CH285030A - Process for the manufacture of a new pain reliever drug. - Google Patents

Process for the manufacture of a new pain reliever drug.

Info

Publication number
CH285030A
CH285030A CH285030DA CH285030A CH 285030 A CH285030 A CH 285030A CH 285030D A CH285030D A CH 285030DA CH 285030 A CH285030 A CH 285030A
Authority
CH
Switzerland
Prior art keywords
methyl
manufacture
pain reliever
phenyl
new pain
Prior art date
Application number
Other languages
German (de)
Inventor
Dr Somogyi J C
E Hofstetter
Original Assignee
Geistlich Soehne 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 Geistlich Soehne Ag filed Critical Geistlich Soehne Ag
Publication of CH285030A publication Critical patent/CH285030A/en

Links

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

Landscapes

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

Description

  

  Verfahren zur Herstellung eines neuen schmerzstillenden Arzneimittels.    Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen  schmerzstillenden Arzneimittels, nämlich des     3-          [N        (ari#iethyl-ss-phenyl)    -     äthyl    -     aminomethyl]        -          4-isopropy        l-norant.ipyrins,    das dadurch ge  kennzeichnet ist, dass man l-Phenyl-2-methyl-         3-halogen-methyl-4-isopropyl-5-pyrazolon        mit          a-Methyl-ss-phenyl-äthylamin    umsetzt.  



  Die Reaktion kann in An- oder Abwesen  heit von Lösungsmitteln erfolgen. Das Pro  dukt soll als Arzneimittel Verwendung fin  den.         1)ie    Reaktion verläuft. wie folgt  
EMI0001.0013     
    <I>Beispiel:</I>    25 Teile     1-Phenyl-2-methyl-3-brommethyl-          4-isopropy1-5-pyrazolon    werden in 50 Teilen  Benzol gelöst. Es werden 22 Teile     a-Methyl-ss-          phenyl-äthylamin    zugegeben. Die Lösung wird  während etwa 15 Minuten unter     Rückfluss    ge  kocht, dann wird das Benzol     abdestilliert    und  der Rückstand mit     Wasser    verrieben.

   Das         Pyrazolon    wird fest und kann nach dem  Trocknen aus     Petroläther    umkristallisiert wer  den; es kristallisiert in feinen weissen Nadeln  vom     Smp.    65 bis 66  C. Es ist in Wasser un  löslich und in den meisten organischen Lö  sungsmitteln löslich. Der     Smp.    seines sauren       nxalates    ist 207 bis 208  C u.     Zers.  



  Process for the manufacture of a new pain reliever drug. The subject of the present patent is a process for the production of a new pain reliever drug, namely 3- [N (ari # iethyl-ss-phenyl) - ethyl - aminomethyl] - 4-isopropyl-norant.ipyrins, which is characterized by that 1-phenyl-2-methyl-3-halo-methyl-4-isopropyl-5-pyrazolone is reacted with a-methyl-ss-phenyl-ethylamine.



  The reaction can take place in the presence or absence of solvents. The product is intended to be used as a medicinal product. 1) the reaction proceeds. as follows
EMI0001.0013
    <I> Example: </I> 25 parts of 1-phenyl-2-methyl-3-bromomethyl-4-isopropy1-5-pyrazolone are dissolved in 50 parts of benzene. 22 parts of a-methyl-ss-phenyl-ethylamine are added. The solution is refluxed for about 15 minutes, then the benzene is distilled off and the residue is triturated with water.

   The pyrazolone becomes solid and can be recrystallized from petroleum ether after drying; it crystallizes in fine white needles with a melting point of 65 to 66 C. It is insoluble in water and soluble in most organic solvents. The m.p. of its acidic nxalates is 207 to 208 C u. Decomp.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von 3-[N(a- Methyl - ss - phenil) - äthyl - aminomethyl ] - 4-iso- propyl-norantipyrin, dadureh gekennzeiehnet, dass man l.-Phenyl-2-methyl-3-halogenmethyl- 4-isopropyl-5-pyrazolon mit a-Methyl-ss-phe- nyl-äthylamin umsetzt. Die neue Verbindung bildet, PATENT CLAIM Process for the production of 3- [N (a-methyl-ss-phenil) -ethyl-aminomethyl] -4-isopropyl-norantipyrine, which is marked that l.-phenyl-2-methyl-3-halomethyl- 4-isopropyl-5-pyrazolone is reacted with a-methyl-ss-phenyl-ethylamine. The new connection forms ein weisses Kristallpulver vom Smp. 65 bis 66 C. Sie ist in Wasser ünlöslieh und in den meisten orga- nisehen Lösungsmitteln löslieh; das saure Oxa- lat schmilzt bei 307 bis 208 C u. Zers. a white crystal powder with a melting point of 65 to 66 C. It is insoluble in water and soluble in most organic solvents; the acidic oxalate melts at 307 to 208 C u. Decomp.
CH285030D 1948-10-08 1948-10-08 Process for the manufacture of a new pain reliever drug. CH285030A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH285030T 1948-10-08
CH275620T 1948-10-08

Publications (1)

Publication Number Publication Date
CH285030A true CH285030A (en) 1952-08-15

Family

ID=25731636

Family Applications (1)

Application Number Title Priority Date Filing Date
CH285030D CH285030A (en) 1948-10-08 1948-10-08 Process for the manufacture of a new pain reliever drug.

Country Status (1)

Country Link
CH (1) CH285030A (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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