NO793581L - PROCEDURE FOR PREPARING A NEW SALT OF ACETYLSALICYLIC ACID - Google Patents
PROCEDURE FOR PREPARING A NEW SALT OF ACETYLSALICYLIC ACIDInfo
- Publication number
- NO793581L NO793581L NO793581A NO793581A NO793581L NO 793581 L NO793581 L NO 793581L NO 793581 A NO793581 A NO 793581A NO 793581 A NO793581 A NO 793581A NO 793581 L NO793581 L NO 793581L
- Authority
- NO
- Norway
- Prior art keywords
- acetylsalicylic acid
- preparing
- procedure
- tert
- ethanol
- Prior art date
Links
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 229960001138 acetylsalicylic acid Drugs 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 title abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000006309 butyl amino group Chemical group 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- UYDSGXAKLVZWIJ-UHFFFAOYSA-N ethyl 2-acetyloxybenzoate Chemical compound CCOC(=O)C1=CC=CC=C1OC(C)=O UYDSGXAKLVZWIJ-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 229940068372 acetyl salicylate Drugs 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- 241000699670 Mus sp. Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 amino acid salts Chemical class 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007935 neutral effect 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
- 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 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000002977 hyperthermial effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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)
Abstract
"Fremgangsmåte for fremstilling av et nytt salt av acetylsalicylsyre""Process for the preparation of a new salt of acetylsalicylic acid"
Description
Foreliggende oppfinnelse vedrorer en fremgangsmåte for fremstilling av 2-: (bert. butylairuno)<etanol-acetylsalicylat, og det særegne ved fremgangsmåten i henhold til oppfinnelsen er at acetylsalicylsyre omsettes med 2- (tertbutylaminoetanol. The present invention relates to a method for the production of 2-: (bert.butylairuno)<ethanol-acetylsalicylate, and the peculiarity of the method according to the invention is that acetylsalicylic acid is reacted with 2-(tert-butylaminoethanol.
Det nye acetylsalcylsyresalt har den fordel at det er vann-opploselig samtidig med at det gir ikke-sure opplosninger. The new acetylsalcylic acid salt has the advantage that it is water-soluble at the same time as it gives non-acidic solutions.
Det er kjent at acetylsalicylsyre/som har velkjente farmakologiske egenskaper som fordelaktig anvendes for humanterapeutiske formål, har den ulempe at den er dårlig vannloselig og dens opplosninger reagerer surt. Dette gjor intravenos tilforsel vanskelig eller langt på vei umulig. It is known that acetylsalicylic acid/which has well-known pharmacological properties which are advantageously used for human therapeutic purposes, has the disadvantage that it is poorly water-soluble and its solutions react acidly. This makes intravenous administration difficult or even impossible.
For å overvinne denne ulempe Ælar en lang rekke opploselige forbindelser avledet fra acetylsalicylsyre blitt foreslått, hvorav de fleste er basiske aminosyresalter. Den foreliggende oppfinnelse tar sikte på å utvide det terapeutiske området som utgjores av slike opploselige forbindelser, ved hjelp av et acetylsalicylsyresalt av en ny type. To overcome this drawback, a wide variety of soluble compounds derived from acetylsalicylic acid have been proposed, most of which are basic amino acid salts. The present invention aims to expand the therapeutic range of such soluble compounds by means of a new type of acetylsalicylic acid salt.
Det salt som fremstilles ved fremgangsmåten i henhold til oppfinnelsen har formelen The salt produced by the method according to the invention has the formula
Og skriver seg således fra kombinasjonen av et mol acetylsalicylsyre og et mol 2- (tert.butylamino)etanol og fremviser folgende fysikalskkjemiske egenskaper. And is thus written from the combination of one mole of acetylsalicylic acid and one mole of 2-(tert.butylamino)ethanol and exhibits the following physicochemical properties.
- molekylvekt: 297.357- molecular weight: 297,357
- smeltepunkt (ror): 123—125°C- melting point (rudder): 123—125°C
- smeltepunkt (oyeblikkelig): 140-142°C- melting point (instantaneous): 140-142°C
Saltet er som nevnt vannopplbselig og pH i en 5% vandig losning er omtrent 5,9, dvs. nesten nbytral pH. As mentioned, the salt is water-soluble and the pH in a 5% aqueous solution is approximately 5.9, i.e. almost neutral pH.
Dette nye salt har en ahalgetisk, antipyretisk og anti-inflamatorisk virkning. This new salt has an analgesic, antipyretic and anti-inflammatory effect.
Ved reaksjonen anvendes reagensene fordelaktig i omtrent stokiometriske mengder, idet hvert av dem foretrukket er opplost i et passende organisk losningsmiddel, som f.eks. etyleter. Reaksjonen foregår tilfredsstillende ved rom-temperatur, slik at det ikke er noen praktisk fordel ved å arbeide ved andre temperaturer. In the reaction, the reagents are advantageously used in roughly stoichiometric amounts, each of them preferably being dissolved in a suitable organic solvent, such as e.g. ethyl ethers. The reaction takes place satisfactorily at room temperature, so that there is no practical advantage in working at other temperatures.
Det folgende éksempel illustrerer fremstillingen av 2-(tert. butylamino)etanol acetylsalicylat. The following example illustrates the production of 2-(tert.butylamino)ethanol acetylsalicylate.
EksempelExample
Acetylsalicylsyre (5,4 g, 0,03 mol) opploses i etyleterrAcetylsalicylic acid (5.4 g, 0.03 mol) is dissolved in ethyl ether
(150 ml) og til denne losning tilsettes en lbsning av 2-(tert.butylamino)etanol (3,5 g, 0,03 mol) i 40 ml etyleter. (150 ml) and to this solution is added a solution of 2-(tert.butylamino)ethanol (3.5 g, 0.03 mol) in 40 ml of ethyl ether.
Det dannes umiddelbart en utfelling. Reaksjonsblandingen omrores i 15 minutter hvoretter den avsuges på filter, A precipitate is immediately formed. The reaction mixture is stirred for 15 minutes, after which it is filtered off with suction,
vaskes med etyleter og tbrkes til konstant vekt under vakuum,washed with ethyl ether and dried to constant weight under vacuum,
i nærvær av fosforsyre anhydrid, til å gi 8,5 g 2-(tert.butyl-amino )etanol-acetylsalicylat som har de ovennevnte fysikalskkjemiske egenskaper. in the presence of phosphoric anhydride, to give 8.5 g of 2-(tert.butyl-amino)ethanol-acetylsalicylate which has the above-mentioned physicochemical properties.
Resultatene av toksdkologiske og farmakologiske undersøkelser som viser de terapeutisk nyttige antipyretiske, analgetiske og antiinflamatoriske aktiviteter av forbindelsen er gitt senere. The results of toxicological and pharmacological studies showing the therapeutically useful antipyretic, analgesic and anti-inflammatory activities of the compound are given later.
Disse resultater er oppsummert i den etterfølgende tabell og der sammenlignet med resultater oppnådd med acetylsalicylsyre. Begge forbindelser har nær beslektede aktiviteter, 'men 2-(tert. ;butylamino)etanol-aeétylsalicylat fremstilt i henhold til den foreliggende oppfinnelse har den fordel at det er omtrent noytralt og vannloselig. Derfor frembyr ikke dets intrave-nose tilforsel noen problemer. De tester som er nevnt i These results are summarized in the following table and there compared with results obtained with acetylsalicylic acid. Both compounds have closely related activities, but 2-(tert.butylamino)ethanol ethyl salicylate prepared according to the present invention has the advantage of being approximately neutral and water-soluble. Therefore, its intranasal administration does not present any problems. The tests mentioned in
tabellen ble gjennomfort på folgende måte:the table was completed in the following way:
-Akutt toksisitet ble bestemt i mus ved oral og intravenos tilforsel. -Den antipyretiske aktivitet ble bestemt i rotter som var gjort hypertermiske ved subkutan tilforsel av olgjær i en dosering på 4 g/kg i henhold til teknikken til Adams, Hepburns og Nicholson (J. Pharm. Pharmacol. 20, 305, 312, 1968). -Acute toxicity was determined in mice by oral and intravenous administration. -The antipyretic activity was determined in rats made hyperthermic by subcutaneous administration of oleaginous yeast at a dosage of 4 g/kg according to the technique of Adams, Hepburns and Nicholson (J. Pharm. Pharmacol. 20, 305, 312, 1968) .
Forbindelsene ble tilfort i maven 17 timer etter gjærinjek-sjonen. The compounds were added to the stomach 17 hours after the yeast injection.
Endringen av frektaltemperatur av de absolutte kontroller, av olgjær-kontrollene og av de behandlede dyr er sammenlignet som en funksjon av tiden. The change in fractal temperature of the absolute controls, of the oleaginous controls and of the treated animals is compared as a function of time.
-Den analgetiske aktivitet ble bestemt ved hjelp av en av de konvensjonelle teknikker for bestemmelse av den nevnte aktivitet, nemlig den såkalte smertetest ("writhing test") i henhold til Linee ogGouret (J. Pharmaco. 4, 3, s. 512 (1972) - The analgesic activity was determined by means of one of the conventional techniques for determining said activity, namely the so-called pain test ("writhing test") according to Linee and Gouret (J. Pharmaco. 4, 3, p. 512 (1972 )
Mus som var blitt holdt fastende i 16 timer ble intraperi-tonealt tilfort 0,25 ml/20 g av en 4% vandig-alkoholisk losning av 0,2 o/oo fenylbenzokinon. Smertebevegelsene for hver mus telles fra det femte til det tiende minutt, idet dyrene ble anvendt i grupper på hver 4 dyr, og testmateri-alene ble tilfort 30 minutter for fenylbenzokinoninjeksjonen. -Den antiinflamatoriske aktivitet ble bestemt oralt, ved å iaktta prosent inhibering av karagenin-indusert odem i rotter etter en periode på 3 timer. Mice that had been fasted for 16 hours were injected intraperitoneally with 0.25 ml/20 g of a 4% aqueous-alcoholic solution of 0.2% phenylbenzoquinone. The pain movements for each mouse are counted from the fifth to the tenth minute, the animals being used in groups of 4 animals each, and the test materials were added 30 minutes before the phenylbenzoquinone injection. -The anti-inflammatory activity was determined orally, by observing the percent inhibition of carrageenan-induced edema in rats after a period of 3 hours.
Odem av bakpoten på rottene induseres ved sub-aponevrotisk injeksjon av 0,05 ml av en 2% karageninlosning i fysiologisk saltlosning. Edema of the hind paw of the rats is induced by sub-aponeurotic injection of 0.05 ml of a 2% carrageenan solution in physiological saline.
I den etterfølgende tabell er resultatene vedrørende saltet fremstilt i henhold til den foreliggende oppfinnelse uttrykt som mol-ekvivalenter av acetylsalicylsyre (syre) og som salt. In the following table, the results regarding the salt produced according to the present invention are expressed as molar equivalents of acetylsalicylic acid (acid) and as salt.
Det fremgår av de ovennevnte undersøkelser at 2-(tert.butyl-amino )etanol-acetylsalicylat er fordelaktig nyttig for humanterapeutiske formål, typisk for behandling av migrene og smerte, og for feber-og inflamatoriske tilstander. It appears from the above-mentioned investigations that 2-(tert.butyl-amino)ethanol-acetylsalicylate is advantageously useful for human therapeutic purposes, typically for the treatment of migraine and pain, and for fever and inflammatory conditions.
For disse anvendelser kan terapeutiske preparater omfattende det nevnte salt som aktiv bestanddel formuleres i enhets-doseform, sammen med vanlige bærere og tilsetningsstoffer. Således kan det terapeutiske preparat sammensettes som tab-letter inneholdende 100-2000 mg, foretrukket 500 mg aktiv bestanddeler (uttrykt som acetylsalecylsyre) eller som et pulver som gjores opploselig med et passende opplosnings-middel (som f.eks. destillert vann) til å gi en løsning for intravenøs injeksjon inneholdende 0,5-2 g aktiv bestanddel (uttrykt som acetylsalecylsyre) idet den daglige dosering er fra 2-4 g. For these applications, therapeutic preparations comprising the aforementioned salt as active ingredient can be formulated in unit dose form, together with usual carriers and additives. Thus, the therapeutic preparation can be composed as tablets containing 100-2000 mg, preferably 500 mg of active ingredients (expressed as acetylsalicylic acid) or as a powder that is made soluble with a suitable solvent (such as, for example, distilled water) to give a solution for intravenous injection containing 0.5-2 g of active ingredient (expressed as acetylsalicylic acid), the daily dosage being from 2-4 g.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| NO793581L true NO793581L (en) | 1980-05-09 |
Family
ID=9214610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO793581A NO793581L (en) | 1978-11-08 | 1979-11-06 | PROCEDURE FOR PREPARING A NEW SALT OF ACETYLSALICYLIC ACID |
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 NO NO793581A patent/NO793581L/en unknown
- 1979-11-06 IT IT7950752A patent/IT7950752A0/en unknown
- 1979-11-07 ZA ZA00795996A patent/ZA795996B/en unknown
- 1979-11-07 JP JP14427479A patent/JPS5566549A/en active Pending
- 1979-11-07 PL PL21946879A patent/PL219468A1/xx unknown
- 1979-11-07 BE BE0/198017A patent/BE879887A/en unknown
- 1979-11-08 AU AU52639/79A patent/AU527562B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| GB2034711A (en) | 1980-06-11 |
| LU81816A1 (en) | 1980-01-25 |
| JPS5566549A (en) | 1980-05-20 |
| AU5263979A (en) | 1980-05-15 |
| FR2440935B1 (en) | 1981-04-17 |
| GB2034711B (en) | 1982-10-27 |
| IT7950752A0 (en) | 1979-11-06 |
| PL219468A1 (en) | 1980-07-14 |
| FI793423A (en) | 1980-05-09 |
| FR2440935A1 (en) | 1980-06-06 |
| DE2944485A1 (en) | 1980-05-29 |
| ES485596A1 (en) | 1980-05-16 |
| AU527562B2 (en) | 1983-03-10 |
| SE7908756L (en) | 1980-05-09 |
| NL7908079A (en) | 1980-05-12 |
| BE879887A (en) | 1980-05-07 |
| ZA795996B (en) | 1980-10-29 |
| DK464479A (en) | 1980-05-09 |
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