CH116465A - Process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2. 3-dimethyl-5-pyrazolone. - Google Patents

Process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2. 3-dimethyl-5-pyrazolone.

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Publication number
CH116465A
CH116465A CH116465DA CH116465A CH 116465 A CH116465 A CH 116465A CH 116465D A CH116465D A CH 116465DA CH 116465 A CH116465 A CH 116465A
Authority
CH
Switzerland
Prior art keywords
sep
phenyl
pyrazolone
acid
compound
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 CH116465A publication Critical patent/CH116465A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C07D239/62—Barbituric acids
    • 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

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

Description

  

  Verfahren zur Herstellung einer     Verbindung    der     Isopropylallylbarbitursüure    mit       1-Phenyl-2    -     3-dimethyl-5-pyrazolon.       Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur     Herstellui3g    einer Ver  bindung der     Isopropylallylbarbitursäure    mit       1-Phenyl-2        #        3-dimetbyl-5-pyrazolon,    welches  darin besteht, dass man     Isopropylallylbarbi-          tursäure    und     1-Phenyl-2    -     3-dimethyl-5-pyra-          zoion,

      gegebenenfalls unter Verwendung eines  Überschusses des einen     Ausgangsstoffes,    in  einem Lösungsmittel auflöst, wobei sich die  Verbindung bildet, welche durch Kristallisa  tion in Freiheit gesetzt wird.  



  Als Lösungsmittel können beispielsweise  verwendet werden:     Alkohol,    Aceton,     Aether,     Benzol, Chloroform, Wasser usw.  



  Die neue Verbindung kristallisiert in  farblosen Nadeln vom Schmelzpunkt 94',  die sich von den Kristallen der Ausgangs  stoffe unterscheiden. Ihre Löslichkeit ist  grösser als diejenige der Komponenten. Ihre  Zusammensetzung entspricht dem Verhältnis  von einem Molekül     Isopropylallylbarbitizrsäure     auf ein Molekül     1-Phenyl-2    -     3-dimethyl-5-          pyrazolon.    Sie soll in der Therapie Verwen  dung finden, da sie wesentlich stärker     anti-          pyretisch    und     analgetisch    wirkt,

   als     1-Phenyl-          2        #        3-dimethyl-5-pyrazolon.            Beispiel:     59 Gewichtsteile     1-Phenyl-2        #        3-dimethyl-          5-pyrazolon    und 34 Gewichtsteile     Isopropylal-          lylbarbitursäure    werden in 40 Gewichtsteilen  Alkohol von 92      /o    unter Erwärmen gelöst.  Beim Abkühlen bilden sich Kristalle, die  nach einigen Tagen vom Lösungsmittel ge  trennt und getrocknet werden. Die Verbin  dung kristallisiert in farblosen Nadeln vom  Schmelzpunkt 94  .



  Process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2 - 3-dimethyl-5-pyrazolone. The present invention relates to a process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2 # 3-dimetbyl-5-pyrazolone, which consists of adding isopropylallylbarbituric acid and 1-phenyl-2-3-dimethyl-5 -pyra- zoion,

      optionally using an excess of one starting material, dissolves in a solvent, the compound being formed which is set free by crystallization.



  Examples of solvents that can be used are: alcohol, acetone, ether, benzene, chloroform, water, etc.



  The new compound crystallizes in colorless needles with a melting point of 94 ', which differ from the crystals of the starting materials. Their solubility is greater than that of the components. Their composition corresponds to the ratio of one molecule of isopropylallylbarbitizric acid to one molecule of 1-phenyl-2 - 3-dimethyl-5-pyrazolone. It should be used in therapy because it has a much stronger anti-pyretic and analgesic effect,

   as 1-phenyl-2 # 3-dimethyl-5-pyrazolone. Example: 59 parts by weight of 1-phenyl-2 # 3-dimethyl-5-pyrazolone and 34 parts by weight of isopropylalylbarbituric acid are dissolved in 40 parts by weight of 92% alcohol with heating. On cooling, crystals form, which are separated from the solvent and dried after a few days. The compound crystallizes in colorless needles with a melting point of 94.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Verbin dung der Isopropylallylbarbitursäure mit 1-Phenyl-2 # 3-dimethyl-5-pyrazolon, dadurch gekennzeichnet, dass man Isopropylallylbar- bitursäure und 1-Phenyl-2 - 3-dimethyl-5- pyrazolon in einem Lösungsmittel auflöst, wobei sich die Verbindung bildet, welche durch Kristallisation in Freiheit gesetzt wird. Die neue Verbindung kristallisiert in farblosen Nadeln vom Schmelzpunkt 94 , die sich von den Kristallen der Ausgangs stoffe unterscheiden. Claim: A process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2 # 3-dimethyl-5-pyrazolone, characterized in that isopropylallylbarbituric acid and 1-phenyl-2 - 3-dimethyl-5-pyrazolone in a solvent dissolves, forming the compound that is set free by crystallization. The new compound crystallizes in colorless needles with a melting point of 94, which differ from the crystals of the starting materials. Ihre Löslichkeit ist grösser als diejenige der Komponenten. Ihre 'Zusammensetzung entspricht dem Verhältnis EMI0002.0001 von <SEP> einem <SEP> Molekül <SEP> Isopropylallylbai-bitursäui@e <tb> auf <SEP> ein <SEP> Molekül <SEP> 1-Phenyl-2 <SEP> # <SEP> 3-dimethy <SEP> l-5 py <SEP> razolon. <SEP> Sie <SEP> soll <SEP> in <SEP> der <SEP> Therapie <SEP> Verwen dung <SEP> finden, <SEP> da <SEP> sie <SEP> wesentlich <SEP> stärker <SEP> anti pyretisch <SEP> und <SEP> analgetisch <SEP> wirkt, <SEP> als <SEP> 1-Plieny <SEP> 1 2 <SEP> # <SEP> 3-diiiiethyl-5-pyrazoloil. Their solubility is greater than that of the components. Their 'composition corresponds to the ratio EMI0002.0001 of <SEP> a <SEP> molecule <SEP> isopropylallylbai-bitursäui @ e <tb> on <SEP> a <SEP> molecule <SEP> 1-phenyl-2 <SEP> # <SEP> 3-dimethy <SEP> l-5 py <SEP> razolon. <SEP> You <SEP> should <SEP> in <SEP> of the <SEP> therapy <SEP> use <SEP>, <SEP> because <SEP> you <SEP> much <SEP> more strongly <SEP> anti pyretic <SEP> and <SEP> analgesic <SEP>, <SEP> as <SEP> 1-Plieny <SEP> 1 2 <SEP> # <SEP> 3-diiiiethyl-5-pyrazoloil. EMI0002.0002 UNTERANSPRUCIIE EMI0002.0003 1. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeichnet, <SEP> dass <SEP> man <SEP> Isopropylallyl barbitursäure <SEP> und <SEP> 1-Phenyl-2 <SEP> # <SEP> 3-dimetliyl- EMI0002.0004 5-pyi,azolon <SEP> in <SEP> nioleku.larein <SEP> Verhältnis <tb> auflüst. <tb> 2. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeiehnet, <SEP> dal,1) <SEP> man <SEP> Isopropylallyl barbitursäure <SEP> und <SEP> 1-Plienyl-2 <SEP> # <SEP> 3-dimethil h-pyrazolon <SEP> unter <SEP> Verwendung <SEP> eines <SEP> Über schusses <SEP> des <SEP> einen <SEP> Ausgangsstoffes <SEP> auflöst. EMI0002.0002 UNDER CLAIMS EMI0002.0003 1. <SEP> method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> that <SEP> man <SEP> isopropylallyl barbituric acid <SEP> and <SEP> 1-phenyl-2 <SEP> # <SEP> 3-dimetliyl- EMI0002.0004 5-pyi, azolon <SEP> in <SEP> nioleku.larein <SEP> ratio <tb> revolves. <tb> 2. <SEP> method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> dal, 1) <SEP> man <SEP> isopropylallyl barbituric acid <SEP> and <SEP> 1-plienyl-2 <SEP> # <SEP> 3-dimethil h-pyrazolone <SEP> below <SEP> Use <SEP> of a <SEP> excess <SEP> of the <SEP> dissolves a <SEP> raw material <SEP>.
CH116465D 1925-05-09 1925-05-09 Process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2. 3-dimethyl-5-pyrazolone. CH116465A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH116465T 1925-05-09

Publications (1)

Publication Number Publication Date
CH116465A true CH116465A (en) 1926-09-01

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ID=4375486

Family Applications (1)

Application Number Title Priority Date Filing Date
CH116465D CH116465A (en) 1925-05-09 1925-05-09 Process for the preparation of a compound of isopropylallylbarbituric acid with 1-phenyl-2. 3-dimethyl-5-pyrazolone.

Country Status (1)

Country Link
CH (1) CH116465A (en)

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