EP2211827A2 - Dérivés d'acides alfa-aminés pour l'amélioration de la solubilité - Google Patents

Dérivés d'acides alfa-aminés pour l'amélioration de la solubilité

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Publication number
EP2211827A2
EP2211827A2 EP08853958A EP08853958A EP2211827A2 EP 2211827 A2 EP2211827 A2 EP 2211827A2 EP 08853958 A EP08853958 A EP 08853958A EP 08853958 A EP08853958 A EP 08853958A EP 2211827 A2 EP2211827 A2 EP 2211827A2
Authority
EP
European Patent Office
Prior art keywords
branched
chain
straight
amino acid
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08853958A
Other languages
German (de)
English (en)
Inventor
Thomas Rudolph
Herwig Buchholz
Michaela Oberle
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP2211827A2 publication Critical patent/EP2211827A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/022—Powders; Compacted Powders
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/26—Optical properties
    • A61K2800/262—Transparent; Translucent
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous

Definitions

  • the present invention relates to the use of ⁇ -amino acid derivatives for solubility improvement of sparingly soluble substances in water or aqueous solutions, as well as mixtures and preferred formulations.
  • Active substances are substances that - occurring or added in relatively small amounts - can develop great physiological effects. They have become indispensable in today's everyday life and play an important role in beauty care as well as in treatment and food intake.
  • Eusolex® 232 phenylbenzimidazole sulfonic acid, 2-
  • Phenylbenzimidazole-5-sulfonic acid for use in cosmetic products, to achieve sufficient solubility.
  • a disadvantage here is the required alkaline pH of the formulation of pH 7 to 8.
  • acidic cosmetics are preferred for reasons of compatibility and the natural-acidic pH of the skin.
  • active substances for example PSBA, but so far can not be used, since it comes here to the recrystallization of the sulfonic acid.
  • the ideal value of a cosmetic formula is pH 5.5 and thus corresponds to the natural pH of the skin.
  • Acids to be formulated in this way are preservatives in the form of the free acid or pharmacologically active substances in the form of the free acid.
  • oxidation-sensitive substances e.g. phenolic substances or vitamins, e.g. Vitamin C and vitamin C derivatives (as disclosed in, for example, WO2008017346), as well as self-tanning substances such as dihydroxyacetone, are known to be oxidized while known to produce oxidation stability with decreasing pH.
  • vitamins e.g. Vitamin C and vitamin C derivatives (as disclosed in, for example, WO2008017346)
  • self-tanning substances such as dihydroxyacetone
  • the object of the present invention is therefore to provide compounds whose use improves the solubility of substances which are sparingly soluble in water when the pH of the solution is below pH 7.
  • a first subject of the present invention is therefore the use of at least one ⁇ -amino acid derivative, its salt or hydrate for improving the solubility of one or more sparingly soluble substances in water or aqueous solutions.
  • the ⁇ -nitrogen atom of the at least one ⁇ -amino acid derivative is quaternary, tertiary or secondary.
  • Particularly poorly soluble substances in the context of this invention are substances whose solubility in water at a temperature between 20 ° and 25 ° C. is less than 1% by weight, when the pH of the solution is below pH 7.
  • the solubility of a substance is preferably improved, its solubility in water in the absence of the ⁇ -amino acid derivative at a temperature between 20 ° and 25 ° C and at a pH of the preparation between 3 and 6.5 less than 1 Wt .-% is.
  • Advantages of the use according to the invention are, in particular, the good skin compatibility and the fact that the use according to the invention of the ⁇ -amino acid derivative makes it possible to use active ingredients which have sufficient solubility only in the alkaline range, also in acidic or neutral cosmetic and dermatological preparations ,
  • the present invention now makes it possible to combine phenylbenzimidazole sulfonic acid (PBSA, Eusolex® 232), which was originally only neutral or alkaline, with acid-sensitive substances such as dihydroxyacetone or vitamin C. In the alkaline would be
  • sufficient solubility in the sense of this invention describes the property of a substance not to crystallize out in the case of product-specific storage. Depending on the application, sufficient solubility is considered to be, in particular, a solubility which provides good efficacy with simultaneous storage stability.
  • a non-amphotensidic betaine, 2-pyrrolidone-5-carboxylic acid and / or a derivative of formiminoglycine is used as at least one ⁇ - amino acid derivative.
  • betaine includes all compounds containing a quaternary ammonium group and an acid radical.
  • the non-amphoteric acid betaine used is particularly preferably trimethylglycine according to the invention.
  • the 2-pyrrolidone-5-carboxylic acid is particularly preferably used:
  • Ectoin Hydroxyectoin Creatine Creatinine Most preferably, ectoine or creatinine is used as formiminoglycine according to the invention.
  • creatinine is used as the ⁇ -amino acid derivative to improve the solubility of one or more sparingly soluble substances in water or aqueous solutions.
  • All ⁇ -amino acid derivatives can also be used according to the invention in the form of their salts or hydrates, for example the creatine hydrate.
  • the solubility of a sparingly soluble substance is selected according to the invention, which is selected from the group chromones, chromanones, flavonoids and organic acids, for example preservatives in the form of the free acid, pharmacological agents in the form of the free acid, cosmetic active ingredients in the form of the free acid.
  • organic acids are aromatic monosulfonic acids.
  • Chromone derivatives are preferably understood as meaning certain chromene-on derivatives which are useful as active ingredients for the preventive treatment of human skin and hair against aging processes and harmful environmental influences. At the same time they show a low irritation potential for the skin, positively influence the water binding in the skin, maintain or increase the elasticity of the skin and thus promote a smoothing of the skin.
  • the sparingly soluble chromene-one whose solubility is improved according to the invention is particularly preferably a compound of the general formula (I)
  • R 1 and R 2 may be identical or different and is H 1 straight-chain or branched C 1 - to C 2 o-alkyl groups or straight-chain or branched Cr to C 2 o-hydroxyalkyl groups
  • R 3 is H or straight-chain or branched C 1 - to C 2 -alkyl groups
  • R 4 is H or OR 7 ,
  • R 5 and R 6 may be identical or different and is H, OH or straight-chain or branched C 3 - to C 2 o-alkenyl groups,
  • R 7 is H or linear or branched C 1 - to C2 0 - alkyl groups, at least two of the substituents R 1, R 2, R 4 to R 6 are different from H.
  • Chromanone derivatives preferably contain certain chromanone derivatives.
  • Skin diseases are suitable, understood. They show a low level at the same time
  • Irritation potential for the skin affect the water binding in the skin positively, maintain or increase the elasticity of the skin and thus promote a
  • R 1 and R 2 may be the same or different and are selected from - H, straight-chain or branched C 1 - to C 2 o-alkyl groups,
  • R 3 , R 4 and R 5 are each independently selected from --H 1 OH 1
  • R 6 ' is H, OH, COOH, COCH 3 , straight-chain or branched C 1 - to C 2 o-alkyl groups,
  • chroman-4-one derivatives of the formula (II) 5,7-dihydroxy-2,2-dimethylchroman-4-one or 6-hydroxy-2,2-dimethylchroman-4-one are particularly preferred more preferably 6-hydroxy-2,2-dimethyl-chroman-4-one.
  • the proportion of one or more compounds selected from chromone or chromanone derivatives in a preparation is preferably from 0.001% by weight to 5% by weight, particularly preferably from 0.01% by weight to 2% by weight, based on the entire preparation.
  • this invention is also understood to mean the aglycones, ie the sugar-free constituents, and the derivatives of the flavonoids and the aglycones.
  • flavonoid is also understood to mean anthocyanidin (cyanidin).
  • Flavonoids are generally poorly soluble compounds, with the exception of, for example, troxerutin and ⁇ -glucosylrutin.
  • the sparingly soluble substance whose solubility is improved according to the invention is preferably isoquercetin or a compound of the general formula (III)
  • R 8 , R 9 and R 10 may be the same or different and each independently represent OH, CH 3 COO, alkoxy or monoglycoside radicals, where the alkoxy radicals may be branched and unbranched and may have 1 to 8 carbon atoms .
  • R 11 is a mono- or diglycoside radical, with this glycoside radical in each case via a group -O-
  • R 12 has the meaning of the radicals R 8 to R 10 , and wherein one or more hydrogen atoms in the OH groups of the glycoside or the radicals are each independently substituted by acetyl or by alkyl radicals having 1 to 8 carbon atoms could be.
  • tiliroside is particularly preferred.
  • the at least one flavonoid for the use according to the invention in corresponding formulations in a total amount of 0.01 wt .-% to 10 wt .-%, more preferably in an amount of 0.1 wt .-% to 5 wt .-% used.
  • Suitable preservatives in the form of the free acid are benzoic acid, benzylic acid, formic acid, propionic acid, salicylic acid or sorbic acid. By solubilizing the ⁇ -amino acid derivative in particular the preservative effect is greatly improved. Creatinine also allows the solution of the preservative in the form of the free acid in preparations with skin-like pH.
  • Aromatic monosulfonic acids are active substances which are suitable inter alia as UV filters, in particular in cosmetics or pharmacy. Their use in cosmetic and dermatological preparations is known.
  • the aromatic monosulfonic acid whose solubility is improved according to the invention, particularly preferably only in the alkaline water-soluble UV filter selected from the group 2-arylbenzimidazole-5-sulfonic acids, 2-hydroxy-4-methoxybenzophenone-5 - sulfonic acid or sulfonic acid derivatives of 3-Benzylidencamphers.
  • Arylbenzimidazolesulfonic acids for example, preferably correspond to the general formula (IV)
  • 2-phenylbenzimidazole-5-sulfonic acid is particularly preferred.
  • Monosulfonic acid derivatives of the 3-benzylidene camphor are, for example, 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid or 2-methyl-5- (oxo-3-bornylidenemethyl) benzenesulfonic acid.
  • solubility of tiliroside, 5,7-dihydroxy-2-methyl-chromen-4-one, or Eusolex® 232 (2-phenylbenzimidazole-5-sulfonic acid) in water or an aqueous solution by use of 2-pyrrolidone-5-carboxylic acid, ectoine, hydroxyectoine, creatine or creatinine.
  • 2-phenyl-benzimidazole-5-sulfonic acid is particularly preferably used as sparingly soluble substance in water or aqueous solutions.
  • a preferred aqueous solution is, for example, a mixture of water and an alcohol, such as methanol, ethanol or propanol, more preferably ethanol.
  • the weight ratio of alcohol to water is preferably between 10: 1 and 1: 100, more preferably weight ratios between 5: 1 and 1:50.
  • embodiments of aqueous solutions which contain no alcohol are also preferred.
  • the solubility of aromatic monsulfonic acids, in particular of 2-phenylbenzimidazole-5-sulfonic acid is particularly preferably improved.
  • An advantage of the particularly preferred combination of creatinine with PBSA is the improvement of the attachment of the UV filter PBSA to hair for improved hair care or hair protection. Furthermore, so effective UV protection of hair dyes or dyed hair against UV-induced color change can be achieved.
  • Another advantage of the particularly preferred combination of creatinine with PBSA is the water resistance of formulations containing this combination. As with the hair care effect described above, creatinine increases the skin's resistance to PBSA. This leads to an improved water resistance of preparations, in particular sunscreen products. The use of this preferred combination of creatinine with PBSA also improves the perspiration or moisture resistance of PBSA-containing products.
  • Another object of the present invention are preparations, preferably cosmetic agents, pharmaceutical compositions, medical devices or foods containing at least one ⁇ -amino acid derivative and at least one sparingly soluble substance, as defined above, wherein the proportion of ⁇ -amino acid derivative in weight percent is greater than the proportion of the sparingly soluble substance in percent by weight, based on the preparation.
  • preparations are preferred in which the ⁇ -amino acid derivative is selected from 2-pyrrolidone-5-carboxylic acid, creatinine,
  • Creatine, ectoine and hydroxyectoine, most preferably creatinine is chosen.
  • preparations are preferred in which the sparingly soluble substance is an aromatic monosulfonic acid.
  • Very particularly preferred preparations contain creatinine and PBSA.
  • the at least one ⁇ -amino acid derivative is present in an amount of from 0.05% by weight to 20% by weight, preferably in an amount of from 0.5% by weight to 10% by weight. and more preferably in an amount of from 1% to 5% by weight.
  • the at least one ⁇ -amino acid derivative and the at least one aromatic monosulfonic acid in a weight percent ratio of 10: 1 to 1, 1: 1, preferably from 5: 1 to 1, 5: 1 contain, very particularly preferred from 3: 1 to 2: 1.
  • An advantage of this preparation according to the invention is that the pH of the aqueous phase of the preparation is less than 7, preferably less than 6.5.
  • the preferred pH range of the aqueous phase of the preparation is from pH 4.5 to 6.5, more preferably from pH 5 to 6.
  • the preparations are usually topically applicable preparations, for example cosmetic or dermatological formulations or medical products.
  • the preparations in this case contain a cosmetically or dermatologically suitable carrier and, depending on the desired property profile, optionally further suitable ingredients.
  • the preparations in this case contain a pharmaceutically acceptable carrier and optionally further pharmaceutical active ingredients. If it is a dietary supplement, then a suitable carrier is to be selected.
  • the preparations are perfumes
  • solvents such as alcohols, oils and, if appropriate, emulsifiers
  • creatinine can be used for the controlled release of these components.
  • agent or formulation is used synonymously in addition to the term preparation. All compounds or components that can be used in the formulations are either known and commercially available or can be synthesized by known methods.
  • Another object of the present invention is a mixture, in particular a solid mixture containing at least one ⁇ -amino acid derivative, preferably selected from 2-pyrrolidone-5-carboxylic acid, creatinine, creatine, ectoine and hydroxyectoine, and at least one sparingly soluble substance, preferably selected from chromones , Chromanones, flavonoids and organic acids, especially aromatic monosulfonic acids.
  • This mixture is particularly suitable for the preparation of a cosmetic, pharmaceutical preparation, a medical device or food preparation.
  • the at least one ⁇ -amino acid derivative and the at least one sparingly soluble substance in a weight percent ratio of 10: 1 to 1, 1: 1, preferably from 5: 1 to 1, 5: 1 contain, very particularly preferred from 3.5: 1 to 2: 1. contain.
  • the mixture according to the invention contains 90% by weight to 11% by weight of at least one ⁇ -amino acid derivative as defined above and 45% by weight to 10% by weight of at least one sparingly soluble substance, such as previously defined.
  • the mixture may also contain other substances, such as release agents.
  • a release agent for example, silica (Aerosiie), Taik, zinc oxide or starch can be used.
  • the sparingly soluble substance in the mixtures according to the invention is very particularly preferably an aromatic monosulfonic acid, preferably selected from the group 2-arylbenzimidazole-5-sulfonic acids of the formula IV, as described above, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid or derivatives of the 3 -Benzylidencamphers.
  • 2-phenylbenzimidazole-5-sulfonic acid and sorbic acid or 2-phenylbenzimidazole-5-sulfonic acid or sorbic acid are particularly preferably selected as sparingly soluble substance in the mixture according to the invention.
  • Creatinine is particularly preferably used as the ⁇ -amino acid derivative in the mixtures according to the invention. Further preferred combinations of embodiments are disclosed in the claims.
  • the mixtures according to the invention can be prepared using techniques which are well known to the person skilled in the art.
  • a suitable solvent preferably in water or an aqueous solution
  • the sparingly soluble substance is introduced and the solvent is removed again using a suitable technique.
  • a distillation, freeze-drying or spray-drying is suitable. Particularly suitable is spray drying.
  • Another object of the invention is therefore also a process for preparing a mixture as described above, characterized in that an ⁇ -amino acid derivative is dissolved in a suitable solvent, the sparingly soluble substance and optionally a release agent is introduced and the solvent is removed.
  • a preferred method for preparing mixtures containing creatinine as ⁇ -amino acid derivative is characterized in that first creatine is dissolved in water at temperatures of 40 ° to 50 0 C, then the sparingly soluble substance and optionally a release agent at temperatures of 40 ° to 50 0th C are registered and the solution is subjected to spray drying.
  • the spray drying is carried out, for example, at a supply air of 160 ° to 240 0 C and an exhaust air of 80 ° to 120 0 C.
  • the preparations or mixtures may comprise or contain, consist essentially of or consist of the said necessary or optional ingredients.
  • pigments In the described preparations and mixtures which comprise according to the invention at least one derivative of an ⁇ -amino acid and at least one sparingly soluble substance, it is also possible for pigments to be present, the layer structure of the pigments not being limited.
  • the color pigment should be skin colored or brownish at a level of from 0.5% to 5% by weight.
  • the selection of a corresponding pigment is familiar to the person skilled in the art.
  • advantageous color pigments are titanium dioxide, mica, iron oxides (eg Fe 2 O 3 , Fe 3 O 4 , FeO (OH)) and / or tin oxide.
  • Advantageous dyes are, for example, carmine, Berlin blue, chrome oxide green, ultramarine blue and / or manganese violet.
  • the Color Index Numbers are taken from the Rowe Color Index, 3rd Edition, Society of Dyers and Colourists, Bradford, England, 1971.
  • 3rd layer substrate pigments z. Mica / metal oxide
  • pearlescent pigments are, for example, pulverulent pigments or castor oil dispersions of bismuth oxychloride and / or titanium dioxide, and Bismuth oxychloride and / or titanium dioxide on mica. Particularly advantageous is z. For example, listed under the CIN 77163 luster pigment.
  • pearlescent pigment types based on mica / metal oxide are also advantageous, for example, are the following pearlescent pigment types based on mica / metal oxide:
  • pearlescent pigments available from Merck under the trade names Timiron®, Colorona®, Dichrona®, Xirona® or Ronastar®.
  • pearlescent pigments which are advantageous in the context of the present invention are obtainable in numerous ways known per se.
  • other substrates except mica can be coated with other metal oxides such.
  • silica and the like As silica and the like.
  • pearlescent pigments which under the Use of SiO 2 are produced.
  • Such pigments which may also have additional gonichromatic effects are, for. B. under the trade name Sicopearl Fantastico available from BASF.
  • preparation or mixture according to the invention may preferably also contain other active substances, such as, for example, repellents, in particular insect repellents, UV filters, aryloximes and parabens.
  • repellent agents belong to the classes of amides, alcohols, esters and ethers.
  • Repellents should usually meet the following conditions: they must not evaporate too quickly and should not penetrate the skin. They must not be primarily irritating or sensitizing to the skin and, moreover, should not be toxic, their effectiveness must also be preserved under the influence of skin fluid and / or UV radiation.
  • Preferred repellents are selected from N, N-diethyl-3-methylbenzamide, 3- (acetyl-butyl-amino) -propionic acid ethyl ester, dimethyl phthalate, butopyronoxyl, 2,3,4,5-bis (2-butylene) -tetrahydro- 2-furaldehyde, N, N-caprylic acid diethylamide, N, N-diethylbenzamide.
  • Parabens are 4-hydroxybenzoic acid esters which are used in free form or as sodium salts for the preservation of preparations in the field of food, cosmetics and pharmaceuticals.
  • the effect of the esters is directly proportional to the chain length of the alkyl radical, but conversely the solubility decreases with increasing chain length.
  • the esters are largely pH independent and operate in a pH range of 3.0-8.0.
  • the antimicrobial mechanism of action is based on damage to the microbial membranes by the surface activity of the PHB esters and on protein denaturation. In addition, interactions with coenzymes occur. The effect is directed against fungi, yeasts and bacteria.
  • the most important as preservatives parabens are 4-hydroxybenzoate, ethyl 4-hydroxybenzoate, propyl 4-hydroxybenzoate, butyl 4-hydroxybenzoate.
  • 2-hydroxy-5-methyllaurophenone oxime which is also referred to as HMLO, LPO or F5
  • HMLO 2-hydroxy-5-methyllaurophenone oxime
  • LPO 2-hydroxy-5-methyllaurophenone oxime
  • Preparations containing 2-hydroxy-5-methyllaurophenone oxime are accordingly suitable for the treatment of skin diseases which are associated with inflammation. It is known that such preparations, e.g. can be used for the treatment of psoriasis, various eczema forms, irritative and toxic dermatitis, UV dermatitis and other allergic and / or inflammatory diseases of the skin and the skin appendages.
  • compositions according to the invention which, in addition to the compound (s) mentioned, additionally contain an aryloxime, preferably 2-hydroxy-5-methyllaurophenone oxime, show surprising anti-inflammatory suitability.
  • the preparations preferably contain from 0.01 to 10% by weight of the aryloxime, and it is particularly preferred if the preparation contains from 0.05 to 5% by weight of aryloxime.
  • the protective effect of preparations against oxidative stress or against the action of radicals can be improved if the preparations contain one or more antioxidants, wherein the skilled person no It is difficult to select suitable fast or delayed-acting antioxidants.
  • the preparation is a preparation for protecting body cells against oxidative stress, in particular for reducing skin aging, characterized in that it contains one or more antioxidants in addition to the other ingredients.
  • antioxidants eg amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles, (eg urocaninic acid) and their derivatives, peptides such as D, L- Carnosine, D-carnosine, L-camosine and their derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, 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, buty
  • R 1 can be selected from the group -C (O) CH 3 , -CO 2 R 3 , -C (O) NH 2 and -C (O) N (R 4 ) 2 ,
  • X is O or NH 1 '
  • R 2 is linear or branched alkyl having 1 to 30 C atoms
  • R 3 is linear or branched alkyl having 1 to 20 C atoms
  • R 4 are each independently of one another H or linear or branched alkyl having 1 to 8 C atoms,
  • R 5 is H or linear or branched alkyl having 1 to 8 C atoms or linear or branched alkoxy having 1 to 8 C atoms and
  • R 6 denotes linear or branched alkyl having 1 to 8 C atoms, preferably derivatives of 2- (4-hydroxy-3,5-dimethoxybenzylidene) malonic acid and / or 2- (4-hydroxy-3,5-dimethoxybenzyl) - malonic acid, more preferably 2- (4-
  • antioxidants are also suitable for use in the cosmetic preparations according to the invention.
  • Known and commercially available mixtures are, for example, mixtures containing as active ingredients lecithin, L - (+) - ascorbyl palmitate and citric acid (eg (eg Oxynex ® AP), natural tocopherols, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (for example Oxynex ® K LIQUID), tocopherol extracts from natural sources, L - (+) - ascorbyl palmitate, L - (+ ) -ascorbic acid and citric acid (for example Oxynex ® L LIQUID), DL- ⁇ -tocopherol, L - (+) - ascorbyl palmitate, citric acid and lecithin (for example Oxynex ® LM) or butylhydroxytoluene (BHT), L - (+) - ascorbyl palmitate and Ci
  • Suitable antioxidants are furthermore compounds of the formula (C)
  • R 1 to R 10 may be the same or different and are selected from H
  • Hydroxy group may be bonded to a primary or secondary carbon atom of the chain and further the alkyl chain may also be interrupted by oxygen, and / or
  • the preparations or mixtures to be used may contain vitamins as further ingredients.
  • vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin Bi), riboflavin (vitamin B 2 ), nicotinamide, Vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D 2 ), vitamin E, DL- ⁇ -tocopherol, tocopherol-E-acetate, tocopherol hydrogen succinate, vitamin Ki, esculin (vitamin P active ingredient), thiamine (vitamin B), Nicotinic acid (niacin), pyridoxine, pyridoxal, pyridoxamine, (vitamin B ⁇ ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B 12 ), particularly preferably vitamin A palmitate, vitamin C and its derivatives, DL- ⁇ -tocopherol,
  • Preferred preparations can also serve for sun protection.
  • Preparations or mixtures according to the invention can therefore contain not only ⁇ -amino acid derivatives and the sparingly soluble substances but also optionally other ingredients, UV filters.
  • UV filters are suitable for combination with the ⁇ -amino acid derivatives to be used according to the invention. Particularly preferred are those UV filters whose physiological harmlessness has already been demonstrated. Both for UVA and UVB filters, there are many well-known and proven substances from the literature, eg
  • Benzylidenecamphor derivatives such as 3- (4'-methylbenzylidene) -dl-camphor (for example Eusolex 6300), 3-benzylidenecamphor (for example Mexoryl® SD), polymers of N - ⁇ (2 and 4) - [2- (oxoborn-3- ylidene) methyl] benzyl ⁇ acrylamide (for example Mexoryl® SW) or N, N 1 N-trimethyl-4- (2-oxobom-3-ylidenemethyl) anilinium methylsulfate (for example Mexoryl® SK).
  • 3- (4'-methylbenzylidene) -dl-camphor for example Eusolex 6300
  • 3-benzylidenecamphor for example Mexoryl® SD
  • polymers of N - ⁇ (2 and 4) - [2- (oxoborn-3- ylidene) methyl] benzyl ⁇ acrylamide for example Mexoryl® SW
  • Benzoyl or dibenzoylmethanes such as 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione (e.g., Eusolex® 9020) or 4-isopropyldibenzoylmethane (e.g., Eusolex® 8020),
  • Benzophenones such as 2-hydroxy-4-methoxybenzophenone (e.g., Eusolex® 4360) or the sodium salt of 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid.
  • Methoxycinnamic acid esters such as octyl methoxycinnamate (e.g., Eusolex® 2292), 4-isoxycinnamate, e.g. as a mixture of isomers (e.g., Neo Heliopan® E 1000),
  • Salicylate derivatives such as 2-ethylhexyl salicylate (e.g., Eusolex® OS), 4-isopropylbenzyl salicylate (e.g., Megasol®) or 3,3,5-trimethylcyclohexyl salicylate (e.g., Eusolex® HMS).
  • phenylbenzimidazole sulfonic acids such as 2-phenylbenzimidazole-5-suifonic acid, 2,2- (1,4-phenylene) bisbenzimidazole-4,6-disulfonic acid or salts thereof (for example Neoheliopan® AP)
  • 2-cyano-3,3-diphenylacrylic acid 2-ethylhexyl ester e.g., Eusolex® OCR
  • Hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate eg Uvinul® UVA Plus, BASF.
  • UVA Plus Ultraviolet® UVA Plus
  • UV filters are also Methoxyflavone en Kunststoffend the German patent application DE-A-10232595.
  • Organic UV filters are usually incorporated in formulations in an amount of 0.5 to 20 percent by weight, preferably 1 to 15 percent by weight.
  • preparations with light protection properties also contain inorganic UV filters.
  • Conceivable inorganic UV filters are those from the group of titanium dioxides, such as coated titanium dioxide (for example Eusolex® T-2000, Eusolex ® T-AQUA, Eusolex® T-AVO), zinc oxides (eg Sachtotec.RTM), iron oxides and also cerium oxides are conceivable.
  • These inorganic UV filters are usually incorporated in an amount of 0.5 to 20 percent by weight, preferably 2 to 10 wt .-%, in cosmetic preparations.
  • Preferred compounds having UV-filtering properties are 3- (4 '- methylbenzylidene) -dl-camphor, 1- (4-tert-butylphenyl) -3- (4-methoxy-phenyl) -Pro-pan-1, 3-dione , 4-isopropyldibenzoylmethane, 2-hydroxy-4-methoxy-benzophenone, octyl methoxycinnamate, SS ⁇ -trimethyl-cyclo-hexyl-salicylate, 4- (dimethylamino) -benzoic acid 2-ethylhexyl ester, 2-cyano-3,3- di-phenyl-2-ethylhexyl acrylate, 2-phenylbenzimidazole-5-sulfonic acid and its potassium, sodium and triethanolamine salts.
  • UV filters can also be used in encapsulated form.
  • organic UV filters in encapsulated form.
  • hydrophilicity of the capsule wall can be adjusted independently of the solubility of the UV filter.
  • hydrophobic UV filters can also be incorporated into purely aqueous preparations.
  • the often perceived as unpleasant oily impression when applying the hydrophobic UV filter containing preparation is suppressed.
  • Certain UV filters in particular dibenzoylmethane derivatives, show only reduced photostability in cosmetic preparations.
  • these filters or compounds that affect the photostability of these filters such as cinnamic acid derivatives, the photostability of the entire formulation can be increased.
  • UV filters it is preferred if one or more of the above-mentioned UV filters are present in encapsulated form. It is advantageous if the capsules so small are that they can not be observed with the naked eye. In order to achieve the above-mentioned effects, it is furthermore necessary for the capsules to be sufficiently stable and not or only to release the encapsulated active ingredient (UV filter) to the environment to a limited extent.
  • Suitable capsules may have walls of inorganic or organic polymers.
  • US Pat. No. 6,242,099 B1 describes the preparation of suitable capsules having walls made of chitin, chitin derivatives or polyhydroxylated polyamines.
  • Particularly preferred capsules have walls which can be obtained by a SolGel process as described in applications WO 00/09652, WO 00/72806 and WO 00/71084.
  • capsules whose walls are made up of silica gel (silica, undefined silicon oxide hydroxide) are preferred.
  • the production of such capsules is known to the skilled worker, for example, from the cited patent applications, whose contents are expressly also part of the subject of the present application.
  • the capsules in preparations to be used according to the invention are preferably present in amounts which ensure that the encapsulated UV filters are present in the preparation in the above-indicated weight percentages.
  • the preparations to be used according to the invention may additionally contain further customary skin-friendly or skin-care active substances.
  • these can be all active ingredients known to the person skilled in the art.
  • Particularly preferred active ingredients are, for example, also so-called compatible solutes. These are substances that are involved in the osmoregulation of plants or microorganisms and can be isolated from these organisms. Under the generic term compatible solutes also the described in the German patent application DE-A-10133202 osmolytes are taken. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and in each case their precursors.
  • osmolytes are in particular substances from the group of polyols, such as, for example, myo-inositol, mannitol or sorbitol and / or one or more of the osmolytically active substances mentioned below Substances understood: taurine, choline, betaine, phosphorylcholine, glycerophosphorylcholine, glutamine, glycine, ⁇ -alanine, glutamate, aspartate, proline, and taurine.
  • polyols such as, for example, myo-inositol, mannitol or sorbitol and / or one or more of the osmolytically active substances mentioned below Substances understood: taurine, choline, betaine, phosphorylcholine, glycerophosphorylcholine, glutamine, glycine, ⁇ -alanine, glutamate, aspartate, proline, and taurine.
  • Precursors of these substances are, for example, glucose, glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids. Precursors are z.
  • compatible solutes as described above, can preferably be used in amounts of up to 15% by weight.
  • the compatible solutes are selected from di-myo-inositol phosphate (DIP), cyclic 2,3-diphosphoglycerate (cDPG), 1, 1-diglycerol phosphate (DGP) 1 ß-mannosylglycerate (Firoin ), ⁇ -mannosylglyceramide (firoin-A) or / and di-mannosyl-di-inositol phosphate (DMIP) or mixtures thereof.
  • DIP di-myo-inositol phosphate
  • cDPG cyclic 2,3-diphosphoglycerate
  • DGP 1, 1-diglycerol phosphate
  • Firoin ß-mannosylglycerate
  • ⁇ -mannosylglyceramide ⁇ -mannosylglyceramide
  • DMIP di-mannosyl-di-inositol phosphate
  • preparations or mixtures according to the invention may contain at least one self-tanner as further ingredient.
  • DHA 1, 3-dihydroxyacetone
  • H 2 C-OH 1, 3-dihydroxyacetone (DHA) Also particularly preferred is a mixture containing dihydroxyacetone and creatinine and PBSA in a creatinine / PBSA mixing ratio of 3: 1.
  • ⁇ -amino acid derivatives and the sparingly soluble substances and optionally further active compounds or else the mixtures according to the invention can be incorporated into preparations in the customary manner, for example by mixing.
  • Suitable preparations for external use for example as a cream, lotion, gel, or as a solution that can be sprayed on the skin.
  • administration formulas such as capsules, dragees, powders, tablet solutions or solutions are suitable.
  • preparations to be used e.g. called: solutions, suspensions, emulsions, PIT emulsions, pastes, ointments, gels, creams, lotions, powders, soaps, surfactant-containing cleaning preparations, oils, aerosols and sprays.
  • Preferred forms of application are also shampoos, sun baths and shower baths, which are also known as so-called "spray tanning, airbrush tanning or sun showers" from commercial self-tanning studios.
  • Preferred excipients come from the group of preservatives, stabilizers, solubilizers, colorants, odor improvers.
  • Ointments, pastes, creams and gels may contain the usual excipients, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth,
  • Cellulose derivatives Polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide or mixtures of these substances.
  • Powders and sprays may contain the usual excipients, for example lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances.
  • Sprays can also contain the usual volatile, liquefied propellants, eg chlorofluorohydrocarbons, propane / butane or dimethyl ether. Also, compressed air is advantageous to use.
  • Solutions and emulsions may contain the usual excipients such as solvents, solubilizers and emulsifiers, e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butylglycol, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerin fatty acid esters, polyethylene glycols and fatty acid esters of sorbitan or mixtures of these substances contain.
  • solvents e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butylglycol, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, g
  • Suspensions may include the usual carriers such as liquid diluents, e.g. Water, ethanol or propylene glycol, suspending agents, e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances.
  • liquid diluents e.g. Water, ethanol or propylene glycol
  • suspending agents e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances.
  • Soaps may contain the usual excipients such as alkali metal salts of fatty acids, salts of fatty acid monoesters, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • excipients such as alkali metal salts of fatty acids, salts of fatty acid monoesters, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • Surfactant-containing cleaning products may include the usual excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic monoesters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates, fatty acid amide ether sulfates, aikylamidobetaines, fatty alcohols,
  • Fatty acid diethanolamides vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acid esters or mixtures of these substances.
  • Facial and body oils may contain the usual excipients such as synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as vegetable oils and oily vegetable extracts, paraffin oils, lanolin oils or mixtures of these substances.
  • synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as vegetable oils and oily vegetable extracts, paraffin oils, lanolin oils or mixtures of these substances.
  • the preferred preparation forms include, in particular, emulsions.
  • Emulsions are advantageous and contain z.
  • Mineral oils mineral waxes - oils, such as triglycerides of capric or caprylic acid, further natural oils such. 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 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.
  • oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the sense of the present invention is advantageously selected from
  • 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, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexadecyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, e.g. B. jojoba oil.
  • the oil phase can be advantageously 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 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 12-18 C-atoms.
  • the fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, for. For example, 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 aqueous phase of the preparations to be used 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, diethylene glycol monomethyl or mono-ethyl ether and analogous products, furthermore lower C-number alcohols, eg. As ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more
  • Thickening agents which may 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 the so-called Carbopoie, for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • Carbopoie 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 are advantageous and contain z.
  • the preparations to be used contain hydrophilic surfactants.
  • the hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and coco amphoacetates.
  • the cosmetic and dermatological preparations can be in various forms. So they can z.
  • Oil-in-water (W / O / W) a gel, a solid stick, an ointment or even an aerosol.
  • Ectoine in encapsulated form, e.g. In collagen matrices and other common encapsulating materials, e.g.
  • wax matrices As encapsulated cellulose, in gelatin, wax matrices or liposomally encapsulated. In particular wax matrices as described in DE-A-43 08 282, have been found to be favorable. Preference is given to emulsions. O / W emulsins are especially preferred. Emulsions, W / O emulsions and O / W emulsions are available in the usual way.
  • emulsifiers for example, the known W / O and O / W emulsifiers can be used. It is advantageous to use other conventional co-emulsifiers in the preferred O / W emulsions.
  • O / W emulsifiers are selected as co-emulsifiers, principally from the group of substances with HLB values of 11-16, very particularly advantageously with HLB values of 14.5-15.5, provided that the O / W Emulsifiers have saturated radicals R and R '. If the O / W emulsifiers have unsaturated radicals R and / or R 1 , or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers may also be lower or higher.
  • fatty alcohol ethoxylates from the group of ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols (cetearyl alcohols). Particularly preferred are: polyethylene glycol (13) stearyl ether (steareth-13),
  • isocetyl ether isoceteth-20
  • polyethylene glycol (12) oleyl ether polyethylene glycol (13) oleyl ether (oleth-13), polyethylene glycol (14) oleyl ether (oleth-14), polyethylene glycol (15) oleyl ether (oleth-15)
  • Polyethylene glycol (12) lauryl ether laureth-12
  • polyethyls n-glycol 14
  • cetyl stearyl ether ceteareth-14
  • polyethylene glycol (15) cetyl stearyl ether ceteareth-15
  • polyethylglycoi (16) cetyl stearyl ether ceteareth-16
  • fatty acid ethoxylates of the following group: polyethylene glycol (20) stearate, polyethylene glycol (21) stearate, polyethylene glycol (22) stearate, polyethylene glycol (23) stearate, polyethylene glycol (24) stearate, polyethylene glycol (25) stearate, polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate, polyethylene glycol (14) isostearate, polyethylene glycol (15) isostearate, polyethylene glycol (16) isostearate, polyethylene glycol (17) isostearate, polyethylene glycol (18) isostearate, polyethylene glycol (19) isostearate, Polyethylene glycol (20) isostearate, polyethylene glycol (21) isostearate, polyethylene glycol (22) isostearate, polyethylene glycol (23) isostearate, polyethylene glycol (24) isostearate, polyethylene glycol (25) isostearate, polyethylene glycol (12) oleate, polyethylene glycol (20) stea
  • Sodium laureth-11-carboxylate can be used.
  • alkyl ether sulfate sodium laureth-4 sulfate can be advantageously used.
  • ethoxylated cholesterol derivative polyethylene glycol (30) cholesteryl ether can be advantageously used.
  • polyethylene glycol (25) soybean oil has been proven.
  • polyethylene glycol glycerol fatty acid esters from the group consisting of polyethylene glycol (20) glyceryl laurate, polyethylene glycol (21) glyceryl laurate, polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23) glyceryl laurate,
  • sorbitan esters from the group of polyether glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.
  • W / O emulsifiers can be used:
  • Fatty alcohols having 8 to 30 carbon atoms monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched
  • W / O emulsifiers are glyceryl monostearate, glyceryl, glyceryl monomyristate, glyceryl, diglyceryl monostearate, Diglycerylmonoisostearat, propylene glycol, propylene glycol monoisostearate, propylene glycol monocaprylate, propylene glycol, sorbitan, sorbitan, sorbitan, Sorbitanmonoisooleat, sucrose, cetyl alcohol, stearyl, arachidyl, behenyl, Isobehenylalkohol, selachyl, Chimyl alcohol, polyethylene glycol (2) stearyl ether (steareth-2), glyceryl monolaurate, glyceryl monocaprinate, glyceryl monocaprylate.
  • compositions which are preferred according to the invention are also suitable for protecting human skin against aging processes as well as against oxidative stress, i. against damage by radicals, as e.g. be generated by sunlight, heat or other influences. It is present in various dosage forms commonly used for this application. Thus, it can be used in particular as a lotion or emulsion, such as cream or milk (O / W, W / O, O / W / O, W / O / W), in the form of oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions, as solid pens or be formulated as an aerosol.
  • a lotion or emulsion such as cream or milk (O / W, W / O, O / W / O, W / O / W)
  • oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions as solid pens or be formulated as an aerosol.
  • the preparation may contain cosmetic adjuvants commonly used in this type of preparation, such as thickeners, emollients, humectants, surfactants, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or or pigments staining the agent itself or the skin, and other ingredients commonly used in cosmetics.
  • cosmetic adjuvants commonly used in this type of preparation, such as thickeners, emollients, humectants, surfactants, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or or pigments staining the agent itself or the skin, and other ingredients commonly used in cosmetics.
  • dispersion or solubilizing agent an oil, wax or other fatty substance, a low monoalcohol or a low polyol or mixtures thereof.
  • a preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and contains, for example, fatty alcohols, fatty acids, fatty acid esters, in particular triglycerides of fatty acids, lanolin, natural and synthetic oils or waxes and emulsifiers in the presence of water.
  • the preparation may also be in the form of an alcoholic gel comprising one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerin, and a thickener, such as silica.
  • the oily-alcoholic gels also contain natural or synthetic oil or wax.
  • the solid sticks consist of natural or synthetic waxes and oils, fatty alcohols, fatty acids, fatty acid esters, lanolin and other fatty substances.
  • blowing agents are generally used, such as alkanes, fluoroalkanes and chlorofluoroalkanes, preferably alkanes.
  • the preparations to be used can be prepared using techniques that are well known to the person skilled in the art.
  • a method for producing a preparation according to the invention may comprise mixing the at least one ⁇ -amino acid derivative with at least one sparingly soluble substance or a mixture according to the invention and a carrier suitable for topical applications, for example, a cosmetically, pharmaceutically or dermatologically suitable carrier.
  • the mixing may result in dissolution, emulsification or dispersion in the carrier.
  • PBSA phenylbenzimidazole sulfonic acid
  • 4% aqueous solutions of ectoine, creatinine and pyrrolidonecarboxylic acid are prepared.
  • the active ingredient PBSA is dispersed in excess in the solution.
  • the pH of the suspension is adjusted to 4.6. Undissolved active ingredient is filtered off after 1 hour of stirring.
  • the dissolved active ingredient content is determined by high performance liquid chromatography. As a comparison, the experiment without solubilizer is used.
  • the solubility at pH 5.7 is determined, i. in this case, it is not reset to pH 4.6.
  • Spray drying gives a white powder which dissolves in water and gives a pH below pH6.
  • Spray drying gives a white powder which dissolves in water and gives a pH below pH6.
  • composition in weight percent 80% ectoine, 20% tiliroside
  • the solvents are in vacuo (60mbar) and a bath temperature of
  • the yellow solid mixture is 48h at 200mbar and 40 ° C in Drying oven dried and placed on a 100 ⁇ m sieve.
  • the ethanol / water mixture can also be spray-dried.
  • composition in weight percent 70% creatinine, 21% isoquercetin, 8.5%
  • composition in weight percent 60% creatinine, 40% sorbic acid. production:
  • mixture M1 2 parts by weight of mixture M1 are homogeneously mixed with 1 part by weight of dihydroxyacetone (DHA).
  • DHA dihydroxyacetone
  • This process preferably takes place under inertized conditions in order to avoid oxidation losses of DHA.
  • Inertized conditions are, for example, the production of the mixture in the absence of UV rays, in the presence of inert gases or even at low temperatures.

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Abstract

L'invention porte sur l'utilisation de dérivés d'acides α-aminés pour améliorer la solubilité de substances peu solubles dans l'eau ou dans des solutions aqueuses, ainsi que des mélanges et des préparations préférées.
EP08853958A 2007-11-29 2008-11-27 Dérivés d'acides alfa-aminés pour l'amélioration de la solubilité Withdrawn EP2211827A2 (fr)

Applications Claiming Priority (2)

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DE102007057543A DE102007057543A1 (de) 2007-11-29 2007-11-29 a-Aminosäurederivate zur Löslichkeitsverbesserung
PCT/EP2008/010045 WO2009068275A2 (fr) 2007-11-29 2008-11-27 DÉRIVÉS D'ACIDES α-AMINÉS POUR L'AMÉLIORATION DE LA SOLUBILITÉ

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EP2211827A2 true EP2211827A2 (fr) 2010-08-04

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US (1) US8293784B2 (fr)
EP (1) EP2211827A2 (fr)
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WO (1) WO2009068275A2 (fr)

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DE102007057543A1 (de) 2009-06-04
US20110039924A1 (en) 2011-02-17

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