BE897217A - NEW ANTI-INFLAMMATORY, ANALGESIC AND ANTIPYRETIC DRUG BASED ON (P-CHLOROBENZOYL-1, METHYL- 2- Methoxy-5) Indole-3 P-Acetamidophenol Acetate - Google Patents

NEW ANTI-INFLAMMATORY, ANALGESIC AND ANTIPYRETIC DRUG BASED ON (P-CHLOROBENZOYL-1, METHYL- 2- Methoxy-5) Indole-3 P-Acetamidophenol Acetate Download PDF

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Publication number
BE897217A
BE897217A BE2/60151A BE2060151A BE897217A BE 897217 A BE897217 A BE 897217A BE 2/60151 A BE2/60151 A BE 2/60151A BE 2060151 A BE2060151 A BE 2060151A BE 897217 A BE897217 A BE 897217A
Authority
BE
Belgium
Prior art keywords
acetamidophenol
chlorobenzoyl
indole
methoxy
acetate
Prior art date
Application number
BE2/60151A
Other languages
French (fr)
Original Assignee
M Richard S A Lab
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 M Richard S A Lab filed Critical M Richard S A Lab
Publication of BE897217A publication Critical patent/BE897217A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof

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

Description

       

   <Desc/Clms Page number 1> 
 



    MEMOIRE DESCRIPTIF    déposé à l'appui d'une demande de
BREVET BELGE formulée par Société Anonyme dite : LABORATOIRE M. RICHARD S. A. pour "Nouveau médicament anti-inflammatoire, analgésique et antipyrétique à base de (p-chlorobenzoyl-1, méthyl-2   méthoxy-5)-   indole-3 acétate de   p-acétamidophénol"   comme
BREVET D'INVENTION. 



  A toute fin utile, la Demanderesse déclare l'existence de la demande de brevet déposée en France le 29 mars 1976 sous le   n  76 09   107, en son nom, non encore accordée à ce jour. 

 <Desc/Clms Page number 2> 

 "Nouveau médicament anti-inflammatoire, analgésique et antipyrétique à base de (p-chlorobenzoyl-1, méthyl-2   méthoxy-5)-   indole-3 acétate de p-acétamidophénol" Dénomination chimique du produit   (p-chlorobenzoyl-l   méthyl-2   méthoxy-5)-indole-3   acétate de p-acétamidophénol. 



  Formule développée 
 EMI2.1 
 
 EMI2.2 
 Formule brute CHNCl Caractères organoleptiques Cristaux blancs solubles dans les solvants organiques aromatiques et hydroxylés, solubles dans l'acétone, peu solubles dans l'éther, insolubles dans l'eau. 



  Point de fusion (capillaire non corrigé)   184-186'après   cristallisation dans un mélange acétone/éther. 

 <Desc/Clms Page number 3> 

 Analyse centésimale 
 EMI3.1 
 
<tb> 
<tb> Théorie <SEP> Résultats
<tb> C <SEP> 66,0 <SEP> 65, <SEP> 44-65, <SEP> 47
<tb> H <SEP> 4,68 <SEP> 4, <SEP> 85-4, <SEP> 68
<tb> N <SEP> 5,70 <SEP> 5, <SEP> 88-5, <SEP> 60
<tb> 
 Toxicité Toxicité   aigue   DL 50 chez la souris 4 g par Kg. 



  Propriétés pharmacologiques Activité anti-inflammatoire : Test au kaolin Le produit à tester a été administré à la dose de 100 mg/kg Pourcentage d'inhibition de l'enflure au bout de 2 heures 29 %
3 heures 60%
4 heures 55 %
5 heures 55 %
6 heures 60 %
Oedème à la carraghénine Produit administré per os à la dose de 100 mg/kg Pourcentage d'inhibition
Ière heure 50 %
2ème heure 40 %
3ème heure 65 %
4ème heure 61 % Activité analgésique :

   Test de siegmund 100 mg/kg per os Pourcentage global d'inhibition 93 % Activité antipyrétique : 100 mg/kg per os chez le lapin Le pourcentage de baisse de température débute vers
3 h 30 après l'ingestion à un taux de 13 % après 4 h 37 %
5 h 59 %
6 h 82 %
7 h 100 % 

 <Desc/Clms Page number 4> 

 Essai chimique du médicament Les tests cliniques effectués avec (p-chlorobenzoyl-l méthyl- 2   méthoxy-5)-indole-3   acétate de p-acétamidophénol ont confirmé l'activité anti-inflammatoire de cette molécule. Sa tolérance clinique s'est révélée particulièrement intéressante. Son action analgésique a pu être objectivée par des essais en double insu, l'activité antipyrétique a également été confirmée. 



  Les essais ont porté sur des posologies variants de 100 mg à 2 g par jour en plusieurs reprises. 



  Forme galénique : Ce médicament pourra être présenté soit à l'état pur, soit en association avec d'autres composants. 



  Usage interne : comprimés, dragées, gélules, capsules de 0,01 à 1 g. 



  Suspensions et solutés buvables et injectables, poudre, granulés, sirops en toutes concentrations. 



  Usage externe : poudre, suspension, solution, crème, pommade, émulsion.



   <Desc / Clms Page number 1>
 



    DESCRIPTIVE MEMORY filed in support of a request for
BELGIAN PATENT formulated by Société Anonyme known as: LABORATOIRE M. RICHARD SA for "New anti-inflammatory, analgesic and antipyretic drug based on (p-chlorobenzoyl-1, 2-methyl-5-methoxy-5) - indole-3 acetate of p-acetamidophenol "   as
PATENT.



  For all practical purposes, the Applicant declares the existence of the patent application filed in France on March 29, 1976 under No. 76 09 107, in its name, not yet granted to date.

 <Desc / Clms Page number 2>

 "New anti-inflammatory, analgesic and antipyretic drug based on (p-chlorobenzoyl-1, 2-methyl-5-methoxy) - indole-3 p-acetamidophenol acetate" Chemical name of the product (p-chlorobenzoyl-1 methyl-2 methoxy-5) -indole-3 p-acetamidophenol acetate.



  Expanded formula
 EMI2.1
 
 EMI2.2
 Raw formula CHNCl Organoleptic characteristics White crystals soluble in aromatic and hydroxylated organic solvents, soluble in acetone, sparingly soluble in ether, insoluble in water.



  Melting point (capillary not corrected) 184-186 'after crystallization from an acetone / ether mixture.

 <Desc / Clms Page number 3>

 Centesimal analysis
 EMI3.1
 
<tb>
<tb> Theory <SEP> Results
<tb> C <SEP> 66.0 <SEP> 65, <SEP> 44-65, <SEP> 47
<tb> H <SEP> 4.68 <SEP> 4, <SEP> 85-4, <SEP> 68
<tb> N <SEP> 5.70 <SEP> 5, <SEP> 88-5, <SEP> 60
<tb>
 Toxicity Acute toxicity LD 50 in mice 4 g per Kg.



  Pharmacological properties Anti-inflammatory activity: Kaolin test The product to be tested was administered at a dose of 100 mg / kg Percentage inhibition of swelling after 2 hours 29%
3 hours 60%
4 hours 55%
5 hours 55%
6 hours 60%
Carrageenan edema Product administered orally at a dose of 100 mg / kg Percentage of inhibition
1st hour 50%
2nd hour 40%
3rd hour 65%
4th hour 61% Analgesic activity:

   Siegmund test 100 mg / kg per os Overall inhibition percentage 93% Antipyretic activity: 100 mg / kg per os in rabbits The percentage drop in temperature begins around
3 h 30 after ingestion at a rate of 13% after 4 h 37%
5 h 59%
6 h 82%
7 h 100%

 <Desc / Clms Page number 4>

 Chemical test of the drug Clinical tests carried out with (p-chlorobenzoyl-1 methyl-2-methoxy-5) -indole-3 p-acetamidophenol acetate confirmed the anti-inflammatory activity of this molecule. Its clinical tolerance has been particularly interesting. Its analgesic action could be objectified by double-blind tests, the antipyretic activity was also confirmed.



  The trials focused on varying dosages of 100 mg to 2 g per day on several occasions.



  Dosage form: This medicine may be presented either in its pure state or in combination with other components.



  Internal use: tablets, dragees, capsules, capsules from 0.01 to 1 g.



  Oral and injectable suspensions and solutions, powder, granules, syrups in all concentrations.



  External use: powder, suspension, solution, cream, ointment, emulsion.

Claims (3)

Revendications.Claims. 1.-Composition pharmaceutique solide ou liquide utilisable en médecine humaine ou vétérinaire, pour traiter par voie orale et rectale, ou par injection intramusculaire ou intraveineuse, ou par voie locale, les syndromes douloureux d'origine inflammatoire associés ou non à des poussées fébriles, caractérisée en ce qu'elle contient comme principe actif le (p-chlorobenzoyl-l méthyl-2 méthoxy-5)-indole-3 acétate de p-acétamidophénol, seul ou associé à d'autres principes actifs. 1.-Solid or liquid pharmaceutical composition usable in human or veterinary medicine, to treat by oral and rectal route, or by intramuscular or intravenous injection, or by local route, painful syndromes of inflammatory origin associated or not with febrile attacks, characterized in that it contains as active ingredient (p-chlorobenzoyl-1 methyl-2-methoxy-5) -indole-3 acetate of p-acetamidophenol, alone or combined with other active ingredients. 2.-Composition selon la revendication 1, caractérisée en ce qu'elle est présentée sous une forme permettant l'administration de 0,1 mg à 500 mg/kg de produit actif par jour. EMI5.1 2. Composition according to claim 1, characterized in that it is presented in a form allowing the administration of 0.1 mg to 500 mg / kg of active product per day.  EMI5.1   3.-Nouveau médicament anti-inflammatoire, analgésique et anti-pyrétique à base de (p-chlorobenzoyl-l méthyl-2 méthoxy- 5)-indole-3 acétate de p-acétamidophénol, substantiellement tel que décrit précédemment. 3.-New anti-inflammatory, analgesic and anti-pyretic drug based on (p-chlorobenzoyl-1 methyl-2 methoxy- 5) -indole-3 acetate p-acetamidophenol, substantially as described above.
BE2/60151A 1976-03-29 1983-07-05 NEW ANTI-INFLAMMATORY, ANALGESIC AND ANTIPYRETIC DRUG BASED ON (P-CHLOROBENZOYL-1, METHYL- 2- Methoxy-5) Indole-3 P-Acetamidophenol Acetate BE897217A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7609107A FR2358145A1 (en) 1976-03-29 1976-03-29 Pharmaceutical compsns. contg. para-acetamido-phenol deriv. - i.e. the (1)-para-chlorobenzoyl-(2)-methyl-(5)-methoxy-indole-(3)-acetate, having antiinflammatory, analgesic, and antipyretic activity

Publications (1)

Publication Number Publication Date
BE897217A true BE897217A (en) 1983-11-03

Family

ID=9171097

Family Applications (1)

Application Number Title Priority Date Filing Date
BE2/60151A BE897217A (en) 1976-03-29 1983-07-05 NEW ANTI-INFLAMMATORY, ANALGESIC AND ANTIPYRETIC DRUG BASED ON (P-CHLOROBENZOYL-1, METHYL- 2- Methoxy-5) Indole-3 P-Acetamidophenol Acetate

Country Status (2)

Country Link
BE (1) BE897217A (en)
FR (1) FR2358145A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57203060A (en) * 1981-06-05 1982-12-13 Kowa Co Piperazine derivative
ES2270634T3 (en) 1999-01-07 2007-04-01 Vanderbilt University CONVERSION OF COX-INHIBITION COMPOUNDS THAT ARE NOT SELECTIVE COH-2 INHIBITORS IN DERIVATIVES THAT ARE SELECTED COX-2 INHIBITORS.
FR2835433B1 (en) * 2002-02-01 2006-02-17 Richard Lab M USE OF 1- (4-CHLOROBENZOYL) -5-METHHOXY-2-METHYL-1H-INDOLE-3ACETIC 4- (ACETYLAMINO) PHENYL ESTER FOR THE PRODUCTION OF A MEDICAMENT FOR INHIBITING COX2 EXCLUSIVELY

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1544673A (en) * 1967-05-26 1968-11-08 Indolylacetylsalicylic esters

Also Published As

Publication number Publication date
FR2358145B1 (en) 1978-12-29
FR2358145A1 (en) 1978-02-10

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