EP1648378A2 - Antimykotischer nagellack - Google Patents
Antimykotischer nagellackInfo
- Publication number
- EP1648378A2 EP1648378A2 EP04767801A EP04767801A EP1648378A2 EP 1648378 A2 EP1648378 A2 EP 1648378A2 EP 04767801 A EP04767801 A EP 04767801A EP 04767801 A EP04767801 A EP 04767801A EP 1648378 A2 EP1648378 A2 EP 1648378A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- nail varnish
- active substance
- varnish according
- nail
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000002966 varnish Substances 0.000 title claims abstract description 33
- 239000013543 active substance Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 229940124532 absorption promoter Drugs 0.000 claims abstract description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
- 230000001857 anti-mycotic effect Effects 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical class NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical class CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Chemical class NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 2
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 2
- 108090000790 Enzymes Chemical class 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 229960000458 allantoin Drugs 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229940088598 enzyme Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical compound ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 abstract 1
- 238000011282 treatment Methods 0.000 description 16
- 208000010195 Onychomycosis Diseases 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 201000005882 tinea unguium Diseases 0.000 description 9
- 239000003429 antifungal agent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 241001480043 Arthrodermataceae Species 0.000 description 5
- 230000037304 dermatophytes Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 229960003749 ciclopirox Drugs 0.000 description 4
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 229940121375 antifungal agent Drugs 0.000 description 3
- 239000002543 antimycotic Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- MQHLMHIZUIDKOO-OKZBNKHCSA-N (2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical compound C1=CC(C(C)(C)CC)=CC=C1C[C@H](C)CN1C[C@@H](C)O[C@@H](C)C1 MQHLMHIZUIDKOO-OKZBNKHCSA-N 0.000 description 1
- 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
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 1
- MBRHNTMUYWQHMR-UHFFFAOYSA-N 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one Chemical compound NCCO.ON1C(=O)C=C(C)C=C1C1CCCCC1 MBRHNTMUYWQHMR-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229940124091 Keratolytic Drugs 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010066901 Treatment failure Diseases 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229960003204 amorolfine Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229940027011 bifonazole / urea Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960004375 ciclopirox olamine Drugs 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 229960004884 fluconazole Drugs 0.000 description 1
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004130 itraconazole Drugs 0.000 description 1
- 230000001530 keratinolytic effect Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 208000026721 nail disease Diseases 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940024986 topical antifungal imidazole and triazole derivative Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q3/00—Manicure or pedicure preparations
- A61Q3/02—Nail coatings
Definitions
- the present invention relates to a nail varnish having antimycotic activity.
- Nail conditions due to fungi are stubborn forms of disease that have so far been unable to be satisfactorily treated.
- fungi onychomycosis
- Various types of nail fungus are grouped under the name of onychomycosis, including those caused by dermatophytes which are the most difficult to treat, while nail fungus caused by yeast has so far been easier to treat. .
- Various routes have been used for the treatment of these yeast infections, but with little success.
- the systemic method which consists of the administration of antifungal agents by the oral route, is a long-term treatment, which can lead to side effects and to the selection of resistant strains.
- the antimycotic molecules used for the oral route are itraconazole, terbinafine and fluconazole (Effendy I. Therapeutic strategies in onychomycosis. Journal of the European Academy of Dermatology and Venereology. 1995, S3-S10). Nail removal by surgery or by chemical action is a very aggressive which gives no guarantee that the nails will grow back in their normal form; on the contrary, the regrowing nails are frequently deformed. Local treatment of the nails with specific substances with antimycotic action has also been envisaged.
- varnishes have the advantage of being easy to apply and of forming a water-insoluble film on the surface of the nail allowing the release of the antimycotic agent within the nail.
- the antimycotic molecules formulated in these nail varnish bases are amorolfine, ciclopiroxolamine and the bifonazole / urea combination (De Chauvin MF, Baran R. and Charasse D. Onychomycosis. III: treatment. Journal de Mycologie Médicale, 2001, 11 (4), 205-215; Fleckman P. Onychomycosis: diagnosis and topical therapy. Dermatologie Therapy, 2002, 15 (2), 71-77).
- Patent EP 855 397 describes antimycotic agents which contain, as active substances, azole derivatives, in particular imidazole and triazole derivatives. These antimycotic agents can be applied in the form of a film soluble in water, manifest a deposition effect and allow a short-term treatment. They are suitable for the treatment of nail fungus and can be used both in solutions and in aerosols which form, after drying, a water-soluble film. The use of such binders in water obviously has the effect that the agent applied is more or less eliminated with each toilet. To facilitate the penetration of antimycotics through the nail, these varnishes often contain keratolytic substances such as urea.
- EP 226 984 describes a nail varnish comprising a film-forming agent insoluble in water and an antimycotic agent.
- the varnish may contain urea but the amount of urea is not specified.
- Application EP 1 138 314 discloses an extended-release film-forming composition for nail varnish comprising an antifungal agent, urea, a humectant such as glycerol or sorbitol, water, a film-forming agent and a solvent comprising minus a volatile component.
- the joint use of urea and glycerol improves the cross-nail passage of the antifungal molecule and the presence of glycerol allows urea to be used at concentrations of less than 1% relative to the total weight of the composition.
- German application DE 10061801 describes a pharmaceutical composition which contains a hydrophilic film-forming agent, water and urea.
- the hydrophilic film-forming agent is polyvinylpyrrolidone in concentrations of 15-25% by weight. Urea is present at a very high concentration, more particularly 75-85% by weight.
- US Patent 5,346,692 describes a nail polish formulation for treating onychomycosis which contains a film-forming agent, an antimycotic agent, urea and a very specific mixture of solvents; the formulations contain a high proportion of urea, preferably 15 to 60% relative to the non-volatile compounds.
- the present invention provides a nail varnish to treat onychomycosis, capable of being applied topically to the infected region of the nail in the form of a film, which allows good release of the active principle and good diffusion of this active principle over the infected regions without attacking the healthy regions of the nail and which contains a small amount of an absorption-promoting agent, preferably urea, despite the absence of a humectant.
- the subject of the invention is therefore a nail varnish with antimycotic action containing: a) 2 to 80% by weight relative to the amount of volatile compounds of at least one l-hydroxy-2-pyridone of general formula ( I)
- RI represents either a straight or branched alkyl group having from 6 to 9 carbon atoms, or a cycloalkyl group having from 3 to 6 carbon atoms
- one of the substituents R2 and R4 represents a hydrogen atom and the other represents a hydrogen atom or a group chosen from methyl and ethyl groups
- R3 represents a straight or branched alkyl group having from 1 to 2 carbon atoms, in free form or in salt form physiologically acceptable, as a substance with antimycotic action
- the nail varnish is characterized in that the active substance with antimycotic action corresponds to formula (I) in which R2 and R4 are each a hydrogen atom.
- the nail varnish contains an active substance with antimycotic action corresponding to formula (I) in which RI represents a cycloalkyl group having 3 to 6 carbon atoms, preferably a group -CH 2 -CH (CH 3 ) -CH 2 -C (CH 3 ) 3 , or a cyclohexyl group.
- the absorption promoter is urea.
- the nail varnish according to the invention relative to the amount of the non-volatile components, that is to say to the sum of the film-forming agents, pigments possibly present, plasticizers and other non-volatile additives, as well as the active substance, this one is generally contained in an amount going from 2 to 80, preferably from 10 to 60 and in particular from 20 to 40% in weight.
- the active substance is contained in an amount ranging from 0.5 to 20, preferably from 2 to 15% by weight relative to the amount of non-volatile components.
- the nail varnishes according to the invention additionally contain, as essential components, one or more film-forming agents which form on the nail after the preparation has dried, a film insoluble in water.
- film-forming agents are chosen from the group comprising acrylic / methacrylic copolymers, polymethacrylate / butyl acrylate, acrylic / acrylate copolymers, polyvinyl alcohol, polyvinylpyrrolidones, polyvinylpyrrolidones / vinyl acetates and vinylpyrrolidones / dimethylaminoethyl methacrylates. It is known that the combination of solvents is of paramount importance for the drying time, the ease of application with a brush and other important properties of the varnish or of the varnish film.
- the solvent system preferably consists of an optimal mixture of solvents with a low boiling point (less than 100 ° C.) and solvents with a medium boiling point (between 100 and up to 150 ° C); possibly with a small proportion of high boiling point solvents (between 150 and up to 200 ° C).
- Water / ethanol, water / isopropyl alcohol or water / butanol mixtures will preferably be chosen as solvent in ratios ranging from 10/90 to 30/70, ratios taking account of the solubility of the active substance and of the film-forming agent chosen.
- the nail varnishes according to the invention can also contain additives commonly used in cosmetics, such as plasticizers based on phthalate, camphor or urea, colorants or colored pigments, pearlescent agents, sedimentation retardants , sulfonamide resins, silicates, perfumes, wetting agents such as sodium dioctylsulfosuccinate, lanolin derivatives, light protection agents such as 2-hydroxy-4-methoxy-benzophenone, substances with antibacterial action .
- the difficulty in carrying out this invention consisted in choosing film-forming agents which are insoluble in water, but soluble in the water / alcohol mixture so that, after drying, the film formed on the nail is insoluble in water. and therefore can resist the action of the toilet.
- the nail varnish according to the invention is also suitable for the prophylactic use against fungal infections of the nail, a sufficiently large deposit of active substance which can be obtained in the nail so that, in the case of fungal contamination, does not notice the appearance of a nail disease caused by fungi.
- the nail polish according to the invention it is possible to achieve a radical cure in the treatment of nail fungus, the nails usually repelling without deformation.
- the present invention is illustrated in more detail with the aid of the following examples.
- Procedure The activity of the compounds used according to the invention has been demonstrated by penetration tests on ox horn. These ox horns were cut so as to obtain keratin disks with a diameter close to 1 cm and a thickness standardized to 0.6 mm. These keratin discs were seeded by a dermatophyte (Trichophyton mentagrophytes). After about 30 days, these dermatophytes have completely colonized the horn discs, both on the surface than in the middle of the substrate, perfectly mimicking the nail fungus phenomenon.
- a dermatophyte Trichophyton mentagrophytes
- compositions according to the invention differ from preparations of the prior art known for the treatment of nails, in that 168 superficial horny layers allow the active substances contained in these preparations to pass in considerable proportion, and that these compositions according to the invention thus exert a lasting action at effective depth.
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)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0309303 | 2003-07-29 | ||
| PCT/FR2004/002019 WO2005011565A2 (fr) | 2003-07-29 | 2004-07-28 | Vernis a ongles a action antimycosique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1648378A2 true EP1648378A2 (de) | 2006-04-26 |
Family
ID=34112705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP04767801A Withdrawn EP1648378A2 (de) | 2003-07-29 | 2004-07-28 | Antimykotischer nagellack |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20060280703A1 (de) |
| EP (1) | EP1648378A2 (de) |
| CA (1) | CA2533720A1 (de) |
| WO (1) | WO2005011565A2 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2892023B1 (fr) * | 2005-10-14 | 2009-09-25 | Galderma Sa | Composition pharmaceutique a base d'amorolfine et d'agent filmogene hydrosoluble pour application ungueale et peri-ungueale |
| FR2937250B1 (fr) * | 2008-10-21 | 2013-05-10 | Fabre Pierre Dermo Cosmetique | Solution filmogene a base d'uree pour le traitement du psorasis de l'ongle |
| US8697753B1 (en) | 2013-02-07 | 2014-04-15 | Polichem Sa | Method of treating onychomycosis |
| KR101580077B1 (ko) * | 2015-03-28 | 2015-12-24 | 한국콜마주식회사 | 시크로피록스 함유 네일락카 조성물 |
| WO2019084293A1 (en) * | 2017-10-25 | 2019-05-02 | Arizona Board Of Regents On Behalf Of The University Of Arizona | COMPOSITIONS AND METHODS FOR ADMINISTERING PHARMACEUTICAL AGENTS |
| CN111279008A (zh) * | 2017-10-27 | 2020-06-12 | 天纳克有限责任公司 | 具有动态热障涂层的内燃机部件以及这种涂层的制造和使用方法 |
| ES2976036B2 (es) * | 2024-03-06 | 2025-08-05 | Univ Madrid Complutense | Potenciación de la acumulación intraungueal de principios activos |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3544983A1 (de) * | 1985-12-19 | 1987-06-25 | Hoechst Ag | Antimykotisch wirksamer nagellack |
| DE4212105A1 (de) * | 1992-04-10 | 1993-10-14 | Roehm Pharma Gmbh | Nagellack zur Behandlung von Onychomykosen |
| WO1997009960A1 (en) * | 1995-09-14 | 1997-03-20 | Sorenson Pharmaceutical, Inc. | Composition and method for treating diseased nails |
| DE50012415D1 (de) * | 2000-01-03 | 2006-05-11 | Karl Kraemer | Zubereitungen zur atraumatischen nagelentfernung |
| US6495124B1 (en) * | 2000-02-14 | 2002-12-17 | Macrochem Corporation | Antifungal nail lacquer and method using same |
-
2004
- 2004-07-28 WO PCT/FR2004/002019 patent/WO2005011565A2/fr not_active Ceased
- 2004-07-28 EP EP04767801A patent/EP1648378A2/de not_active Withdrawn
- 2004-07-28 US US10/565,936 patent/US20060280703A1/en not_active Abandoned
- 2004-07-28 CA CA002533720A patent/CA2533720A1/fr not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005011565A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005011565A2 (fr) | 2005-02-10 |
| US20060280703A1 (en) | 2006-12-14 |
| CA2533720A1 (fr) | 2005-02-10 |
| WO2005011565A3 (fr) | 2005-03-31 |
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