WO2014183973A1 - Préparations stabilisées à teneur en acide ascorbique et en ions phosphate - Google Patents

Préparations stabilisées à teneur en acide ascorbique et en ions phosphate Download PDF

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Publication number
WO2014183973A1
WO2014183973A1 PCT/EP2014/058486 EP2014058486W WO2014183973A1 WO 2014183973 A1 WO2014183973 A1 WO 2014183973A1 EP 2014058486 W EP2014058486 W EP 2014058486W WO 2014183973 A1 WO2014183973 A1 WO 2014183973A1
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Prior art keywords
weight
preparations
cosmetic
dermatological
ascorbic acid
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PCT/EP2014/058486
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German (de)
English (en)
Inventor
Kerstin Heike
Juliane Schade
Julia Eckert
Jens Treu
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Beiersdorf Ag
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Publication of WO2014183973A1 publication Critical patent/WO2014183973A1/fr

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    • 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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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

Definitions

  • the present invention relates to the use of phosphate ions for the protection of ascorbic acid and / or generally ascorbyl compounds against oxidation, in particular in cosmetic and dermatological preparations.
  • the present invention relates to cosmetic preparations with effective protection against harmful oxidation dationsluien in the skin, but also for the protection of cosmetic preparations themselves or to protect the components of cosmetic preparations from harmful oxidation processes.
  • the present invention further relates to antioxidant active substance combinations, 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 invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological skin lesions, such as, for example, Skin aging, especially skin aging caused by oxidative processes.
  • the present invention particularly preferably relates to active ingredients and preparations containing such active ingredients for the recycling of oxidized vitamin E, protection against UV-related skin damage (erythema), stimulation of collagen synthesis, strengthening of dermo-epidermal junction zone (skin tightening), visible improvement of the skin condition premature aging of the skin (improvement of the complexion, anti-wrinkle effect), and stimulation of ceramide synthesis.
  • the present invention further relates to active compound combinations and preparations which are used for the prophylaxis and treatment of the photosensitive skin, in particular photodermatoses. The damaging effect of the ultraviolet part of solar radiation on the skin is well known.
  • UVC range rays with a wavelength less than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema simple sunburn or even more or less severe burns.
  • UVA range it is important to have available filter substances, since its rays can cause reactions in photosensitive skin. It has been proven that UVA radiation leads to damage to 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 reactions. The damaging influence of UVB radiation can be amplified by UVA radiation.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin metabolism.
  • photochemical reaction products are radical compounds, for example hydroxy radicals.
  • undefined radical Photoproducts that form in the skin itself may display uncontrolled sequelae due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule, can also occur on UV irradiation, as can short-lived epoxides and many others. Singlet oxygen, for example, is distinguished from the normally present one
  • oxidative stress which is understood as stressing the living cell by accumulating cell-damaging oxidized compounds such as, for example, lipid hydroperoxides, hydrogen peroxide or reactive oxygen compounds such as singlet oxygen, hydroxyl, and peroxide anions.
  • oxidative stress can z. B. by radiation exposure, xenobiotics, heavy metal ions or other causes. He plays a role in the development of some diseases.
  • antioxidants and / or radical scavengers can be incorporated in the cosmetic or dermatological formulations.
  • antioxidants and radical scavengers are known.
  • vitamin E a substance with known antioxidant activity, in cosmetic formulations, but here too the effect achieved lags far behind the hoped-for effect.
  • excellent antioxidants are selected from the group of ascorbic acid and the ascorbyl compounds.
  • L-ascorbic acid ⁇ (R) -5 - [(S) -1,2-dihydroxyethyl] -3,4-dihydroxy-5-H-furan-2-one, vitamin C ⁇ is characterized by the structural formula
  • Ascorbic acid is an endiol and has a strong reducing effect as a reductone. Ascorbic acid is sensitive to heat and is decomposed in particular in the presence of heavy metal traces and in an alkaline medium by light and atmospheric oxygen, in pure, dry state, however, it is relatively resistant to light, air and heat.
  • Ascorbyl compounds preferably ascorbyl esters of fatty acids, more preferably ascorbyl palmitate, are often used in cosmetic and dermatological preparations, since the sensitivity of these compounds to oxidative influence on ascorbic acid is greatly reduced and these compounds are usually better oil-soluble, which can offer galenic advantages.
  • Ascorbyl compounds in the narrower sense are in particular the ascorbyl esters of the general structure
  • R may represent a branched or unbranched alkyl radical having up to 25 carbon atoms.
  • compositions in particular cosmetic or dermatological preparations containing a) at least 1, preferably at least 2 wt .-% of ascorbic acid and / or
  • Ascorbyl compounds based on the total weight of the preparations b) one or more water-soluble phosphates, in particular orthophosphates c) 4-tert-butyl-4'-methoxydibenzoylmethane
  • the phosphate or phosphates in particular alkali metal phosphates, particularly preferably the potassium phosphate, are advantageously present in cosmetic or dermatological preparations, preferably at 0.001% by weight to 10% by weight, preferably from 0.05% by weight to 5% by weight. %, particularly preferably from 0.1 to 2.0% by weight, based on the total weight of the preparations.
  • Hydrogen phosphates and dihydrogen phosphates also apply as "phosphate" in the context of the present invention.
  • the ascorbyl compound or the ascorbyl compounds, in particular vitamin C is or are advantageously according to the invention in cosmetic or dermatological preparations to 1, preferably at least 2 wt .-% to 20 wt .-%, particularly preferably to 3 wt .-% to 5 wt .-%, based on the total weight of the preparations.
  • 4-tert-butyl-4'-methoxydibenzoylmethane is advantageously present in cosmetic or dermatological preparations, preferably up to 10% by weight, preferably from 0.05% by weight to 5% by weight, particularly preferably 0.1%. 2.0 wt .-%, based on the total weight of the preparations.
  • the active ingredient combinations used in cosmetic or dermatological preparations according to the invention have higher stability than the active ingredients used individually, which relates in particular to the ascorbyl compounds and more particularly the vitamin C.
  • active compound combinations according to the invention as an antioxidant and its use for the control and / or prophylaxis of the skin aging caused by oxidative stress and inflammatory reactions onen.
  • the cosmetic or dermatological preparations according to the invention may be composed as usual and used for the treatment, care and cleansing of the skin and / or the hair and as a make-up product in decorative cosmetics. They preferably contain 0.001% by weight to 10% by weight, preferably 0.05% by weight to 5% by weight, in particular 0.1% to 2.0% by weight, based on the total weight of the preparations, on active compound combinations used according to the invention.
  • Complexing agents are known auxiliaries of cosmetology or medical galenics. By complexing of interfering metals such as Mn, Fe, Cu and others, for example, unwanted chemical reactions in cosmetic or dermatological preparations can be prevented.
  • Complexing agents in particular chelators, form complexes with metal atoms, which in the presence of one or more polybasic complexing agents, ie chelators, represent metallacycles.
  • Chelates represent compounds in which a single ligand occupies more than one coordination site on a central atom. In this case, normally stretched compounds are closed by complex formation via a metal atom or ion into rings. The number of bound ligands depends on the coordination number of the central metal. The prerequisite for chelation is that the metal-reactive compound contain two or more atomic groups acting as electron donors.
  • the complexing agent (s) can advantageously be selected from the group of the customary compounds, preference being given to at least one substance selected from the group consisting of tartaric acid and its anions, citric acid and its anions, aminopolycarboxylic acids and their anions (such as, for example, ethylenediaminetetraacetic acid (EDTA) and theirs Anions, nitrilotriacetic acid (NTA) and their anions, hydroxyethylenediaminotriacetic acid (HOEDTA) and their anions,
  • EDTA ethylenediaminetetraacetic acid
  • NTA nitrilotriacetic acid
  • HOEDTA hydroxyethylenediaminotriacetic acid
  • the complexing agent (s) according to the invention are advantageously present in cosmetic or dermatological preparations, preferably at from 0.01% by weight to 10% by weight, preferably from 0.05% by weight to 5% by weight, particularly preferably 0.1 - 2.0 wt .-%, based on the total weight of the preparations.
  • Cosmetic and dermatological preparations are applied according to the invention in the usual manner for cosmetics on the skin and / or hair in sufficient quantity.
  • Cosmetic and dermatological preparations according to the invention can be present in various forms. So they can e.g. a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water type (O / W), a multiple emulsion, for example of the water-in-oil-in-water type. Water (W / O / W), a gel, a solid stick, an ointment or even an aerosol. It is also advantageous to present isoquercitrin in encapsulated form, e.g. in
  • Collagen matrices and other common encapsulating materials e.g. as cellulase encapsulations, in gelatin, wax matrices or liposomally encapsulated.
  • wax matrices as described in DE-OS 43 08 282 have been found to be favorable.
  • the cosmetic and dermatological preparations according to the invention may comprise cosmetic adjuvants conventionally used in such preparations, for example preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moistening and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • compounds according to the invention may also contain further antioxidants and / or radical scavengers.
  • antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocaninic acid) and derivatives thereof, peptides such as D, L-carnosine, D-carnosine, L-carnosine.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocaninic acid
  • peptides such as D, L-carnosine, D-carnosine, L-carnosine.
  • Carnosine and its derivatives eg anserine
  • carotenoids eg ⁇ -carotene, ⁇ -carotene, lycopene
  • chlorogenic acid and its derivatives eg dihydrolipoic acid
  • lipoic acid and its derivatives eg dihydrolipoic acid
  • aurothioglucose propylthiouracil and other thiols (eg Thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl,
  • Cholesteryl and glyceryl esters and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (eg buthionine sulfoximines, homocysteinesulfoximine, buthionine sulfones, penta, hexa, Heptathioninsulfoximin) in very low tolerated dosages (eg pmol to ⁇ / kg), (metal) chelators (eg ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid , Bile extracts, bilirubin, biliver
  • the amount of the aforementioned 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 of the preparation.
  • vitamin E and / or its derivatives represent the additional antioxidant (s)
  • vitamin A or vitamin A derivatives, or carotenes or derivatives thereof, constitute the additional antioxidant (s) it is advantageous if their respective concentrations are in the range from 0.001 to 10% by weight, based on the total weight of the formulation , to choose.
  • Emulsions according to the invention are advantageous and contain, for example, the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as is customarily used for such a type of formulation.
  • Oils such as triglycerides of capric or caprylic acid, further natural oils such as e.g. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or lower esters of fatty alcohols with alkanoic acids
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present 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 having a chain length of 3 to 30 carbon 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 consisting of isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isobutyl stearate and isopropyl stearate.
  • nonyl isononanoate 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and also synthetic, semisynthetic and natural mixtures of such esters, for example jojoba oil.
  • the oil phase can be advantageously selected 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 the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12 to 18 carbon atoms.
  • the fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, such as 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 are also advantageous to use in the context of the present invention. It may also be advantageous, if appropriate, to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • synthetic, semi-synthetic and natural oils such as 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 are also advantageous to use in the context of the present invention. It may also be advantageous, if appropriate, 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 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, Ci2-i5-alkyl benzoate, caprylic-capric acid triglyceride, dicaprylyl ether.
  • Ci2-i5-alkyl benzoate and 2-ethylhexyl isostearate mixtures of Ci2-i5-alkyl benzoate and isotridecyl isononanoate and mixtures of C 12- i5-alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffinol, 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
  • other silicone oils are also advantageous for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • mixtures of cyclomethicone and isotridecyl isonanoate, of cyclomethicone and 2-ethylhexyl isostearate are particularly advantageous.
  • Phosphates especially orthophosphates
  • the aqueous phase of the preparations according to the invention advantageously contains alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, di - ethylene glycol monomethyl or monoethyl ether and analogous products, furthermore low C-number alcohols, eg Ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickening agents, which or which can be advantageously selected from the group of silica, aluminum silicates, polysaccharides or their derivatives, e.g.
  • Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose particularly advantageous from the group of polyacrylates, preferably a polyacrylate from the group of so-called Carbopols, for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • Carbopols for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • Emulsions of the invention are advantageous and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an above-mentioned oil in the presence of a thickener which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • a thickener which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • Suitable propellants for preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or mixed with one another. Also, compressed air is advantageous to use.
  • preparations according to the invention may also contain other substances which absorb UV radiation in the UVA and / or UVB range, the total amount of filter substances being, for example, from 0.1% by weight to 30% by weight, preferably from 0.5 to 10 Wt .-%, in particular 1, 0 to 6.0 wt .-%, based on the total weight of the preparations, in order to provide cosmetic preparations that protect the hair or the skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for hair or skin.
  • UVB filter substances these may be oil-soluble or water-soluble.
  • oil-soluble UVB filters according to the invention are, for example:
  • 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
  • 4-aminobenzoic acid derivatives preferably (2- ethylhexyl) 4- (dimethylamino) benzoate, 4- (dimethylamino) benzoic acid amyl ester;
  • Esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycinnamic acid isopentyl ester;
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomenthyl salicylate,
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably di (2-ethylhexyl) 4-methoxybenzalmalonate, - 2,4,6-trianilino (p-carbo-2'-ethyl-1 '-hexyloxy) -1, 3,5-triazine.
  • Advantageous water-soluble UVB filters are e.g.
  • Salts of 2-phenylbenzimidazole-5-sulfonic acid such as its sodium, potassium or triethanolammonium salt, and the sulfonic acid itself;
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
  • Sulfonic acid derivatives of the 3-benzylidene camphor such as, for example, 4- (2-oxo-3-bomylidene-methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and its salts, and di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and its salts (the debranching 10-sulfato compounds, for example the corresponding sodium, potassium or triethanolammonium salt), also referred to as benzene-1, 4-di (2-oxo-3-bomylidenemethyl-10-sulfonic acid
  • UVB filters which can be used in combination with the active compound combinations according to the invention should of course not be limiting.
  • the invention also provides the use of a combination of the active substance combinations used according to the invention with at least one UVB filter as antioxidant or the use of a combination of the active compound combinations used according to the invention with at least one UVB filter as antioxidant in a cosmetic or dermatological preparation.
  • UVA filters which have hitherto usually been present in cosmetic preparations.
  • Cosmetic and dermatological preparations with an effective content of active ingredient combinations used according to the invention may also contain inorganic pigments which are commonly used in cosmetics for the protection of the skin from UV rays. These are oxides of titanium, zinc, zirconium, silicon, manganese, cerium and mixtures thereof, as well as modifications in which the oxides are the active agents. Particular preference is given to pigments based on titanium dioxide.
  • a method for measuring the UVA protection performance is currently also being worked on in the COLI PA because the industry demands a uniform method.
  • the COLIPA is the umbrella organization of the European cosmetics industry. a. Recommendations regarding the execution of the measurement method.
  • the UVA / UVB balance is the basis of the method discussed there. It is modified to include a pre-irradiation with UV light to include some special UV filter systems. So far, the products have been tested without pre-irradiation.
  • the ratio of UV-A to UV-B protection is at least 1: 3, more preferably at least 2: 3.
  • the cosmetic and dermatological substances contain active ingredients and auxiliaries customarily used for this type of preparations for hair care and hair treatment as adjuvants are preservatives, surface-active substances, substances for preventing foaming , Thickeners, emulsifiers, fats, oils, waxes, organic solvents, bactericides, perfumes, dyes or pigments. the purpose of which is to dye the hair or the cosmetic or dermatological preparation itself, electro- lytes, substances against the greasing of hair.

Abstract

Préparations, notamment préparations cosmétiques ou dermatologiques contenant a) au moins 1, de préférence au moins 2 % en poids d'acide ascorbique et/ou de composés ascorbyle, par rapport au poids total des préparations, b) un ou plusieurs phosphates, notamment des orthophosphates, hydrosolubles, c) 4-tert-butyl-4'-méthoxydibenzoylméthane.
PCT/EP2014/058486 2013-05-14 2014-04-25 Préparations stabilisées à teneur en acide ascorbique et en ions phosphate WO2014183973A1 (fr)

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DE102013208865.5A DE102013208865A1 (de) 2013-05-14 2013-05-14 Stabilisierte Zubereitungen mit einem Gehalt an Ascorbinsäure und Phosphationen
DE102013208865.5 2013-05-14

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WO2016078854A1 (fr) * 2014-11-19 2016-05-26 Beiersdorf Ag Préparations contenant de l'acide ascorbique, de l'ubidécarénone et des ions phosphate pour un remodelage amélioré de la peau ou contre la cellulite
US10941205B2 (en) 2015-10-02 2021-03-09 Hoffmann-La Roche Inc. Bispecific anti-human A-beta/human transferrin receptor antibodies and methods of use
US11584793B2 (en) 2015-06-24 2023-02-21 Hoffmann-La Roche Inc. Anti-transferrin receptor antibodies with tailored affinity
US11603411B2 (en) 2015-10-02 2023-03-14 Hoffmann-La Roche Inc. Bispecific anti-human CD20/human transferrin receptor antibodies and methods of use

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US11603411B2 (en) 2015-10-02 2023-03-14 Hoffmann-La Roche Inc. Bispecific anti-human CD20/human transferrin receptor antibodies and methods of use
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