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WO2009030306A1 - Combinaisons de substances actives à base d'énoxolone et d'érythrulose, et préparations cosmétiques ou dermatologiques contenant ces combinaisons de substances actives - Google Patents

Combinaisons de substances actives à base d'énoxolone et d'érythrulose, et préparations cosmétiques ou dermatologiques contenant ces combinaisons de substances actives Download PDF

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Publication number
WO2009030306A1
WO2009030306A1 PCT/EP2008/005724 EP2008005724W WO2009030306A1 WO 2009030306 A1 WO2009030306 A1 WO 2009030306A1 EP 2008005724 W EP2008005724 W EP 2008005724W WO 2009030306 A1 WO2009030306 A1 WO 2009030306A1
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WO
WIPO (PCT)
Prior art keywords
skin
erythrulose
preparations
cosmetic
active substance
Prior art date
Application number
PCT/EP2008/005724
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German (de)
English (en)
Inventor
Sabrina Ahlheit
Cathrin Scherner
Christoph Smuda
Rainer Wolber
Michael WÖHRMANN
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
Publication of WO2009030306A1 publication Critical patent/WO2009030306A1/fr

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Classifications

    • 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
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation

Definitions

  • the present invention relates to active ingredient combinations, in particular those for browning the human skin, as well as cosmetic and dermatological preparations containing such drug combinations.
  • UVC region the so-called UVC region
  • UVB region rays in the range between 290 nm and 320 nm, the so-called UVB region, cause erythema simple sunburn or even more or less severe burns.
  • UVA range it is important to have filter substances available, since its rays can cause damage. It has thus been proven that UVA radiation leads to damage of the elastic and collagenous fibers of the connective tissue, causing the skin to age prematurely, and that it is the cause of numerous phototoxic and photoallergic effects.
  • UVA radiation can also cause skin damage by damaging the skin's own keratin or elastin. This reduces the elasticity and water retention capacity of the skin, i. The skin becomes less supple and tends to wrinkle.
  • the strikingly high prevalence of skin cancer in areas of strong sunlight indicates that damage to the genetic information in the cells is evidently also caused by sunlight, especially UV-A radiation.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin metabolism.
  • such photochemical reaction products are radic compounds, e.g. Hydroxyl radicals.
  • Undefined radical photoproducts which are formed in the skin itself, can also show uncontrolled sequelae due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule, can also be seen on UV irradiation, as can short-lived epoxides and many others.
  • Singlet oxygen for example, is distinguished from the normally present triplet oxygen (radical ground state) by increased reactivity. However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • UV radiation counts as ionizing radiation. There is thus the risk that ionic species may also be formed on exposure to UV radiation, which in turn may intervene oxidatively in the biochemical processes.
  • the pigmentation of human skin is essentially caused by the presence of melanin.
  • Melanin and its breakdown products (melanoids), carotene, degree of haemorrhage and the nature and thickness of the stratum corneum and other skin layers make skin shades different from virtually white (with reduced filling or in the absence of blood vessels) or yellowish to light brown-reddish, bluish to brown Nuances and finally appear almost black.
  • the individual skin regions show different depth of color due to different amounts of melanin. According to recent findings, the distribution of melanin in the skin has At least as much influence on the color appearance (browning) as the amount of melanin.
  • the natural melanin protects the skin from penetrating UV radiation.
  • melanin With strong pigmentation (for example, in colored people, but also in fair-skinned persons after some UV irradiation), melanin is also found in the stratum spinosum and even in the stratum corneum. It weakens the UV radiation by up to approx. 90% before it reaches the corium.
  • Skin type I never tans, always gets a sunburn.
  • Skin type II hardly tans, easily gets sunburned.
  • Skin type IM tans average good.
  • Skin type IV tans easily and persistently, almost never gets sunburned.
  • Skin type V Dark, often almost black, skin never gets sunburned.
  • Carotene is stored in the subcutaneous adipose tissue by regular intake of carotene preparations, the skin gradually turns orange to yellow-brown.
  • a slight skin tone can be achieved (eg extracts of fresh green walnut shells, henna)
  • the staining can also be done by way of chemical modification of the skin's hom für with so-called self-tanning preparations.
  • the most important active ingredient is dihydroxyacetone (DHA).
  • DHA dihydroxyacetone
  • Dihydroxyacetone can be referred to as ketotriose and reacts as reducing sugar with the amino acids of the skin or the free amino and imino groups of keratin via a series of intermediates in the sense of a Maillard reaction to brown-colored substances, so-called melanoids, which occasionally melanoidins to be named.
  • the glycyrrhetinic acid isolable from licorice is the aglycone of glycyrrhizin (which is the 2 ⁇ -glucuronido- ⁇ -glucuronide of glycyrrhetinic acid).
  • Glycyrrhetinic acid is used as an anti-inflammatory agent.
  • Glycyrrhizinic acid 3-hemisuccinate serves as an anticoagulant.
  • Glycyrrhizin has an anti-inflammatory effect and is used in the form of liquorice juice (Sirupus Iquiritiae) as a cough suppressant and expectorant.
  • Glycyrrhetinic acid and glycyrrhizin are known to the person skilled in the art as active ingredients having a skin-lightening activity.
  • glycyrrhetinic acid is preferred according to the invention for glycyrrhizin, but it may also be advantageously replaced by it partially or completely.
  • the erythrulose according to the invention is preferred to the dihydroxyacetone, but may also be advantageously replaced by this partially or completely.
  • the weight ratios of glycyrrhetinic acid and / or glycyrrhizin on the one hand and erythrulose on the other hand are selected from the range from 10: 1 to 1: 100 in the active substance combinations or preparations.
  • Particularly preferred weight ratios of glycyrrhetinic acid and / or glycyrrhizin on the one hand and erythrulose on the other hand in the active substance combinations or the preparations containing them are from the range from 1: 30 to 1: 7.5, very particularly preferably from the range from 1:20 to 1: 10 selected.
  • Cosmetic or dermatological preparations according to the invention preferably contain 0.001-10% by weight of glycyrrhetinic acid and / or glycyrrhizin.
  • cosmetic or dermatological preparations according to the invention preferably contain 0.1-3% by weight of erythrulose.
  • cosmetic or dermatological preparations according to the invention 0.1 to 3 wt .-% of dihydroxyacetone.
  • a preferred embodiment of the present invention relates to preparations containing 0.001-10% by weight of glycyrrhetinic acid and / or glycyrrhizin and 0.1-3% by weight of dihydroxyacetone and / or 0.1-3% of erythrulose.
  • Preferred ratios of glycyrrhetinic acid and dihydroxyacetone are between 10: 1 to 1: 100, more preferably between 1: 30 and 1: 7.5, most preferably between 1:20 and 1:10.
  • Cosmetic or dermatological preparations according to the invention particularly preferably contain 0.01-1% by weight of glycyrrhetinic acid and / or glycyrrhizin and 0.5-2% by weight of dihydroxyacetone and / or erythrulose, with a combination of dihydroxyacetone and erythrulose in the ratio 1: 5 to 5: 1, based on the total composition of the preparations.
  • cosmetic or dermatological preparations containing 0.05 to 0.25% by weight of glycyrrhetinic acid and 0.75 to 1.75% by weight of erythrulose, based on the total composition of the preparations.
  • the formulations of the invention showed that a) the skin barrier is strengthened b) skin moisture is increased c) in particular unwanted pigmentation disorders such as melasma, various forms of post-inflammatory hyperpigmentation due to, for example, scars or sunburns, Age spots, freckles, liver spots, vitiligo, etc. are alleviated or eliminated. d) skin wrinkles are reduced.
  • the use of preparations according to the invention furthermore surprisingly also led to an improvement in the contours of the skin and to an increased elasticity, in particular on the weak connective tissue areas of the body such as, for example, the legs, the stomach and the abdomen.
  • Emulsions according to the invention for the purposes of the present invention are advantageous and contain e.g. Fats, oils, waxes and / or other fatty substances, as well as water and one or more emulsifiers, as they are commonly used for such a type of formulation.
  • Medicinal topical compositions according to the present invention usually contain one or more drugs in effective concentration.
  • drugs for the sake of simplicity, reference is made to the clear distinction between cosmetic and medical use and corresponding products to the statutory provisions of the Federal Republic of Germany (for example, Cosmetics Regulation, Food and Medicines Act).
  • the cosmetic and / or dermatological formulations according to the invention may be composed as usual and used for the treatment of the skin and / or the hair in the sense of a dermatological treatment or a treatment in the sense of nourishing cosmetics. NEN. But they can also be used in make-up products in decorative cosmetics or in the cosmetic and dermatological cleaning products.
  • the moire (s) selected from the group are glycerol, lactic acid and / or lactates, in particular sodium lactate, butylene glycol, propylene glycol, biosaccharide gum-1, glycine soya, ethylhexyloxyglycerol, pyrrolidonecarboxylic acid and urea , It is furthermore particularly advantageous to use polymeric moisturizers from the group of water-soluble, water-swellable or water-gellable polysaccharides. For example, hyaluronic acid, chitosan and a fucose-rich polysaccharide, which are filed in the Chemical Abstracts under the registration number 178463-23-5 and z.
  • glycerol as a moisturizer, preferably in a concentration of 0.05 to 30% by weight, particularly preferably 1 to 10% by weight, in each case based on the total weight of the preparation ,
  • the solvents used can be: water or aqueous solutions, furthermore oils, such as triglycerides of capric or caprylic acid, but preferably castor oil, fats, waxes and other natural and synthetic fatty substances, preferably Esters of fatty acids with low C-number alcohols, eg with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids, but also 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 monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products.
  • oils such as triglycerides of capric or caprylic acid, but
  • mixtures of the abovementioned solvents are used, as may be an advantageous further constituent of alcohol in the case of alcoholic solvents.
  • Cosmetic and dermatological preparations according to the invention can be present in various forms, such as are usually used for this type of preparation.
  • they may contain a solution, a water-in-oil (W / O) or oil-in-water (O / W) emulsion, or a multiple emulsions such as water-in-oil-in-water (W / O / W), oil-in-water-in-oil (O / W / O), a gel, a hydrodispersion, a lamellar phase , a liquid isotropic solution phase, a micellar phase, a solid or dispersed mono- or polyhexagonal phase, a solid or dispersed mono- or poly-cubic phase, an isotropic phase, a crystalline phase, a solid stick, or else Represent aerosol.
  • the active compounds according to the invention can also be used with particular advantage in microemulsions, for example as described in German Offenlegungsschrift DE-195 9 079.
  • the oil phase of the preparations according to the invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols a chain length of 3 to 30 C atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having 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, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2 Hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semisynthetic and natural mixtures of such esters, eg 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 fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12-18, carbon atoms.
  • the fatty acid triglycerides can be advantageously selected from the group of synthetic, semi-synthetic 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.
  • the oil phase is advantageously selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 2- i 5 alkyl benzoate, caprylic-capric acid triglyceride, dicaprylyl ether.
  • Particularly advantageous are mixtures of C 12 -i 5 alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 12-15 -alkyl benzoate and isotridecyl isononanoate and mixtures of C 12-15 - benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffin oil, squalane and squalene are to be used advantageously in the context of the present invention.
  • the oil phase may further comprise 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 silicone oils.
  • cyclomethicone octamethylcyclotetrasiloxane
  • silicone oils are also advantageous 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 particularly advantageous.
  • the content of the oil phase is between 1 and 50 wt .-%, based on the total weight of the preparations, preferably 2.5 to 30 wt .-%, particularly preferably 5 to 15 wt .-%.
  • the cosmetic and / or dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics and dermatological agents.
  • active ingredients to be used in the context of the present invention are those which improve the condition of the skin, in particular active ingredients for the treatment and / or care of aging skin, for example those which reduce the development of wrinkles or even existing wrinkles.
  • active ingredients for the treatment and / or care of aging skin for example those which reduce the development of wrinkles or even existing wrinkles.
  • biochinones in particular ubiquinone (Q10), folic acid and its derivatives (in particular tetrahydrofolic acid and dihydrofolic acid), niacin and its derivatives (in particular niacinamide), creatine and creatinine, carnitine, biotin, isoflavone, hop and hops malt extracts ,
  • agents that promote the restructuring of connective tissue such as natural and synthetic isoflavonoids and isoflavonoid-containing plant extracts - such.
  • the formulations are particularly suitable as active ingredients for supporting the skin functions in dry skin (such as, for example, vitamin C, biotin, carnitine, green tea extracts, eucalyptus oil, urea and mineral salts (such as, for example, NaCl, marine minerals). and osmolytes (such as inositol, betaine, quaternary ammonium compounds)).
  • active ingredients for supporting the skin functions in dry skin
  • active ingredients such as, for example, vitamin C, biotin, carnitine, green tea extracts, eucalyptus oil, urea and mineral salts (such as, for example, NaCl, marine minerals).
  • osmolytes such as inositol, betaine, quaternary ammonium compounds
  • active ingredients which can be used individually or in combination: Ubiquinone. Folic acid, creatine, carnitine and I-soflavone.
  • active ingredients for alleviating irritative skin conditions have proven to be particularly advantageous.
  • agents such as sericosides, various extracts of licorice, licochalcone, especially licochalcone A, silymarin, silyphos, dexpanthenol, inhibitors of prostaglandin metabolism, in particular the Cycloo xygenase and leukothene metabolism, in particular 5-lipoxygenase, but also the 5-Lipoxvgenase Inhibitor protein, FLAP.
  • the abovementioned active substances are furthermore particularly suitable for creating or renewing an (energy) depot and for activating the repair (repair) of different cellular structures, in particular of the DNA.
  • Licochalcones in particular licochalcone A, and dexpanthenol, which can be used individually or in combination, are very particularly advantageous.
  • compositions are also obtained when antioxidants are used as additives or active ingredients.
  • the preparations advantageously contain one or more antioxidants.
  • antioxidants As favorable, but nevertheless optional to be used antioxidants all suitable or common for cosmetic and dermatological applications or conventional antioxidants can be used.
  • water-soluble antioxidants can be used, such as vitamins, eg. As ascorbic acid and its derivatives - in particular ascorbyl palmitate, Na and Mg ascorbyl phosphate and ascorbyl acetate - and rutinic acid and derivatives thereof, in particular alpha glucosylrutin, quercetin and isoquercetin.
  • vitamins eg. As ascorbic acid and its derivatives - in particular ascorbyl palmitate, Na and Mg ascorbyl phosphate and ascorbyl acetate - and rutinic acid and derivatives thereof, in particular alpha glucosylrutin, quercetin and isoquercetin.
  • antioxidants are also vitamin E and its derivatives (especially vitamin E acetate), vitamin A and its derivatives (especially vitamin A palmitate) and carnosine, butylhydroxytoluene, butylated hydroxyanisole, beta-alanine and carotenoids (especially beta-carotene) and phytoene.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30 wt .-%, particularly preferably 0.05 to 20 wt .-%, in particular 0.1 to 10 wt .-%, based on the total weight the preparation.
  • Vitamin E acetate 0.1 0.1
  • Vitamin E acetate 0.1 0.1 0.1

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
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Abstract

La présente invention concerne des combinaisons de substances actives à base a) d'énoxolone et/ou de glycyrrhizine et b) d'érythrulose, ainsi qu'éventuellement c) de dihydroxyacétone.
PCT/EP2008/005724 2007-08-31 2008-07-14 Combinaisons de substances actives à base d'énoxolone et d'érythrulose, et préparations cosmétiques ou dermatologiques contenant ces combinaisons de substances actives WO2009030306A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007041475.9 2007-08-31
DE102007041475A DE102007041475A1 (de) 2007-08-31 2007-08-31 Wirkstoffkombination aus Glycyrrhetinsäure und Erythrulose und kosmetische oder dermatologische Zubereitungen, diese Wirkstoffkombination enthaltend

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WO2009030306A1 true WO2009030306A1 (fr) 2009-03-12

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WO (1) WO2009030306A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009018334A1 (de) * 2009-04-23 2010-10-28 Beiersdorf Ag Verwendung von Glycyrrhetinsäure und/oder Derivaten zur Herstellung kosmetischer oder dermatologischer Zubereitungen zur Prophylaxe von Schäden an der hauteigenen DNA und/oder zur Reparatur bereits eingetretener Schäden an der heuteigenen DNA

Citations (4)

* Cited by examiner, † Cited by third party
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FR2612776A1 (fr) * 1987-03-25 1988-09-30 Thorel Jean Procede et composition de bronzage en deux phases
US6451293B1 (en) * 1997-03-05 2002-09-17 Pentapharm Ag Combination of erythrulose and a reducing sugar with self-tanning properties
DE10221811A1 (de) * 2002-05-16 2003-11-27 Beiersdorf Ag Malzextrakt enthaltende kosmetischen Zubereitung
WO2007101559A1 (fr) * 2006-03-01 2007-09-13 Beiersdorf Ag Utilisation d'acide glycyrrhétique et/ou de glycyrrhizine pour préparer des formulations cosmétiques pour le brunissement de la peau

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Publication number Priority date Publication date Assignee Title
DE1959079A1 (de) 1969-11-25 1971-07-08 Stavebni Strojirenstvi A Lehka Foerdervorrichtung fuer rohe Ziegeleierzeugnisse
FR2781668B1 (fr) * 1998-07-31 2001-06-01 Oreal Procede de traitement de la peau et patch pour la mise en oeuvre du procede
FR2799650B1 (fr) * 1999-10-14 2001-12-07 Oreal Procede pour limiter la penetration dans la peau et/ou les fibres keratiniques d'un agent cosmetique et/ou pharmaceutique actif
AU2002308248A1 (en) * 2001-03-09 2002-09-24 Pentapharm Ltd Topical preparations and food preparations comprising a pyridoxine-alpha-d-glucose
FR2854897B1 (fr) * 2003-05-12 2007-05-04 Sederma Sa Compositions cosmetiques ou dermopharmaceutiques pour reduire les signes du vieillissement cutane.
US20050089486A1 (en) * 2003-09-24 2005-04-28 Ralph Spindler Self-tanning compositions and method of using the same
DE10354052A1 (de) * 2003-11-17 2005-06-16 Beiersdorf Ag Kosmetikum mit empfindlichen Inhaltsstoffen
EP1773366A4 (fr) * 2004-06-22 2009-11-11 E L Management Corp Composition de film dissoluble

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2612776A1 (fr) * 1987-03-25 1988-09-30 Thorel Jean Procede et composition de bronzage en deux phases
US6451293B1 (en) * 1997-03-05 2002-09-17 Pentapharm Ag Combination of erythrulose and a reducing sugar with self-tanning properties
DE10221811A1 (de) * 2002-05-16 2003-11-27 Beiersdorf Ag Malzextrakt enthaltende kosmetischen Zubereitung
WO2007101559A1 (fr) * 2006-03-01 2007-09-13 Beiersdorf Ag Utilisation d'acide glycyrrhétique et/ou de glycyrrhizine pour préparer des formulations cosmétiques pour le brunissement de la peau

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