US20040039030A1 - Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis - Google Patents

Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis Download PDF

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US20040039030A1
US20040039030A1 US10606229 US60622903A US2004039030A1 US 20040039030 A1 US20040039030 A1 US 20040039030A1 US 10606229 US10606229 US 10606229 US 60622903 A US60622903 A US 60622903A US 2004039030 A1 US2004039030 A1 US 2004039030A1
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pyridone
methyl
example
alkyl
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Manfred Bohn
Karl Kraemer
Astrid Markus
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Medicis Pharmaceutical Corp
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Hoechst AG
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/006Antidandruff preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4412Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/852Dandruff
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/857Dermatitis
    • Y10S514/861Eczema
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/857Dermatitis
    • Y10S514/863Psoriasis
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/857Dermatitis
    • Y10S514/864Seborrhea
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/88Hair treatment, application to head or scalp
    • Y10S514/881Shampoo

Abstract

Compounds of the formula (I) are disclosed and are suitable for the treatment of seborrheic dermatitis.
Figure US20040039030A1-20040226-C00001

Description

  • [0001]
    Seborrheic dermatitis is understood as meaning a disorder of the scalp which differs from simple dandruff by the presence of erythema as a sign of inflammation, by the greater degree of scaling with occasional itching and burning, and by the occurrence of eczematous changes to other body sites. It can occur in the form of patches, but also more frequently affects the whole scalp and often includes, beyond the hairline, the forehead, around the neck and the ears. In severe cases, the scalp can have a secondary infection, and the changes can then exhibit a spongy consistency, vesicle and crust formation and can weep.
  • [0002]
    Seborrheic dermatitis frequently occurs even in infancy and usually remits spontaneously at an age of 8-12 months. The scalp changes consisting of erythema, scaling and occasionally vesicles and crusts in infants can regress spontaneously within a few weeks, intermittently reoccur or persist during the entire childhood. They are frequently combined with a similar. process around the eyelids, nose and ears. Later, the condition usually occurs after puberty and can last for the whole life or even increase in strength. Approximately 1-3% of the population are affected by this illness.
  • [0003]
    It is known that 1-hydroxy-2-pyridones and their salts exhibit activity against normal dandruff which is characterized by a clinically noninflammatory scaling of the scalp occurring in nearly all people (DE 22 34 009).
  • [0004]
    The most promising type of treatment of seborrheic dermatitis until now was the topical application of corticosteroid preparations, but more recently topical therapy with antimycotic substances has gained importance.
  • [0005]
    While corticosteroid preparations display their activity exclusively via an effect on the inflammatory process, the antimycotic substances such as ketoconazole are active exclusively against the yeast fungi of the strain Pityrosporum which is assumed to be the cause of seborrheic dermatitis. The 1-hydroxy-2-pyridones according to the invention, however, combine the properties of both classes of substance in one substance and exhibit both antiinflammatory action and antimycotic activity against Pityrosporum strains.
  • [0006]
    In comparison to ketoconazole, the substances according to the invention —even afteronly a short topical contact time—concentrate rapidly in the skin layers which are relevant for fungal growth and thus contribute to a rapid cure.
  • [0007]
    While ketoconazole is inactive in vitro against gram-positive bacteria (Kinsman et al., J. Med. Microbiol. (1983) 16, No. 2, IV), the hydroxy-pyridones according to the invention exhibit activity against gram-positive and gram-negative aerobic and anaerobic bacteria (Dittmar et al., Arzneim.-Forschung, (1981) 31 (11), No. 8a, pp. 1317-1322). With respect to the treatment of secondarily infected cases, this is an extremely important finding.
  • [0008]
    Compared with ketoconazole, the compounds used according to the invention furthermore have very crucial. advantages with respect to their processing possibilities in pharmaceutical preparations. On account of their solubility in water, alcohols and aqueous-alcoholic solutions, the preparation of hair lotions and transparent gel preparations is possible without problems.
  • [0009]
    The preparations according to the invention can also be employed for the treatment of Pityriasis versicolor, a superficial, noninflammatory skin fungus disorder on the trunk.
  • [0010]
    The invention therefore relates to the use of 1-hydroxy-2-pyridones of the formula I
    Figure US20040039030A1-20040226-C00002
  • [0011]
    in which R1, R2 and R3, which are identical or different, are a hydrogen atom or alkyl having 1-4 carbon atoms, and
  • [0012]
    R4 is a saturated hydrocarbon radical having 6 to 9 carbon atoms or a radical of the formula II
    Figure US20040039030A1-20040226-C00003
  • [0013]
    where
  • [0014]
    X is S or O,
  • [0015]
    Y is a hydrogen atom or up to 2 halogen atoms such as chlorine and/or bromine,
  • [0016]
    Z is a single bond or the bivalent radicals O, S, —CR2—(R═H or (C1-C4)-alkyl) or other bivalent radicals having 2-10 carbon and, if appropriate, oxygen and/or sulfur atoms linked in the form of a chain, where—if the radicals contain 2 or more oxygen and/or sulfur atoms—the latter must be separated from one another by at least 2 carbon atoms and where 2 adjacent carbon atoms can also be linked to one another by a double bond and the free valences of the carbon atoms are saturated by H and/or (C1-C4)-alkyl groups,
  • [0017]
    Ar is an aromatic ring system having up to two rings which can be substituted by up to three radicals from the group consisting of fluorine, chlorine, bromine, methoxy, (C1-C4)-alkyl, trifluoromethyl and trifluoromethoxy, in free or in salt form,
  • [0018]
    for the production of a pharmaceutical for the treatment of seborrheic dermatitis.
  • [0019]
    In the radicals “Z”, the carbon chain members are preferably CH2 groups. If the CH2 groups are substituted by C1-C4-alkyl groups, CH3 and C2H5 are preferred substituents. Exemplary radicals “Z” are:
  • [0020]
    —O—, —S—, —CH2—, —(CH2)m—(m=2-10), —C(CH3)2—, —CH2O—, —OCH2—, —CH2S—, —SCH2—, —SCH(C2H5)—, —CH═CH—CH2O—, —O—CH2—CH═CH—CH2O—, —OCH2—CH2O—, —OCH2—CH2CH2O—, —SCH2CH2CH2S—, —SCH2CH2CH2CH2O—, —SCH2CH2OCH2CH2O —, —SCH2CH2OCH2CH2O —CH2CH2S— or —S—CH2—C(CH3)2—CH2—S—.
  • [0021]
    The radical “S” is a sulfur atom, the radical “O” is an oxygen atom. The term “Ar” denotes phenyl or fused systems such as naphthyl, tetrahydro- naphthyl and indenyl, and also isolated systems as such, which are derived from biphenyl, diphenylalkanes, diphenyl ethers and diphenyl thioethers.
  • [0022]
    In the formula I, the hydrocarbon radial R4 is an alkyl or cyclohexyl radical which can also be bonded to the pyridone ring via a methylene or ethylene group or can contain an endomethyl group. R4 can also be an aromatic radical which, however, is preferably bonded to the pyridone radical via at least one aliphatic carbon atom.
  • [0023]
    Important representatives of the class of compounds characterized by the formula I are:
  • [0024]
    6-[4-(4-chlorophenoxy)phenoxymethyl]-1-hydroxy-4-methyl-2-pyridone, 6-[4-(2,4-dichlorophenoxy)phenoxymethyl]-1-hydroxy4-methyl-2-pyridone, 6-(biphenyl4-oxymethyl)-1-hydroxy4-methyl-2-pyridone, 6-(4-benzyl-phenoxymethyl)-1-hydroxy4-methyl-2-pyridone, 6-[4-(2,4-dichlorobenzyl-oxy)phenoxymethyl]-1-hydroxy4-methyl-2-pyridone, 6-[4-(4-chloro-phenoxy)phenoxymethyl]-1-hydroxy-3,4-dimethyl-2-pyridone, 6-[4-(2,4-dichlorobenzyl)phenoxymethyl]-1-hydroxy-3,4-dimethyl-2-pyridone, 6-[4-cinnamyloxy)phenoxymethyl]-1-hydroxy4-methyl-2-pyridone, 1-hydroxy4-methyl-6-[4-(4-trifluoromethylphenoxy)phenoxymethyl]-2-pyridone, 1hydroxy-4-methyl-6-cyclohexyl-2-pyridone, 1-hydroxy4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone, 1-hydroxy4-methyl-6-n-hexyl-, -6-iso-hexyl-, -6-n-heptyl- or -6-isoheptyl-2-pyridone, 1-hydroxy4-methyl-6-octyl- or -6-isooctyl-2-pyridone, in particular 1-hydroxy4-methyl-6-cyclohexyl-methyl- or -6-cyclohexylethyl-2-pyridone, where the cyclohexyl radical can in each case also carry a methyl radical, 1-hydroxy4-methyl-6-(2-bicyclo-[2,2,1]heptyl)-2-pyridone, 1-hydroxy-3,4-dimethyl-6-benzyl- or -6-dimethyl-benzyl-2-pyridone or 1-hydroxy4-methyl-6-(β-phenylethyl)-2-pyridone.
  • [0025]
    The term “saturated” in this case designates those radicals which contain no aliphatic multiple bonds, i.e. no ethylenic or acetylenic bonds.
  • [0026]
    The abovementioned compounds of the formula I can be employed either in free form or as salts, use in free form is preferred.
  • [0027]
    If organic bases are used, poorly volatile bases are preferably employed, for example low molecular weight alkanolamines such as ethanolamine, diethanolamine, N-ethylethanolamine, N-methyidiethanolamine, triethanol-amine, diethylaminoethanol, 2-amino-2-methyl-n-propanol, dimethylamino-propanol, 2-amino-2-methylpropanediol, triisopropanolamine. Further poorly volatile bases which may be mentioned are, for example, ethylenediamine, hexamethylenediamine, morpholine, piperidine, piperazine, cyclohexylamine, tributylamine, dodecylamine, N,N-dimethyldodecylamine, stearylamine, oleylamine, benzylamine, dibenzylamine, N-ethylbenzylamine, dimethylstearylamine, N-methylmorpholine, N-methylpiperazine, 4-methylcyclohexylamine, N-hydroxyethylmorpholine. The salts of quaternary ammonium hydroxides such as trimethylbenzylammonium hydroxide, tetramethylammonium hydroxide or tetraethylammonium hydroxide can also be used, furthermore guanidine and its derivatives, in particular its alkylation products. However, it is also possible to employ as salt-forming agents, for example, low molecular weight alkylamines such as methylamine, ethylamine or triethylamine. Suitable salts for the compounds to be employed according to the invention are also those with inorganic cations, for example alkali metal salts, in particular sodium, potassium or ammonium salts, alkaline earth metal salts such as, in particular, the magnesium or calcium salts, as well as salts with bi- or tetravalent cations, for example the zinc, aluminum or zirconium salt.
  • [0028]
    The active compounds to be employed in the preparations of the compound of the formula I can be prepared, for example, according to processes given in U.S. Pat. No. 2,540,218.
  • [0029]
    For the use according to the invention of the compounds mentioned, liquid to semisolid pharmaceutical preparations, in particular hair lotions, shampoos, liquid soaps, as well as cream, ointment and gel preparations, are suitable.
  • [0030]
    In this case, these are always preparations which, depending on their actual intended use, are applied to the skin and/or to the scalp for a shorter or longer time. Due to the addition of the compounds according to the invention, an effective treatment of the seborrheic dermatitis is brought about.
  • [0031]
    If the preparations according to the invention are present as shampoo, they can be in clear liquid or opaque liquid form, in cream form or even gelatinous. The surfactants on which these shampoos are based can be of anionic, cationic, nonionic or amphoteric nature and can also be present as a combination of these substances.
  • [0032]
    Preferably, however, anionic surfactants are employed on their own or as a mixture with other anionic surfactants as base surfactants - if appropriate with addition of amphoteric surfactants as cosurfactant.
  • [0033]
    As the sole detergent substances, amphoteric surfactants are virtually insignificant, since their foaming behavior, thickenability and partly also skin and eye mucous membrane tolerability are only moderate. In combination with various anionic surfactants, however, precisely these properties are synergistically improved. This explains the relatively great importance of the amphoteric surfactants for the optimization of anionic shampoo bases.
  • [0034]
    Nonionic surfactants can also be employed as cosurfactants.
  • [0035]
    Examples of anionic detergent substances of this type which may be mentioned are: (C10-C20)-alkyl- and -alkylenecarboxylates, alkyl ether carboxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, alkylol-amide sulfates and sulfonates, fatty acid alkylamide polyglycol ether sulfates, alkanesulfonates and hydroxyalkanesulfonates, olefinsulfonates, acyl esters of isothionates, α-sulfofatty acid esters, alkylbenzosulfonates, alkylphenol glycol ether sulfonates, sulfosuccinates, sulfosuccinic acid hemiesters and diesters, fatty alcohol ether phosphates, protein-fatty acid condensation products, alkylmonoglyceride sulfates and sulfonates, alkylglyceride ether sulfonates, fatty acid methyltaurides, fatty acid sarcosinates or sulforicinoleates. These compounds and their mixtures are used in the form of their water-soluble or water-dispersible salts, for example the sodium, potassium, magnesium, ammonium, mono-, di- and triethanolammonium as well as analogous alkylolammonium salts.
  • [0036]
    Examples of amphoteric surfactants which can be added to the shampoos are: N-((C12-C18)-alkyl)-β-aminopropionates and N-((C12-C18)-alkyl)-β-iminodipropionates as alkali metal and mono-, di- and trialkylol-ammonium salts; N-acylamidoalkyl-N,N-dimethylacetobetaine, preferably N-((C8-C18)-acyl)amidopropyl-N,N-dimethylacetobetaine; (C12-C18)-alkyl-dimethylsulfopropylbetaine; amphoteric surfactants based on imidazoline (trade name: Miranol®, Steinapon®), preferably the sodium salt of 1-(β-carboxymethyloxyethyl)-1-(carboxymethyl)-2-laurylimidazolinium; amine oxides, e.g. (C12-C18)-alkyldimethylamine oxide or fatty acid amidoalkyldimethylamine oxide.
  • [0037]
    Suitable nonionic surfactants which can be employed as detergent substances are, for example: fatty alcohol ethoxylates (alkyl polyethylene glycols); alkylphenol polyethylene glycols; alkylmercaptan. polyethylene glycols; fatty amine ethoxylates (alkylamino polyethylene glycols); fatty acid ethoxylates (acyl polyethylene glycols), polypropylene glycol ethoxylates (Pluronic®); fatty acid alkylolamides (fatty acid amide polyethylene glycols); sucrose esters; alkyl polyglucosides; sorbitol esters and polyglycol ether.
  • [0038]
    Suitable cationic surfactants are, for example, quaternary ammonium salts such as di-((C10-C24)-alkyl)dimethylammonium chloride or bromide, preferably di-((C12-C18)-alkyl)dimethylammonium choride or bromide; (C10-C24)-alkyldimethylethylammonium chloride or bromide; (C10-C24)-alkyltrimethylammonium chloride or bromide, preferably cetyltrimethyl-ammonium chloride or bromide and (C20-C22)-alkyltrimethylammonium chloride or bromide; (C10-C24)-alkyldimethylbenzylammonium chloride or bromide; preferably (C12-C18)-alkyldimethylbenzylammonium chloride; N-((C10-C18)-alkyl)pyridinium chloride or bromide, preferably N-((C12-C16)-alkyl)pyridinium chloride or bromide; N-((C10-C18)-alkyl)isoquinolinium chloride, bromide or monoalkylsulfate; N-((C12-C18)-alkylolaminoformyl-methyl)pyridinium chloride; N-((C12-C18)-alkyl)-N-methylmorpholinium chloride, bromide or monoalkylsulfate, N-((C12-C18)-alkyl)-N-ethyl-morpholinium chloride, bromide or monoalkylsulfate; (C16-C18)-alkyl-pentaoxethylammonium chloride; diisobutylphenoxyethoxyethyldimethyl-benzylammonium chloride; salts of N,N-diethylaminoethylstearylamide and -oleylamide with hydrochloric acid, acetic acid, lactic acid, citric acid, phosphoric acid; N-acylamidoethyl-N,N-diethyl-N-methylammonium chloride, bromide or monoalkylsulfate and N-acylamidoethyl-N,N-diethyl-N-benzylammonium chloride, bromide or monoalkylsulfate, where acyl is preferably stearyl or oleyl.
  • [0039]
    The preparations according to the invention can additionally contain further additives, e.g. aromatic substances, cblorants, opacifiers and pearl luster agents, for example esters of fatty acids and polyols, magnesium and zinc salts of fatty acids, dispersions based on copolymers, thickeners such as sodium, potassium or ammonium chloride, sodium sulfate, fatty acid alkylolamides, cellulose derivatives of natural gums, collagen hydrolyzates, furthermore fats, oils, fatty alcohols, silicones, substances having a keratolytic and keratoplastic action. for example sulfur, salicylic acid or enzymes.
  • [0040]
    The shampoos are prepared in a manner known per se by mixing together of the individual components and a further processing—if necessary —suited to the particular type of preparation. Some of these various possible preparations are described by way of example in the working examples.
  • [0041]
    The preparations according to the invention can also be present in the form of aqueous and aqueous-alcoholic hair lotions, and also those in gel form and in aerosol form as spray or foam. Alcohols employed are preferably ethanol and isopropyl alcohol.
  • [0042]
    Further preparations which may be mentioned in which the 1-hydroxy-2-pyridones can be used according to the invention are, for example, cream and ointment preparations, products which are primarily used for the treatment of hairless head and body parts.
  • [0043]
    The preparation of all these preparations is also carried out—as already mentioned in the case of shampoo—in a manner known per se with addition of the active compound employed according to the invention. Of the abovementioned 1-hydroxy-2-pyridones, the preparations according to the invention can contain one compound or even several in combination.
  • [0044]
    The pH of the preparations is in the skin-physiological range of approximately pH 4.5 to 6.5. Whereas, when using the compounds in salt form, the adjustment of the pH range mentioned has to be carried out using organic acids, this measure is not necessary when using the free compounds.
  • [0045]
    In the preparations according to the invention, the active compounds is incorporated in amounts which are customarily between approximately 0.05 and approximately 10%. Within this range, the concentrations of the specific preparations depend on their intended use. Certain preparation forms such as concentrates, which are to be diluted before use, can have considerably higher concentrations.
  • [0046]
    If they are preparations which remain on the skin and on the scalp, for example gel preparations, ointments, creams or hair lotions, lower concentrations will be employed, for example from about 0.05% to about 1%, preferably from 0.1 to 0.5%. In higher concentrations, they will expediently be used when they are preparations which, optionally after dilution, only act on the scalp for a short time, for example shampoos or liquid soaps. In these cases, for example, concentrations of approximately 0.2 to approxi- mately 10%, preferably from approximately 0.5% to approximately 2%, can be expedient.
  • [0047]
    The following quantitative data relate to the weight, if not stated otherwise.
  • EXAMPLE 1
  • [0048]
    A preparation according to the invention has the following composition:
  • [0049]
    Shampoo (based on anionic detergent substances)
    1-Hydroxy-4-methyl-6-cyclohexyl-2(1H)pyridone  1.00%
    Sodium lauryl diglycol ether sulfate (27% strength solution) 40.00%
    Disodium lauryl polyglycol ether sulfosuccinate (33% strength 10.00%
    solution)
    Sodium chloride  2.50%
    Water 46.50%
  • EXAMPLE 2
  • [0050]
    A preparation according to the invention has the following composition:
  • [0051]
    Shampoo (based on anionic detergent substance with amphoteric surfactant as cosurfactant)
    1-Hydroxy-4-methyl-6-cyclohexyl-2(1H)pyridone  1.00%
    Sodium lauryl diglycol ether sulfate (27% strength solution) 36.00%
    Cocamidopropylbetaine (30% strength solution)  6.00%
    Sodium chloride  3.30%
    Water 53.70%
  • EXAMPLE 3
  • [0052]
    A preparation according to the invention has the following composition:
  • [0053]
    Shampoo (based on anionic detergent substance with nonionic surfactant as cosurfactant)
    1-Hydroxy-4-methyl-6-cyclohexyl-2(1H)pyridone  1.50%
    Sodium lauryl diglycol ether sulfate (27% strength solution) 30.00%
    Lauryl alcohol polyglucoside  8.00%
    Sodium chloride  2.00%
    Water 58.50%
  • EXAMPLE 4
  • [0054]
    A preparation according to the invention has the following composition:
  • [0055]
    Liquid soap
    1-Hydroxy-4-methyl-6-cyclohexyl-2(1H)pyridone  1.00%
    Sodium lauryl diglycol ether sulfate (27% strength solution) 35.00%
    Cocamidopolyglycol ether sulfate magnesium salt (30% strength  8.00%
    solution)
    Cocamidopropylbetaine (30% strength solution) 10.00%
    Lauryl alcohol glycol ether  2.00%
    Sodium chloride  2.00%
    Water 42.00%
  • EXAMPLE 5
  • [0056]
    A preparation according to the invention has the following composition:
  • [0057]
    Hair lotion
    1-Hydroxy-4-methyl-6-[4-(4-chlorophenoxy)phenoxymethyl]-  0.05%
    2(1H)pyridone
    2-Propanol 60.00%
    Water 39.95%
  • EXAMPLE 6
  • [0058]
    A preparation according to the invention has the following composition:
  • [0059]
    Gel preparation
    1-Hydroxy-4-methyl-6-cyclohexyl-2(1H)pyridone  0.75%
    2-Propanol 15.00%
    2-Octyldodecanol  7.50%
    Carbomer 4,000,000  0.50%
    Polysorbate 60  1.50%
    Sodium hydroxide  0.18%
    Water 74.57%
  • EXAMPLE 7
  • [0060]
    A preparation according to the invention has the following composition:
  • [0061]
    Cream preparation
    1-Hydroxy-4-methyl-6-cyclohexyl-2(1H)-pyridone,  1.00%
    aminoethatnol salt 1:1
    2-Octyldodecanol  7.50%
    Liquid paraffin  7.50%
    Stearyl alcohol  7.50%
    Cetyl alcohol  7.50%
    Polysorbate 60  3.00%
    Sorbitan monostearate  2.00%
    Lactic acid, 90% strength  0.51%
    Water 63.49%
  • EXAMPLE 8
  • [0062]
    In a clinical study with a total of 180 patients, it was possible to show that the symptoms of seborrheic dermatitis of the scalp (severe scaling, inflammation, itching) can be effectively treated by a 1-2×weekly treatment with a 1% strength ciclopirox shampoo preparation over a period of 4 weeks.
  • EXAMPLE 9
  • [0063]
    In a clinical study, it was possible to successfully treat 180 patients with seborrheic dermatitis of the scalp, of the face and of the upper body by application of a 0.77% strength ciclopirox gel preparation over a period of 4 weeks.

Claims (13)

  1. 1. The use of 1-hydroxy-2-pyridones of the formula I
    Figure US20040039030A1-20040226-C00004
    in which R1, R2 and R3, which are identical or different, are a hydrogen atom or alkyl having 1-4 carbon atoms, and
    R4 is a saturated hydrocarbon radical having 6 to 9 carbon atoms or a radical of the formula II
    Figure US20040039030A1-20040226-C00005
    where
    X is S or O,
    Y is a hydrogen atom or up to 2 halogen atoms such as chlorine and/or bromine,
    Z is a single bond or the bivalent radicals O, S, —CR2—(R═H or (C1-C4)-alkyl) or other bivalent radicals having 2-10 carbon and, if appropriate, oxygen and/or sulfur atoms linked in the form of a chain, where—if the radicals contain 2 or more oxygen and/or sulfur atoms—the latter must be separated from one another by at least 2 carbon atoms and where 2 adjacent carbon atoms can also be linked to one another by a double bond and the free valences of the carbon atoms are saturated by H and/or (C1-C4)-alkyl groups,
    Ar is an aromatic ring system having up to two rings which can be substituted by up to three radicals from the group consisting of fluorine, chlorine, bromine, methoxy, (C1-C4)-alkyl, trifluoromethyl and trifluoromethoxy, in free or in salt form, for the production of a pharmaceutical for the treatment of seborrheic dermatitis.
  2. 2. The use as claimed in claim 1, wherein the compound of the formula I is employed in which Ar is a bicyclic system which is derived from biphenyl, diphenylalkane or diphenyl ether.
  3. 3. The use as claimed in claim 1 or 2, wherein the compound of the formula I contains a cyclohexyl radical in the position R4.
  4. 4. The use as claimed in one or more of claims 1 to 3, wherein the compound of the formula I contains an octyl radical of the formula —CH2—CH(CH3)—CH2—C(CH3)3 in the position R4.
  5. 5. The use as claimed in claim 1, wherein 1-hydroxy-4-methyl-6-[4-(4-chlorophenoxy)phenoxymethyl]-2(1H)pyridone, 1-hydroxy-4-methyl-6-cyclohexyl-2(1H)pyridone or 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)pyridone is employed.
  6. 6. The use as claimed in one or more of claims 1 to 5, wherein the pharmaceutical is a hair lotion, shampoo or a cream, ointment or gel preparation.
  7. 7. The use as claimed in claim 6, wherein anionic, cationic, nonionic or amphoteric surfactants are employed on their own or as a mixture with other surfactants.
  8. 8. The use as claimed in claim 7, wherein the surfactant employed is at least one anionic surfactant on its own or as a mixture with other anionic surfactants and/or amphoteric surfactants.
  9. 9. The use as claimed in one or more of claims 1 to 8, wherein the pharmaceutical has a pH of 4.5 to 6.5.
  10. 10. A pharmaceutical preparation comprising a 1-hydroxy-2-pyridone of the formula I as claimed in claim 1 and at least one anionic, cationic, nonionic or amphoteric surfactant or a mixture of these surfactants.
  11. 11. A pharmaceutical preparation as claimed in claim 10, wherein the surfactant employed is at least one anionic surfactant on its own or as a mixture with other anionic surfactants and/or amphoteric surfactants.
  12. 12. A pharmaceutical preparation as claimed in claim 10 or 11, wherein the preparation has a pH of 4.5 to 6.5.
  13. 13. A pharmaceutical preparation as claimed in one or more of claims 10 to 12, wherein the 1-hydroxy-2-pyridone of the formula I is employed in a concentration of 0.2% to 10%, preferably of 0.5% to 2%.
US10606229 1996-09-27 2003-06-26 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis Abandoned US20040039030A1 (en)

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DE1996139818 DE19639818A1 (en) 1996-09-27 1996-09-27 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US7719498 true 1998-12-04 1998-12-04
US10606229 US20040039030A1 (en) 1996-09-27 2003-06-26 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis

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US10606229 US20040039030A1 (en) 1996-09-27 2003-06-26 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US12563774 US20110112150A2 (en) 1996-09-27 2009-09-21 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US13018417 US7981909B2 (en) 1996-09-27 2011-01-31 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US13177710 US8227490B2 (en) 1996-09-27 2011-07-07 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US13555352 US20120329835A1 (en) 1996-09-27 2012-07-23 Use of 1-hydroxy-2- pyridones for the treatment of seborrheic dermatitis

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US7719498 Division 1998-12-04 1998-12-04

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US13018417 Expired - Lifetime US7981909B2 (en) 1996-09-27 2011-01-31 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US13177710 Expired - Lifetime US8227490B2 (en) 1996-09-27 2011-07-07 Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040081677A1 (en) * 1996-09-27 2004-04-29 Aventis Pharma Deutschland Gmbh. Antimycotic gel having high active compound release
US20060078577A1 (en) * 2004-10-08 2006-04-13 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
US20060078580A1 (en) * 2004-10-08 2006-04-13 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
US20110112153A1 (en) * 1996-09-27 2011-05-12 Manfred Bohn Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
WO2012075396A3 (en) * 2010-12-02 2012-12-27 The University Of Kansas Prodrugs of 6-cyclohexyl-1-hydroxy-4- methylpyridin-2(1h)-one and derivatives thereof

Citations (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3883545A (en) * 1968-08-31 1975-05-13 Hoechst Ag Certain 1-hydroxy-2-pyridones
US3968118A (en) * 1968-08-31 1976-07-06 Hoechst Aktiengesellschaft Process for the manufacture of 1-hydroxy-2-pyridones
US4185106A (en) * 1972-07-11 1980-01-22 Hoechst Aktiengesellschaft Pyridones as antidandruff agents
US4699924A (en) * 1983-02-01 1987-10-13 Lever Brothers Company Skin treatment composition
US4711775A (en) * 1972-07-11 1987-12-08 Hoechst Aktiengesellschaft Cosmetic compositions
US4797109A (en) * 1988-02-25 1989-01-10 Methode Electronics, Inc. Coiled wire interconnector
US4797409A (en) * 1986-04-18 1989-01-10 Hoechst Aktiengesellschaft 1-hydroxy-2-pyridones, a process for their preparation, and medicaments which contain them, and intermediates formed in the preparation of the 1-hydroxy-2-pyridones
US4957730A (en) * 1985-12-19 1990-09-18 Hoechst Aktiengesellschaft Antimycotic nail varnish
US5066484A (en) * 1990-04-30 1991-11-19 Revlon, Inc. Nail enamels containing glyceryl, glycol or citrate esters
US5071639A (en) * 1988-03-22 1991-12-10 Shiseido Company Ltd. Nail cosmetic composition
US5120530A (en) * 1989-02-24 1992-06-09 Hoffmann-La Roche Inc. Antimicotic nail varnish containing amorolfine in quaternary ammonium acrylic copolymer
US5132107A (en) * 1986-07-07 1992-07-21 Lange Bouke J Two-phase cleansing, conditioning and medicinal treatment shampoo
US5264206A (en) * 1987-06-16 1993-11-23 Hoechst Aktiengesellschaft Nail lacquer with antimycotic activity, and a process for the preparation thereof
US5346692A (en) * 1992-04-10 1994-09-13 Roehm Pharma Gmbh Nail lacquer for the treatment of onychomycosis
US5356907A (en) * 1989-10-17 1994-10-18 Roussel Uclaf 1-cycloalkylpyridones as analgesics
US5494658A (en) * 1993-01-05 1996-02-27 Hoechst Aktiengesellschaft Antidandruff agents and cosmetic preparations
US5495658A (en) * 1993-07-16 1996-03-05 Sanden Corp. Method of making cylindrical ferromagnetic body and cover assembly for rotor of DC motor
US5510100A (en) * 1993-06-10 1996-04-23 L'oreal Oil-in-water emulsions containing an auto-emulsifiable composition based on a fatty alcohol and on an alkyl polyoside and a co-emulsifying agent
US5603939A (en) * 1992-11-12 1997-02-18 L'oreal Film-forming cosmetic composition based on a chlorinated graft copolymer resulting from the grafting of a chlorinated polyolefin and acrylic, styrene and/or vinyl type unsaturated monomers
US5609854A (en) * 1995-06-06 1997-03-11 Elizabeth Arden Company, Division Of Conopco, Inc. Thickened and stabilized cosmetic emulsion compositions
US5612327A (en) * 1993-09-01 1997-03-18 Teijin Limited 1α,24-(OH)2 -cholecalciferol emulsion composition and method for treating psoriasis
US5650145A (en) * 1994-05-05 1997-07-22 L'oreal Dermatological/cosmetic compositions comprising antifungal and antibacterial compounds and reduction of hair loss therewith
US5675013A (en) * 1993-10-18 1997-10-07 Olin Corporation 1-hydroxy-6-substituted pyridine-2-ones and 1-hydroxy-6-substituted pyridine-2-thiones for biocidal use
US5683681A (en) * 1994-04-07 1997-11-04 L'oreal Cosmetic compositions for application to the nail
US5753600A (en) * 1989-10-09 1998-05-19 Kao Corporation Liquid detergent composition
US5756108A (en) * 1994-11-10 1998-05-26 L'oreal Oily phase in an aqueous phase dispersion stabilized by cubic gel particles and method of making
US5814322A (en) * 1994-07-11 1998-09-29 L'oreal Gelled cosmetic and/or dermatological composition which is rich in solvent and which contains hollow particles, and its applications
US5866105A (en) * 1991-05-23 1999-02-02 Novartis Ag Pharmaceutical composition
US6162420A (en) * 1993-05-18 2000-12-19 Hoechst Aktiengesellschaft Use of glyceryl triacetate for treating onychomycoses
US6455551B1 (en) * 1996-10-30 2002-09-24 Aventis Pharma Deutschland Gmbh Use of 1-hydroxy-2-pyridones for treating mucosa diseases which are difficult to treat
US6469033B1 (en) * 1996-09-27 2002-10-22 Aventis Pharma Deutschland Gmbh Use of 1-hydroxy-2-pyridones for the treatment of skin diseases
US6514490B2 (en) * 1997-04-14 2003-02-04 Janssen Pharmaceutica N.V. Compositions containing an antifungal and a cationic agent
US20030086881A1 (en) * 2000-03-09 2003-05-08 Aventis Pharma Deutschland Gmbh Antiinfective combinations and their use for the topical treatment of fungal infections of the toenails and fingernails
US20040081677A1 (en) * 1996-09-27 2004-04-29 Aventis Pharma Deutschland Gmbh. Antimycotic gel having high active compound release

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172149A (en) * 1978-01-30 1979-10-23 Westwood Pharmaceuticals, Inc. Method for treating living skin exhibiting excessive sebum secretion
JPS6040403B2 (en) 1979-11-02 1985-09-11 Ss Pharmaceutical Co
DE3140954A1 (en) 1981-10-15 1983-05-05 Hoechst Ag Use of 1-hydroxy-2-pyridones for the prophylaxis and treatment of acne
JPS63405B2 (en) 1981-12-26 1988-01-07 Lion Corp
US4948576A (en) 1983-02-18 1990-08-14 Johnson & Johnson Consumer Products, Inc. Detergent compositions
JPH0577648B2 (en) 1984-09-13 1993-10-27 Kao Corp
GB8523839D0 (en) * 1985-09-27 1985-10-30 Procter & Gamble Shampoo compositions
GB8524508D0 (en) 1985-10-04 1985-11-06 Beecham Group Plc Composition
DE3687458T2 (en) 1985-11-04 1993-07-29 Owen Galderma Lab Inc nails film forming arzneimitteltraeger for administration of medicines to
US5641475A (en) 1987-05-15 1997-06-24 Tristrata, Inc. Antiodor, antimicrobial and preservative compositions and methods of using same
LU86944A1 (en) 1987-07-17 1989-03-08 Oreal Composition based on derivatives of hydroxypyridone to reduce hair loss
LU86945A1 (en) 1987-07-17 1989-03-08 Oreal pharmaceutical and cosmetics has basic pyridones and antibacterial agents
GB8724285D0 (en) 1987-10-16 1987-11-18 Procter & Gamble Shampoo compositions
EP0496434B1 (en) 1987-10-22 1999-02-03 THE PROCTER & GAMBLE COMPANY Photoprotection compositions comprising chelating agents
DE3738405A1 (en) 1987-11-12 1989-05-24 Henkel Kgaa sebosuppressive preparations
DE3826914A1 (en) 1988-08-09 1990-02-15 Henkel Kgaa Color stabilization of antimicrobial preparations
US5116603A (en) 1989-01-31 1992-05-26 Yissum Research Development Company Of The Hebrew University Of Jerusalem Oral antifungal preventative, and method of use
FR2685638B1 (en) 1991-12-31 1995-04-21 Biorga Sa Laboratoires
FR2685867B1 (en) 1992-01-07 1995-06-09 Thorel Jean Compositions against peeling of the epidermis and scalp.
FR2694694B1 (en) 1992-08-13 1994-10-28 Thorel Jean Noel active composition for the treatment of psoriasis, especially scalp psoriasis.
JPH0680567A (en) 1992-09-01 1994-03-22 Kao Corp Agent for prevention and treatment of dandruff
DE69314656D1 (en) 1992-09-08 1997-11-20 Procter & Gamble Mild, substantially colorless shampoo composition
DE4336434A1 (en) 1993-10-26 1995-04-27 Hoechst Ag Pharmaceutical composition for parenteral, enteral and dermal administration of practically insoluble drugs and processes for their preparation
US5480904A (en) 1993-10-28 1996-01-02 Eli Lilly And Company Methods for inhibiting uterine fibrosis
JPH09510185A (en) 1993-12-23 1997-10-14 ザ、プロクター、エンド、ギャンブル、カンパニー Tissue Moisturizing and antimicrobial composition
JP3103274B2 (en) 1994-06-01 2000-10-30 花王株式会社 Sebum secretion inhibitor
FR2722689B1 (en) 1994-07-20 1996-10-04 Fabre Pierre Dermo Cosmetique New combination product comprising an antifungal agent and crotamiton as a potentiator of the activity of the antifungal agent, and dermatological compositions and / or cosmetics including the
US5696164A (en) 1994-12-22 1997-12-09 Johnson & Johnson Consumer Products, Inc. Antifungal treatment of nails
WO1996029056A1 (en) 1995-03-17 1996-09-26 Gebro Broschek Gmbh Topically applied pharmaceutical composition, method of preparing it and its use
US6075017A (en) * 1995-03-21 2000-06-13 Ramot University Authority For Applied Research And Industrial Development Ltd. Compositions for the treatment of dandruff
WO1996029045A1 (en) 1995-03-21 1996-09-26 Ramot University Authority For Applied Research And Industrial Development Ltd. Compositions for the treatment of dandruff
WO1997020560A1 (en) 1995-12-04 1997-06-12 Hoechst Aktiengesellschaft Use of 1-hydroxy-2-pyridones for treating mucosa diseases which are difficult to treat
US20040039030A1 (en) * 1996-09-27 2004-02-26 Hoechst Akeengesellschaft Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
EP0983037B1 (en) 1998-02-09 2003-05-02 MacroChem Corporation Antifungal nail lacquer
US6231875B1 (en) 1998-03-31 2001-05-15 Johnson & Johnson Consumer Companies, Inc. Acidified composition for topical treatment of nail and skin conditions
US6120756A (en) * 1998-08-19 2000-09-19 Philip I. Markowitz Topical anionic salicylate for disorders of the skin

Patent Citations (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968118A (en) * 1968-08-31 1976-07-06 Hoechst Aktiengesellschaft Process for the manufacture of 1-hydroxy-2-pyridones
US3883545A (en) * 1968-08-31 1975-05-13 Hoechst Ag Certain 1-hydroxy-2-pyridones
US4711775A (en) * 1972-07-11 1987-12-08 Hoechst Aktiengesellschaft Cosmetic compositions
US4185106A (en) * 1972-07-11 1980-01-22 Hoechst Aktiengesellschaft Pyridones as antidandruff agents
US4699924A (en) * 1983-02-01 1987-10-13 Lever Brothers Company Skin treatment composition
US4957730A (en) * 1985-12-19 1990-09-18 Hoechst Aktiengesellschaft Antimycotic nail varnish
US4797409A (en) * 1986-04-18 1989-01-10 Hoechst Aktiengesellschaft 1-hydroxy-2-pyridones, a process for their preparation, and medicaments which contain them, and intermediates formed in the preparation of the 1-hydroxy-2-pyridones
US5132107A (en) * 1986-07-07 1992-07-21 Lange Bouke J Two-phase cleansing, conditioning and medicinal treatment shampoo
US5264206A (en) * 1987-06-16 1993-11-23 Hoechst Aktiengesellschaft Nail lacquer with antimycotic activity, and a process for the preparation thereof
US4797109A (en) * 1988-02-25 1989-01-10 Methode Electronics, Inc. Coiled wire interconnector
US5071639A (en) * 1988-03-22 1991-12-10 Shiseido Company Ltd. Nail cosmetic composition
US5120530A (en) * 1989-02-24 1992-06-09 Hoffmann-La Roche Inc. Antimicotic nail varnish containing amorolfine in quaternary ammonium acrylic copolymer
US5753600A (en) * 1989-10-09 1998-05-19 Kao Corporation Liquid detergent composition
US5559130A (en) * 1989-10-17 1996-09-24 Roussel Uclaf Pyrrolidinyl pyridones for treating pain
US5356907A (en) * 1989-10-17 1994-10-18 Roussel Uclaf 1-cycloalkylpyridones as analgesics
US5395843A (en) * 1989-10-17 1995-03-07 Roussel-Uclaf Pyridones
US5066484A (en) * 1990-04-30 1991-11-19 Revlon, Inc. Nail enamels containing glyceryl, glycol or citrate esters
US5866105A (en) * 1991-05-23 1999-02-02 Novartis Ag Pharmaceutical composition
US5346692A (en) * 1992-04-10 1994-09-13 Roehm Pharma Gmbh Nail lacquer for the treatment of onychomycosis
US5603939A (en) * 1992-11-12 1997-02-18 L'oreal Film-forming cosmetic composition based on a chlorinated graft copolymer resulting from the grafting of a chlorinated polyolefin and acrylic, styrene and/or vinyl type unsaturated monomers
US5494658A (en) * 1993-01-05 1996-02-27 Hoechst Aktiengesellschaft Antidandruff agents and cosmetic preparations
US6162420A (en) * 1993-05-18 2000-12-19 Hoechst Aktiengesellschaft Use of glyceryl triacetate for treating onychomycoses
US5510100A (en) * 1993-06-10 1996-04-23 L'oreal Oil-in-water emulsions containing an auto-emulsifiable composition based on a fatty alcohol and on an alkyl polyoside and a co-emulsifying agent
US5495658A (en) * 1993-07-16 1996-03-05 Sanden Corp. Method of making cylindrical ferromagnetic body and cover assembly for rotor of DC motor
US5612327A (en) * 1993-09-01 1997-03-18 Teijin Limited 1α,24-(OH)2 -cholecalciferol emulsion composition and method for treating psoriasis
US5675013A (en) * 1993-10-18 1997-10-07 Olin Corporation 1-hydroxy-6-substituted pyridine-2-ones and 1-hydroxy-6-substituted pyridine-2-thiones for biocidal use
US5683681A (en) * 1994-04-07 1997-11-04 L'oreal Cosmetic compositions for application to the nail
US5650145A (en) * 1994-05-05 1997-07-22 L'oreal Dermatological/cosmetic compositions comprising antifungal and antibacterial compounds and reduction of hair loss therewith
US5814322A (en) * 1994-07-11 1998-09-29 L'oreal Gelled cosmetic and/or dermatological composition which is rich in solvent and which contains hollow particles, and its applications
US5756108A (en) * 1994-11-10 1998-05-26 L'oreal Oily phase in an aqueous phase dispersion stabilized by cubic gel particles and method of making
US5609854A (en) * 1995-06-06 1997-03-11 Elizabeth Arden Company, Division Of Conopco, Inc. Thickened and stabilized cosmetic emulsion compositions
US6469033B1 (en) * 1996-09-27 2002-10-22 Aventis Pharma Deutschland Gmbh Use of 1-hydroxy-2-pyridones for the treatment of skin diseases
US20040081677A1 (en) * 1996-09-27 2004-04-29 Aventis Pharma Deutschland Gmbh. Antimycotic gel having high active compound release
US6455551B1 (en) * 1996-10-30 2002-09-24 Aventis Pharma Deutschland Gmbh Use of 1-hydroxy-2-pyridones for treating mucosa diseases which are difficult to treat
US6514490B2 (en) * 1997-04-14 2003-02-04 Janssen Pharmaceutica N.V. Compositions containing an antifungal and a cationic agent
US20030086881A1 (en) * 2000-03-09 2003-05-08 Aventis Pharma Deutschland Gmbh Antiinfective combinations and their use for the topical treatment of fungal infections of the toenails and fingernails

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060121118A1 (en) * 1996-09-27 2006-06-08 Aventis Pharma Deutschland Gmbh Antimycotic gel having high active compound release
US7026337B2 (en) 1996-09-27 2006-04-11 Aventis Pharma Deutschland Gmbh Antimycotic gel having high active compound release
US7981909B2 (en) 1996-09-27 2011-07-19 Medicis Pharmaceutical Corporation Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US20110112153A1 (en) * 1996-09-27 2011-05-12 Manfred Bohn Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis
US20040081677A1 (en) * 1996-09-27 2004-04-29 Aventis Pharma Deutschland Gmbh. Antimycotic gel having high active compound release
US7740875B2 (en) 2004-10-08 2010-06-22 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
US20060078580A1 (en) * 2004-10-08 2006-04-13 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
US7776349B2 (en) 2004-10-08 2010-08-17 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
US20060078579A1 (en) * 2004-10-08 2006-04-13 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
US20060078577A1 (en) * 2004-10-08 2006-04-13 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications
WO2012075396A3 (en) * 2010-12-02 2012-12-27 The University Of Kansas Prodrugs of 6-cyclohexyl-1-hydroxy-4- methylpyridin-2(1h)-one and derivatives thereof
US8609637B2 (en) 2010-12-02 2013-12-17 The University Of Kansas Prodrugs of 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-(1H)-one and derivatives thereof
US9243014B2 (en) 2010-12-02 2016-01-26 The University Of Kansas Method of treatment with prodrugs of 6-cyclohexyl-1-hydroxy-4-methylpyridin in-2-1H-one and derivatives thereof

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US20110112153A1 (en) 2011-05-12 application
US20110269801A1 (en) 2011-11-03 application
US20100076031A1 (en) 2010-03-25 application

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