NO176503B - Fremgangsmåte for fremstilling av neglelakk - Google Patents
Fremgangsmåte for fremstilling av neglelakk Download PDFInfo
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- NO176503B NO176503B NO900882A NO900882A NO176503B NO 176503 B NO176503 B NO 176503B NO 900882 A NO900882 A NO 900882A NO 900882 A NO900882 A NO 900882A NO 176503 B NO176503 B NO 176503B
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- copolymer
- phenyl
- dimethyl
- methyl
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- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 11
- 239000013543 active substance Substances 0.000 claims abstract description 12
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
- 239000002966 varnish Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 229920001577 copolymer Polymers 0.000 claims description 18
- 230000000843 anti-fungal effect Effects 0.000 claims description 8
- 229940121375 antifungal agent Drugs 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- MQHLMHIZUIDKOO-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical compound C1=CC(C(C)(C)CC)=CC=C1CC(C)CN1CC(C)OC(C)C1 MQHLMHIZUIDKOO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- UFLFSJVTFSZTKX-UHFFFAOYSA-N 2,2-dimethylmorpholine Chemical compound CC1(C)CNCCO1 UFLFSJVTFSZTKX-UHFFFAOYSA-N 0.000 claims 1
- 150000001253 acrylic acids Chemical class 0.000 claims 1
- HSZDQROOAWTFFJ-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-phenylpropan-2-yl)phenyl]propyl]morpholine Chemical compound C=1C=C(C(C)(C)C=2C=CC=CC=2)C=CC=1CC(C)CN1CC(C)OC(C)C1 HSZDQROOAWTFFJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920003134 Eudragit® polymer Polymers 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- XYAUIVRRMJYYHR-UHFFFAOYSA-N acetic acid;propane-1,2,3-triol Chemical class CC(O)=O.OCC(O)CO XYAUIVRRMJYYHR-UHFFFAOYSA-N 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K8/34—Alcohols
-
- 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
-
- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q3/00—Manicure or pedicure preparations
- A61Q3/02—Nail coatings
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Biotechnology (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Massaging Devices (AREA)
- Finger-Pressure Massage (AREA)
- Magnetic Treatment Devices (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Insulated Conductors (AREA)
- Impact Printers (AREA)
- Nonmetallic Welding Materials (AREA)
Description
Foreliggende oppfinnelse vedrører fremgangsmåte ved fremstilling av en neglelakk som inneholder minst ett antimykotisk virksomt stoff og minst en vannuløselig filmdanner.
Formålet ved oppfinnelsen er å oppnå en forbedring av kvaliteten på preparater av ovennevnte art, og således især når det gjelder følgende egenskaper: God gjennomtrengningshastighet, god hudfordragelighet, god flyte-evne, god strykeevne, kort inntørkningstid, bare middels høy glans, tilstrekkelig stor hardhet og lang holdbarhet (ca 3-4 dager).
Dette mål oppnås ifølge oppfinnelsen ved det som er angitt i krav l<*>s karakteriserende del. Ytterligere karakteriserende trekk er angitt i underkravene.
Som vannuløselig filmdanner anvendes et kopolymerisat av akryl- og metakrylsyreestere med lavt innhold av kvartære ammoniumgrupper. Slike kopolymerisater er kjent f.eks. fra US patentskriftet 2677679 og DAS 1627751.
Det er hensiktsmessig med et så stort innhold av kvartære ammoniumgrupper i kopolymerisatet at det molare forhold av ammoniumgrupper til de øvrige nøytrale (inneholder ikke ammoniumgrupper) akrylsyre- hhv. metakrylsyreestere (-COOR<2> i formel I nedenfor) ligger mellom ca 1:20 og 1:40.
Den gjennomsnittlige molekylvekt er ca 150.000. Slike kopolymerisater kan karakteriseres ved følgende del-formel, hvor R-l betyr hydrogen eller metyl, og R2 betyr metyl eller etyl
Slike substanser fins å kjøpe i handelen som 12,5% lakk-løsninger og også som løsningsmiddelfrie faste stoffer under betegnelsen EUDRAGIT<®> RL og RS, (se R6mpp's Chemie-lexikon, 8. opplag, s. 1211). Slike substanser kan også blandes med hverandre alt etter behov.
Anvendelsen av slike kopolymerisater gir på grunn av sin svelleevne og gjennomtrengelighet høy diffusjonshastighet og høy gjennomtrengningshastighet for virkestoffet.
Anvendelsen av slike kopolymerisater gir lakken i tillegg til ovennevnte egenskaper høy resistens mot mekaniske skader og mot vekkvasking, og det i hele pH-området. Dette muliggjør at lakkfilmen som inneholder den antimykotisk virksomme substans, kan forbli på neglen i flere dager, og derfor er tidsrommet mellom to påføringer flere dager.
I preparatet fremstilt ifølge oppfinnelsen er kopolymerisatet og det antimykotisk virksomme stoff og eventuelt ytterligere tilsetningstoffer, såsom bløtgjørere, inndunstningsforhalere eller -påskyndere, med fordel oppløst i et inert organisk løsningsmiddel, især etanol eller metylenklorid.
Som bløtgjørere kan nevnes: Glyserinacetater som triace-tin, ftalater, eller bløtgjørere på kamferbasis. Foruten de foretrukne løsningsmidler, nemlig etanol og metylenklorid, kan f.eks. også aceton og isopropanol anvendes.
Eksempler på inndunstningsforhalere er toluen, butanol, butylacetat, amylalkohol og amylacetat, og som eksempel på en inndunstningspåskynder kan nevnes etylacetat.
Det antimykotisk virksomme stoff som fins i preparatet fremstilt ifølge oppfinnelsen kan være 4-[3-[p-(a,a-di-metylbenzyl)-fenyl]-2-metyl-propyl]-2,6-dimetyl-morfolin eller 4-[3-[p-(1,1-dimetylpropyl)-fenyl]-2-metylpropyl]-2,6-dimetyl-morfolin i saltform, især i form av hydrokloridet eller nitratet. Foretrukket er cis-isomerene av disse forbindelser. Disse cis-isomerer er kjent fra den européiske patentpublikasjon nr. 24 334, nemlig den som er nevnt som nummer to, under betegnelsen 4-[3-(p-tert.amyl-fenyl)-2-metylpropyl]-2,6-dimetyl-morfolin. Anvendelsen av cis-isomeren av denne forbindelse, i form av hydrokloridet, er særlig foretrukket.
En særlig foretrukket utførelsesform av preparatet fremstilt ifølge oppfinnelsen inneholder det antimykotisk virksomme stoff, altså det ovennevnte morfolinderivat, i en mengde på ca 0,25 til 10 vekt%, især en mengde på ca 5 vekt%, med hensyn til totalvekten.
I henhold til en fordelaktig utførelsesform av preparatet fremstilt ifølge oppfinnelsen inneholder preparatet det vannuløselige kopolymerisat i en mengde av ca 2-30 vekt%, fortrinnsvis 10-20 vekt%, særlig foretrukket ca 12,5 vekt%.
Fremgangsmåten ifølge oppfinnelsen ved fremstilling av preparatet består i at man blander kopolymerisatet i oppløst form med virkestoffet og eventuelle tilsetningsstoffer, såsom bløtgjørere, inndunstningspåskyndere, inndunstningsforhalere og lign.
Eksempel 1
Et preparat fremstilt ifølge oppfinnelsen som inneholder metylenklorid som løsningsmiddel, har følgende sammenset-ning:
Eksempel 2
Et preparat fremstilt ifølge oppfinnelsen som inneholder etanol som løsningsmiddel, oppviser følgende sammenset-ning:
Virkestoffet som er anvendt i eksemplene ovenfor, er cis-4-[3-[p-(a,a-dimetylbenzyl)-fenyl]-2-metyl-propyl]-2,6-dimetyl-morfolinhydroklorid eller cis-4-[3-[p-(1,l-di-metylpropyl)-fenyl]-2-metylpropyl]-2,6-dimetyl-morfolinhydroklorid, og EUDRAGIT<®> RL 100 er et kopolymerisat av akryl- og metakrylestere som inneholder ammoniumgrupper i et molart forhold på 1:20 (se firmaprospekt fra Røhm Pharma GMBH, Weiterstadt, BRD: "EUDRAGIT® RL und RS An-wendung in der Arzneimittelherstellung" 1982). Istedenfor dette kopolymerisat kan også andre strukturelt lignende kopolymerisater anvendes, f.eks. et kopolymerisat av trimetylmetakryloksyetylammoniumklorid, metakrylsyre-metylester og akrylsyreetylester med et lavt innhold av ammoniumgrupper.
Claims (5)
1. Fremgangsmåte ved fremstilling av en neglelakk som inneholder minst ett antimykotisk virksomt stoff og minst en vannuløselig filmdanner,
karakterisert ved at man som antimykotisk virksomt stoff anvender et salt av 4-[3-[p-(a,a-dimetyl-benzyl) -fenyl]-2-metyl-propyl]-2,6-dimetyl-morfolin eller 4-[3-[p-(1,1-dimetylpropyl)-fenyl]-2-metyl-propyl]-2,6-dimetyl-morfolin, i en mengde av 0,25-10 vekt%, især 5 vekt%, med hensyn til totalvekten, og som vannuløselig filmdanner anvender et kopolymerisat av akryl- og metakrylsyreestere med lavt innhold av kvartære ammoniumgrupper, i en mengde av 2-30 vekt%, fortrinnsvis 10-20 vekt%, særlig foretrukket 12,5 vekt%, og at man blander kopolymerisatet i oppløst form med det antimykotisk virksomme stoff og eventuelle tilsetningsstoffer, såsom bløt-gjørere, inndunstningspåskyndere, inndunstningsforhalere og lignende.
2. Fremgangsmåte ifølge krav 1, karakterisert ved at man som kopolymerisat anvender et slikt hvor ammoniumgruppenes molare forhold til de øvrige nøytrale akrylsyre- hhv. metakrylsyreestere i kopolymerisatet ligger mellom ca 1:20 og ca 1:40.
3. Fremgangsmåte ifølge krav 1 eller 2, karakterisert ved at det anvendte kopoly-merisats gjennomsnittlige molekylvekt er ca 150.000.
4. Fremgangsmåte ifølge krav 1, 2 eller 3, karakterisert ved at man som antimykotisk virksomt stoff anvender cis-4-[3-[p-(a,a-dimetylbenzyl)-fenyl]-2-metyl-propyl]-2,6-dimetyl-morfolin-hydroklorid.
5. Fremgangsmåte ifølge krav 1, 2 eller 3, karakterisert ved at man som antimykotisk virksomt stoff anvender cis-4-[3-[p-(l,1-dimetylpropyl)-fenyl]-2-metylpropyl]-2,6-dimetylmorfolin-hydroklorid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH69089 | 1989-02-24 | ||
| CH404589 | 1989-11-09 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO900882D0 NO900882D0 (no) | 1990-02-23 |
| NO900882L NO900882L (no) | 1990-08-27 |
| NO176503B true NO176503B (no) | 1995-01-09 |
| NO176503C NO176503C (no) | 1995-04-19 |
Family
ID=25685381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO900882A NO176503C (no) | 1989-02-24 | 1990-02-23 | Fremgangsmåte for fremstilling av neglelakk |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5120530A (no) |
| EP (1) | EP0389778B1 (no) |
| JP (1) | JP2579694B2 (no) |
| KR (1) | KR0125940B1 (no) |
| AT (1) | ATE105172T1 (no) |
| AU (1) | AU626990B2 (no) |
| CA (1) | CA2008775C (no) |
| DE (1) | DE59005574D1 (no) |
| DK (1) | DK0389778T3 (no) |
| DZ (1) | DZ1398A1 (no) |
| ES (1) | ES2052990T3 (no) |
| FI (1) | FI97198C (no) |
| HK (1) | HK26697A (no) |
| HU (1) | HU210500B (no) |
| IE (1) | IE63531B1 (no) |
| IL (1) | IL93434A (no) |
| IS (1) | IS1851B (no) |
| MC (1) | MC2087A1 (no) |
| MX (1) | MX171740B (no) |
| NO (1) | NO176503C (no) |
| NZ (1) | NZ232588A (no) |
| PH (1) | PH26925A (no) |
| PT (1) | PT93252B (no) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU219480B (hu) * | 1991-05-23 | 2001-04-28 | Novartis Ag. | Eljárás gombás körömmegbetegségek ellen helyileg alkalmazható, allil-amin-származékot tartalmazó gyógyászati készítmények előállítására |
| DE4212105A1 (de) * | 1992-04-10 | 1993-10-14 | Roehm Pharma Gmbh | Nagellack zur Behandlung von Onychomykosen |
| DE19518262A1 (de) * | 1995-05-18 | 1996-11-21 | Hoechst Ag | Die Verwendung von Glyceryltriacetat zur Behandlung von Onychomykosen |
| DK128494A (da) * | 1994-11-08 | 1996-05-09 | Edel K Seidenschnur | Behandling af keratinøse og psoriatiske sygdomstilstande med neglelak indeholdende vitamin D metabolit, eller derivat, og/eller vitamin A derivat |
| DE19643831A1 (de) | 1996-10-30 | 1998-05-07 | Hoechst Ag | Verwendung von 1-Hydroxy-2-pyridonen zur Behandlung von schwer therapierbaren Schleimhauterkrankungen |
| KR980000415A (ko) * | 1996-06-29 | 1998-03-30 | 이능희 | 무좀방지 효과가 있는 네일락카 조성물 |
| DE19639816A1 (de) | 1996-09-27 | 1998-04-02 | Hoechst Ag | Antimykotische Mittel mit hoher Wirkstofffreisetzung |
| DE19639817A1 (de) | 1996-09-27 | 1998-04-02 | Hoechst Ag | Verwendung von 1-Hydroxy-2-pyridonen zur Behandlung von Hautinfektionen |
| US20040039030A1 (en) * | 1996-09-27 | 2004-02-26 | Hoechst Akeengesellschaft | Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis |
| RO118174B1 (ro) * | 1997-08-21 | 2003-03-28 | Aventis Pharma Deutschland Gmbh | Lac de unghii şi utilizarea acestuia |
| US6224887B1 (en) | 1998-02-09 | 2001-05-01 | Macrochem Corporation | Antifungal nail lacquer and method using same |
| US6495124B1 (en) | 2000-02-14 | 2002-12-17 | Macrochem Corporation | Antifungal nail lacquer and method using same |
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1990
- 1990-01-29 CA CA002008775A patent/CA2008775C/en not_active Expired - Lifetime
- 1990-02-15 AT AT9090102973T patent/ATE105172T1/de not_active IP Right Cessation
- 1990-02-15 DE DE59005574T patent/DE59005574D1/de not_active Expired - Lifetime
- 1990-02-15 ES ES90102973T patent/ES2052990T3/es not_active Expired - Lifetime
- 1990-02-15 DK DK90102973.6T patent/DK0389778T3/da not_active Application Discontinuation
- 1990-02-15 EP EP90102973A patent/EP0389778B1/de not_active Expired - Lifetime
- 1990-02-16 MC MC902111A patent/MC2087A1/xx unknown
- 1990-02-16 MX MX019534A patent/MX171740B/es unknown
- 1990-02-19 IL IL9343490A patent/IL93434A/en not_active IP Right Cessation
- 1990-02-19 AU AU49947/90A patent/AU626990B2/en not_active Expired
- 1990-02-19 FI FI900809A patent/FI97198C/fi active IP Right Grant
- 1990-02-19 NZ NZ232588A patent/NZ232588A/xx unknown
- 1990-02-19 HU HU90847A patent/HU210500B/hu unknown
- 1990-02-21 KR KR1019900002110A patent/KR0125940B1/ko not_active IP Right Cessation
- 1990-02-21 JP JP2038528A patent/JP2579694B2/ja not_active Expired - Lifetime
- 1990-02-21 DZ DZ900032A patent/DZ1398A1/fr active
- 1990-02-22 US US07/483,479 patent/US5120530A/en not_active Expired - Lifetime
- 1990-02-22 PH PH40088A patent/PH26925A/en unknown
- 1990-02-22 IS IS3556A patent/IS1851B/is unknown
- 1990-02-23 IE IE66990A patent/IE63531B1/en not_active IP Right Cessation
- 1990-02-23 PT PT93252A patent/PT93252B/pt active IP Right Grant
- 1990-02-23 NO NO900882A patent/NO176503C/no not_active IP Right Cessation
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1997
- 1997-03-06 HK HK26697A patent/HK26697A/xx not_active IP Right Cessation
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| MK1K | Patent expired |