NL7908079A - NEW SALT OF ACETYLSALICYLIC ACID AND PHARMACEUTICAL PREPARATION CONTAINING THIS SALT. - Google Patents
NEW SALT OF ACETYLSALICYLIC ACID AND PHARMACEUTICAL PREPARATION CONTAINING THIS SALT. Download PDFInfo
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- NL7908079A NL7908079A NL7908079A NL7908079A NL7908079A NL 7908079 A NL7908079 A NL 7908079A NL 7908079 A NL7908079 A NL 7908079A NL 7908079 A NL7908079 A NL 7908079A NL 7908079 A NL7908079 A NL 7908079A
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- Prior art keywords
- salt
- acetylsalicylic acid
- tert
- ethanol
- butylamino
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims description 21
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims description 18
- 229960001138 acetylsalicylic acid Drugs 0.000 title claims description 15
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 5
- IUXYVKZUDNLISR-UHFFFAOYSA-N 2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCCO IUXYVKZUDNLISR-UHFFFAOYSA-N 0.000 claims description 4
- 230000000202 analgesic effect Effects 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 230000001754 anti-pyretic effect Effects 0.000 claims description 4
- 239000002221 antipyretic Substances 0.000 claims description 4
- 238000001990 intravenous administration Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 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
- 229940102223 injectable solution Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 241000700159 Rattus Species 0.000 description 4
- 125000006309 butyl amino group Chemical group 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- 206010030113 Oedema Diseases 0.000 description 2
- 229940068372 acetyl salicylate Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 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
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000002977 hyperthermial effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
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- 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)
Description
S 5652-1 P & C ^S 5652-1 P & C ^
Nieuw zout van acetylsalicylzuur, alsmede farmaceutisch preparaat dat dit zout bevat.New salt of acetylsalicylic acid, as well as a pharmaceutical preparation containing this salt.
De uitvinding heeft betrekking op een nieuw zout van acetylsalicyl-zuur, welk zout het voordeel biedt oplosbaar in water te zijn en niet-zure oplossingen te geven.The invention relates to a new salt of acetylsalicylic acid, which salt has the advantage of being water-soluble and giving non-acidic solutions.
Het is bekend dat acetylsalicylzuur, waarvan de farmacologische eigen-5 schappen bekend zijn en dat therapeutisch met voordeel voor mensen toegepast kan worden, het nadeel heeft dat het weinig oplosbaar in water en zuur is. Dit maakt de intraveneuze toediening van salicylzuur moeilijk zó niet onmogelijk.It is known that acetylsalicylic acid, the pharmacological properties of which are known and which can be used therapeutically advantageously for humans, has the drawback of being sparingly soluble in water and acid. This makes the intravenous administration of salicylic acid difficult, if not impossible.
Om dit nadeel te verzachten heeft men verschillende oplosbare deriva-10 ten van acetylsalicylzuur voorgesteld, waarvan het grootste deel gevormd wordt door basische zouten van aminozuren. De uitvinding verruimt het gebied van oplosbare therapeutisch werkzame verbindingen door het verschaffen van een zout van acetylsalicylzuur van een ander type.To alleviate this drawback, various soluble derivatives of acetylsalicylic acid have been proposed, the majority of which are basic salts of amino acids. The invention broadens the range of soluble therapeutically active compounds by providing a salt of acetylsalicylic acid of another type.
De uitvinding verschaft het zout van acetylsalicylzuur en 2-(tert.bu-15 tylamino)ethanol, welk zout wordt voorgesteld door de formule van het formuleblad.The invention provides the salt of acetylsalicylic acid and 2- (tert.bu-tylamino) ethanol, which salt is represented by the formula of the formula sheet.
De onderhavige verbinding bestaat dus uit een combinatie van een mol acetylsalicylzuur en een mol 2-(tert.butylamino)ethanol, welke verbinding f de onderstaande fysicochemische eigenschappen bezit: 20 molecuulgewicht: 297, 357; smeltpunt (buis): 123® - 125®C; smeltpunt (direkt): 140® - 142®C.Thus, the present compound consists of a combination of a mole of acetylsalicylic acid and a mole of 2- (tert.butylamino) ethanol, which compound f has the following physicochemical properties: molecular weight: 297, 357; melting point (tube): 123® - 125®C; melting point (direct): 140® - 142®C.
De onderhavige verbinding is oplosbaar in water. De pH van een waterige 5 gew.%'s oplossing bedraagt circa 5,9, dat wil zeggen de oplossing 25 is ongeveer neutraal.The present compound is soluble in water. The pH of an aqueous 5% by weight solution is about 5.9, that is, the solution is about neutral.
Het onderhavige nieuwe zout bezit een analgetische, antipyretische en anti-ontstekings-werking.The present new salt has an analgesic, antipyretic and anti-inflammatory action.
Men kan het onderhavige nieuwe zout bereiden door acetylsalicylzuur en 2-(tert.butylamino)ethanol met elkaar om te zetten. Met voordeel ge-30 bruikt men de reactiecomponenten in stoechiometrische hoeveelheden, waarbij elk van de reactiecomponenten bij voorkeur is opgelost in een geschikt organisch oplosmiddel, zoals diethylether. De reactie verloopt op bevredigende wijze bij de temperatuur van de omgeving, zodat het geen enkel voordeel heeft in de praktijk van deze temperatuur af te wijken.The present new salt can be prepared by reacting acetylsalicylic acid and 2- (tert.butylamino) ethanol together. Advantageously, the reactants are used in stoichiometric amounts, each of the reactants preferably being dissolved in a suitable organic solvent, such as diethyl ether. The reaction proceeds satisfactorily at the ambient temperature, so that there is no advantage in deviating from this temperature in practice.
35 Het onderstaande voorbeeld licht de bereiding van het zout van acetyl salicylzuur en 2-(tert.butylamino)ethanol toe.The example below illustrates the preparation of the salt of acetyl salicylic acid and 2- (tert.butylamino) ethanol.
790 8 0 79 •f / - 2 -790 8 0 79 • f / - 2 -
VOORBEELDEXAMPLE
In 150 ml diethylether loste men 5,4 g (0,03 mol) acetylsalicylzuur op. Aan deze oplossing werd een oplossing van 3,5 g 2-(tert.butylamino)-ethanol (0,03 mol) in 40 ml diethylether toegevoegd. Er verscheen onmid-5 delijk een neerslag. Men roerde het mengsel gedurende 15 minuten? vervolgens werd afgezogen, met diethylether gewassen en onder verlaagde druk en in aanwezigheid van fosforpentoxide tot constant gewicht gedroogd. Men verkreeg 8,5 g van het acetylsalicylaat van 2-(tert.butylamino) ethanol met de bovengenoemde fysicochemische eigenschappen.5.4 g (0.03 mol) of acetylsalicylic acid were dissolved in 150 ml of diethyl ether. To this solution was added a solution of 3.5 g of 2- (tert.-butylamino) -ethanol (0.03 mol) in 40 ml of diethyl ether. A precipitate appeared immediately. The mixture was stirred for 15 minutes? it was then aspirated, washed with diethyl ether and dried to constant weight under reduced pressure and in the presence of phosphorus pentoxide. 8.5 g of the acetylsalicylate of 2- (tert.butylamino) ethanol having the above physicochemical properties were obtained.
10 Microanalyse % berekend % gevonden C 60,59 60,53 H 7,80 7,78 N 4,71 4,61 0 26,90 15 Hieronder zijn de resultaten gegeven van het toxicologisch en farma cologisch onderzoek, waaruit de therapeutisch waardevolle antipyretische, analgetische en anti-ontstekingswerkzaamheid van de onderhavige verbinding blijkt.10 Microanalysis% calculated% found C 60.59 60.53 H 7.80 7.78 N 4.71 4.61 0 26.90 15 Below are the results of the toxicological and pharmacological research, from which the therapeutically valuable antipyretic , analgesic and anti-inflammatory activity of the present compound.
Deze resultaten zijn samengevat in de onderstaande tabel, waarin ze 20 yergeleken worden met de resultaten die verkregen zijn met acetylsalicylzuur. De werkzaamheden van de twee verbindingen lopen niet sterk uiteen, maar het door de uitvinding verschafte acetylsalicylaat van 2-(tert.butyl-amino)ethanol heeft het voordeel dat het praktisch neutraal is en in water oplosbaar. Derhalve geeft de intraveneuze toediening van het zout geen 25 enkel probleem. De in de tabel vermelde proeven werden als volgt uitgevoerd: De acute toxiciteit werd bepaald door orale en intraveneuze toediening aan muizen.These results are summarized in the table below, in which they are compared to the results obtained with acetylsalicylic acid. The activities of the two compounds are not very different, but the acetyl salicylate of 2- (tert-butylamino) ethanol provided by the invention has the advantage of being practically neutral and water-soluble. Therefore, the intravenous administration of the salt presents no problem whatsoever. The tests listed in the table were performed as follows: The acute toxicity was determined by oral and intravenous administration to mice.
De antipyretische werkzaamheid werd bepaald voor ratten die hyperthermisch waren gemaakt door subcutane toediening van biergist in een dosis van 30 4 g/kg, volgens de methode van Adams, Hepburns en Nicholson (J. Pharm.Antipyretic efficacy was determined for rats rendered hyperthermic by subcutaneous administration of brewer's yeast at a dose of 4 g / kg, according to the method of Adams, Hepburns and Nicholson (J. Pharm.
Pharmacol. 20, 305, 312, 1968).Pharmacol. 20, 305, 312, 1968).
De toediening vond intragastrisch plaats 17 uren na het injecteren van de gist.Administration was done intragastrically 17 hours after yeast injection.
Men vergeleek de ontwikkeling van de rectale temperatuur van de ratten als 35 functie van de tijd bij "absolute" controledieren, controledieren waaraan biergist was -toegediend en de behandelde dieren.The development of the rectal temperature of the rats as a function of time was compared in "absolute" control animals, control animals administered brewer's yeast and the treated animals.
De analgetische werkzaamheid werd bepaald volgens een hiervoor klassieke methode, namelijk de "kronkelproef" ("writhing test") volgens Linee en Gouret (J. Pharmacol 4_, 3, blz. 512 (1972)).The analgesic activity was determined by a classical method above, namely the "writhing test" according to Linee and Gouret (J. Pharmacol 4, 3, p. 512 (1972)).
790 8 0 79 -. * - 3 -790 8 0 79 -. * - 3 -
Aan muizen, die men gedurende 16 uren had laten vasten, werd intraperito-naal 0,25 ml/20 g van een oplossing van 0,2 %o fenylbenzochinon in waterige alcohol (4 %) toegediend. Men telde het aantal kronkelingen van iedere muis van de 5e tot de 10e minuut. De muizen waren verdeeld in groepen van 5 4 en de te onderzoeken materialen werden 30 minuten vóór het injecteren van fenylbenzochinon toegediend.Mice, which had been fasted for 16 hours, were administered intraperitoneally 0.25 ml / 20 g of a solution of 0.2% o phenyl benzoquinone in aqueous alcohol (4%). The number of squiggles of each mouse was counted from the 5th to the 10th minute. The mice were divided into groups of 5 and the materials to be tested were administered 30 minutes before phenyl benzoquinone injection.
De anti-ontstekingswerkzaamheid werd bepaald door orale toediening, waarbij het percentage remming van het carrageenine-oedeem bij ratten na 3 uren werd waargenomen. Het oedeem aan de achterpoot van de rat werd opgewekt 10 door subaponeurotisch injecteren van 0,05 ml van een 2 %'s oplossing van carrageenine in fysiologisch serum.Anti-inflammatory activity was determined by oral administration, with the percent inhibition of carrageenin edema in rats observed after 3 hours. The hind paw edema of the rat was induced by subaponeurotic injection of 0.05 ml of a 2% solution of carrageenin in physiological serum.
In de onderstaande tabel zijn de resultaten voor wat betreft het zout volgens de uitvinding uitgedrukt in molairequivalenten van acetylsalicyl-zuur (zuur) en als het zout. < 790 80 79 / e ,--- - 4 - \ o cm *-< η \ in oo τι* 10 \ 1=¾ *· *· *·In the table below, the results for the salt of the invention are expressed in molar equivalents of acetylsalicylic acid (acid) and as the salt. <790 80 79 / e, --- - 4 - \ o cm * - <η \ in oo τι * 10 \ 1 = ¾ * · * · * ·
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0 ϋ o > ft N 0) id Λ! I N Id O0 ϋ o> ft N 0) id Λ! I N Id O
(dp -P ·Ρ M O N G O > -P ,¾ P(dp -P · Ρ M O N G O> -P, ¾ P
1¾ ft XftH-PP H Ai Ο -P P P ft 0 GO) idPPftH-CifUid tiiics c ω ,y rtisoi ___J_ <! SII I ___ 790 8 0 79 „ 01¾ ft XftH-PP H Ai Ο -P P P ft 0 GO) idPPftH-CifUid tiiics c ω, y rtisoi ___J_ <! SII I ___ 790 8 0 79 „0
*—) t-H . CM* -) t-H. CM
- 5 - "W.- 5 - "W.
Uit het bovenstaande blijkt dat het zout van acetylsalicylzuur en 2-(tert.hutylamino)ethanol met voordeel therapeutisch kan worden toege-. past voor mensen, met name voor het behandelen van migraine en andere pijnen, koorts en ontstekingen.From the above, it appears that the salt of acetylsalicylic acid and 2- (tert.hutylamino) ethanol can advantageously be added therapeutically. suits people, especially for treating migraines and other pains, fever and inflammation.
5 Bij deze toepassingen kan het geneesmiddel, dat het onderhavige zout als actief bestanddeel bevat, met gebruikelijke dragers of aanlengmiddelen bereid worden in de vorm van eenheidsdoses. Dit preparaat kan bijvoorbeeld de vorm hebben van gecomprimeerde tabletten van 500 mg, uitgedrukt als acetylsalicylzuur of van een op te lossen poeder dat met een geschikt op-10 losmiddel, zoals apyrogeen gedestilleerd water, een oplossing voor intraveneuze injectie vormt, bijvoorbeeld een oplossing die 0,5 - 2 g actief bestanddeel (uitgedrukt als acetylsalicylzuur) bevat, waarbij de dagelijkse dosis 2 - 4 g bedraagt.In these applications, the medicament containing the present salt as an active ingredient can be prepared in unit dose form with conventional carriers or extenders. This preparation may be, for example, in the form of 500 mg compressed tablets, expressed as acetylsalicylic acid, or of a powder to be dissolved which, with a suitable solvent, such as apyrogen distilled water, forms a solution for intravenous injection, for example a solution containing 0 1.5 g of active ingredient (expressed as acetylsalicylic acid), the daily dose being 2-4 g.
« « 790 80 79«« 790 80 79
Claims (5)
Applications Claiming Priority (2)
| 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 |
| FR7831588 | 1978-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7908079A true NL7908079A (en) | 1980-05-12 |
Family
ID=9214610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7908079A NL7908079A (en) | 1978-11-08 | 1979-11-05 | NEW SALT OF ACETYLSALICYLIC ACID AND PHARMACEUTICAL PREPARATION CONTAINING THIS SALT. |
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 BE BE0/198017A patent/BE879887A/en unknown
- 1979-11-07 PL PL21946879A patent/PL219468A1/xx unknown
- 1979-11-07 JP JP14427479A patent/JPS5566549A/en active Pending
- 1979-11-07 ZA ZA00795996A patent/ZA795996B/en unknown
- 1979-11-08 AU AU52639/79A patent/AU527562B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PL219468A1 (en) | 1980-07-14 |
| AU527562B2 (en) | 1983-03-10 |
| GB2034711B (en) | 1982-10-27 |
| ES485596A1 (en) | 1980-05-16 |
| ZA795996B (en) | 1980-10-29 |
| IT7950752A0 (en) | 1979-11-06 |
| FR2440935A1 (en) | 1980-06-06 |
| DE2944485A1 (en) | 1980-05-29 |
| NO793581L (en) | 1980-05-09 |
| SE7908756L (en) | 1980-05-09 |
| LU81816A1 (en) | 1980-01-25 |
| DK464479A (en) | 1980-05-09 |
| JPS5566549A (en) | 1980-05-20 |
| AU5263979A (en) | 1980-05-15 |
| FI793423A (en) | 1980-05-09 |
| GB2034711A (en) | 1980-06-11 |
| FR2440935B1 (en) | 1981-04-17 |
| BE879887A (en) | 1980-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |