LU81816A1 - NOVEL SALT OF ACETYLSALICYLIC ACID, PREPARATION METHOD THEREOF AND THERAPEUTIC APPLICATIONS - Google Patents
NOVEL SALT OF ACETYLSALICYLIC ACID, PREPARATION METHOD THEREOF AND THERAPEUTIC APPLICATIONS Download PDFInfo
- Publication number
- LU81816A1 LU81816A1 LU81816A LU81816A LU81816A1 LU 81816 A1 LU81816 A1 LU 81816A1 LU 81816 A LU81816 A LU 81816A LU 81816 A LU81816 A LU 81816A LU 81816 A1 LU81816 A1 LU 81816A1
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- acetylsalicylic acid
- preparation
- therapeutic applications
- novel salt
- salt
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- 150000003839 salts Chemical class 0.000 title description 9
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 229940068372 acetyl salicylate Drugs 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003907 antipyretic analgesic agent Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 9
- 241000700159 Rattus Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- UYDSGXAKLVZWIJ-UHFFFAOYSA-N ethyl 2-acetyloxybenzoate Chemical compound CCOC(=O)C1=CC=CC=C1OC(C)=O UYDSGXAKLVZWIJ-UHFFFAOYSA-N 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- -1 amino acid salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000002977 hyperthermial effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
- C07C65/10—Salicylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
v La présente invention est relative à un nouveau sel de l'acide acétylsalicylique présentant l'avantage d'être hydrosoluble, en donnant des solutions non acides.The present invention relates to a new salt of acetylsalicylic acid having the advantage of being water-soluble, giving non-acidic solutions.
On sait que l'acide acétylsalicylique dont les proprié -5 tés pharmacologiques sont bien connues et mises à profit en thérapeutique humaine, présente l'inconvénient d'être peu soluble dans l'eau et acide.It is known that acetylsalicylic acid, the pharmacological properties of which are well known and used in human therapy, has the drawback of being sparingly soluble in water and acid.
rr
Ceci rend son administration par voie intra-veineuse difficile, sinon impossible.This makes its administration intravenously difficult, if not impossible.
Pour pallier cet inconvénient il a été proposé divers 10 composés solubles dérivant de l'acide acétylsalicylique, la plupart étant des sels d'amino-acides basiques. L'invention se propose d'enrichir l'arsenal thérapeutique formé par ces composés solubles à l'aide d'un sel d'acide acétylsalicylique' d ' un J type différent.To overcome this drawback, various soluble compounds have been proposed derived from acetylsalicylic acid, most of which are basic amino acid salts. The invention proposes to enrich the therapeutic arsenal formed by these soluble compounds using a salt of acetylsalicylic acid 'of a different type.
Elle a ainsi pour objet l'acétylsalicylate de 15 2-(terbutylamino) éthanol.It thus relates to acetylsalicylate of 2- (terbutylamino) ethanol.
Ce sel répond à la formule.This salt meets the formula.
acooH. (ch3)3-c-nh-ch2-ch2ohacooH. (ch3) 3-c-nh-ch2-ch2oh
O.-CO-CHO.-CO-CH
vv
Il résulte ainsi de la combinaison d'une mole d'acide 20 acétylsalicylique et d'une mole de 2-(terbutylamino) éthanol et présente les caractéristiques physicochimiques suivantes.It thus results from the combination of one mole of acetylsalicylic acid and one mole of 2- (terbutylamino) ethanol and has the following physicochemical characteristics.
- poids moléculaire : 297, 357 ; - point de fusion (tube) : 123-125°C ; - point de fusion(instantanée) : 140-142°C.- molecular weight: 297, 357; - melting point (tube): 123-125 ° C; - melting point (instantaneous): 140-142 ° C.
25 Il est soluble dans l'eau. Le pH de la solution aqueuse à 5 p. 100 est d'environ 5, 9, c'est-à-dire voisin de la neutralité.25 It is soluble in water. The pH of the aqueous solution at 5 p. 100 is about 5, 9, that is to say close to neutrality.
Ce nouveau sel est doué d'une activité analgésique, antipyrétique et anti-inflammatoire.This new salt is endowed with analgesic, antipyretic and anti-inflammatory activity.
On peut lé préparer en faisant réagir l'acide acétylsa-30 licylique sur le 2-(terbutylamino) éthanol. Avantageusement les réactifs Μ 2 ' sont mis en oeuvre en des proportions sensiblement stoechiométriques, chacun d'eux étant de préférence dissous dans un solvant organique approprié, tel l'éther éthylique. La réaction se déroule de manière satisfaisante à la température ambiante, en sorte qu'il n'y a aucun 5 intérêt à s'en écarter dans la pratique.It can be prepared by reacting acetylsa-licylic acid on 2- (terbutylamino) ethanol. Advantageously, the reagents Μ 2 ′ are used in substantially stoichiometric proportions, each of them preferably being dissolved in an appropriate organic solvent, such as ethyl ether. The reaction proceeds satisfactorily at room temperature, so there is no point in deviating from it in practice.
L'exemple suivant illustre la préparation de l'acétylsalicylate de 2-(terbutyiamino) éthanol.The following example illustrates the preparation of 2- (terbutyiamino) ethanol acetylsalicylate.
Exemple :Example:
Dans 150 ml d'éther éthylique on dissout 5, 4 g 10 d'acide acétylsalicylique (0, 03 mole). A cette solution, on ajoute une solution de 3, 5 g de 2-(ter butyl amino) éthanol (0, 03 mole) dans 40 ml d'éther éthylique.5.4 g of acetylsalicylic acid (0.03 mole) are dissolved in 150 ml of ethyl ether. To this solution is added a solution of 3.5 g of 2- (ter butyl amino) ethanol (0.03 mole) in 40 ml of ethyl ether.
Il apparaît immédiatement un précipité. On maintient sous agitation 15 minutes, puis on essore, lave à l'éther 15 éthylique et sèche jusqu'à poids constant sous vide en présence d'anhydride phosphorique.A precipitate immediately appears. Stirring is continued for 15 minutes, then it is filtered, washed with ethyl ether and dried to constant weight under vacuum in the presence of phosphoric anhydride.
On obtient 8, 5 g d'acétylsalicylate de 2-(terbutylamino) éthanol présentant les caractéristiques physicochimiques énoncées plus haut.8.5 g of 2- (terbutylamino) ethanol acetylsalicylate are obtained, having the physicochemical characteristics stated above.
20 Microanalyse - · % théorique % trouvé C 60,59 60,53 H 7,80 7,78 N 4,71 4,61 25 O 26, 9020 Microanalysis - ·% theoretical% found C 60.59 60.53 H 7.80 7.78 N 4.71 4.61 25 O 26, 90
On donnera ci-après les résultats des études toxicologiques et pharmacologiques mettant en évidence les activités antipyrétique, analgésique et anti-inflammatoire du composé qui le rendent précieux en thérapeutique.The results of the toxicological and pharmacological studies showing the antipyretic, analgesic and anti-inflammatory activities of the compound which make it valuable in therapy will be given below.
30 Ces résultats sont résumés dans le tableau qui suit et comparés dans ce dernier avec ceux obtenus avec l'acide acétylsalicylique. Les deux composés sont d'activités voisines, mais l'acétylsalicylate de 2-(terbutylaminoéthanol) selon l'invention présente l'avantage d'être pratiquement neutre et hydrosoluble. De ce fait , son administration par 35 voie intraveineuse n'offre aucun problème. Les tests mentionnés dans le > .These results are summarized in the following table and compared therewith with those obtained with acetylsalicylic acid. The two compounds are of similar activity, but the acetylsalicylate of 2- (terbutylaminoethanol) according to the invention has the advantage of being practically neutral and water-soluble. Therefore, its administration intravenously does not present any problem. The tests mentioned in>.
3 ’ tableau ont été effectués comme suit : -La toxicité aiguë a été déterminée chez la souris par voie orale et par voie intraveineuse.3 'table were carried out as follows: -Acute toxicity was determined in mice orally and intravenously.
-L'activité antipyrétique a été déterminée sur des rats rendus 5 . hyperthermiques par injection sous cutanée de levure de bière à la dose de 4 g/kg, selon la technique d'Adams, Hepburns et Nicholson (J. Pharm, Pharmacol. 20, 305, 312, 1968),-The antipyretic activity was determined on rats rendered 5. hyperthermic by subcutaneous injection of brewer's yeast at a dose of 4 g / kg, according to the technique of Adams, Hepburns and Nicholson (J. Pharm, Pharmacol. 20, 305, 312, 1968),
Les traitements sont administrés par voie intragas-trique 17 heures après l’injection de levure.Treatments are administered intragastrically 17 hours after the yeast injection.
10 On compare l’évolution de la température rectale des rats en fonction du temps des témoins absolus, des témoins "levure de bière" et des animaux traités.10 The evolution of the rectal temperature of the rats is compared as a function of the time of the absolute controls, the "brewer's yeast" controls and the animals treated.
-L’activité analgésique a été déterminée par une des techniques classiques d'étude de cette activité, le "writhing test", selon Linee et Gouret 15 (J. Pharmaco. 4 , 3, p. 512 (1972).-The analgesic activity was determined by one of the classical techniques for studying this activity, the "writhing test", according to Linee and Gouret 15 (J. Pharmaco. 4, 3, p. 512 (1972).
Des souris à jeun depuis 16 heures, reçoivent par voie intrapéritonéale 0, 25 ml/20 g d'une solution hydro-alcoolique à 4 % de phénylbenzoquinone à 0, 2 °/°°, On compte les étirement s-torsions de chaque souris de la 5e à la 10e minute, les animaux étant groupés par 4 20 et les produits à essayer étant administrés 30 minutes avant l'injection de phénylbenzoquinone.Fasting mice for 16 hours, receive 0.25 ml / 20 g of a 4% phenylbenzoquinone hydroalcoholic solution at 0.2 ° / 0 ° intraperitoneally. The s-twists of each mouse are counted from the 5th to the 10th minute, the animals being grouped by 4 20 and the products to be tested being administered 30 minutes before the injection of phenylbenzoquinone.
- L‘activité anti-inflammatoire a été déterminée par voie orale en observant le pourcentage d’inhibition de l’oedème à la carrageenine du . rat au bout de 3 heures.- The anti-inflammatory activity was determined orally by observing the percentage of inhibition of carrageenin edema. rat after 3 hours.
25 L’oedème de la patte arrière du rat est provoqué par injection sous-apcnévrotique de 0, 05 ml d’une solution de carragee-nine à 2 % dans le sérum physiologique.25 The rat's hind paw edema is caused by sub-apneurotic injection of 0.05 ml of a 2% carrageenan solution in physiological saline.
Dans le tableau ci-dessous les résultats en ce qui concerne le sel selon l’invention sont exprimés en équivalent moléculaire 30 d’acide acétylsalicylique (acide) et en sel (sel).In the table below, the results with regard to the salt according to the invention are expressed in molecular equivalent of acetylsalicylic acid (acid) and in salt (salt).
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n ffl r~ V ü H 1 1 ü ΐ Φ ! Il « « H < <* <3^0 :| H . n H · . . Il « u « n Λ 5n ffl r ~ V ü H 1 1 ü ΐ Φ! It "" H <<* <3 ^ 0: | H. n H ·. . It "u" n Λ 5
Il résulte de ce qui précède que l'acétylsalicylate de ’ 2-(terbutylamino) éthanol est utilisable avantageusement en thérapeutique humaine, notamment pour le traitement des migraines et des douleurs, des états fiévreux et des états inflammatoires.It follows from the above that ’2- (terbutylamino) ethanol acetylsalicylate can be advantageously used in human therapy, in particular for the treatment of migraines and pain, feverish and inflammatory states.
5 Dans ces indications, le médicament comportant ce sel, à titre de principe actif, peut être formulé en doses unitaires avec les véhicules et excipients usuels. C'est ainsi que ce médicament peut prendre la forme de comprimés à 500 mg exprimés en acide acétylsalicy- ’ lique ou de poudre à solubiliser pour former avec un solvant approprié, tel-10 le de l'eau distillée apyrogène, une solution pour injection intraveineuse.In these indications, the medicament comprising this salt, as active ingredient, can be formulated in unit doses with the usual vehicles and excipients. Thus, this medicament can take the form of 500 mg tablets expressed as acetylsalicylic acid or powder to be dissolved to form with a suitable solvent, such as pyrogen-free distilled water, a solution for injection. intravenous.
* contenant de 0, 5 à 2 g de principe actif exprimé en acide acétylsalicylique par litre, la posologie journalière étant de 2 à 4 grammes.* containing 0.5 to 2 g of active ingredient expressed as acetylsalicylic acid per liter, the daily dosage being 2 to 4 grams.
> »> »
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7831588 | 1978-11-08 | ||
| FR7831588A FR2440935A1 (en) | 1978-11-08 | 1978-11-08 | NOVEL SALT OF ACETYLSALICYLIC ACID, PREPARATION METHOD THEREOF AND THERAPEUTIC APPLICATIONS THEREOF |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU81816A1 true LU81816A1 (en) | 1980-01-25 |
Family
ID=9214610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU81816A LU81816A1 (en) | 1978-11-08 | 1979-10-24 | NOVEL SALT OF ACETYLSALICYLIC ACID, PREPARATION METHOD THEREOF AND THERAPEUTIC APPLICATIONS |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5566549A (en) |
| AU (1) | AU527562B2 (en) |
| BE (1) | BE879887A (en) |
| DE (1) | DE2944485A1 (en) |
| DK (1) | DK464479A (en) |
| ES (1) | ES485596A1 (en) |
| FI (1) | FI793423A (en) |
| FR (1) | FR2440935A1 (en) |
| GB (1) | GB2034711B (en) |
| IT (1) | IT7950752A0 (en) |
| LU (1) | LU81816A1 (en) |
| NL (1) | NL7908079A (en) |
| NO (1) | NO793581L (en) |
| PL (1) | PL219468A1 (en) |
| SE (1) | SE7908756L (en) |
| ZA (1) | ZA795996B (en) |
-
1978
- 1978-11-08 FR FR7831588A patent/FR2440935A1/en active Granted
-
1979
- 1979-10-23 SE SE7908756A patent/SE7908756L/en not_active Application Discontinuation
- 1979-10-24 LU LU81816A patent/LU81816A1/en unknown
- 1979-10-30 GB GB7937546A patent/GB2034711B/en not_active Expired
- 1979-10-31 ES ES485596A patent/ES485596A1/en not_active Expired
- 1979-11-01 FI FI793423A patent/FI793423A/en not_active Application Discontinuation
- 1979-11-02 DK DK464479A patent/DK464479A/en not_active Application Discontinuation
- 1979-11-03 DE DE19792944485 patent/DE2944485A1/en not_active Withdrawn
- 1979-11-05 NL NL7908079A patent/NL7908079A/en not_active Application Discontinuation
- 1979-11-06 IT IT7950752A patent/IT7950752A0/en unknown
- 1979-11-06 NO NO793581A patent/NO793581L/en unknown
- 1979-11-07 ZA ZA00795996A patent/ZA795996B/en unknown
- 1979-11-07 JP JP14427479A patent/JPS5566549A/en active Pending
- 1979-11-07 BE BE0/198017A patent/BE879887A/en unknown
- 1979-11-07 PL PL21946879A patent/PL219468A1/xx unknown
- 1979-11-08 AU AU52639/79A patent/AU527562B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DK464479A (en) | 1980-05-09 |
| ZA795996B (en) | 1980-10-29 |
| SE7908756L (en) | 1980-05-09 |
| GB2034711B (en) | 1982-10-27 |
| NO793581L (en) | 1980-05-09 |
| NL7908079A (en) | 1980-05-12 |
| AU5263979A (en) | 1980-05-15 |
| FI793423A (en) | 1980-05-09 |
| DE2944485A1 (en) | 1980-05-29 |
| AU527562B2 (en) | 1983-03-10 |
| ES485596A1 (en) | 1980-05-16 |
| FR2440935B1 (en) | 1981-04-17 |
| GB2034711A (en) | 1980-06-11 |
| JPS5566549A (en) | 1980-05-20 |
| FR2440935A1 (en) | 1980-06-06 |
| IT7950752A0 (en) | 1979-11-06 |
| PL219468A1 (en) | 1980-07-14 |
| BE879887A (en) | 1980-05-07 |
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