EP1686952A1 - Utilisation de licochalcone a ou d'un extrait contenant de la licochalcone a a base de radix glycyrrhizae inflatae pour lutter contre le vieillissement de la peau - Google Patents

Utilisation de licochalcone a ou d'un extrait contenant de la licochalcone a a base de radix glycyrrhizae inflatae pour lutter contre le vieillissement de la peau

Info

Publication number
EP1686952A1
EP1686952A1 EP04764150A EP04764150A EP1686952A1 EP 1686952 A1 EP1686952 A1 EP 1686952A1 EP 04764150 A EP04764150 A EP 04764150A EP 04764150 A EP04764150 A EP 04764150A EP 1686952 A1 EP1686952 A1 EP 1686952A1
Authority
EP
European Patent Office
Prior art keywords
skin
acid
preparations
cosmetic
licocalchone
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.)
Ceased
Application number
EP04764150A
Other languages
German (de)
English (en)
Inventor
Thomas Blatt
Ute Breitenbach
Stefan Gallinat
Ludger Kolbe
Christopher Mummert
Franz STÄB
Rainer Wolber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beiersdorf AG
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 EP19160989.0A priority Critical patent/EP3524236A1/fr
Publication of EP1686952A1 publication Critical patent/EP1686952A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K31/12—Ketones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61P17/04—Antipruritics
    • 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
    • A61P17/08—Antiseborrheics
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to cosmetic or dermatological and dermatological preparations containing active ingredients for the care and protection of the skin, in particular skin aged or aging due to intrinsic and / or extrinsic factors, and the use of such active ingredients and combinations of such active ingredients in the field cosmetic and dermatological skin care.
  • Cosmetic skin care primarily means that the natural function of the skin as a barrier against environmental influences (e.g. dirt, chemicals, microorganisms) and against the loss of the body's own substances (e.g. water, natural fats, electrolytes) is strengthened or restored.
  • environmental influences e.g. dirt, chemicals, microorganisms
  • loss of the body's own substances e.g. water, natural fats, electrolytes
  • the aim of skin care is also to compensate for the loss of fat and water in the skin caused by daily washing. This is especially important when the natural regeneration ability is insufficient.
  • skin care products are intended to protect against environmental influences, especially sun and wind, and to delay skin aging.
  • Chronological skin aging is caused, for example, by endogenous, genetically determined factors.
  • the following structural damage and functional disorders occur in the epidermis and dermis due to aging, which can also fall under the term "senile xerosis”: a) dryness, roughness and formation of dry wrinkles, b) itching and c) reduced regreasing due to sebum glands (eg after washing).
  • Exogenous factors such as UV light and chemical pollutants can be cumulative and e.g. accelerate or complement the endogenous aging processes.
  • exogenous factors e.g. the following structural damage and functional disorders in the skin that go beyond the extent and quality of the damage with chronological aging:
  • the present invention relates in particular to products for the care of naturally aged skin and for the treatment of the consequential damage caused by light aging, in particular the phenomena listed under a) to g).
  • Products for the care of aged skin are known per se. They contain e.g. Retinoids (vitamin A acid and / or its derivatives) or vitamin A and / or its derivatives.
  • Retinoids vitamin A acid and / or its derivatives
  • their effect on structural damage is limited in scope.
  • the use of products containing vitamin A acid often causes severe erythematous skin irritation. Retinoids can therefore only be used in low concentrations.
  • the present invention relates to cosmetic preparations with effective protection against harmful oxidation processes in the skin, but also to protect cosmetic preparations themselves or to protect the constituents of cosmetic preparations from harmful oxidation processes.
  • the present invention further relates to antioxidants, preferably those which are used in skin-care cosmetic or dermatological preparations.
  • the invention also relates to cosmetic and dermatological preparations containing such antioxidants.
  • the present relates Invention of cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological skin changes such as skin aging, in particular skin aging caused by oxidative processes.
  • the present invention relates to active substance combinations and preparations which are used for the prophylaxis and treatment of light-sensitive skin, in particular photodermatoses.
  • UVC range rays with a wavelength shorter than 290 nm
  • Numerous compounds are known for protection against UVB radiation, which are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, saiicylic acid, benzophenone and also 2-phenylbenzimidazole.
  • UVA range It is also important to have filter substances available for the range between about 320 nm and about 400 nm, the so-called UVA range, since their rays can cause reactions in light-sensitive skin. It has been proven that UVA radiation damages the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it can be seen as the cause of numerous phototoxic and photoallergic reactions. The damaging influence of UVB radiation can be intensified by UVA radiation.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products interfere with the skin's metabolism.
  • photochemical reaction products are predominantly free radical compounds, for example hydroxy radicals.
  • Undefined radical photo products which are created in the skin itself, can also display uncontrolled subsequent reactions due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule can occur with UV radiation, just as short-lived epoxies and many others.
  • Singlet oxygen for example, is characterized by increased reactivity compared to the triplet oxygen that is normally present (radical ground state). However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species also develop when exposed to UV, which in turn can then oxidatively intervene in the biochemical processes.
  • antioxidants and / or free radical scavengers can be incorporated into the cosmetic or dermatological formulations.
  • vitamin E a substance with a known antioxidative effect, in light protection formulations, but the effect achieved here also falls far short of the hoped-for effect.
  • the object of the invention was therefore also to create cosmetic, dermatological and pharmaceutical active substances and preparations and light protection formulations which are used for the prophylaxis and treatment of light-sensitive skin, in particular photodermatoses, preferably PLD.
  • Erythematous skin symptoms also appear as a side effect with certain skin diseases or irregularities. For example, the typical rash in the appearance of acne is usually more or less reddened.
  • Mainly antioxidants are used as protective substances against the spoilage of them containing preparations used.
  • undesirable oxidation processes can also occur in human and animal skin. Such processes play an essential role in skin aging.
  • antioxidants and / or free radical scavengers can be incorporated into cosmetic or dermatological formulations.
  • antioxidants and radical scavengers are known.
  • vitamin E a substance with a known antioxidant activity in light protection formulations, but the effect achieved here still lags far behind the hoped-for effect.
  • the object of the present invention was therefore to find ways which avoid the disadvantages of the prior art.
  • the effect of remedying the damage associated with endogenous, chronological and exogenous skin aging and prophylaxis should be permanent, sustainable and without the risk of side effects.
  • the object of the present invention was to remedy these shortcomings.
  • active ingredient used according to the invention or cosmetic or topical dermatological preparations with an effective content of active ingredient used according to the invention is surprisingly an effective treatment, but also a prophylaxis of deficient or hypoactive skin conditions or deficient or hypoactive conditions of skin appendages from signs of premature aging of the skin (eg wrinkles, age spots, telangiectasia) and / or skin appendages, from environmental ones (smoking, smog, reactive oxygen species, free radicals) ) and especially light-related negative changes in the skin and skin appendages.
  • the active ingredient according to the invention or cosmetic or topical dermatological preparations with an effective content of the active ingredient according to the invention also surprisingly serves to stimulate the synthesis of collagen, hyaluronic acid, elastin to stimulate the intracellular DNA synthesis, particularly in the case of deficient or hypoactive skin conditions.
  • a use according to the invention is particularly advantageous, characterized in that the preparations as a whole are 0.0001 to 5% by weight, in particular 0.001 to 1% by weight contain in particular 0.005 to 0.15% by weight of licochalcon A, based on the total weight of the preparation.
  • a use according to the invention is also particularly advantageous, characterized in that the preparations contain 0.001 to 10% by weight, in particular 0.05 to 5% by weight, very particularly 0.01 to 2% by weight, of one or more polyols , based on the total weight of the preparation.
  • preparations contain licocalchon as a constituent of plant extracts, in particular of Radix Glycyrrhizae inflatae.
  • the plant species Glycyrrhiza inflata belongs to the genus Glycyrrhiza, which belongs to the Fabaceae (pea family) plant family.
  • the drug Radix Glycyrrhizae inflatae i.e. the root of the plant, is used, for example, in femostic medicine.
  • the use of the drug as an anti-inflammatory is also known.
  • Licochalcon A Licochalcon A, which is characterized by the following structural formula:
  • a combination of licochalcon A water, if appropriate one or more polyols is also according to the invention.
  • cosmetic or dermatological preparations for the treatment and prophylaxis of the symptoms of intrinsic and / or extrinsic skin aging and for the treatment and prophylaxis of the harmful effects of ultraviolet radiation on the skin.
  • the cosmetic or dermatological preparations contain 0.001 to 10% by weight, in particular 0.05 to 5% by weight, very particularly 0.01 to 2% by weight, of an aqueous extract from Radix Glycyrrhizae inflatae , based on the total weight of the preparation.
  • the cosmetic or dermatological preparations contain 0.001 to 10% by weight, in particular 0.05 to 5% by weight, very particularly 0.01 to 2% by weight, of one or more ethoxylated or propoxylated raw materials , based on the total weight of the preparation.
  • the cosmetic or dermatological preparations contain 0.001 to 10% by weight, in particular 0.05 to 5% by weight, very particularly 0.01 to 2% by weight, of one or more polyols, based on the total weight of the preparation.
  • butylene glycol as the polyol.
  • Licochalcone A in other vehicle systems in a concentration of 0.0001 to 5% by weight, in particular 0.001 to 1% by weight, very particularly 0.005-0.05% by weight.
  • preparations containing the active compound combinations according to the invention, customary antioxidants can be used.
  • the antioxidants are advantageously selected from the group consisting of amino acids (for example glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (for example urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-camosine, L- Carnosine and its derivatives (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, pro pylthiouracil and other thiols (e.g.
  • amino acids for example glycine, histidine, tyrosine, tryptophan
  • imidazoles for example urocanic acid
  • peptides such as D, L-carnosine, D-camosine, L
  • thioredoxin glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -Linoleyl, cholesteryl and glyceryl esters) as well as their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthionine sulfoximines, pentane, sulfonimine, , Hexa-, heptathione sulfoximine) in very low tolerable doses e.g. pmol to ⁇ mol / kg
  • metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (e.g. citric acid, lactic acid, Malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g.
  • ⁇ -linolenic acid linoleic acid, oleic acid
  • folic acid and its derivative e alanine diacetic acid, flavonoids, polyphenols, catechins, vitamin C and derivatives (e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g.
  • vitamin E acetate as well as coniferyl benzoate of benzoin, rutinic acid and its derivatives, ferulic acid Derivatives, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguajak resin acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (eg ZnO, ZnSO 4 ) selenium and its derivatives (eg selenium methionine derivatives), stilbene Stilbene oxide, trans-stilbene oxide) and the derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances which are suitable according to the invention.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05 to 20% by weight, in particular 1 to 10% by weight, based on the total weight of the preparation ,
  • the prophylaxis or the cosmetic or dermatological treatment with the active ingredient used according to the invention or with the cosmetic or topical dermatological preparations with an effective content of active ingredient used according to the invention is carried out in the usual way, namely in such a way that the active ingredient used according to the invention or the cosmetic or topical dermatological preparations with an effective content of active ingredient used according to the invention is applied to the affected skin areas.
  • the active ingredient used according to the invention can advantageously be incorporated into conventional cosmetic and dermatological preparations, which come in various forms can be present.
  • they can be a solution, an emulsion of the water-in-oil (W / O) or oil-in-water (OW) type, or multiple emulsions, for example of the water-in-oil-in-water type (W / O / W) or oil-in-water-in-oil (O / W / O), a hydrodispersion or lipodispersion, a gel, a solid stick or an aerosol.
  • W / O water-in-oil
  • OW oil-in-water
  • O oil-in-water-in-oil
  • Emulsions according to the invention in the sense of the present invention are advantageous and contain e.g. Fats, oils, waxes and / or other fat bodies, as well as water and one or more emulsifiers, as are usually used for such a type of formulation.
  • Medical topical compositions in the sense of the present invention contain in the rule in one or more medicaments in an effective concentration.
  • cosmetic or topical dermatological compositions in the for the purposes of the present invention, depending on their structure, they are used, for example, as skin protection cream, cleansing milk, sunscreen lotion, nutritional cream, day or night cream, etc. It may be possible and advantageous to use the compositions according to the invention as the basis for pharmaceutical formulations.
  • cosmetic and dermatological preparations which are in the form of a sunscreen are also favorable.
  • these preferably additionally contain at least one UVA filter substance and / or at least one UVB filter substance and / or at least one inorganic pigment.
  • UV-A or UV-B filter substances are usually incorporated into day creams.
  • Preparations according to the invention can advantageously contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances, for example. 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1 to 6% by weight, based on the total weight of the preparations.
  • the UVB filters can be oil-soluble or water-soluble.
  • oil-soluble substances are: 3-benzylidene camphor and its derivatives, for example 3- (4-methylbenzylidene) camphor, 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid (2- ethylhexyl) ester, 4- (dimethylamino) benzoeklareamylester; Esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycinnamic acid isopentyl ester; - esters of salicylic acid, preferably salicylic acid (2-ethylhexyl) ester, salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomethyl ester; Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'
  • 2-phenylbenzimidazole-5-sulfonic acid and its salts for example sodium, potassium or triethanoammonium salts, sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and their salts; Sulfonic acid derivatives of 3-benzylidene camphor, such as 4- (2-oxo-3-bornylidene-methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and their salts.
  • 2-phenylbenzimidazole-5-sulfonic acid and its salts for example sodium, potassium or triethanoammonium salts
  • sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and their salts
  • Sulfonic acid derivatives of 3-benzylidene camphor such as 4- (2-oxo
  • UVB filters which can be used according to the invention, is of course not intended to be limiting.
  • the invention also relates to the combination of a UVA filter according to the invention with a UVB filter or a cosmetic or dermatological preparation according to the invention which also contains a UVB filter.
  • UVA filters in preparations according to the invention which are usually contained in cosmetic and / or dermatological preparations.
  • Such filter substances are preferably derivatives of dibenzoylmethane, in particular 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione and 1-phenyl-3- (4th '-isopropylphenyl) propane-1,3-dione. Preparations containing these combinations are also the subject of the invention.
  • the same amounts of UVA filter substances that were mentioned for UVB filter substances can be used.
  • Cosmetic and / or dermatological preparations in the sense of the present invention can also contain inorganic pigments which are usually used in cosmetics to protect the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum, cerium and mixtures thereof, as well as modifications in which the oxides are the active agents. Pigments based on titanium dioxide are particularly preferred. The amounts mentioned for the above combinations can be used.
  • the cosmetic and dermatological preparations according to the invention can contain cosmetic active ingredients, auxiliaries and / or additives, as are usually present in such Preparations are used, for example antioxidants, preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic active ingredients for example antioxidants, preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols
  • the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion
  • solvents water or aqueous solutions 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 low C alcohols, e.g.
  • Water can also be a component of alcoholic solvents.
  • the oil phase of the emulsions, ologels or hydrolodispersions or lipodispersions in the sense of the present invention 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 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 C-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-ethylhexyl palmitate Ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate as well as synthetic, semi-synthetic and natural mixtures of such esters, for example jojoba oil.
  • the oil phase can advantageously be chosen from the group of branched and unbranched hydrocarbons and waxes, the silicone oils, the dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also the fatty acid triglycerides, especially 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 carbon atoms.
  • the fatty acid triglycerides can, for example, advantageously be selected from the group of synthetic, semisynthetic and natural oils, e.g. Olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
  • 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, octyldodecanol, isotridecylisononanoate, isoeicosane, 2-ethylhexyl cocoate, C 2 -i 5 -alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
  • hydrocarbons paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
  • the oil phase can advantageously also have a content of 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 advantageous as to be used according to the invention.
  • reversible silicone oil used.
  • other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • the aqueous phase of the preparations according to the invention advantageously advantageously contains - alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or - monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analog products, furthermore alcohols of low C number, for example Ethanol, isopropanol, 1, 2-propanediol, glycerol and, in particular, one or more thickeners, 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 polyacrylates, preferably a polyacrylate from the group of so-called carbopoles, for example carbopoles of types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • Gels used in the present invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener, which is preferably silicon dioxide or an aluminum silicate in the case of oily alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oily alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • Fixed pens contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters.
  • Common raw materials which are suitable for use as cosmetic sticks in the sense of the present invention are liquid oils (for example paraffin oils, castor oil, isopropyl myristate), semi-solid components (for example petroleum jelly, lanolin), solid components (for example beeswax, ceresin and microcrystalline) Waxes or ozokerite) and high-melting waxes (e.g. carnauba wax, candelilla wax)
  • Suitable blowing agents for cosmetic and / or dermatological preparations which can be sprayed from aerosol containers in the sense of the present invention are the customary known volatile, liquefied blowing agents, 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.
  • Cosmetic preparations within the meaning of the present invention can also be present as gels which, in addition to an effective content of the active ingredient according to the invention and solvents usually used for this, preferably water, or organic thickeners, e.g. Gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic thickeners, e.g. B. aluminum silicates such as bentonite, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • the thickener is in the gel e.g. in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
  • Phenylene-1,4-bis (monosodium, -2-benzimidazyl-5,7-disulfonic acid) 1.00
  • Phenylene-1,4-bis (monosodium, -2-benzimidazyl-5,7-disulfonic acid) 2.00
  • Phenylene-1,4-bis (monosodium, -2-benzimidazyl-5,7-disulfonic acid) 0.50
  • Titanium dioxide 3.00

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Abstract

L'invention concerne l'utilisation de licochalcone A ou d'un extrait contenant de la licochalcone A à base de Radix Glycyrrhizae inflatae dans des préparations cosmétiques ou dermatologiques destinées au traitement thérapeutique et prophylactique des symptômes du vieillissement de la peau intrinsèque et/ou extrinsèque, ainsi que pour le traitement thérapeutique et prophylactique des effets nocifs des rayons ultraviolets sur la peau.
EP04764150A 2003-09-12 2004-08-16 Utilisation de licochalcone a ou d'un extrait contenant de la licochalcone a a base de radix glycyrrhizae inflatae pour lutter contre le vieillissement de la peau Ceased EP1686952A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP19160989.0A EP3524236A1 (fr) 2003-09-12 2004-08-16 Utilisation du licochalchone a ou d'un extrait du radix glycyrrhizae inflatae contenant du licochalchone a contre le vieillissement cutané

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10342212A DE10342212A1 (de) 2003-09-12 2003-09-12 Verwendung von Licocalchon A oder eines Licocalchon A enthaltenden Extraktes aus Radix Glycyrrhizae inflatae gegen Hautalterung
PCT/EP2004/009158 WO2005027866A1 (fr) 2003-09-12 2004-08-16 Utilisation de licochalcone a ou d'un extrait contenant de la licochalcone a a base de radix glycyrrhizae inflatae pour lutter contre le vieillissement de la peau

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP19160989.0A Division EP3524236A1 (fr) 2003-09-12 2004-08-16 Utilisation du licochalchone a ou d'un extrait du radix glycyrrhizae inflatae contenant du licochalchone a contre le vieillissement cutané

Publications (1)

Publication Number Publication Date
EP1686952A1 true EP1686952A1 (fr) 2006-08-09

Family

ID=34258619

Family Applications (2)

Application Number Title Priority Date Filing Date
EP19160989.0A Withdrawn EP3524236A1 (fr) 2003-09-12 2004-08-16 Utilisation du licochalchone a ou d'un extrait du radix glycyrrhizae inflatae contenant du licochalchone a contre le vieillissement cutané
EP04764150A Ceased EP1686952A1 (fr) 2003-09-12 2004-08-16 Utilisation de licochalcone a ou d'un extrait contenant de la licochalcone a a base de radix glycyrrhizae inflatae pour lutter contre le vieillissement de la peau

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP19160989.0A Withdrawn EP3524236A1 (fr) 2003-09-12 2004-08-16 Utilisation du licochalchone a ou d'un extrait du radix glycyrrhizae inflatae contenant du licochalchone a contre le vieillissement cutané

Country Status (5)

Country Link
US (1) US20070196289A1 (fr)
EP (2) EP3524236A1 (fr)
JP (1) JP2007505056A (fr)
DE (1) DE10342212A1 (fr)
WO (1) WO2005027866A1 (fr)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10224387A1 (de) 2002-06-01 2003-12-11 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem aufbereiteten Extrakt aus Radix Glycyrrhizae inflatae
DE10352369A1 (de) * 2003-11-10 2005-06-09 Beiersdorf Ag Verwendung von Licocalchon A oder eines Licocalchon A enthaltenden Extraktes aus Radix Glycyrrhizae inflatae gegen postinflammatorische Hyperpigmentierung
DE10356164A1 (de) * 2003-12-02 2005-08-04 Beiersdorf Ag Wirkstoffkombinationen aus Licochalcon A oder einem Extrakt aus Radix Clycyrrhizae inflatae, enthaltend Licochalcon A, Phenoxyethanol und gewünschtenfalls Glycerin
US8158362B2 (en) 2005-03-30 2012-04-17 Decode Genetics Ehf. Methods of diagnosing susceptibility to myocardial infarction and screening for an LTA4H haplotype
US8613910B2 (en) 2005-07-27 2013-12-24 Merck Patent Gmbh Flavonoids as synergists for enhancing the action of self-tanning substances
WO2007012356A1 (fr) * 2005-07-27 2007-02-01 Merck Patent Gmbh Flavonoides utilises comme synergistes pour renforcer l'effet de substances autobronzantes
DE102006010589A1 (de) * 2006-03-06 2007-09-13 Beiersdorf Ag Kosmetische oder dermatologische Emulsionen enthaltend Licocalchon A oder einen Licocalchon A enthaltenden Extraxt aus Radix Glycyrrhizae inflatae
US20090092561A1 (en) * 2007-10-09 2009-04-09 Lupia Joseph A Body-care and household products and compositions comprising specific sulfur-containing compounds
RU2448723C1 (ru) * 2008-05-23 2012-04-27 Нисихара Ко., Лтд. Средство, способствующее экспрессии белка bcl-2, средство, ингибирующее апоптоз, и средство, предотвращающее повреждение днк эпидермальных клеток ультрафиолетом
WO2009141915A1 (fr) * 2008-05-23 2009-11-26 有限会社西原 Expresseur de protéine bcl-2, inhibiteur d'apoptose et agent préventif pour une lésion de l'adn par uv dans des cellules épidermiques
DE102008048328A1 (de) 2008-09-16 2010-04-15 Beiersdorf Ag UV-Filter haltige O/W-Wirkstoffemulsion
DE202008018656U1 (de) 2008-09-16 2017-11-07 Beiersdorf Ag UV-Filter haltige O/W-Wirkstoffemulsion
US20100260695A1 (en) * 2009-04-09 2010-10-14 Mary Kay Inc. Combination of plant extracts to improve skin tone
JP2013035762A (ja) * 2011-08-05 2013-02-21 Minofuaagen Seiyaku:Kk 皮膚炎治療剤及び皮膚掻痒治療剤
MX2018001778A (es) * 2015-08-13 2018-06-06 Arch Personal Care Products Lp Concentrado para paño limpiador humedo.
WO2017131954A1 (fr) * 2016-01-27 2017-08-03 Elc Management Llc Composition de soins personnels comprenant un mélange pour la restauration capillaire
CN106389519A (zh) * 2016-11-30 2017-02-15 郑州仁宏医药科技有限公司 一种治疗白发脱发的西药复方制剂及其制备方法
CA3107838A1 (fr) 2018-07-30 2020-02-06 Unilever Global Ip Limited Compositions comprenant des ingredients botaniques actifs
CN115317386A (zh) * 2022-09-21 2022-11-11 江西沁华蔓医药科技有限公司 提拉紧致抗衰老精华液及其制备方法
CN115531276A (zh) * 2022-11-09 2022-12-30 江西沁华蔓医药科技有限公司 透皮保湿精华液及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001163718A (ja) * 1999-12-10 2001-06-19 Maruzen Pharmaceut Co Ltd 皮脂分泌抑制剤および皮膚外用剤
DE10124475A1 (de) * 2001-05-19 2002-11-21 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an einer oder mehreren Kethohexosen

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4144325A (en) 1976-11-10 1979-03-13 Voyt Walter F Method of and composition for preventing sunburn while affording tanning
US4248861A (en) 1979-02-21 1981-02-03 Schutt Steven R Skin treatment methods
JPS6396120A (ja) * 1986-10-14 1988-04-27 Matsuura Yakugiyou Kk 日焼け止め化粧品
JP2584423B2 (ja) * 1987-12-15 1997-02-26 丸善製薬株式会社 紫外線吸収剤
JPH02142717A (ja) * 1988-11-22 1990-05-31 Kanebo Ltd 養毛化粧料
JP2794433B2 (ja) * 1989-02-02 1998-09-03 丸善製薬株式会社 甘草疎水性フラボノイド製剤
JPH02204495A (ja) * 1989-02-02 1990-08-14 Maruzen Kasei Co Ltd 甘草疎水性フラボノイドの抽出法
JPH02221229A (ja) * 1989-02-22 1990-09-04 Momotani Jiyuntenkan:Kk ヒアルロニダーゼ・インヒビター
JPH05310586A (ja) * 1992-05-15 1993-11-22 Soken Kk 糠およびふすまからの活性酸素消去剤
DE4303983C2 (de) * 1993-02-11 1998-01-22 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an anorganischen Mikropigmenten
JP3808947B2 (ja) * 1996-09-04 2006-08-16 花王株式会社 油性固形化粧料
JPH10182416A (ja) * 1996-12-20 1998-07-07 Rashieru Seiyaku Kk 化粧料組成物
EP0998939A1 (fr) * 1998-09-09 2000-05-10 The School Of Pharmacy, University Of London Extraits de plantes à base de chalcone utilisables en thérapie
JP4563521B2 (ja) * 1998-12-24 2010-10-13 丸善製薬株式会社 コラーゲン産生促進剤および皮膚外用剤
US6214352B1 (en) * 2000-01-06 2001-04-10 Matsukawa Kagaku Co., Ltd. Tyrosinase inhibiting agent
US20020197289A1 (en) * 2001-03-23 2002-12-26 L'oreal Compositions and methods for combating the appearance of ageing
JP5024978B2 (ja) * 2001-09-14 2012-09-12 丸善製薬株式会社 抗酸化剤
JP2003238379A (ja) * 2002-02-08 2003-08-27 Maruzen Pharmaceut Co Ltd 皮膚化粧料および頭髪化粧料
KR20020062237A (ko) * 2002-04-18 2002-07-25 김대도 박하 팩
DE10224387A1 (de) * 2002-06-01 2003-12-11 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem aufbereiteten Extrakt aus Radix Glycyrrhizae inflatae
JP3648730B2 (ja) * 2002-08-27 2005-05-18 株式会社豊▲凛▼ 皮膚化粧料
DE10352367A1 (de) * 2003-11-10 2005-06-09 Beiersdorf Ag Verwendung von Licochalkon A gegen Rosacea
DE10352369A1 (de) * 2003-11-10 2005-06-09 Beiersdorf Ag Verwendung von Licocalchon A oder eines Licocalchon A enthaltenden Extraktes aus Radix Glycyrrhizae inflatae gegen postinflammatorische Hyperpigmentierung
DE10356164A1 (de) * 2003-12-02 2005-08-04 Beiersdorf Ag Wirkstoffkombinationen aus Licochalcon A oder einem Extrakt aus Radix Clycyrrhizae inflatae, enthaltend Licochalcon A, Phenoxyethanol und gewünschtenfalls Glycerin
DE10356869A1 (de) * 2003-12-03 2005-07-07 Beiersdorf Ag Tensidhaltige Zubereitung mit Licochalcon A
DE10357452A1 (de) * 2003-12-03 2005-06-30 Beiersdorf Ag Kosmetische Zubereitungen mit einem Gehalt an Licochalcon A oder einem Extrakt aus Radix Glycyrrhizae inflatae, enthaltend Licochalcon A, und organischen Verdicker
DE10357046A1 (de) * 2003-12-04 2005-06-30 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen enthaltend eine Kombination aus grünem Farbstoff und antiinflammatorischem Wirkstoff

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001163718A (ja) * 1999-12-10 2001-06-19 Maruzen Pharmaceut Co Ltd 皮脂分泌抑制剤および皮膚外用剤
DE10124475A1 (de) * 2001-05-19 2002-11-21 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an einer oder mehreren Kethohexosen

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200165, Derwent World Patents Index; AN 2001-574426 *
See also references of WO2005027866A1 *

Also Published As

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WO2005027866A1 (fr) 2005-03-31
DE10342212A1 (de) 2005-04-07
JP2007505056A (ja) 2007-03-08
EP3524236A1 (fr) 2019-08-14
US20070196289A1 (en) 2007-08-23

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