FR2473039A1 - Ortho-acetyl:oxy-phenyl-propionic acid - having analgesic and platelet aggregation inhibiting activity - Google Patents

Ortho-acetyl:oxy-phenyl-propionic acid - having analgesic and platelet aggregation inhibiting activity Download PDF

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Publication number
FR2473039A1
FR2473039A1 FR8000349A FR8000349A FR2473039A1 FR 2473039 A1 FR2473039 A1 FR 2473039A1 FR 8000349 A FR8000349 A FR 8000349A FR 8000349 A FR8000349 A FR 8000349A FR 2473039 A1 FR2473039 A1 FR 2473039A1
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France
Prior art keywords
analgesic
platelet aggregation
propionic acid
acetyl
phenyl
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
FR8000349A
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French (fr)
Inventor
Marcel Richard
Jean-Jacques Serrano
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Richard SA Laboratoire M
Original Assignee
Richard SA Laboratoire M
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 Richard SA Laboratoire M filed Critical Richard SA Laboratoire M
Priority to FR8000349A priority Critical patent/FR2473039A1/en
Publication of FR2473039A1 publication Critical patent/FR2473039A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring

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

Abstract

3-o-Acetyloxyphenyl propionic acid (I) is new. Used as analgesic and platelet aggregation inhibitor its toxicity has LD50 of 1540 mg/kg p.o.(mouse). (I) gave 78% and 40% protection to mice in the phenyl benzoquinone and hot plate tests, dosage not stated. In rats and rabbits (I) showed 60% inhibition of A.P. platelet aggregation at 100 mg/kg.

Description

Nouvelle substance utilisable en thérapeutique comme agent anti agrégant plaquettaire et analgésique.New substance usable in therapy as an anti-platelet aggregating agent and analgesic.

L'invention concerne la molécule : acide acétyl-mélilotique C11 H12 04 PM = 208, ou acide acetyl-o-hydroxyphényl-3-propionique de formule développée :

Figure img00010001
The invention relates to the molecule: acetyl-melilotic acid C11 H12 04 PM = 208, or acetyl-o-hydroxyphenyl-3-propionic acid of structural formula:
Figure img00010001

Caractéristiques de cette substance : poudre cristalline blanche point de fusion 47/490C - très peu soluble dans l'eau - soluble dans les solvants organiques.Characteristics of this substance: white crystalline powder melting point 47 / 490C - very slightly soluble in water - soluble in organic solvents.

Caractéristiques analytiques
Analyse pour C11H12O4 (208)
Calculé, % : C 63,46; H 5,77
Trouvé, % % : C 63,81; H 5,02
C 63,83; H 5,03
U.V. (alcool 950) : #max : 262 nm.Analytical characteristics
Analysis for C11H12O4 (208)
Calculated,%: C 63.46; H 5.77
Found,%%: C 63.81; H 5.02
C 63.83; H 5.03
UV (alcohol 950): #max: 262 nm.

max
I.R. (KBr) : 1750 cm-1 (CO acétate) ; 1200 cm-1 (acétate); 1690 cm-1
(acide).max
IR (KBr): 1750 cm-1 (CO acetate); 1200 cm-1 (acetate); 1690 cm-1
(acid).

RMN (D20, NaOD) : acétate : 1,90 ppm (3 H). NMR (D20, NaOD): acetate: 1.90 ppm (3 H).

Rf (CCM, silicagel) (CHC13/MeOH 9/1) = 0,62.Rf (TLC, silica gel) (CHC13 / MeOH 9/1) = 0.62.

Essais toxicologiques : déterminés par voie orale chez la souris mâle par la méthode de Behrens et Karber.Toxicological tests: determined orally in male mice by the method of Behrens and Karber.

DL 50 = 1540 mg/kg
Essais pharmacologiques: activité analgésique - test 9 la phénylbenzoquinone et test à la plaque chauffante sur souris, respectivement 78 et 40% de protection.LD 50 = 1540 mg / kg
Pharmacological tests: analgesic activity - test 9 phenylbenzoquinone and hot plate test on mice, 78 and 40% protection respectively.

Activité anti-agrégante plaquettaire (sur rats et lapins) agrégation provoquée par agent agrégant 1'A D P - inhibition de 60% à 100 mg/kg. Anti-aggregation activity in platelets (on rats and rabbits) aggregation caused by an aggregating agent A D P - 60% inhibition at 100 mg / kg.

Indications thérapeutiques majeures
Traitement préventif et curatif des états pathologiques circulatoires. Prévention et traitement des thrombogeavascu- laires.Major therapeutic indications
Preventive and curative treatment of circulatory pathological conditions. Prevention and treatment of pulmonary thrombosis.

Traitement des manifestations douloureuses,
Présentation :
Administration interne : ampoules injectables et buvables, gélules, comprimés, poudres, granulés, suppositoires (substance pure ou associée à d'autres éléments médicamentaux).Treatment of painful manifestations,
Presentation :
Internal administration: injectable and drinkable ampoules, capsules, tablets, powders, granules, suppositories (pure substance or combined with other medicinal elements).

Administration externe crème, pommådes, solutés, émulsion (substance pure ou associée à d'autres éléments médicamenteux). External administration cream, ointments, solutes, emulsion (pure substance or combined with other medicinal elements).

Claims (3)

REVENDICATIONS 1 - Produit chimique nouveau, caractérisé en ce qu'il a pour formule : 1 - New chemical product, characterized in that it has the formula:
Figure img00030001
Figure img00030001
 2 - Médicament à usage vétérinaire et humain, caractérisé en ce qu'il comporte, comme produit actif, le produit chimique nouveau selon la revendication 1. 2 - Medicinal product for veterinary and human use, characterized in that it comprises, as active product, the new chemical product according to claim 1. 3 - Médicament selon la revendication 2, caractérisé en ce qu'il est conditionné pour entre utilisé par voie orale, parentérale, rectale ou locale externe.  3 - Medication according to claim 2, characterized in that it is packaged for between used orally, parenterally, rectally or locally externally.
FR8000349A 1980-01-07 1980-01-07 Ortho-acetyl:oxy-phenyl-propionic acid - having analgesic and platelet aggregation inhibiting activity Withdrawn FR2473039A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR8000349A FR2473039A1 (en) 1980-01-07 1980-01-07 Ortho-acetyl:oxy-phenyl-propionic acid - having analgesic and platelet aggregation inhibiting activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8000349A FR2473039A1 (en) 1980-01-07 1980-01-07 Ortho-acetyl:oxy-phenyl-propionic acid - having analgesic and platelet aggregation inhibiting activity

Publications (1)

Publication Number Publication Date
FR2473039A1 true FR2473039A1 (en) 1981-07-10

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Family Applications (1)

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FR8000349A Withdrawn FR2473039A1 (en) 1980-01-07 1980-01-07 Ortho-acetyl:oxy-phenyl-propionic acid - having analgesic and platelet aggregation inhibiting activity

Country Status (1)

Country Link
FR (1) FR2473039A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0153538A1 (en) * 1984-02-23 1985-09-04 Laboratoire Marcel Richard Société anonyme dite Derivatives of melilotic acid, and medicaments containing them

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2995598A (en) * 1958-02-27 1961-08-08 Smith Miller & Patch Inc Beta(ortho-acetoxyphenyl)propionic acid and salts thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2995598A (en) * 1958-02-27 1961-08-08 Smith Miller & Patch Inc Beta(ortho-acetoxyphenyl)propionic acid and salts thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0153538A1 (en) * 1984-02-23 1985-09-04 Laboratoire Marcel Richard Société anonyme dite Derivatives of melilotic acid, and medicaments containing them

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