WO2000010556A1 - Utilisation de composes azotes quaternaires pour la prophylaxie et le traitement de l'eczema atopique surinfecte - Google Patents

Utilisation de composes azotes quaternaires pour la prophylaxie et le traitement de l'eczema atopique surinfecte Download PDF

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Publication number
WO2000010556A1
WO2000010556A1 PCT/EP1999/005425 EP9905425W WO0010556A1 WO 2000010556 A1 WO2000010556 A1 WO 2000010556A1 EP 9905425 W EP9905425 W EP 9905425W WO 0010556 A1 WO0010556 A1 WO 0010556A1
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Prior art keywords
acid
sodium
derivatives
oil
advantageously
Prior art date
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PCT/EP1999/005425
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German (de)
English (en)
Inventor
Gunhild Hamer
Bernd Traupe
Florian Wolf
Heiner Max
Original Assignee
Beiersdorf Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Priority to EP99938370A priority Critical patent/EP1104295A1/fr
Publication of WO2000010556A1 publication Critical patent/WO2000010556A1/fr

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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
    • A61K31/74—Synthetic polymeric materials
    • A61K31/785—Polymers containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline

Definitions

  • Atopic eczema generally begins with itching, reddening, scaling, oozing and crusting, whereby the areas of the skin that are affected, depending on the age of the patient, assume certain characteristic accumulations. Complications in the appearance of atopic eczema are often superinfections with various pathogens men, especially Staphylococcus aureus, which affects approximately 90% of all atopics with eczematous manifestation.
  • Conventional treatment methods therefore include, in addition to anti-inflammatory agents (e.g. hydrocortisone), also external substances such as various antibiotics in the narrower sense or agents with antimicrobial or antimycotic properties in the broader sense (e.g. gentian violet).
  • anti-inflammatory agents e.g. hydrocortisone
  • external substances such as various antibiotics in the narrower sense or agents with antimicrobial or antimycotic properties in the broader sense (e.g. gentian violet).
  • the conventionally used active ingredients usually have the disadvantage that they either have more or less serious side effects, resistance or intolerance, or that they have an unsanitary appearance (e.g. severe skin discoloration with gentian violet).
  • antibiotics In individual cases, it is easily possible to fight superinfections with antibiotics, but mostly such substances have the disadvantage of unpleasant side effects. For example, patients are often allergic to penicillins, which is why appropriate treatment would be prohibited in such a case. Furthermore, topically administered antibiotics have the disadvantage that they not only free the skin flora from the secondary pathogen, but also severely impair the physiological skin flora and the natural healing process is slowed down again in this way.
  • the object of the present invention was to eliminate the disadvantages of the prior art and to make available substances and preparations containing such substances, the use of which can cure superinfections, the physiological skin flora not suffering any appreciable losses.
  • quaternary ammonium compounds is sometimes used synonymously for “quaternary nitrogen compounds”.
  • quaternary ammonium compounds or preparations containing quaternary ammonium compounds are extremely suitable for reducing superinfected atopic eczema or for alleviating the symptoms of superinfected eczema.
  • Quaternary ammonium compounds with at least one long alkyl chain such as distearyldimethylammonium chloride (DSDMA)
  • DSDMA distearyldimethylammonium chloride
  • Predominantly short-chain quaternary ammonium compounds have microbicidal properties and are therefore used in fungicidal and bactericidal disinfectants or as algicides.
  • the quaternary ammonium compounds used according to the invention can advantageously be selected from the group of quaternary surfactants.
  • alkyl betaine, alkyl amidopropyl betaine and alkyl amidopropyl hydroxysulfain are advantageous.
  • the cationic surfactants used in the invention can be furthermore preferably selected from the group of quaternary ammonium compounds, especially benzyltrialkylammonium chlorides or bromides, such as benzyl zyldimethylstearylammoniumchlorid, further Alkyltriaikylammoniumsalze, for example cetyltrimethylammonium chloride or bromide, xyethylammoniumchloride Alkyldimethylhydro- or bromides, dialkyldimethylammonium chlorides or - bromides , Alkylamidethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl or cetylpyrimidinium chloride, imidazoline derivatives and compounds with a cationic character such as amine
  • the preparations according to the invention are particularly advantageously characterized in that the quaternary nitrogen compounds are present in concentrations of 0.001-99.00% by weight, preferably 0.01-50.00% by weight, particularly preferably 0.1-10.00% by weight .-%, each based on the total weight of the composition.
  • Dermatological preparations according to the invention can be in the form of aerosols, that is to say from aerosol containers, squeeze bottles or preparations sprayable by a pump device, or in the form of liquid compositions that can be applied by means of roll-on devices, but also in the form of W / O that can be applied from normal bottles and containers. or O / W emulsions, e.g. Creams or lotions.
  • the preparations can advantageously be in the form of tinctures, shampoos, washing, showering or bathing preparations or powders.
  • ethanol and isopropanol, glycerol and propylene glycol, skin-caring fat or fat-like substances, such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol can be used as conventional cosmetic carriers for the production of the dermatological preparations according to the invention in such a way
  • Preparations customary proportions are used as well as Schieimbiidigen substances and thickeners, such as hydroxyethyl or hydroxypropyl cellulose, polyacrylic acid, polyvinylpyrrolidone, but also in small amounts cyclic silicone oils (polydimethylsiloxanes) and liquid polymethylphenylsiloxanes of low viscosity.
  • the lipid phase can advantageously be selected from the following group of substances: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil;
  • Fats, waxes and other natural and synthetic fat bodies preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids; Alkyl benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiioxanes and mixed forms thereof.
  • the oil phase of preparations according to the invention in the form of oils, emulsions, oleogels or hydrodispersions or lipodispersions is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms. Atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms, from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from the group of isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononylisononanoate, 2-xyl-ethylhexyl palmitate Hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oieate, erucylerucate and synthetic, semisynthetic and natural mixtures of such esters, for example Jojoba oil.
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, in particular the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms.
  • the fatty acid triglycerides can, for example, advantageously be selected from the group of synthetic, semisynthetic and natural oils, for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like, in particular evening primrose oil and borage oil.
  • synthetic, semisynthetic and natural oils for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like, in particular evening primrose oil and borage oil.
  • any mixtures of such oil and wax components can also be used advantageously for the purposes of the present invention. It may also be advantageous to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • the oil phase is advantageously selected from the group consisting of 2-ethylhexyl isostearate, octyldodanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12-1 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
  • hydrocarbons paraffin oil, squaian and squaien can be used advantageously for the purposes of the present invention.
  • the oil phase can advantageously also contain cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
  • Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention.
  • other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • Mixtures of cyclomethicone and isotridecyl isononanoate, cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
  • the aqueous phase of the preparations according to the invention advantageously advantageously contains alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or mono - Butyl ether, diethylene glycol monomethyl or monoethyl ether and similar products, furthermore alcohols with a low C number, for example Ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickening agents, which one or more can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates, polysaccharides or their derivatives, e.g.
  • Hyaluronic acid, xanthan gum, hydroxypropyl methyl cellulose particularly advantageously from the group of the polyacrylates, preferably a polyacrylate from the group of the so-called carbopoles, for example carbopoles of the types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • Solid pins used in the present invention contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters.
  • Suitable propellants for dermatological preparations according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
  • hydrocarbons propane, butane, isobutane
  • Non-ionogenic types such as polyoxyethylene fatty alcohol ethers, for example cetylstearyl alcohol polyethylene glycol ethers with 12 or 20 attached ethylene oxide units per molecule, cetostearyl alcohol and sorbitan esters and sorbitan ester and ethylene oxide compounds (for example sorbitan ethyl monostearate and monostearate) and long-chain, high molecular weight waxy polyglycol ethers have been found to be suitable.
  • polyoxyethylene fatty alcohol ethers for example cetylstearyl alcohol polyethylene glycol ethers with 12 or 20 attached ethylene oxide units per molecule
  • cetostearyl alcohol and sorbitan esters and sorbitan ester and ethylene oxide compounds for example sorbitan ethyl monostearate and monostearate
  • long-chain, high molecular weight waxy polyglycol ethers have been found to be suitable.
  • Cleaning agents can also be advantageous embodiments of the present invention. This is particularly advantageous since some quaternary nitrogen compounds have surfactant properties.
  • Surfactants are amphiphilic substances that can dissolve organic, non-polar substances in water. Due to their specific molecular structure with at least one hydrophilic and one hydrophobic part of the molecule, they ensure a reduction in the surface tension of the water, wetting of the skin, facilitating the removal and removal of dirt, easy rinsing and, if desired, foam regulation.
  • hydrophilic parts of a surfactant molecule are mostly polar functional groups, for example -COO " , -OSO 3 2" , -SO 3 " , while the hydrophobic parts generally represent non-polar hydrocarbon residues.
  • Surfactants are generally of type and charge of the hydrophilic part of the molecule. There are four groups:
  • B + any cation, eg Na +
  • Non-ionic surfactants do not form ions in an aqueous medium.
  • Anionic surfactants to be used advantageously are acylamino acids (and their salts), such as
  • acylglutamates for example sodium acylglutamate, di-TEA-palmitoylaspartate and sodium caprylic / capric glutamate,
  • acyl peptides for example palmitoyl-hydrolyzed milk protein, sodium cocoyl-hydrolyzed soy protein and sodium / potassium cocoyl-hydrolyzed collagen,
  • Sarcosinates for example myristoyl sarcosin, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
  • taurates for example sodium lauroyl taurate and sodium methyl cocoyl taurate
  • carboxylic acids for example lauric acid, aluminum stearate, magnesium alkanolate and zinc undecyienate,
  • ester carboxylic acids for example calcium stearoyl lactylate, laureth-6 citrate and sodium PEG-4 lauramide carboxylate,
  • ether carboxylic acids for example sodium laureth-13 carboxylate and sodium PEG-6 cocamide carboxylate,
  • Phosphoric acid esters and salts such as, for example, DEA-oleth-10-phosphate and di-laureth-4 phosphate, Sulfonic acids and salts such as
  • acyl isethionates e.g. Sodium / ammonium cocoyl isethionate
  • alkyl sulfonates for example sodium coconut monoglyceride sulfate, sodium C ⁇ 2-14 olefin sulfonate, sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate,
  • Sulfosuccinates for example dioctyl sodium sulfosuccinate, disodium laureth sulfosuccinate, disodium lauryl sulfosuccinate and disodium undecylenamido MEA sulfosuccinate
  • sulfuric acid esters such as
  • alkyl ether sulfate for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium myreth sulfate and sodium C ⁇ 2-13 pareth sulfate,
  • Alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate.
  • the large remaining group of quaternary nitrogen surfactants is represented by the group of active substances on which the invention is based.
  • acyl- / dialkylethylenediamine for example sodium acylamphoacetate, disodium acylamphodipropionate, disodium alkylamphodiacetate, sodium acylamphohydroxypropylsulfonate, disodium acylamphodiacetate and sodium acylamphopropionate,
  • N-alkylamino acids for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • Non-ionic surfactants to be used advantageously 1. alcohols,
  • alkanolamides such as cocamides MEA / DEA / MIPA
  • amine oxides such as cocoamidopropylamine oxide
  • esters which are formed by esterification of carboxylic acids with ethyl oxide, glycerol, sorbitol or other alcohols,
  • ethers for example ethoxylated / propoxylated alcohols, ethoxyated / propoxylated esters, ethoxyated / propoxylated glycerol esters, ethoxyated / propoxylated cholesterols, ethoxylated / propoxylated triglyceride esters, ethoxylated propoxylated lanolin, ethoxylated / propoxylated polysiloxanes and propoxylated POs Lauryl glucoside, decyl glycoside and cocoglycoside.
  • compositions according to the invention can be up to 80% by weight, based on the total weight of the preparations.
  • the dermatological preparations according to the invention the pH of which is preferably e.g. is adjusted to 4.0 to 7.5, in particular 5.0 to 6.5, by customary buffer mixtures, perfume, dyes, antioxidants, suspending agents, buffer mixtures or other customary cosmetic or dermatological base materials are added.
  • antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • antioxidants are advantageously selected from the group consisting of Amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids , Carotenes (e.g. ⁇ -carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, liponic acid and their derivatives (e.g.
  • Amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine)
  • carotenoids e.g.
  • thiols e.g. thioredoxin, glutathione, cysteine, cystine, Cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, paimitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters
  • salts dilaurylthiodi - propionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthioninsulfoximines, homocysteine sulfoximine, buthioninsulfones, penta
  • thiols e.g. thioredoxin, glutathione, cysteine
  • ⁇ -hydroxy fatty acids e.g. cftronic acid, lactic acid, malic acid
  • humic acid e.g. bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives eg ascorbyl palmitate, Mg-ascorbyl phosphate, as - corby acetate
  • tocopherols and derivatives eg vitamin E acetate
  • vitamin A and derivatives vitamin A and derivatives (vitamin A palmitate) as well as coniferyl benzoate of benzoin
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the preparation .
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to have their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation, to choose.
  • the pH of the dermatological preparations according to the invention is less than 8. pH values that are slightly higher than 7 but less than 7.5 can generally be tolerated. In any case, it is easy to determine for a given fatty acid mixture by simply trying it out, without inventive step, which exact upper pH limit is to be observed.
  • the pH of the formulations according to the invention is advantageously adjusted to less than 8 in the acidic to very weakly alkaline range, preferably from 4.0 to 7.5, particularly preferably from 5.0 to 6.5.
  • auxiliary additives and carriers and possibly perfume to be used can easily be determined by a person skilled in the art by simply trying them out, depending on the type of product in question.
  • the dermatological preparations according to the invention are prepared in a customary manner, usually simply by mixing with stirring, optionally with gentle heating. It has no difficulties.
  • fat phase and water phase e.g. prepared separately, optionally with heating and then emulsified.
  • the suspension bases for this can advantageously be selected from the group Silicic acid gels (eg those available under the trade name Aerosil®), kieselguhr, talc, modified starch, titanium dioxide, silk powder, nylon powder, polyethylene powder and related substances.
  • Titanium dioxide 1.00

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

Utilisation de composés azotés quaternaires pour la prophylaxie et le traitement de l'eczéma atopique surinfecté.
PCT/EP1999/005425 1998-08-19 1999-07-29 Utilisation de composes azotes quaternaires pour la prophylaxie et le traitement de l'eczema atopique surinfecte WO2000010556A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP99938370A EP1104295A1 (fr) 1998-08-19 1999-07-29 Utilisation de composes azotes quaternaires pour la prophylaxie et le traitement de l'eczema atopique surinfecte

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998137549 DE19837549A1 (de) 1998-08-19 1998-08-19 Verwendung quaternärer Stickstoffverbindungen zur Prophylaxe und Behandlung des superinfizierten Ekzems
DE19837549.2 1998-08-19

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WO2000010556A1 true WO2000010556A1 (fr) 2000-03-02

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EP (1) EP1104295A1 (fr)
DE (1) DE19837549A1 (fr)
WO (1) WO2000010556A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006054312A1 (fr) * 2004-11-16 2006-05-26 Munisekhar Medasani Composé de type ammonium pour le traitement de psoriasis et d'eczéma
WO2017195783A1 (fr) * 2016-05-09 2017-11-16 株式会社ナノエッグ Composition pour le traitement ou la prévention de la dermatite atopique

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DE19918324A1 (de) * 1999-04-22 2000-10-26 Mann Gerhard Chem Pharm Fab Pharmazeutische Zusammensetzung wirksam gegen durch Bakterien, Viren, Pilze, Hefen und Protozoen verursachte Krankheitszustände
DE10140361B4 (de) * 2001-08-17 2009-07-16 Rüdiger Bode Verwendung einer Biguanide enthaltenden Zubereitung zur Hufpflege
DE10147186A1 (de) * 2001-09-25 2003-04-24 Beiersdorf Ag Wirkstoffkombinationen aus Polyhexamethylenbiguanid-Hydrochlorid und Distearyldimethylammoniumchlorid und Zubereitungen, solche Wirkstoffkombinationen enthaltend

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006054312A1 (fr) * 2004-11-16 2006-05-26 Munisekhar Medasani Composé de type ammonium pour le traitement de psoriasis et d'eczéma
WO2017195783A1 (fr) * 2016-05-09 2017-11-16 株式会社ナノエッグ Composition pour le traitement ou la prévention de la dermatite atopique
JP2019151663A (ja) * 2016-05-09 2019-09-12 株式会社ナノエッグ アトピー性皮膚炎を治療または予防するための組成物

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EP1104295A1 (fr) 2001-06-06

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