3-dimethyl-4-isopropyl-5-pyr-          azolon    leicht zu einer wohl definierten, gut       kristallierenden    Verbindung zusammen  treten, wenn sie in innige     Berührung,    ge  bracht werden.

   Die Einwirkung kann durch  Zusammenschmelzen von     Salicylsäure    und       1-Phenyl    - 2,3 -     dimethyl-4-isopropyl-5-pyrazo-          lon    oder durch Erwärmen dieser Ausgangs  stoffe in einem     indifferenten        Lösungsmittel     durchgeführt werden. Die Komponenten  treten dabei in molekularem Verhältnis zu-         sammen.       Die Verbindung von     Salicylsäure    mit     l-          Phenyl        -2,3-dimethyl        -4-isopropyl-5-pyrazolon     bildet farblose Kristalle vom Schmelzpunkt  72 bis 73  .

   In Wasser ist sie schwer löslich;  leicht löst sie sich in den meisten der     ge-          bräuchlichen    organischen Lösungsmittel, wie  Alkohol, Benzol, Essigäther. Durch     Um-          kristallisieren    wird die Verbindung nicht       verändert.       Die     Verbindung    von     Salicylsäure    mit     1-          Phenyl        -2,3-dimethyl        -4-isopropyl-5-pyrazolon     wirkt insbesondere bei rheumatischen Affek  tionen stark und anhaltend, schmerzlindernd.

    Sie ist darin sowohl der     .Salieylsäure,    als  auch den bekannten     analgetisch    wirkenden  Verbindungen der     Pyrazolongruppe,    wie  zum Beispiel dem     sälicylsauren        Antipyrin,     weit überlegen. Gegenüber der     Salicylsäure     hat sie     ausserdem    noch den     Vorzug,        dass    sie  den Magen gar nicht reizt, also auch von  empfindlichen Patienten anstandslos er  tragen wird. Sie soll als Arzneimittel ver  wendet werden.

      <I>Beispiel 1:</I>  Man     vermischt    138 Gewichtsteile     Salicyl-          säure    mit 230 g     1-Phenyl-2,3-dimethyl-4-          isopropyl-5-pyrazolon    und übergiesst mit       2,8,0    Gewichtsteilen Alkohol. Beim     .gelinden     Erwärmen geht alles in Lösung. Die fil  trierte Lösung wird unter Rühren mit etwa      300 Teilen Wasser versetzt. Die neue Ver  bindung kristallisiert in farblosen Kristallen.  Sie ist sofort rein. Sie schmilzt bei 72 bis  73  . Die Ausbeute ist nahezu quantitativ.

    <I>Beispiel 2:</I>  In<B>160</B> Gewichtsteilen Benzol löst man       unter    schwachem Erwärmen 13,8 Gewichts  teile     Salicylsäure    und 230 Gewichtsteile     1-          Phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolon.     Zu der filtrierten, noch nicht völlig erkal  teten Lösung fügt man bis zur schwachen       Trübung        etwa    210 Gewichtsteile niedrig sie  denden     Petroläther    zu. Nach dem vollstän  digen Abkühlen werden die     schmelzpunkts-          reinen    Kristalle abgetrennt. Die Ausbeute ist       praktisch        quantitativ.  



  Method for preparing a salieylsic acid compound. It has been found that salicylic acid and 1.-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone easily come together to form a well-defined, well-crystallizing compound when they are brought into intimate contact.

   The action can be carried out by melting together salicylic acid and 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone or by heating these starting materials in an inert solvent. The components come together in a molecular ratio. The compound of salicylic acid with 1-phenyl -2,3-dimethyl -4-isopropyl-5-pyrazolone forms colorless crystals with a melting point of 72 to 73.

   It is sparingly soluble in water; It dissolves easily in most of the common organic solvents such as alcohol, benzene, and acetic ether. Recrystallization does not change the connection. The combination of salicylic acid with 1-phenyl -2,3-dimethyl -4-isopropyl-5-pyrazolone has a strong and persistent analgesic effect, particularly in rheumatic affections.

    It is far superior to salicylic acid as well as to the known analgesic compounds of the pyrazolone group, such as, for example, salicylic acid antipyrine. Compared to salicylic acid, it also has the advantage that it does not irritate the stomach at all, so even sensitive patients can easily carry it. It is intended to be used as a medicinal product.

      Example 1: 138 parts by weight of salicylic acid are mixed with 230 g of 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone and 2.8 parts by weight of alcohol are poured over them. When heated gently, everything goes into solution. About 300 parts of water are added to the filtered solution while stirring. The new compound crystallizes in colorless crystals. She is in immediately. It melts at 72 to 73. The yield is almost quantitative.

    <I> Example 2: </I> In 160 parts by weight of benzene, 13.8 parts by weight of salicylic acid and 230 parts by weight of 1-phenyl-2,3-dimethyl-4-isopropyl-5 are dissolved with gentle heating -pyrazolone. About 210 parts by weight of low-boiling petroleum ether are added to the filtered, not yet completely cooled solution. After complete cooling, the crystals with a pure melting point are separated off. The yield is practically quantitative.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer Salicyl- säureverbindung, dadurch gekennzeichnet, dass man Salicylsäure und 1-Phenyl-2,3-di- methyl-4-isopropyl-5-pyrazolon aufeinander einwirken lässt. Die Verbindung von Salicylsäure mit 1- Phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolon bildet farblose Kristalle vom Schmelzpunkt 72 bis 73 . In Wasser ist sie schwer löslich; leicht löst sie sich in den meisten der ge bräuchlichen organischen Lösungsmittel, wie Alkohol, Benzol, Essigäther. PATENT CLAIM: Process for the preparation of a salicylic acid compound, characterized in that salicylic acid and 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone are allowed to act on one another. The compound of salicylic acid with 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone forms colorless crystals with a melting point of 72 to 73. It is sparingly soluble in water; it dissolves easily in most of the common organic solvents such as alcohol, benzene and vinegar ether. Durch Um kristallisieren wird die Verbindung nicht verändert. Die Verbindung von Salicylsäure mit 1- Phenyl -2,3-dimethyl -4-isopropyl-5-pyrazolon wirkt insbesondere bei rheumatischen Affek tionen stark und anhaltend, schmerzlindernd. Sie ist darin sowohl der Salicylsäure, als auch den bekannten analgetisch wirkenden Verbindungen der Pyrazolongruppe, wie zum Beispiel dem salicylsauren Antipyrin, weit überlegen. Recrystallization does not change the connection. The combination of salicylic acid with 1-phenyl -2,3-dimethyl -4-isopropyl-5-pyrazolone has a strong and persistent analgesic effect, particularly in rheumatic affections. It is far superior to salicylic acid as well as to the known analgesic compounds of the pyrazolone group, such as salicylic acid antipyrine. Gegenüber der Salicylsäure hat sie ausserdem noch den Vorzug, dass sie den Magen gar nicht reizt, also auch von emp findlichen Patienten anstandslos ertragen wird. Sie soll als Arzneimittel verwendet werden. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Einwir kung von Salicylsäure auf 1.-Phenyl-2,3- dimethyl-4-isopropyl-5-pyrazolon in einem Lösungsmittel durchführt. Compared to salicylic acid, it also has the advantage that it does not irritate the stomach at all, meaning that sensitive patients can tolerate it without any problem. It is intended to be used as a medicine. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that the action of salicylic acid on 1.-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone is carried out in a solvent.
CH183066D 1935-01-29 1935-01-29 Method for preparing a salicylic acid compound. CH183066A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH183066T 1935-01-29

Publications (1)

Publication Number Publication Date
CH183066A true CH183066A (en) 1936-03-15

Family

ID=4432004

Family Applications (1)

Application Number Title Priority Date Filing Date
CH183066D CH183066A (en) 1935-01-29 1935-01-29 Method for preparing a salicylic acid compound.

Country Status (1)

Country Link
CH (1) CH183066A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2472565A1 (en) * 1979-11-09 1981-07-03 Toho Pharma Co Ltd N - ((ISOPROPYL-4-METHYL-2-PHENYL-1-PYRAZOLONE-5-YL-3) METHYL) ACETOXY-2-BENZAMIDE, PROCESS FOR PREPARING THE SAME, AND MEDICAMENTS CONTAINING THE SAME

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2472565A1 (en) * 1979-11-09 1981-07-03 Toho Pharma Co Ltd N - ((ISOPROPYL-4-METHYL-2-PHENYL-1-PYRAZOLONE-5-YL-3) METHYL) ACETOXY-2-BENZAMIDE, PROCESS FOR PREPARING THE SAME, AND MEDICAMENTS CONTAINING THE SAME

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