DK155975B - Kosmetisk praeparat til brug ved behandling af acne - Google Patents
Kosmetisk praeparat til brug ved behandling af acne Download PDFInfo
- Publication number
- DK155975B DK155975B DK130979AA DK130979A DK155975B DK 155975 B DK155975 B DK 155975B DK 130979A A DK130979A A DK 130979AA DK 130979 A DK130979 A DK 130979A DK 155975 B DK155975 B DK 155975B
- Authority
- DK
- Denmark
- Prior art keywords
- peroxide
- treatment
- acne
- thenoyl
- cosmetic
- Prior art date
Links
- 206010000496 acne Diseases 0.000 title claims description 14
- 239000002537 cosmetic Substances 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- 208000002874 Acne Vulgaris Diseases 0.000 title claims description 5
- 150000002978 peroxides Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000654 additive Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- -1 pomade Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000186429 Propionibacterium Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000001574 biopsy Methods 0.000 description 2
- 230000002995 comedolytic effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 239000011547 Bouin solution Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 241000282806 Rhinoceros Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011327 histological measurement Methods 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/38—Percompounds, e.g. peracids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
- i -
DK 155975 B
Opfindelsen angår et kosmetisk præparat beregnet til behandling af acne, og dette præparat er ejendommeligt ved et indhold af thenoylperoxid.
5 Thenoylperoxid med den i kravet anførte formel er allerede beskrevet som kemisk stof. Det er især blevet benyttet til polymerisation af styren (MONATS, 1949, 8_0, 739), men hidtil har man ikke anvist nogen kosmetisk anvendelse af denne forbindelse.
10
Det har imidlertid nu vist sig, at forbindelsen har anti-bakterielle og comedolytiske (comedon = hudorm) egenskaber, som gør forbindelsen velegnet i kosmetiske præparater.
15 Præparatet egner sig især til behandling af acne, når læsionerne (comedoner og pustuler) er fremkommet.
Det kosmetiske præparat ifølge opfindelsen indeholder især 2-20% aktiv forbindelse.
20
Præparatet kan administreres lokalt og kan til dette formål foreligge som opløsning, emulsion, creme, pomade, pudder, lotion og gelé.
25 De kosmetiske præparater fremstilles efter gængse metoder.
Den aktive bestanddel kan inkorporeres deri sammen med gængs benyttede tilsætningsstoffer såsom polyethylenglyco-ler, voks, fedtstoffer, stearinderivater, talkum, alkoholer såsom stearyl- og ketostearylalkoholer, vegetabilske olier 30 såsom mandelolie, mineralolier, fugtemidler, fortykkelsesmidler, konserveringsmidler, parfume, farvestoffer eller andre kendte tilsætningsstoffer. Visse tilsætningsstoffer, som reagerer på en uønsket måde med thenoylperoxid, bør dog undgås. Det gælder fx umættede fedtstoffer.
35 - 2 -
DK 755975B
Den sædvanlige dosis, som afhænger af brugeren og dennes kosmetiske problem, kan fx være 1-4 påføringer pr. dag af en pomade med 2-20% aktivt stof.
5 Specielt kan de omhandlede præparater indeholde 0,2-20% aktivt stof, og de kan påføres huden i form af fx opløsninger, emulsioner, creme, pomade, pudder, lotioner, geleer, sæbe, toiletmælk, masker, aerosoler eller badeolie.
10 De kosmetiske præparater kan fremstilles på gængs måde.
Det skal bemærkes, at et stof, som er nært beslægtet med thenoylperoxid, nemlig benzoylperoxid, finder anvendelse til behandling af acne, men benzoylperoxid frembyder van-15 skeligheder ved brugen på grund af sin ustabilitet. Denne forbindelse eksploderer let i tør tilstand ved en temperatur på 70-80°C, og præparater, som indeholder forbindelsen, nedbrydes ofte ved opbevaring (J. Pharm. Sci. 1977, 66, 718).
20
Thenoylperoxid har en spontan sønderdelingshastighed ved 75 °C, som kun er halvt så stor som for benzoylperoxid (J.
Org. Chem. 1962, 27, 410), og det sønderdeles ikke eksplosivt før temperaturer over 130°C.
25
Det er blevet påvist (Canad. Med. Ass. J. 1965, 9J3, 252), at egenskaberne af benzoylperoxid er bundet til peroxidationskraften af denne forbindelse ved langsom frigørelse af oxygen efter påføring på huden.
30
Man måtte da vente, at thenoylperoxid skulle have en mindre kosmetisk effekt end effekten af benzoylperoxid, fordi det er mere stabilt end dette.
35 Det har imidlertid nu vist sig på overraskende måde, at thenoylperoxid er mindst lige så aktivt som benzoylperoxid.
»
DK 155975B
- 3 - l
Thenoylperoxid udgør således takket være sin store stabilitet en forbindelse, som har meget betydelige fordele i forhold til det hidtil benyttede benzoylperoxid.
5 Disse fordele fremgår af nedenstående forsøgsrapporter, som illustrerer egenskaberne af thenoylperoxid.
Kosmetisk undersøgelse af thenoylperoxid 1) Antibakteriel og antifungisk aktivitet 10 De minimale inhiberende koncentrationer (MIC) bestemmes ved metoden med seriefortyndinger i væskeformet miljø for Pro-pionibacterium aenes og i gelosemiljø for oval Pityrospo-rum.
MIC pq/liter 15 Forbindelser Propionibacterium aenes oval Pityrosporum thenoylperoxid 12,5-37,5 250 benzoylperoxid 25 -50 2) Comedolytisk aktivitet
Grupper på 3 hårløse hunmus ("rhinoceros"), som frembyder 20 spontane comedoner, modtager daglig en kutan påføring af 0,1 ml acetone indeholdende thenoylperoxid i 10%'s opløs- 2 ning. Denne påføring sker på ca. 1 cm . En kontrolgruppe modtager opløsningsmidlet under samme betingelser. Behandlingen omfatter 15 påføringer. 24 timer efter den sidste 25 foretages en stor biopsi i den behandlede zone, og den fikser es i Bouin's opløsning.
Biopsierne skæres derpå i 5 μ tykkelse i paraffin vinkelret på hudoverfladen og farves med hemalun-eosin.
30
Der foretages derpå histologiske målinger på 30 comedoner taget tilfældigt i hver gruppe. Diameteren af mundingen (d) og den store diameter (D) bestemmes som angivet på følgende skema: fr 35
DK 155975B
- 4 - Når snittet ikke passerer mundingen af comedonen, defineres (d) til værdien O.
Antallet af målte comedoner er tilstrækkelig stor til at 5 eliminere indflydelsen hidrørende fra, hvorledes snittet rammer, i sammenligning med forholdet d/D for de forskellige grupper.
Resultater
10 Måling af mundingen og den store diameter af comedoner: Behandling d* D* Forhold d/D
Kontrol 8,7+1,5 25 ±2,2 0,35 thenoylperoxid 21,1+1,7 23,5+1,6 0,90 benzoylperoxid 14,7+2,1 27,0+1,8 0,54 15 * Udtrykt i arbitrære enheder under hensyn til tykkelsen af genstanden og af den skærm, som målingen udføres på.
Disse resultater viser, at gennemsnitscomedonen hos kontroldyrene fremviser en mindre munding end hos de med theno-20 ylperoxid behandlede dyr, medens den store diameter er uændret. Denne ændring af forholdet d/D i retning mod værdien 1, dvs. omdannelsen af lukkede comedoner til åbne comedoner, muliggør udpresningen af comedonens hornvæv, et fænomen, som hyppigt iagttages ved mikroskopisk undersøgelse.
25
Eksempel på kosmetisk præparat
Man fremstiller en pomade indeholdende: thenoylperoxid 10 g ethanol 40 g 30 - polyglycolether af mættet fedtalkohol 10 g
Carbopol 940 (carboxyvinylpolymer) diisopropanolamin dinatrisumsalt af EDTA
vand ad 100 g i 35 - 5 -
DK 155975 B
Yderligere eksempler på kosmetiske præparater 1) Man fremstiller en gelé til lokal påføring indeholdende : thenoylperoxid 10 g 5 - tilsætningsstof ad 100 g (enkeltheder vedrørende tilsætningsstof: carboxypolymethylen, triethanolamin, ethanol, polyoxyethylen-2,3-laurylether, propylenglycol, vand) 10 2) Man fremstiller en gelé til lokal påføring indeholden de: thenoylperoxid 5 g tilsætningsstof ad 100 g (enkeltheder vedrørende tilsætningsstof: hydroxypropylmethylcellulose og silicat, natriumhydroxid, poiyoxyethylen-4-lauryl-ether, propylenglycol, vand) 20
Claims (2)
1. Kosmetisk præparat beregnet til behandling af acne, kendetegnet ved et indhold af thenoylperoxid med formlen r\ O ^CO-O-O-CO^ 10
2. Kosmetisk præparat ifølge krav 1, kendetegnet ved et indhold på 0,2-20%, især 2-20% aktiv bestanddel. 15
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7809616 | 1978-03-31 | ||
| FR7809616A FR2420972A1 (fr) | 1978-03-31 | 1978-03-31 | Application du peroxyde de thenoyle a titre de medicament |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK130979A DK130979A (da) | 1979-10-01 |
| DK155975B true DK155975B (da) | 1989-06-12 |
| DK155975C DK155975C (da) | 1989-10-30 |
Family
ID=9206538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK130979A DK155975C (da) | 1978-03-31 | 1979-03-30 | Kosmetisk praeparat til brug ved behandling af acne |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0004810B1 (da) |
| JP (1) | JPS55361A (da) |
| AU (1) | AU524669B2 (da) |
| CA (1) | CA1144072A (da) |
| DE (1) | DE2967592D1 (da) |
| DK (1) | DK155975C (da) |
| FR (1) | FR2420972A1 (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0918149D0 (en) | 2009-10-16 | 2009-12-02 | Jagotec Ag | Improved medicinal aerosol formulation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE687356A (da) * | 1966-09-23 | 1967-03-01 | ||
| FR6698M (da) * | 1967-08-03 | 1969-02-10 | ||
| FR2043477A1 (en) * | 1969-05-20 | 1971-02-19 | Investigations Sci Pharm | Magnesium thenoate |
-
1978
- 1978-03-31 FR FR7809616A patent/FR2420972A1/fr active Granted
-
1979
- 1979-03-28 EP EP79400198A patent/EP0004810B1/fr not_active Expired
- 1979-03-28 DE DE7979400198T patent/DE2967592D1/de not_active Expired
- 1979-03-29 JP JP3634879A patent/JPS55361A/ja active Granted
- 1979-03-30 DK DK130979A patent/DK155975C/da not_active IP Right Cessation
- 1979-03-30 CA CA000324696A patent/CA1144072A/fr not_active Expired
- 1979-03-30 AU AU45663/79A patent/AU524669B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE2967592D1 (en) | 1986-05-28 |
| DK155975C (da) | 1989-10-30 |
| AU524669B2 (en) | 1982-09-30 |
| FR2420972A1 (fr) | 1979-10-26 |
| EP0004810B1 (fr) | 1986-04-23 |
| CA1144072A (fr) | 1983-04-05 |
| JPS55361A (en) | 1980-01-05 |
| EP0004810A2 (fr) | 1979-10-17 |
| EP0004810A3 (en) | 1979-10-31 |
| JPH0130806B2 (da) | 1989-06-22 |
| DK130979A (da) | 1979-10-01 |
| FR2420972B1 (da) | 1980-12-26 |
| AU4566379A (en) | 1979-10-04 |
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