NO793581L - Fremgangsmaate for fremstilling av et nytt salt av acetylsalicylsyre - Google Patents
Fremgangsmaate for fremstilling av et nytt salt av acetylsalicylsyreInfo
- 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)
- 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)
Abstract
"Fremgangsmåte for fremstilling av et nytt salt av acetylsalicylsyre"
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.
Det nye acetylsalcylsyresalt har den fordel at det er vann-opploselig samtidig med at det gir ikke-sure opplosninger.
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.
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.
Det salt som fremstilles ved fremgangsmåten i henhold til oppfinnelsen har formelen
Og skriver seg således fra kombinasjonen av et mol acetylsalicylsyre og et mol 2- (tert.butylamino)etanol og fremviser folgende fysikalskkjemiske egenskaper.
- molekylvekt: 297.357
- smeltepunkt (ror): 123—125°C
- smeltepunkt (oyeblikkelig): 140-142°C
Saltet er som nevnt vannopplbselig og pH i en 5% vandig losning er omtrent 5,9, dvs. nesten nbytral pH.
Dette nye salt har en ahalgetisk, antipyretisk og anti-inflamatorisk virkning.
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.
Det folgende éksempel illustrerer fremstillingen av 2-(tert. butylamino)etanol acetylsalicylat.
Eksempel
Acetylsalicylsyre (5,4 g, 0,03 mol) opploses i etyleterr
(150 ml) og til denne losning tilsettes en lbsning av 2-(tert.butylamino)etanol (3,5 g, 0,03 mol) i 40 ml etyleter.
Det dannes umiddelbart en utfelling. Reaksjonsblandingen omrores i 15 minutter hvoretter den avsuges på filter,
vaskes med etyleter og tbrkes til konstant vekt under vakuum,
i nærvær av fosforsyre anhydrid, til å gi 8,5 g 2-(tert.butyl-amino )etanol-acetylsalicylat som har de ovennevnte fysikalskkjemiske egenskaper.
Resultatene av toksdkologiske og farmakologiske undersøkelser som viser de terapeutisk nyttige antipyretiske, analgetiske og antiinflamatoriske aktiviteter av forbindelsen er gitt senere.
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
tabellen ble gjennomfort på folgende måte:
-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).
Forbindelsene ble tilfort i maven 17 timer etter gjærinjek-sjonen.
Endringen av frektaltemperatur av de absolutte kontroller, av olgjær-kontrollene og av de behandlede dyr er sammenlignet som en funksjon av tiden.
-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)
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.
Odem av bakpoten på rottene induseres ved sub-aponevrotisk injeksjon av 0,05 ml av en 2% karageninlosning i fysiologisk saltlosning.
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.
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.
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.
Claims (2)
1. Fremgangsmåte for fremstilling av 2-(tert.butylamino) etanol-acetylsalicylat,
karakterisert ved at acetylsalicylsyre omsettes med 2-(tert.butylamino)étanol.
2. Fremgangsmåte som angitt i krav 1, karakterisert ved at begge reagensror anvendes i stort sett stokiornetriske mengder, idet hvert reagens er opplost i et passende organisk løsningsmiddel som f.eks. etyleter.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7831588A FR2440935A1 (fr) | 1978-11-08 | 1978-11-08 | Nouveau sel de l'acide acetylsalicylique, son procede de preparation et ses applications therapeutiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO793581L true NO793581L (no) | 1980-05-09 |
Family
ID=9214610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO793581A NO793581L (no) | 1978-11-08 | 1979-11-06 | Fremgangsmaate for fremstilling av et nytt salt av acetylsalicylsyre |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5566549A (no) |
| AU (1) | AU527562B2 (no) |
| BE (1) | BE879887A (no) |
| DE (1) | DE2944485A1 (no) |
| DK (1) | DK464479A (no) |
| ES (1) | ES485596A1 (no) |
| FI (1) | FI793423A (no) |
| FR (1) | FR2440935A1 (no) |
| GB (1) | GB2034711B (no) |
| IT (1) | IT7950752A0 (no) |
| LU (1) | LU81816A1 (no) |
| NL (1) | NL7908079A (no) |
| NO (1) | NO793581L (no) |
| PL (1) | PL219468A1 (no) |
| SE (1) | SE7908756L (no) |
| ZA (1) | ZA795996B (no) |
-
1978
- 1978-11-08 FR FR7831588A patent/FR2440935A1/fr active Granted
-
1979
- 1979-10-23 SE SE7908756A patent/SE7908756L/xx not_active Application Discontinuation
- 1979-10-24 LU LU81816A patent/LU81816A1/fr unknown
- 1979-10-30 GB GB7937546A patent/GB2034711B/en not_active Expired
- 1979-10-31 ES ES485596A patent/ES485596A1/es not_active Expired
- 1979-11-01 FI FI793423A patent/FI793423A/fi not_active Application Discontinuation
- 1979-11-02 DK DK464479A patent/DK464479A/da not_active Application Discontinuation
- 1979-11-03 DE DE19792944485 patent/DE2944485A1/de not_active Withdrawn
- 1979-11-05 NL NL7908079A patent/NL7908079A/nl not_active Application Discontinuation
- 1979-11-06 IT IT7950752A patent/IT7950752A0/it unknown
- 1979-11-06 NO NO793581A patent/NO793581L/no unknown
- 1979-11-07 ZA ZA00795996A patent/ZA795996B/xx unknown
- 1979-11-07 JP JP14427479A patent/JPS5566549A/ja active Pending
- 1979-11-07 BE BE0/198017A patent/BE879887A/fr 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 (da) | 1980-05-09 |
| ZA795996B (en) | 1980-10-29 |
| SE7908756L (sv) | 1980-05-09 |
| GB2034711B (en) | 1982-10-27 |
| NL7908079A (nl) | 1980-05-12 |
| AU5263979A (en) | 1980-05-15 |
| FI793423A (fi) | 1980-05-09 |
| DE2944485A1 (de) | 1980-05-29 |
| AU527562B2 (en) | 1983-03-10 |
| ES485596A1 (es) | 1980-05-16 |
| FR2440935B1 (no) | 1981-04-17 |
| GB2034711A (en) | 1980-06-11 |
| JPS5566549A (en) | 1980-05-20 |
| LU81816A1 (fr) | 1980-01-25 |
| FR2440935A1 (fr) | 1980-06-06 |
| IT7950752A0 (it) | 1979-11-06 |
| PL219468A1 (no) | 1980-07-14 |
| BE879887A (fr) | 1980-05-07 |
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