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
• • 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
  • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
  • A61K31/19—Carboxylic acids, e.g. valproic acid
• • 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
  • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
  • A61K31/19—Carboxylic acids, e.g. valproic acid
  • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
• • 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
  • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
  • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• • 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
  • A61K8/36—Carboxylic acids; Salts or anhydrides 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
• • 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
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
  • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
• • 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
  • A61K8/602—Glycosides, e.g. rutin
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P37/00—Drugs for immunological or allergic disorders
  • A61P37/02—Immunomodulators
  • A61P37/04—Immunostimulants
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P37/00—Drugs for immunological or allergic disorders
  • A61P37/08—Antiallergic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • 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
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/52—Stabilizers
  • A61K2800/522—Antioxidants; Radical scavengers
• • 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
  • A61Q19/001—Preparations for care of the lips
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/19—Sheets or webs edge spliced or joined
  • Y10T428/192—Sheets or webs coplanar
  • Y10T428/193—Double faced corrugated sheets or webs connected
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/19—Sheets or webs edge spliced or joined
  • Y10T428/192—Sheets or webs coplanar
  • Y10T428/195—Beveled, stepped, or skived in thickness

Definitions

• the present invention relates to active compounds and formulations comprising such active compounds for cosmetic or dermatological treatment and/or prophylaxis of inflammatory, allergic or autoimmune-reactive symptoms, and protecting cells which participate in the immune response of the skin.
• the skin As a barrier organ in the human organism, the skin, especially the epidermis, is particularly subjected to external effects. According to current scientific understanding, the skin represents an immunological organ which, as an immunocompetent peripheral compartment, plays its own role in inductive, effective and regulatory immune processes of the total organism.
• UVC range rays having a wavelength below 290 nm
• UVB range rays in the range between 290 and 320 nm
• the narrower range around 308 nm is stated as a maximum for the erythema activity of sunlight.
• UVA range UV range
• UVA radiation also leads to damage to the elastic and collagenic fibres of connective tissue, which causes the skin to age prematurely (so-called photoageing), and that it is to be regarded as a cause of numerous phototoxic toxic and photoallergic reactions.
• the damaging influence of UVB radiation may be intensified by UVA radiation.
• UVB radiation is of particular interest in the development of topical sunscreen compositions, since the action spectrum for the acutely inflammatory processes (sunburn) and chronic damage (photoageing) is located here.
• UVB-induced immunosuppression a serious change in the intraepidermal immunological situation may furthermore occur under the action of UVB, this being called UVB-induced immunosuppression.
• UVB-induced immunosuppression a serious change in the intraepidermal immunological situation may furthermore occur under the action of UVB, this being called UVB-induced immunosuppression.
• far-reaching changes in the immunological processes of the skin with both local and systemic effects are possible consequences here.
• Immunosuppression generally is the suppression or attenuation of the reactivity of the immune system.
• UVB-induced immunosuppression can be classified into local and systemic effects. In the end, it includes a large number of the most diverse aspects, all of which comprise reduction of the normal immunological defence mechanisms of the skin. The increased tumour growth was thus already related to the immunosuppressive action of UVB light very early on using the model of mice irradiated with UVE.
• This UVB-induced immunosuppresion is nowadays discussed as the mechanism by means of which UVB-induced neoplastic cells, which are in themselves highly immunogenic, withdraw from immunological defence and therefore their own destruction.
• intercellular adhesion molecule-1 on epidermal keratinocytes is suppressed as a consequence of a dermatologically relevant UVB exposure.
• This glycoprotein on the cell surface also called ICAM-1 is one of the most important cellular communication structures, via which direct cellcell contacts between epidermal keratinocytes and leukocytes, such as, for example, T-lymphocytes and monocytes, are regulated.
• UVB-induced immunosuppression thus concerns a broad spectrum of immunological dysfunctions which result in a reduction in the defence reactions which normally proceed.
• such photochemical reaction products are chiefly free-radical compounds, for example hydroxyl radicals or superoxide radical anions.
• Undefined free-radical photo products which are formed in the skin itself can also show uncontrolled secondary reactions because of their high reactivity.
• singlet oxygen a non-radical excited state of the oxygen molecule, may also occur under UV irradiation, as may shortlived epoxides and many other reactive oxygen species.
• Singlet oxygen for example, is distinguished from the triplet oxygen normally present (free-radical ground state) by an increased reactivity. Nevertheless, excited, reactive (free-radical) triplet states of the oxygen molecule also exist.
• vitamin E or vitamin E esters substances of known antioxidative action, in light protection formulations.
• the background was always UV protection by absorption of light or protection against photo-oxidative processes.
• the activity of vitamin E from topical vehicles was weak.
• a high dosage also provided no remedy, since a more prooxidative action was achieved, especially with vitamin E.
• substances according to the invention chosen from the group consisting of flavonoids and their glucosides, from the group of cinnamic acid derivatives and from the group of tocopherols and their derivatives are particularly advantageous.
• Japanese Laid-Open Specification Hei-06-138,941 indeed describes oral formulations having a content of water-soluble glucosides, which can be chosen, for example, from the group consisting of a-glucosylrutin, u-glucosylmyrictrin, a-glucosylisoquercitrin and a-glucosylquercitrin.
• Japanese Laid-Open Specification Hei-04-10 363,395 describes a process for preventing decomposition of perfume constituents which is distinguished, inter alia, by an addition of a-glucosylrutin to the corresponding formulations.
• European Laid-Open Specification 586 303 and European Laid-Open Specification 595 694 furthermore describe the use of flavonoids as antioxidants or light protection substances in cosmetics. It is furthermore known from US-A 4,144,325 and 4,248,861 and from numerous other documents to employ vitamin E in cosmetic and dermatological light protection formulations. However, the use according to the invention of vitamin E and its derivatives for cosmetic or dermatological prophylaxis of the immunosuppression induced by UVB radiation was not made obvious by the prior art.
• the invention relates to the use of cosmetic and dermatological formulations having
• Active compound combinations b) their use and formulations which comprise these are preferred.
• the invention also relates to the use of the active compound according to the invention for the purposes mentioned and their use as immunomodulating or immunoprotective active compounds, in particular in cosmetic and dermatological formulations.
• the active compounds and formulations according to the invention are used for protection of immunocompetent cells, such as Langerhans cells, and for protection of cell constituents.
• Topical formulations are preferred.
• Preferred flavonoids according to the invention are, for example, hydroxylated flavones, flavanones, isoflavones or chalcones, and in each case also glycosides thereof, as well as these non-hydroxylated base structures and parent substances.
• flavonoids according to the invention are also designated A) below, the cinnamic acid derivatives according to the invention are designated B) and the antioxidants according to the invention are also designated C).
• the flavonoids A) are preferably chosen from the group consisting of substances of the generic structural formulae
• Z 1 -Z 5 independently of one another are chosen from the group consisting of H, OH and O-alkyl, wherein the alkyl groups can be branched and unbranched and can contain 1-10 C atoms, and wherein Gly is chosen from the group consisting of mono- and oligoglycoside radicals, or can also be H.
• Preferred glycoside radicals are those mentioned below for Gly 1 -Gly 3 .
• flavonoids according to the invention are advantageously chosen from the group consisting of substances of the following formulae:
• Z 1 -Z 5 have the abovementioned meanings and Gly 1 , Gly 2 and Gly 3 are monlglycoside radicals.
• Gly 1 , Gly 2 and Gly 3 are monlglycoside radicals.
• allosyl, altrosyl, apiosyl, arabinosyl, biosidyl, galactosyl, gulosyl, glucoronidyl, idosyl, mannosyl, talosyl and xylosyl are also advantageously to be used, where appropriate. It may also be advantageous according to the invention to use pentosyl radicals.
• flavone glycoside or glycosides from the group consisting of alpha-glucosyl-rutin, alpha-glucosylmyrictrin, alpha-glucosylisoquer-citrin and alpha-glucosylquercitrin.
• Compounds such as alpha-glycosylrutin, alpha-glycosylhesperidin, alpha-glycosylnaringin, alpha-manno-sylrutin and alpha-rhamnosylrutin are furthermore particularly preferred according to the invention.
• flavonoids in which the phenolic OH function on C9 is present in the free form (so-called chalcones) . It is particularly advantageous to use neohesperidin dihydrochalcone from this group.
• flavonoid or flavonoids from the group consisting of quercitin, rutin, chrysin, kaempferol, myricetin, rhamnetin, apigenin, luteolin, naringin, hesperidin, naringenin, hesperitin, morin, phloridzin, diosmin, fisetin, vitexin, neohesperidin dihydrochalcone, flavone, glycosylrutin and genistein.
• the flavonoids which are particularly preferred according to the invention are chrysin, naringin, hesperidin, naringenin, hesperetin, morin, phloridzin, diosmin, neohesperidin dihydrochalcone, flavone and, in particular, alpha-glucosylrutin of the formula
• flavonoid-containing plant extracts can be aqueous-alcoholic or aqueous-glycolic extracts and dry extracts obtained by the customary methods.
• citrous fruit peel or kernel extract for example Citricidal/Synthapharm
• soya extract for example Phytodermin/Chem. Laboratorium Dr. Kurt Richter GmbH
• Sophora japonica extract for example Sophorine/Solabia
• Scotch thistle extract for example Psoralen Silymarin/Mani GmbH Chemische für
• cat's-foot blossom extract for example spinach extract and a mixed plant extract of passion flower, blackcurrant and vine leaves (AE Complex/Solabia).
• Suitable cinnamic acid derivatives are, for example, hydroxycinnamic acids and derivatives thereof, it being possible for the derivatives to be, for example, those defined below.
• the acids or salts thereof can be used, preferably the physiologically tolerated salts, for example water-soluble salts (sodium or potassium salts).
• Ferulic acid is regarded as a particularly advantageous cinnamic acid derivative in the context of the present invention.
• Ferulic acid (4-hydroxy-3-methoxy-cinnamic acid, caffeic acid 3-methyl ether) is characterized by the structural formula
• E-ferulic acid In the context of the present invention, it is preferable to use E-ferulic acid. However, it is also advantageous, where appropriate, to employ Z-ferulic acid or any desired mixtures of E- and Z-ferulic acid.
• caffeic acid Another derivative of cinnamic acid which is preferred according to the invention is caffeic acid, which is distinguished by the structure
• derivatives of caffeic acid or ferulic acid is to be understood as meaning their cosmetically or pharmacologically acceptable esters, salts and base adducts, in particular those such as are described above for the cinnamic acid derivatives.
• Preferred combinations according to the invention are combinations of one or more substances from the group consisting of the abovementioned flavonoids or combinations of one or more representatives of the flavonoids with a derivative of cinnamic acid, or also the combination with several cinnamic acid derivatives.
• the weight ratio of the cinnamic acid derivatives to the flavonoid or flavonoids is advantageously 25:1 to 1:25, preferably 5:1 to 1:5, particularly preferably about 2:1 to 1:2.
• Formulations with combinations b) which comprise alpha-glucosylrutin and/or ferulic acid are particularly preferred.
• the compounds of group A or those of the combination of active compounds A) and B) can be present as the sole active compounds in the formulations according to the invention.
• the formulations according to the invention can also additionally and preferably have a content of an antioxidant or several antioxidants C).
• the antioxidants C) according to the invention can advantageously be chosen from the group consisting of tocopherols and derivatives thereof.
• the tocopherols also called vitamin E, are derived from the parent substance tocol (2-methyl-2-(4,8,12-trimethyltridecyl)-chroman-6-ol).
• the configuration 2R,4‘R,8‘R is attributed to ⁇ -tocopherol, which occurs naturally the most frequently and is the most important. It is occasionally also called RRR- ⁇ -tocopherol.
• the tocopherol derivatives which are preferred according to the invention are a-tocopherol and its esters, in particular a-tocopheryl acetate. Esters of acids having 2-18, in particular 2-8 C atoms are preferred.
• vitamin E and/or derivatives thereof are the antioxidant or antioxidants, it is advantageous to choose the particular concentrations thereof from the range from 0.001 to 10% by weight, based on the total weight of the formulation.
• antioxidants C) from the group consisting of amino acids (for example glycine, histidine, tyrosine and tryptophan) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotenoids, carotenes (for example ⁇ -carotene, ⁇ -carotene and lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propyl-thiouracil, thioredoxin and glutathione, and furthermore (metal)chelators (for example ⁇ -hydroxy-fatty acids, palmitic acid, phytic acid and lactoferrin), a-hydroxyacids (for example citric acid, lactic acid
• amino acids for example glycine
• the amount of the abovementioned antioxidants C) (one or more compounds) in the formulations 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 formulation.
• the cosmetic and/or dermatological formulations according to the invention can have the customary composition and can be used for prophylaxis and/or for treatment of the skin in the context of a dermatological treatment or prophylaxis and/or treatment in the context of cosmetics. However, they can also be used in make-up products of decorative cosmetics.
• the cosmetic and dermatological formulations according to the invention preferably comprise 0.001% by weight to 30% by weight, preferably 0.01% by weight to 10% by weight, but in particular 0.1% by weight to 6% by weight, based on the total weight, of one or more substances A) according to the invention or of the combination of A) and B).
• the weight content of active compounds from the group consisting of flavonoids and derivatives thereof and the group consisting of cinnamic acid and its derivatives can be varied in a wide range of ratios in the combinations.
• the weight ratio of the active compounds is preferably 20:1 to 1:20, in particular 10:1 to 1:10, particularly preferably 2:1 to 1:2.
• the weight content of active compounds from the group consisting of flavonoids and derivatives thereof and the group consisting of tocopherol and its derivatives can likewise be varied within a wide range of ratios in the combinations.
• the weight ratio of the active compounds is preferably 20:1 to 1:20, in particular 10:1 to 1:10, particularly preferably 2:1 to 1:2.
• the weight ratios can preferably be varied within the following limits: 20:1 to 1:20, in particular 10:1 to 1:10, particularly preferably 2:1 to 1:2.
• the formulations according to the invention preferably combinations of flavonoids and derivatives thereof, cinnamic acid and derivatives thereof and vitamin E and derivatives thereof, are applied to the skin in a sufficient amount in the manner customary for cosmetics or dermatological agents.
• Cosmetic formulations according to the invention for protection of the skin can be in various forms, such as are usually employed, for example, for this type of formulation. They can thus be, for example, a solution, an emulsion of the water-in-oil (W/o) type or of the oil-in-water (O/W) type, or a multiple emulsion, for example of the water-in-oil-in-water (W/O/W) type, a gel, a hydrodispersion, an anhydrous ointment, a solid stick or also an aerosol.
• the cosmetic formulations according to the invention can comprise cosmetic auxiliaries such as are usually used in such formulations, for example UV/A and UV/B filters, preservatives, bactericides, perfumes, agents for preventing foaming, dyestuffs, pigments which have a colouring action, thickeners, surface-active substances, emulsifiers, softening substances, humidifying and/or humectant substances, fats, oils, waxes or other customary constituents of a cosmetic formulation, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
• cosmetic auxiliaries such as are usually used in such formulations, for example UV/A and UV/B filters, preservatives, bactericides, perfumes, agents for preventing foaming, dyestuffs, pigments which have a colouring action, thickeners, surface-active substances, emulsifiers, softening substances, humidifying and/or humectant substances, fats, oils
• the cosmetic or dermatological formulation is a solution or lotion
• solvents which can be used are:
• oils such as triglycerides of capric or of caprylic acid, or liquid triglycerides of natural origin
• fats, waxes and other natural and synthetic fatty substances preferably esters of fatty acids with alcohols of low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids
• silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof
• alcohols, diols or polyols of low C number and ethers thereof 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.
• Emulsions according to the invention for example in the form of a sunscreen cream, a sunscreen lotion or a sunscreen milk, are advantageous and comprise, for example, the fats, oils, waxes and other fatty substances mentioned, as well as water and an emulsifier such as is usually used for such a type of formulation.
• Gels according to the invention usually comprise alcohols of low C number, for example ethanol, isopropanol, 1,2-propanediol, glycerol and water, or an above-mentioned oil, in the presence of a thickener, which is preferably silicon dioxide or an aluminium silicate in the case of oily-alcohol gels and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
• alcohols of low C number for example ethanol, isopropanol, 1,2-propanediol, glycerol and water, or an above-mentioned oil
• a thickener which is preferably silicon dioxide or an aluminium silicate in the case of oily-alcohol gels and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
• Anhydrous cosmetic and dermatological formulations such as ointments or skin oils, according to the invention are advantageous and comprise, for example, the fats, oils, silicone oils, waxes and other fatty substances mentioned.
• Solid sticks according to the invention comprise, for example, naturally occurring or synthetic waxes, fatty alcohols or fatty acid esters. Lip care sticks are preferred.
• Suitable propellants for cosmetic or dermatological formulations according to the invention which can be sprayed from aerosol containers are the customary known readily volatile, liquefied propellants, for example hydrocarbons (propane, butane and isobutane), which can be employed by themselves or as a mixture with one another. Compressed air can also advantageously be used.
• propellant gases which are non-toxic per se and which would be suitable in principle for the present invention, but which should nevertheless be omitted because of an unacceptable action on the environment or other concomitant circumstances, in particular fluorohydrocarbons and fluorochlorohydrocarbons (CFCs).
• the formulations according to the invention can furthermore preferably comprise substances which absorb UV radiation in the UVB range, the total amount of the filter substances being, 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 formulation, in order to provide cosmetic formulations which protect the skin from the entire range of ultraviolet radiation. They can also be used as sunscreen agents.
• the UVB filters can be oil-soluble or water-soluble. Oil-soluble substances which may be mentioned are, for example:
• 3-benzylidenecamphor derivatives preferably 3-(4-methylbenzylidene) camphor and 3-benzylidenecamphor;
• esters of cinnamic acid preferably 2-ethylhexyl 4-methoxycinnamate and isopentyl 4-methoxycinnamate;
• esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate and homomenthyl salicylate;
• esters of benzalmalonic acid preferably di(2-ethylhexyl) 4-methoxybenzalmalonate
• Water-soluble substances which may be mentioned are, for example:
• salts of 2-phenylbenzimidazole-5-sulphonic acid such as its sodium, potassium or its triethanolammonium salt, and the sulphonic acid itself;
• sulphonic acid derivatives of 3-benzylidenecamphor such as, for example, 4-(2-oxo-3-bornylidenemethyl)-benzenesulphonic acid, 2-methyl-5-(2-oxo-3-bornylidenemethyl) -benzenesulphonic acid and its salts.
• UVB filters which can be used in combination with the active compounds according to the invention, is not of course intended to be limiting.
• the invention also relates to the combination of one or more active compounds according to the invention with one or more UVB filters, and cosmetic or dermatological formulations according to the invention which also comprise one or more UVB filters.
• UVA filters which have usually been contained to date in cosmetic and/or dermatological formulations.
• These substances are preferably derivatives of dibenzoylmethane, in particular 1- (4′-tert-butylphenyl) -3- (4, -methoxyphenyl) propane-1,3-dione and 1-phenyl-3-(4′-isopropylphenyl) propane-1,3-dione.
• the invention also relates to these combinations and formulations which comprise these combinations. The amounts used for the UVB combination can be employed.
• Cosmetic formulations comprising active compounds according to the invention can also comprise inorganic pigments which are usually used in cosmetics for protecting the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminium and cerium and mixtures thereof, as well as modifications in which the oxides are the active agents.
• the pigments are particularly preferably those based on titanium dioxide.
• the invention also relates to these combinations of UVA filters and/or UVB filters and pigment and to formulations which comprise this combination.
• the amounts mentioned for the above combinations can be used.
• Example 1 W/O cream % by weight Paraffin oil 10.00 Petrolatum 4.00 Wool wax alcohol 1.00 PEG 7-hydrogenated castor oil 3.00 Aluminium stearate 0.40 Diosmin 0.50 Ferulic acid 0.50 Glycerol 2.00 Water, preservative and perfume to 100.00
• Example 2 W/O cream % by weight Paraffin oil 20.00 Petrolatum 4.00 Glucose sesquiisostearate 2.00 Aluminium stearate 0.40 ⁇ -Glucosylrutin 1.00 Caffeic acid 0.50 Vitamin E acetate 1.00 Glycerol 5.00 Water, preservative and perfume to 100.00
• Example 3 O/W lotion % by weight Paraffin oil 8.00 Isopropyl palmitate 3.00 Petrolatum 4.00 Cetearyl alcohol 2.00 PEG 40-castor oil 0.50 Sodium cetearyl sulphate 0.50 Sodium carbomer 0.40 Ferulic acid 0.50 Phloridzin 0.20 Glycerol 3.00 ⁇ -Tocopherol 0.20 Octyl methoxycinnamate 5.00 Butylmethoxydibenzoylmethane 1.00 Water, preservative and perfume to 100.00
• Example 4 O/W cream % by weight Paraffin oil 7.00
• avocado oil 4.00 Glyceryl monostearate 2.00
• Sophora japonica extract 0.80 Sophorine/Solabia
• Example 5 Lip care stick % by weight Hydrogenated castor oil 4.00 Ceresin 8.00 Beeswax 4.00 Carnauba wax 2.00 Petrolatum 40.00 ⁇ -Glycosylrutin 0.10 ⁇ -Carotene 0.10 Caffeic acid 0.30 Paraffin oil, pigments and dyestuffs to 100.00
• Example 6 Lip care stick % by weight Isopropyl lanolate 10.00 Acetylated lanolin 4.00 Beeswax, bleached 9.00 Carnauba wax 4.00 Petrolatum 40.00 Morin 0.10 Tocopheryl acetate 0.10 Ferulic acid 0.10 Paraffin oil, pigments and dyestuffs to 100.00
• Example 7 Liposome-containing gel % by weight Lecithin 6.00 Shea butter 3.00 Ferulic acid 0.50 Neohesperidin dihydrochalcone 0.10 Tocopherol 0.20 Biotin 0.08 Sodium citrate 0.50 Glycine 0.20 Urea 0.20 Sodium PCA 0.50 Hydrolysed collagen 2.00 Xanthan gum 1.40 Sorbitol 3.00 Water, preservative and perfume to 100.00
• Example 8 Gel % by weight Carbopol 934 P 2.00 Triethanolamine 3.00 Ferulic acid 0.50 Hesperitin 0.10 Tocopherol acetate 0.20 Polyoxyethylene sorbitan fatty acid ester 0.50 (Tween 20) Glycerol 2.00 Sodium PCA 0.50 Hydrolysed collagen 2.00 Water, preservative and perfume to 100.00
• Example 11 Sunscreen emulsion % by weight Cyclomethicone 2.00 Cetearyl alcohol + 2.50 PEG 40-hydrogenated castor oil + Sodium cetearyl sulphate Glyceryl lanolate 1.00 Caprylic acid/capric acid triglyceride 0.10 Laurylmethicone copolyol 2.00 Octyl stearate 3.00 Castor oil 4.00 Glycerol 3.00 Acrylamide/sodium acrylate copolymer 0.30 Hydroxypropylmethylcellulose 0.30 Octyl methoxycinnamate 5.00 Butyl-methoxy-dibenzoylmethane 0.50 Sophora japonica extract 0.70 (Sophorine/Solabia) Tocopheryl acetate 1.00 Na 3 HEDTA 1.50 Perfume, preservative, dyestuffs as desired H 2 O, completely desalinated to 100.00
• Example 12 Sunscreen emulsion % by weight Cyclomethicone 2.00 Cetearyl alcohol + 2.50 PEG 40-hydrogenated castor oil + Sodium cetearyl sulphate Glyceryl lanolate 1.00 Caprylic acid/capric acid triglyceride 0.10 Laurylmethicone copolyol 2.00 Octyl stearate 3.00 Castor oil 4.00 Glycerol 3.00 Acrylamide/sodium acrylate copolymer 0.30 Hydroxypropylmethylcellulose 0.30
• Example 9 Sunscreen emulsion % by weight Cyclomethicone 2.00 Cetyldimethicone copolyol 0.20 PEG 22-dodecyl copolymer 3.00 Paraffin oil (DAB 9) 2.00 Caprylic acid/capric acid triglyceride 5.80 Octylmethoxycinnamate 5.80 Butyl-methoxy-dibenzoylmethane 4.00 Hesperidin 0.50 Tocopheryl acetate 0.50 ZnSO 4 0.70 Na 4 EDTA 0.30 Perfume, preservative, dyestuffs as desired H 2 O, completely desalinated to 100.00
• Example 10 Sunscreen emulsion % by weight Cyclomethicone 2.00 Cetyldimethicone copolyol 0.20 PEG 22-dodecyl copolymer 3.00 Paraffin oil (DAB 9) 2.00 Caprylic acid/capric acid triglyceride 5.80 Octyl methoxycinnamate 5.80 Butyl-methoxy-dibenzoylmethane 4.00 Naringin 0.25 Ferulic acid 0.50 Tocopherol 0.50 ZnSO 4 0.70 Na 4 EDTA 0.30 Perfume, preservative, dyestuffs as desired H 2 O, completely desalinated to 100.00 Octyl methoxycinnamate 5.00 Butyl-methoxy-dibenzoylmethane 0.75 Extract of passion flower, blackcurrant 2.50 and grape leaves (AE Complex/Solabia) Ferulic acid 0.30 Na 3 HEDTA 1.50 Perfume, preservative, dyestuffs as desired H 2 O,
• Example 13 Massage cream % by weight Stearyl alcohol 2.00 Petrolatum 4.00 Dimethicone 2.00 Isopropyl palmitate 6.00 Cetearyl alcohol 4.00 PEG 40-hydrogenated castor oil 2.00 Tocopherol 0.50 Scotch thistle extract 0.30 (Pronalen Silymarin/Mani GmbH) Glycerol 3.00 Water, preservative and perfume to 100.00
• Example 14 Hair lotion % by weight Ethanol 40.00 Diisopropyl adipate 0.10 Perfume 0.10 PEG 40-hydrogenated castor oil 0.20 Naringenin 0.10 Tocopheryl acetate 0.10 Dyestuff, preservative as desired Water to 100.00
• Example 15 Hair lotion % by weight Isopropyl alcohol 45.00 Cat's-foot blossom extract (Helicrysum) 1.00 Propylene glycol 0.50 Perfume, dyestuff, preservative as desired Water to 100
• Example 16 Spray formulation % by weight Naringenin 0.10 Tocopherol 0.10 Ferulic acid 0.05 Ethanol 28.20 Perfume as desired Propane/butane 25/75 to 100
• UVB-MLR The UVB mixed lymphocyte reaction method
• the UVB-MLR is a method of analyzing the effects of test substances on UVB-induced suppression of a cellular immune response. It is a modification of the MLR, an immunological in vitro standard method which serves as a measure of the activation and functionalization of the T-lymphocyte system.
• test substances were added to the cell cultures in various concentrations.
• a Phillips TL 20W/12 lamp was used as the source of irradiation.
• Mononuclear cells from the peripheral blood of two healthy human donors are purifed by means of density gradient centrifugation and cultured together in microtitre plates.
• the individual culture here is composed of 3.0 x 105 stimulator cells treated with mitocytin (donor A) and 2.5 x 5 responder cells (donor B) (incubation at 37° C., 7.5% of CO 2 , 10% of FCS (foetal calf serum) in RPMI 1640 medium).
• the stimulator cells are arrested physiologically by the treatment with mitocytin, so that only they act as a cellular antigen for the responder cells, proliferation of which is determined via the incorporation of 3 H-thymidine.
• the responder cells are no longer recognized as an antigen by the stimulator cells.
• 3 H-thymidine is analyzed after separation of all the cells, that is to say stimulator and responder cells.
• the amount of 3 H-thymidine incorporated correlates with the ability to give an immune response; the less 3 H-thymidine incorporated, the greater the UVB immunosuppression.
• the stimulator cells are irradiated with the corresponding UVB dose before their incubation with the responder cells.
• the corresponding test substance is present in the culture medium during the irradiation.

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