EP1871339A1 - Uv schutz - Google Patents

Uv schutz

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Publication number
EP1871339A1
EP1871339A1 EP06742521A EP06742521A EP1871339A1 EP 1871339 A1 EP1871339 A1 EP 1871339A1 EP 06742521 A EP06742521 A EP 06742521A EP 06742521 A EP06742521 A EP 06742521A EP 1871339 A1 EP1871339 A1 EP 1871339A1
Authority
EP
European Patent Office
Prior art keywords
branched
chain
formula
compound
compounds
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Withdrawn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
EP06742521A
Other languages
German (de)
English (en)
French (fr)
Inventor
Thomas Rudolph
Herwig Buchholz
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
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE102005018184A external-priority patent/DE102005018184A1/de
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP1871339A1 publication Critical patent/EP1871339A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K8/362—Polycarboxylic 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
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    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
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    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P27/02—Ophthalmic agents
    • 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]
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers
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    • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
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    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant

Definitions

  • the present invention relates to the use of compounds which themselves do not exhibit significant UV absorption in the UV-A or UV-B range but are reactive under use conditions to produce UV-A or UV-B protection during exposure Application, corresponding novel compounds and preparations, and corresponding preparation process for compounds and preparations.
  • a field of application of the compounds according to the invention is, for example, cosmetics.
  • the task of nourishing cosmetics is to preserve the impression of a youthful skin if possible.
  • Another approach is to protect the skin from environmental influences that lead to permanent damage and thus aging of the skin. The idea is to intervene preventively and thereby delay the aging process.
  • An example are UV filters, which by absorption of certain wavelength ranges a
  • Skin damage is caused not only by sunlight, but also by other external influences, such as cold or heat.
  • the skin is subject to natural aging, which causes wrinkles and relieves the elasticity of the skin.
  • UV protection could be provided that allows low UV doses to pass, but diminishes their detrimental effect and activates itself at higher doses of radiation.
  • the object of the invention is therefore to provide a composition which, if necessary, has a protective action against UV rays and / or a protective effect against oxidative stress
  • a first subject of the present invention is therefore the use of compounds which themselves have no significant UV
  • UV-A or UV-B range Show absorption in the UV-A or UV-B range, but are reactive under application conditions to produce UV-A or UV-B protection during use.
  • UV protection can take place according to various mechanisms.
  • preferred compounds react with reactive species, such as radicals, to form products that provide UV-A or UV-B protection.
  • reactive species such as radicals
  • Another class of compounds to be used according to the invention is used under conditions of use of
  • Skin enzymes reacted, forming products that provide UV-A or UV-B protection.
  • Another class of compounds to be used according to the invention is decomposed under application conditions by the introduction of heat, thus forming products which provide UV-A or UV-B protection.
  • Particularly preferred according to the invention is the use of compounds of the formula I.
  • a 1 -A 3 each independently represents a benzyl radical or a radical - (CH 2 O) n (CH 2 ) o (O) pH, where m and o each independently represent an integer from the
  • Z 1 and Z 2 is independently O, S, CR 7 R 8 , NR 7 or a single bond,
  • R 7 and R 8 are each independently selected from H, OH, straight or branched Cr to C 2 o-alkoxy groups, straight-chain or branched C 1 - to 2 o-alkyl groups, straight-chain or branched C 3 - to C 2 o-alkenyl groups straight chain or branched Cr to C 2 o-hydroxyalkyl groups, wherein the 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, straight or branched Cr to C 20 hydroxyalkoxy groups, wherein the hydroxy group (n) may be bonded to a primary or secondary carbon atoms of the chain and further the alkyl chain may also be interrupted by oxygen, or salts of the compounds of formula I is.
  • R 2 to R 6 are each independently selected from H,
  • Oxygen may be interrupted, straight-chain or branched Cr to C 2 o-hydroxyalkoxy groups, wherein the hydroxy group (s) may be bonded to a primary or secondary carbon atoms of the chain and further the alkyl chain may also be interrupted by oxygen, wherein one of the radicals R 2 to R 6 is also a branched or unbranched Ci- 2 -alkoxy or branched or unbranched C-2
  • Polysiloxane is bound, stand, or salts of the compounds of formula Ia is used.
  • Z 1 in the compound of the formula Ia is a single bond. In this case, the formula Ia simplifies too
  • All counterions for salts according to the invention may be any anions which are harmless for the corresponding purpose. It is advantageous if it is salts of strong acids. It is particularly preferred according to the invention, when the salts are chlorides or bromides.
  • the compounds described can be used according to the invention as an active ingredient for topical application or for the preparation of cosmetic or dermatological preparations or for the production of household products. The compounds described can be used for product protection.
  • product protection means in particular the protection of oxidation-sensitive formulation constituents, such as organic or inorganic dyes, antioxidants, vitamins, perfume components, oil components or matrix constituents, such as emulsifiers, thickeners, film formers and surfactants.
  • oxidation-sensitive formulation constituents such as organic or inorganic dyes, antioxidants, vitamins, perfume components, oil components or matrix constituents, such as emulsifiers, thickeners, film formers and surfactants.
  • oxygen radicals activatable precursor for UV filters.
  • Subject of the invention is also the
  • Another object of the present invention are the new compounds of formula I or Ia.
  • R 3 and R 5 are each independently selected from H, straight-chain or branched C r to C 20 -
  • Alkoxy groups straight or branched Cr to 2 o-alkyl groups, straight or branched C 3 - to C 2 o-alkenyl groups, straight-chain or branched Cr to C 2 o-hydroxyalkyl groups, wherein the hydroxy group may be bonded to a primary or secondary carbon atom of the chain and further through the alkyl chain
  • Particularly preferred may be in a variant of the invention, the use of at least one compound of formula I, which is characterized in that at least one group of R 2 , R 4 and R 6 is OH. These compounds show a particularly pronounced antioxidant performance.
  • the use of at least one compound of the formula I may be preferred, which is characterized in that at least one group of R 3 and R 5 is t-butyl. These compounds show a particularly pronounced antioxidant performance.
  • Compound of the formula I or Ia with long-chain Hydrocarbon radicals in particular branched long-chain hydrocarbon radicals may be preferred. These compounds are often particularly readily miscible with carriers, in particular oils, and can thus be used particularly easily in formulations. It is particularly preferred in this variant of the invention, when R 1 is a branched or unbranched C 7-3 -alkyl or C 6 hydroxyalkyl -3O-.
  • R 4 is a branched or unbranched Ci- 2 -alkoxy or branched or unbranched C2-20- alkyleneoxy
  • a spacer which is bonded via an Si atom to an oligo- or polysiloxane chain which contains one or more compounds of the formula I, where R 4 is preferably a propanyloxy-,
  • At least one compound of formula I which is selected from 4-hydroxy-phenyl-propionic acid, 4-hydroxyphenyl-propionic acid 2-ethyl-hexyl ester, A-hydroxy-3,5-dimethoxy-benzyl-malonic acid di-2-ethylhexyl ester, A-methoxy-benzyl-malonic acid di-2-ethyl-hexyl ester, 4-methoxy-phenyl-propionic acid 2-ethylhexyl ester, 4-hydroxy-3,5-dimethoxy-phenyl 2-ethylhexyl propionate, 3,4,5-trimethoxybenzyl malonic acid di-2-ethylhexyl ester, 2-ethylhexyl 4-hydroxy-3-methoxy-2-phenylpropionate, 4-hydroxy 3-Methoxybenzyl malonic acid di-2-ethylhexyl ester, 3,4-dihydroxybenzyl malonic
  • At least one compound of the formula I in which Z 1 is NH and X is -C ( O) -Z 2 -R 1 , where both radicals -Z 2 -R 1 are identical, and R 2 to R 6 are each independently preferably H, hydroxy or methoxy.
  • a 1 -A 3 are each independently a radical - (CH 2 ) o (O) pH, where o is 1, 2, or 3 and p stands for 0 or 1.
  • a further subject of the invention are preparations containing at least one compound of the formula I.
  • the preparations are usually either topically applicable preparations, for example cosmetic or dermatological formulations, foods or dietary supplements or household products.
  • the preparations in this case contain a cosmetically or dermatologically, food-grade or household-suitable carrier and, depending on the desired profile of properties, optionally further suitable ingredients.
  • Advantages of the compounds according to the invention or use of compounds according to the invention or of the compositions according to the invention can be in particular:
  • the UV absorption which occurs upon activation in particular UV irradiation
  • preferred compounds of the formula I are suitable for improving galenic properties, such as, for example, the skin sensation, of preparations,
  • preferred compounds of formula I show good solubility and solvent properties, preferably e.g. as a solvent for crystalline components, a preferred group of compounds according to the invention can also cause skin tanning or improve the action of skin-tanning substances, such as dihydroxyacetone,
  • an antioxidant activity against free radicals e.g. by UV light or by thermolytic processes, such as smoking, such as e.g. against the superoxide radical anion or the NO radical, or against reactive
  • Oxygen species e.g. against singlet oxygen and peroxides
  • preferred compounds of the formula I are suitable for generating or increasing ("boosf effect") sun protection factors such as SPF, SPF 1 PPD or IPD, or radical protection factors, a product-stabilizing effect on cosmetic, pharmaceutical, in particular dermatological products or household products or Food and nutritional supplements, in particular those containing colorants, consistency or odors,
  • PEG polyglycerol
  • PG polyglycerol
  • PEG or PG-containing emulsifiers as mentioned below in this application, or a reduction in the damaging effect of the degradation products of autooxidizable polyethyleneglycol (PEG) or polyglycerol (PG) derivatives, a stabilizing effect on dyes, consistency or odors , or on antioxidants or vitamins, and UV filters and titanium dioxide-containing pigments, in particular in cosmetic, pharmaceutical, in particular dermatological or household products or foods and dietary supplements, - while most antioxidants are ineffective after reaction with radicals, show preferred compounds of the formula I after this reaction UV-filtering effect and set their own
  • Preferred compounds of the invention with antioxidant properties can also be used for pigmentation control, since they can have a whitening effect on skin areas.
  • Pigments that can accelerate conversion of more preferred compounds of formula I to the UV absorbing oxidation products Pigments that can accelerate conversion of more preferred compounds of formula I to the UV absorbing oxidation products.
  • preferred compounds described herein are colorless or only slightly colored and thus do not or only to a slight extent discolorations of the preparations.
  • preparations comprising at least one carrier suitable for cosmetic or dermatological preparations or household products and at least one compound which itself does not show any significant UV absorption in the UV-A or UV-B range but is reactive under application conditions and UV -A- or UV-B protection produced, another object of the present invention.
  • Preferred preparations contain the compounds of the formula I or Ia described in detail above. In this case, it is particularly preferred according to the invention if the preparation comprises at least one compound of the formula I ena or 1 enb
  • the preparation comprises at least one compound of the formula Ia Ena or Ia Enb
  • radicals X, Y, Z 1 and Z 2 and R 1 -R 6 in the at least one compound of formula I and the at least one compound of formula I ena or I enb or the at least one compound are identical according to formula Ia and the at least one compound according to formula Ia ena or Ia enb.
  • the compound of formula I or Ia as a reservoir for the UV absorption potential of the compound of formula I ena or I enb or
  • Ia ena or Ia enb serve. That the use of the compounds of the formula I or Ia thus enables a reduction of the use concentration of the UV filter according to formula I ena or I enb or Ia ena or Ia enb or the replica of the UV filter according to formula I ena or I enb or Ia ena or Ia enb by UV-induced oxidation of the compounds of formula I can thus compensate for the loss of power that many compounds of the formulas I ena or I enb or Ia ena or Ia enb suffer UV irradiation as a result of photoreactions Replication of the UV filter according to formula I ena or I enb or Ia ena or Ia enb by UV-induced oxidation of the compounds of formula I or Ia can so in
  • At least one compound of the formula I ena or eneneb or la ena or la enb is a compound selected from 4-hydroxycinnamic acid, 4-hydroxycinnamic acid 2-ethylhexyl ester, 4-Hydroxy-3,5-dimethoxy-benzylidene-malonic acid di-2-ethylhexyl ester, 4-methoxy-benzylidene-malonic acid di-2-ethylhexyl ester,
  • the compounds which themselves do not exhibit significant UV absorption in the UV-A or UV-B range, but are reactive under application conditions and produce UV-A or UV-B protection, are typically present in amounts of 0.01 in accordance with the invention to 20 wt .-%, preferably in amounts of
  • the compounds according to the invention may be able to develop their positive effect as radical scavengers on the skin particularly well, it may be preferable to allow the compounds according to the invention to penetrate into deeper skin layers.
  • the compounds according to the invention can have sufficient lipophilicity in order to be able to penetrate through the outer skin layer into epidermal layers.
  • appropriate transport means for example liposomes, can be provided in the preparation, which make possible a transport of the compounds according to the invention through the outer skin layers.
  • a systemic transport of the compounds of the invention is conceivable.
  • the preparation is then, for example, designed to be suitable for oral administration.
  • the substances of the formula I act as radical scavengers.
  • Radicals are generated exogenously not only by sunlight, but also by the action of reactive substances, such as ozone, nitrogen oxides (eg cigarette smoke) or heavy metal contamination (eg in the diet). Further examples are anoxia, which blocks the flow of electrons upstream of the cytochrome oxidases and causes the formation of superoxide radical ions; Inflammation, inter alia, with the formation of
  • Superoxide anions are accompanied by the membrane NADPH oxidase of leukocytes, but which are also associated with the formation (by disproportionation in the presence of ferrous ion) of the hydroxy radicals and other reactive species normally involved in the phenomenon of phagocytosis; as well as lipid autooxidation generally through a
  • Hydroxyl radical is initiated and provides lipidic alkoxy radicals and hydroperoxides.
  • the compounds or preparations according to the invention are generally suitable for immune protection and for the protection of DNA and RNA.
  • preferred compounds of the present invention are also useful in the treatment of skin diseases associated with a keratinization disorder involving differentiation and cell proliferation, particularly for the treatment of acne vulgaris, acne comedonica, polymorphic acne, rosaceae acne , the nodular acne, the acne conglobata, age-related acne, acne, such as acne solaris, acne-induced acne or acne professionalis, for the treatment of other disorders of keratinization, especially of the ichthyoses, the ichtyosi-forms conditions, of the Darrier disease, the
  • the dermis or epidermis which may be of viral origin, such as Verruca vulgaris. Veruca plana, Epidermodysplasia verruciformis, oral papillomatosis, Papillo-matosis florida, and growths caused by UV radiation, in particular epithelioma baso-cellulare and epithelioma spinocellulare, for the treatment of other skin diseases, such as dermatitis bullosa and the collagen-related diseases, for the treatment of certain ocular diseases, in particular corneal diseases, for the elimination or control of photodamaging and aging associated with aging, for the reduction of pigmentation and keratosis actinica and for the treatment of all diseases associated with normal conditions Aging or light-induced aging, for the prevention or healing of wounds / scars of the atrophy of the epidermis and / or dermis caused by locally or systemically applied corticosteroids and any other types of dermal atrophy, for the prevention or treatment of Disorders of
  • Cancerous conditions or precancerous conditions for the treatment of inflammatory diseases, such as arthritis, for the treatment of all viral diseases of the skin or other areas of the body, for the prevention or treatment of alopecia, for the treatment of skin diseases or diseases of other body with an immunological component, for the treatment of cardiovascular diseases, such as atherosclerosis or hypertension, as well as insulin-independent diabetes, for the treatment of skin problems caused by UV radiation.
  • inflammatory diseases such as arthritis
  • alopecia for the treatment of skin diseases or diseases of other body with an immunological component
  • cardiovascular diseases such as atherosclerosis or hypertension
  • insulin-independent diabetes for the treatment of skin problems caused by UV radiation.
  • 2,2-diphenyl-1-picrylhydrazyl is a solution-free radical.
  • the unpaired electron leads to a strong absorption band at 515 nm, the solution is dark violet in color.
  • the antiradical property of the substance to be tested is determined by determining the concentration at which 50% of the 2,2-diphenyl-1-picrylhydrazyl used reacted with the radical scavenger. This concentration is expressed as EC- 50 , a value that should be considered as a substance property under the given measurement conditions.
  • the examined substance is compared with a standard (eg tocopherol).
  • the EC 50 value is a measure of the capacity of each compound to catch radicals. The lower the EC 50 value, the higher the capacity to catch radicals. For the purposes of this invention is said to catch from a large or high capacity radicals when the ECso value is lower than that of tocopherol.
  • antioxidants Another important aspect of the effect of the antioxidants is the time this EC 50 value is reached. This time, measured in minutes, gives the r E c 5 o value, which gives an idea of the rate at which these antioxidants trap radicals. For the purpose of these inventions, antioxidants which reach this value within less than 60 minutes are considered to be fast, those which reach the EC 50 value only after more than 120 minutes have a delayed effect.
  • a low AE (x10 3 ) is in the range up to about 10, an average AE is spoken in the range of 10 to 20, and a high AE is present according to the invention at values above 20.
  • fast-acting antioxidants with those with a slow or delayed action.
  • Typical weight ratios of the fast-acting antioxidants to delayed-acting antioxidants are in the range from 10: 1 to 1:10, preferably in the range from 10: 1 to 1: 1, and for skin-protecting preparations particularly preferably in the range from 5: 1 to
  • compositions show weight ratios of the fast-acting antioxidants to time-delayed antioxidants in the range 1: 1 to 1:10, preferably in the range 1: 2 to 1: 8.
  • the preparation is therefore a preparation for the protection of body cells against oxidative stress, in particular for reducing skin aging, characterized in that it preferably contains one or more further compounds in addition to the one or more compounds according to formula I.
  • antioxidants There are many known and proven substances in the literature that can be used as antioxidants, eg amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles, (eg urocanic acid) and their derivatives, peptides like DL-camosine, D-
  • Camosin L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ß-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 theirs
  • 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 their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthionine sulfoximines,
  • Homocysteine sulfoximine, buthione sulfone, penta-, hexa-, heptathionine sulfoximine) in very low tolerated dosages eg pmol to ⁇ mol / kg
  • furthermore (metal) chelators eg ⁇ -hydroxyfatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), Tocopherols and derivatives (eg vitamin E acetate), vitamin A and derivatives (eg vitamin A palmitate) and benzylic resin coniferyl benzoate,
  • 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 (for example 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
  • antioxidants are usually used with compounds of the invention in such compositions in ratios in the range of 1000: 1 to 1: 1000, preferably in amounts of 100: 1 to 1: 100.
  • the preparations according to the invention may contain vitamins as further ingredients. Preference is given to vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin B 1 ),
  • Vitamin B 2 Riboflavin (vitamin B 2 ), nicotinic acid amide, 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 Bi), nicotinic acid (niacin), pyridoxine, pyridoxal, pyridoxamine, (vitamin B 6 ), pantothenic acid, biotin, folic acid and cobalamin (vitamin Bi 2 ) in the cosmetic preparations according to the invention, particularly preferably vitamin - A-palmitate, retinol, vitamin C and its derivatives, DL- ⁇ -tocopherol, tocopherol-E-acetate, nicotinic acid, pantothenic acid and biotin. Vitamins are thereby in compounds of the invention usually in
  • antioxidants such as beta-carotene and tocopherol
  • Compounds to UV-deficient compounds can accelerate.
  • the compounds of the invention to be used according to the invention generally have a UV absorption in the UV-A and / or UV-B range after irradiation.
  • the compounds according to the invention to be used in accordance with the invention are precursors of broadband UV filters which are used alone or in combination with other UV filters.
  • Filters can be used.
  • Other compounds which are likewise preferred according to the invention are precursors of UV filters having an absorption maximum in the boundary region between the UV-B and the UV-A radiation.
  • As a UV-A-I filter therefore, they advantageously supplement the absorption spectrum of commercially available UV-B or UV-A-1 filters.
  • straight-chained or branched Cr to C 2 o-alkoxy groups in particular the long-chain alkoxy functions, such as ethylhexyloxy groups, increase the oil-solubility of the compounds.
  • Some of such compounds are as oil components and can be easily incorporated into the preparation or can act as a solvent for other formulation ingredients.
  • the preparations according to the invention may also contain poorly soluble or non-soluble compounds according to the invention in the preparation matrix.
  • the compounds are preferably dispersed in finely divided form in the cosmetic preparation.
  • Particularly preferred preparations according to the invention also contain pure UV filters in addition to the compounds according to the invention.
  • Dibenzoylmethane derivatives used in UVB filters, or the cinnamic acid derivatives used in particular as UVB filters in combination with the compounds according to the invention have an additional advantage:
  • the UV-sensitive dibenzoylmethane derivatives and cinnamic acid derivatives are additionally stabilized by the presence of the compounds according to the invention.
  • Another object of the present invention is therefore the use of the compounds of the formula I for the stabilization of dibenzoylmethane derivatives and / or cinnamic acid derivatives in preparations.
  • UV filters are suitable for combination with the compounds according to the invention.
  • UV filters whose physiological harmlessness has already been demonstrated.
  • UVA and UVB filters there are many known and proven substances in the literature, e.g.
  • Benzylidene camphor derivatives such as 3- (4'-methylbenzylidene) dl camphor (eg Eusolex® 6300), 3-benzylidene camphor (eg Mexoryl® SD), polymers of N - ⁇ (2 and 4) - [(2-oxobom-3-) yliden) methyl] benzyl ⁇ -acrylamide (eg Mexoryl® SW), N, N, N-trimethyl-4- (2-oxobrom-3-ylidenemethyl) anilinium methylsulfate (eg Mexoryl® SK) or (2-oxobrom-3-yl) yliden) toluene-4-sulfonic acid (eg
  • Benzoyl or dibenzoylmethanes such as 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione (e.g., Eusolex® 9020) or A-isopropyldibenzoylmethane (e.g., Eusolex® 8020),
  • Benzophenones such as 2-hydroxy-4-methoxybenzophenone (e.g., Eusolex® 4360) or 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its sodium salt (e.g., Uvinul® MS-40),
  • Methoxycinnamic acid esters such as octyl methoxycinnamate (e.g., Eusolex® 2292), isopentyl 4-methoxycinnamate, e.g. as a mixture of isomers (e.g., Neo Heliopan® E 1000),
  • Salicylate derivatives such as 2-ethylhexyl salicylate (e.g., Eusolex® OS), A-
  • Isopropylbenzyl salicylate e.g., Megasol®
  • 3,3,5-trimethylcyclohexylsalicylate e.g., Eusolex® HMS
  • 4-aminobenzoic acid and derivatives such as 4-aminobenzoic acid, A- (dimethylamino) benzoic acid 2-ethylhexyl ester (eg Eusolex® 6007), ethoxylated 4-aminobenzoic acid ethyl ester (eg Uvinul® P25), Phenylbenzimidazole sulfonic acids, such as 2-phenylbenzimidazole-5-sulfonic acid and its potassium, sodium and triethanolamine salts (eg Eusolex® 232), 2,2- (1,4-phenylene) bisbenzimidazole-4,6-disulfonic acid or salts thereof ( eg Neoheliopan® AP) or 2,2- (1,4-phenylene) bisbenzimidazole-6-sulfonic acid;
  • A- (dimethylamino) benzoic acid 2-ethylhexyl ester eg Eusolex® 6007)
  • Hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate e.g., Uvinul® UVA Plus, BASF.
  • organic UV filters are usually incorporated in an amount of 0.5 to 10 weight percent, preferably 1-8%, in cosmetic formulations.
  • UV filters are also Methoxyflavone enschend the older German patent application DE-A-10232595.
  • Organic UV filters are usually incorporated in an amount of 0.5 to 20 percent by weight, preferably 1-15%, in cosmetic formulations.
  • inorganic UV filters are those from the group of titanium dioxides such as coated titanium dioxide (eg Eusolex® T-2000, Eusolex ® T-AQUA, Eusolex ® T-AVO), zinc oxides (eg Sachtotec®), iron oxides or cerium oxides conceivable.
  • coated titanium dioxide eg Eusolex® T-2000, Eusolex ® T-AQUA, Eusolex ® T-AVO
  • zinc oxides eg Sachtotec®
  • iron oxides or cerium oxides conceivable.
  • These inorganic UV filters are usually incorporated in an amount of 0.5 to 20 weight percent, preferably 2-10%, 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-methoxybenzophenone, octyl methoxycinnamate, 3,3,5-trimethyl-cyclo-hexyl-salicylate, 4- (dimethylamino) -benzoic acid-2-ethyl- hexyl ester, 2-cyano-3,3-di-phenyl-2-ethylhexyl acrylate, 2-phenyl-benzimidazole-5-sulfonic acid and their potassium, sodium and triethanolamine salts.
  • optimized compositions can be the combination of the organic UV filters 4'-methoxy-6-hydroxyflavone with 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione and 3- (4 ' -
  • Methylbenzylidene -dl camphor. This combination results in a broadband protection that can be achieved by adding inorganic UV filters, such as
  • Titanium dioxide microparticles can still be added.
  • UV filters and the compounds according to the invention 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 or of the compound of the formula I.
  • hydrophobic UV filters or compounds according to the invention can also be incorporated into purely aqueous preparations.
  • UV filters in particular dibenzoylmethane derivatives, show only reduced photostability in cosmetic preparations.
  • UV filter and the associated irritation potential when applied directly to the human skin prevents this effect.
  • encapsulation of individual UV filters or compounds according to the invention or other ingredients can result in problems with the preparation arising from the interaction of individual preparation constituents, such as crystallization processes, precipitation and agglomeration, since the interaction is prevented. Therefore, it is preferred according to the invention if one or more of the abovementioned UV filters or compounds according to the invention are present in encapsulated form. It is advantageous if the capsules are so small that they can not be observed with the naked eye. To achieve the above effects, it is still necessary that the
  • Capsules are sufficiently stable and donate the encapsulated active ingredient (UV filter) not or only to a small extent to the environment.
  • Suitable capsules may have walls of inorganic or organic polymers.
  • Capsules which are particularly preferred for use in accordance with the invention have walls which can be obtained by a SolGel process, as described in applications WO 00/09652, WO 00/72806 and WO 00/71084.
  • Undefined silicon oxide hydroxide are constructed.
  • 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 according to the invention are preferably present in amounts which ensure that the encapsulated UV filters are present in the preparation in the amounts indicated above.
  • the preparations according to the invention may additionally contain further customary skin-sparing or skin-care active substances.
  • these can be all active ingredients known to the person skilled in the art.
  • Particularly preferred active ingredients are pyrimidinecarboxylic acids and / or aryloximes.
  • Pyrimidinecarboxylic acids occur in halophilic microorganisms and play a role in the osmoregulation of these organisms
  • enzymes against denaturing conditions such as salts, extreme pH, surfactants, urea, guanidinium chloride and other compounds.
  • Ectoine and ectoine derivatives such as hydroxyectoine can be used to advantage in medicines.
  • hydroxyectoine can be used for the manufacture of a medicament for the treatment of skin diseases.
  • Other uses of hydroxyectoine and other ectoine derivatives are typically in areas where e.g. Trehalose is used as an additive. So may ectoin derivatives, such as
  • Hydroxyectoin as a protective substance in dried yeast and bacterial cells use.
  • pharmaceutical products such as non-glycosylated, pharmaceutically active peptides and proteins e.g. t-PA can be protected with Ectoin or its derivatives.
  • EP-A-0 671 161 describes in particular that ectoine and hydroxy ectoine are used in cosmetic preparations, such as powders, soaps, surfactant-containing
  • a pyrimidinecarboxylic acid according to the formula below is preferably used,
  • R 1 is a radical H or CI-8-alkyl
  • R 2 is a radical H or C 1-4 -alkyl
  • R 3 , R 4 , R 5 and R 6 are each independently a radical from the group H, OH, NH 2 and C1-4 alkyl.
  • Preference is given to using pyrimidinecarboxylic acids in which R 2 is a methyl or an ethyl group and R 1 or R 5 and R 6 are H.
  • pyrimidinecarboxylic acids ectoine ((S) -1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoine ((S 1 S) -1, 4,5,6- Tetrahydro-5-hydroxy-2-methyl-4-pyrimidine-carboxylic acid) used.
  • the preparations according to the invention preferably contain such pyrimidinecarboxylic acids
  • the pyrimidinecarboxylic acids are preferably used in ratios of 100: 1 to 1: 100 to the compounds of the invention, with ratios in the range 1: 10 to 10: 1 are particularly preferred.
  • 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 accompany inflammation. It is known that such preparations can be used, for example, for the therapy of psoriasis, different forms of eczema, 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 of the formula I, additionally contain an aryloxime, preferably 2-hydroxy-5-methyllaurophenone oxime, show surprising antiinflammatory suitability.
  • the preparations preferably contain 0.01 to 10 wt .-% of the aryloxime, wherein it is particularly preferred when the preparation contains 0.05 to 5% by weight of aryloxime.
  • the preparation according to the invention contains at least one
  • Suitable self-tanning agents include trioses and tetroses, such as the following compounds:
  • juglone 5-hydroxy-1,4-naphthoquinone
  • Lawson 2-hydroxy-1,4-naphthoquinone
  • the flavonoid diosmetin and its glycosides or sulfates can also be used. These compounds can be in the form of Substances or plant extracts are used.
  • diosmetin may preferably be used in the form of a chrysanthemum extract.
  • DHA 1, 3-dihydroxyacetone
  • the said self-tanner may be used alone or as a mixture. It is particularly preferred when DHA is used in admixture with another of the above-mentioned self-tanner.
  • compositions are either known and commercially available or may be synthesized by known methods.
  • the one or more compounds according to the invention can be incorporated in the usual way into cosmetic or dermatological preparations. Suitable preparations for an external
  • Dosage formulations such as capsules, dragees, powders, tablet solutions or solutions are suitable.
  • preparations according to the invention e.g. called: solutions, suspensions, emulsions, PIT emulsions, pastes,
  • Ointments gels, creams, lotions, powders, soaps, surfactant-containing cleaning preparations, oils, aerosols and sprays.
  • Other applications are e.g. Sticks, shampoos and shower baths. Any customary carrier substances, adjuvants and optionally further active ingredients can be added to the preparation.
  • Preferable excipients come from the group of preservatives, antioxidants, stabilizers, solubilizers, vitamins, 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.
  • 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 carriers, e.g. Lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances.
  • Sprays may additionally contain the usual propellants, e.g. Chlorofluorocarbons, propane / butane or dimethyl ether.
  • 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,
  • solvents e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylglycol, oils, in particular cottonseed oil,
  • Suspensions may be the customary carriers such as liquid diluents, for example water, ethanol or propylene glycol, suspending agents, for example 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 for example water, ethanol or propylene glycol
  • suspending agents for example 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 carriers such as alkali salts of fatty acids,
  • Surfactant-containing cleaning products may include the usual carriers such as
  • 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
  • the preferred preparation forms according to the invention include in particular emulsions.
  • Emulsions of the invention are advantageous and contain z.
  • the lipid phase can advantageously be selected from the following substance group:
  • mineral oils mineral waxes - oils such as triglycerides of capric or caprylic acid, furthermore natural
  • Oils such as 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 low C-alkanoic acids or with fatty 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 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 acid and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon 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, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexadecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semisynthetic and natural mixtures of such esters, eg. B. jojoba oil.
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and fatty acid triglycerides, in particular the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of one chain length from 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. 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 selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethyl hexylcocoat, C 2 -i 5 alkyl benzoate, caprylic-capric acid triglyceride, Dicap- rylether.
  • Particularly advantageous are mixtures of C 2 -i 5 alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 2-15 alkyl benzoate and isotridecyl isononanoate and mixtures of C 2 -i 5 alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffin oil, squalane and squalene are to be used advantageously in the context of the present invention.
  • the oil phase can also have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or silicone oils.
  • cyclomethicone (octamethylcyclotetrasiloxane) is used as the silicone oil to be used according to the invention.
  • other silicone oils are also advantageous for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • mixtures of cyclomethicone and Iso tridecylisononanoat from cyclomethicone and 2-Ethylhexylisostearat.
  • 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, diethylene - Glykolmonomethyl- or -monoethylether and analogous products, also low C-number alcohols, z.
  • 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 organic solvent.
  • Emulsions of the invention are advantageous and contain z.
  • the preparations according to the invention contain hydrophilic surfactants.
  • hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and cocoamphoacetates.
  • R represents a branched or unbranched alkyl radical having 4 to 24 carbon atoms and wherein DP means a mean Glucosyl michsgrad of up to 2.
  • the value DP represents the degree of glucosidation of the alkylglucosides used in the invention and is defined as
  • pi, p 2 , P 3 ... Or pi represent the proportion of products which are mono-, di-trisubstituted ... times glucosylated in weight percentages.
  • the value DP takes into account the fact that alkylglucosides, as a rule, are mixtures of mono- and oligoglucosides. According to the invention, a relatively high content of monoglucosides, typically of the order of 40-70% by weight, is advantageous.
  • Alkylglylcosides used particularly advantageously according to the invention are selected from the group octylglucopyranoside, nonylglucopyranoside, decyl glucopyranoside, undecyl glucopyranoside, dodecyl glucopyranoside, tetradecyl glucopyranoside and hexadecyl glucopyranoside.
  • Salary of the active ingredients used in the invention for example, Plantaren ® 1200 (Henkel KGaA), Oramix ® NS 10 (Seppic).
  • acyl lactylates are advantageously selected from the group of substances which are defined by the structural formula
  • R 1 denotes a branched or unbranched alkyl radical having 1 to 30 carbon atoms and M + is selected from the group of the alkali ions and the group of the ammonium ions substituted by one or more alkyl and / or by one or more hydroxyalkyl radicals or corresponds to half the equivalent of an alkaline earth metal ion.
  • sodium is advantageous, for example the product Pathionic ® ISL from the American Ingredients
  • R 2 is a branched or unbranched alkyl radical having 1 to 30 carbon atoms.
  • R 2 is a branched or unbranched alkyl radical having 6 to 12 carbon atoms.
  • Capramidopropylbetaine for example the product Tego ® Betaine is advantageous, for example 810 from Th. Goldschmidt AG.
  • compositions according to the invention are advantageously characterized in that the hydrophilic or surfactant (s) in concentrations of
  • the cosmetic and dermatological preparations according to the invention are applied to the skin and / or the hair in a quantity sufficient in the manner customary for cosmetics.
  • Cosmetic and dermatological preparations according to the invention can be present in various forms. So they can z. Legs
  • Encapsulating materials e.g. As cellulose encapsulations, in gelatin,
  • Wax matrices or liposomally encapsulated In particular, wax matrices as described in DE-OS 4308 282, have been found to be favorable. Preference is given to emulsions. O / W emulsions are particularly 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 further customary co-emulsifiers in the preferred O / W emulsions according to the invention.
  • suitable co-emulsifiers are, for example, O / W emulsifiers, primarily 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 W emulsifiers have saturated radicals R and R 1 . If the O / W emulsifiers have unsaturated radicals R and / or R ', 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), polyethylene glycol (14) stearyl ether
  • Step-14 polyethylene glycol (15) stearyl ether (steareth-15),
  • isosteareth-12 polyethylene glycol (13) isostearyl ether (isosteareth-13), polyethylene glycol (14) isostearyl ether (isosteareth-14), polyethylene glycol (15) isostearyl ether (isosteareth-15), polyethylene glycol (16) - isostearyl ether (isosteareth- 16), polyethylene glycol (17) isostearyl ether (isosteareth-17), polyethylene glycol (18) isostearyl ether (isosteareth-18),
  • cetyl stearyl ether (Ceteareth-18), polyethylene glycol (19) cetyl stearyl ether (Ceteareth-19), polyethylene glycol (20) cetyl stearyl ether (Ceteareth-20).
  • 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 (13) oleate, polyethylene glycol (14) oleate, polyethylene glycol (15) oleate, polyethylene glycol (16) oleate, polyethylene glycol (17) oleate, polyethylene glycol ( 18) oleate, polyethylene glycol (19) oleate,
  • 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, polyethylene glycol (6) glyceryl caprate / citrate, polyethylene glycol (20 ) glyceryl oleate, polyethylene glycol (20) glyceryl isostearate, polyethylene glycol (18) glyceryl oleate (cocoate).
  • polyethylene glycol (20) glyceryl laurate polyethylene glycol (21) glyceryl laurate
  • polyethylene glycol (22) glyceryl laurate polyethylene glycol (23) glyceryl laurate
  • polyethylene glycol (6) glyceryl caprate / citrate polyethylene glycol (20 ) glyceryl oleate
  • sorbitan esters from the group of polyethylene 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 having a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids a chain length of 8 to 24, in particular 12-18 C-atoms, monoglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 8 to 24, in particular 12-18 C-atoms, diglycerol ethers saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 8 to 24, in particular 12 to 18, carbon atoms,
  • W / O emulsifiers are glyceryl monostearate, glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate, diglyceryl monostearate, diglyceryl monoisostearate, propylene glycol monostearate, propylene glycol monoisostearate, propylene glycol monocaprylate, propylene glycol monolaurate, sorbitan monoisostearate, sorbitan monolaurate,
  • Preparations preferred according to the invention are particularly 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 pins or present as
  • 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 pins or present as
  • Aerosol be made up.
  • 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 pigments which stain 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 pigments which stain 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, in addition to the compound or compounds according to the invention, for example fatty alcohols, fatty acids, fatty acid esters, in particular triglycerides of fatty acids,
  • oily lotions based on natural or synthetic oils and waxes, lanolin,
  • Fatty acid esters in particular triglycerides of fatty acids, or oily alcoholic lotions based on a lower alcohol, such as ethanol, or a glycerol, such as propylene glycol, and / or a polyol, such as glycerol, and oils, waxes and fatty acid esters, such as triglycerides of fatty acids.
  • the preparation of the invention 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.
  • a preparation is formulated as an aerosol
  • the customary propellants such as alkanes, fluoroalkanes and chlorofluoroalkanes
  • the cosmetic preparation may also be used to protect the hair against photochemical damage to prevent changes in hues, discoloration or damage of a mechanical nature. In this case, it is suitably carried out as a shampoo, lotion, gel or emulsion for rinsing, wherein the respective
  • a preparation for hairdressing and treatment, as a lotion or gel for brushing or laying a wave of water, as hair lacquer, perming agent, dyeing or decolorizing the hair.
  • the formulation with photoprotective properties may contain, in addition to the compound (s) of the invention, various adjuvants used in this type of mediator, such as surfactants, thickeners, polymers, emollients, preservatives, foam stabilizers, electrolytes, organics
  • Solvents silicone derivatives, oils, waxes, anti-grease agents, dyes and / or pigments which dye the agent itself or the hair or other ingredients commonly used for hair care.
  • this preparation contains at least one compound of formula I, wherein R 1 is a radical R a or R b
  • a 1 -A 3 are each independently a radical - (CH 2 ) O (O) P H, where o is 1, 2, or 3 and p is 0 or 1, and it is most preferred that the at least one compound according to Formula I is a compound selected from the compounds Iah, and Ib to Iv, as described above, is.
  • UV absorption in the UV-A or UV-B range shows, but under
  • Application conditions is reactive and produces UV-A or UV-B protection, with a cosmetically or dermatologisch or for food or household products suitable carrier is mixed, and the
  • preparations according to the invention can be prepared using techniques which are well known to the person skilled in the art.
  • the mixing may result in dissolution, emulsification or dispersion of the compound of the invention in the carrier.
  • the compound of the formula I is prepared by hydrogenating at least one compound of the formula I ena or enb
  • molecular hydrogen suitable for hydrogenation of the compounds of formula I ena or I enb is used, the hydrogenation is preferably carried out in the presence of a catalyst or catalyst system.
  • Suitable catalysts for the hydrogenation are all common homogeneous and heterogeneous catalysts, particularly preferred as
  • Catalyst at least one noble metal preferably selected from the elements Pt, Pd and Rh, or a transition metal, such as Mo, W, Cr, but especially Fe, Co and Ni, either used individually or in a mixture.
  • the catalyst (s) or catalyst mixtures may also be supported on supports such as carbon, activated carbon,
  • Alumina, barium carbonate, barium sulfate, calcium carbonate, strontium carbonate or diatomaceous earth may also be used in the form of the Raney compound, for example Raney nickel. If the catalysis is carried out in a homogeneous process, it is preferred if one or more catalysts are used
  • complex compounds of said metals such as the Wilkinson catalyst [chloro-tris (triphenylphosphine) rhodium] is used. It is also possible to use salts of said metals which can be reduced in situ by a reducing agent and generate in situ a finely divided metal (O) species.
  • suitable noble metal salts are palladium acetate, palladium bromide or palladium chloride; suitable reducing agents are, for example, hydrogen, hydrazine, sodium borohydride or formates.
  • a heterogeneous catalyst wherein it is particularly preferred as a catalyst in the inventive
  • Method Pd or Pt preferably on activated charcoal, for example, 5 wt .-% Pd or Pt on C, use.
  • the hydrogenation is usually carried out at a temperature in the range of 20 - 15O 0 C. Furthermore, the hydrogenation is advantageous in a
  • Suitable solvents are protic solvents, in particular the conventional protic solvents known to the person skilled in the art, such as water, lower alcohols, such as, for example, methanol, ethanol and isopropanol, and primary and secondary amines and mixtures of such protic solvents, where it may be particularly preferred
  • Solvent water is used.
  • Suitable solvents for this reaction are common aprotic solvents.
  • Dimethylformamide, dimethyl sulfoxide and N-methyl-pyrrolidone can be used.
  • the hydrogenation is carried out in bulk, i. no additional solvent is required.
  • the workup can be carried out by conventional methods.
  • the catalyst can be filtered off, the filtrate can be freed from the solvent, for. B. by heating at compared to
  • reaction products can likewise be carried out by customary methods, for example by recrystallization from a suitable solvent, or by chromatographic methods.
  • compounds according to the invention can have a stabilizing effect on the preparation. When used in corresponding products, they therefore remain stable for longer and do not change their galenic and sensory properties. In particular, even with prolonged use or prolonged storage, the effectiveness of the ingredients, such as vitamins, obtained. Among other things, this is particularly advantageous in compositions for protecting the skin against the action of UV rays, since these cosmetics are exposed to particularly high levels of exposure to UV radiation.
  • the foods that can be fortified according to the present invention with one or more compounds of the invention include all materials that are suitable for consumption by animals or for the
  • the foodstuffs may be solid or liquid, ie as a beverage.
  • Further objects of the present invention are accordingly the use of a compound according to formula I as Food supplement for human or animal nutrition and preparations containing food or dietary supplements and containing appropriate carriers.
  • Foods which can be fortified according to the present invention with one or more compounds according to the invention are, for example, foods derived from a single natural source, e.g. Sugar, unsweetened juice, nectar or puree from a single plant species, e.g. unsweetened apple juice (including a mixture of different types of apple juice), grapefruit juice,
  • Wheat flour or oat bran Mixtures of such foods are also suitable for being fortified according to the present invention with one or more compounds according to the invention, for example multi-vitamin preparations, mineral-substance mixtures or sweetened juice.
  • multi-vitamin preparations for example multi-vitamin preparations, mineral-substance mixtures or sweetened juice.
  • foods that can be enriched according to the present invention with one or more compounds of the invention are also suitable for being fortified according to the present invention with one or more compounds according to the invention, for example multi-vitamin preparations, mineral-substance mixtures or sweetened juice.
  • Food preparations for example prepared cereals, biscuits, mixed drinks, foods specially prepared for children, such as yoghurt, dietary foods, low calorie foods or animal feeds.
  • the foods that can be fortified according to the present invention with one or more compounds of the invention thus include all edible combinations of carbohydrates,
  • Lipids, proteins, inorganic elements, trace elements, vitamins, water or active metabolites of plants and animals Lipids, proteins, inorganic elements, trace elements, vitamins, water or active metabolites of plants and animals.
  • the foods which can be fortified according to the present invention with one or more compounds of the invention are preferably administered orally, e.g. in the form of food, pills, tablets, capsules, powders, syrups, solutions or suspensions.
  • the foods according to the invention enriched with one or more compounds according to the invention can be prepared with the aid of
  • compounds according to the invention are also suitable as medicament ingredients. They have a supportive or substitutive effect on natural
  • the compounds of the invention may be partially compared in their action with radical scavengers such as vitamin C, compounds of the invention may be used for example for the preventive treatment of inflammation and allergies of the skin and in certain cases for the prevention of certain cancers.
  • compounds of the invention are suitable for the preparation of a medicament for the treatment of inflammations, allergies and irritations, in particular of the skin.
  • drugs can be produced in an action as a vein tonic, as an agent for increasing the strength of blood capillaries, as an inhibitor of cuperose, as an inhibitor of chemical, physical or actinic erythema, as a means of treating sensitive skin, as a decongestant, as a dehydrating agent, as a means for Slimming, as anti-wrinkle agents, as stimulators of the synthesis of extracellular matrix components, as a tonicityener for improving skin elasticity and as
  • preferred compounds of the present invention exhibit antiallergic and antiinflammatory and antiirritative effects. They are therefore suitable for the preparation of medicaments for the treatment of inflammation or allergic reactions.
  • Benzylmalonic acid derivatives or phenylpropionic acid derivatives such as 4-Alkylenoxy-benzyl malonic acid diethyl ester included.
  • FIG. 1 shows the change in the UV spectrum of 4-hydroxy-3,5-dimethoxy-benzyl-malonic acid di-2-ethylhexyl ester (from Example 1)
  • the curves represent the unirradiated substance (0 kJ / m 2 irradiated), irradiated after 15 min irradiation (86 kJ / m 2 ), after 65 min irradiation (373 kJ / m 2 irradiated), after 235 min irradiation (1349 kJ / irradiated m 2 ) and after 405 min irradiation (2325 kJ / m 2 irradiated).
  • the spectra are recorded on a Carry 300 bio spectrometer.
  • the irradiation is carried out by means of an Atlas Sun Test CPS, xenon lamp with UV special glass filter at a power of 95.69 W / m 2 in the range 290-400 nm. After only 65 minutes, a significantly increased UV absorption of the compound in the UV-A range (E max in the range 320-340 nm), which increases further with prolonged irradiation.
  • Example 3a Oxidation in UV light in the presence of further
  • FIG. 2 shows the change in the UV / VIS spectrum of emulsions containing 0.5% by weight of beta-carotene and 4% by weight of 4-hydroxy-3,5-dimethoxybenzylmalonic acid di-2-ethyl- hexyl ester (curves A and B) in
  • the curves represent the unirradiated emulsions (curves A and C) and the emulsions after 90 minutes of irradiation (curves B and D).
  • the spectra are recorded on a Carry 50 spectrometer.
  • exemplary formulations for cosmetic preparations which contain compounds according to Example 1 or 2.
  • Corresponding preparations can be prepared in the same way with all compounds according to the invention.
  • UV-Pearl, OMC stands for the preparation with the INCI name: Water (for EU: Aqua), Ethylhexyl Methoxycinnamate, Silica, PVP, Chlorphenesin, BHT; this formulation is commercially available under the designation Eusolex®UV Pearl TM OMC from Merck KGaA, Darmstadt.
  • Phase B Heat phase B to 75 ° C, phase C to 80 ° C. Add Phase B slowly to Phase C with stirring. Cool with stirring to 65 ° C and homogenize. Cool to 40 ° C and add phases D, E and F to Phase B / C with stirring and homogenize again. Now add the pearlescent pigment with stirring. Cool to room temperature and adjust the pH to 6.0-6.5.
  • hair mascara preparations can be prepared which have the following modifications:
  • Example 6 Conditioner with IR3535®
  • Method of preparation Mix phases A and B separately. Add phase B to phase A with stirring. Add phase C.
  • conditioner preparations can be produced which have the following modifications:
  • phase A water Disperse the pearlescent pigment and Titriplex III in phase A water. Heat the components of phases A and B to 75 ° C. Add phase B to phase A with stirring and homogenize. Cool to 40 0 C and add the ingredients of Phase C. Cool to 30 0 C and turn. homogenize for approx. 30 sec. Adjust the pH to 3.6-4.0.
  • FIGS. 1a and 1b are identical to FIGS. 1a and 1b:
  • FIG. 1 shows a section of FIG. 1a
  • FIG. 1 shows the change in the UV spectrum of 4-hydroxy-3,5-dimethoxybenzyl malonic acid di-2-ethylhexyl ester upon irradiation with UV light
  • the curves represent the unirradiated substance (0 kJ / m 2 irradiated), irradiated after 15 min irradiation (86 kJ / m 2 ), after 65 min irradiation (373 kJ / m 2 irradiated), after 235 irradiation (1349 kJ / m 2 irradiated) and after 405 min irradiation (2325 kJ / m 2 irradiated).
  • the spectra are recorded on a Cary 300 bio spectrometer.
  • FIG. 2 is a diagrammatic representation of FIG. 1
  • FIG. 2 shows the change in the UV / VIS spectrum of emulsions containing 0.5% by weight of beta-carotene and 4% by weight of 4-hydroxy-3,5-dimethoxybenzylmalonic acid di-2-ethyl- hexyl ester (curves A and B) in

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EP1871339A1 (de) * 2005-04-19 2008-01-02 Merck Patent GmbH Uv schutz
DE102007005186A1 (de) 2007-01-29 2008-07-31 Merck Patent Gmbh Partikuläres UV-Schutzmittel
DE102007013366A1 (de) 2007-03-16 2008-09-18 Merck Patent Gmbh Verwendung von Chroman-4-on-Derivaten
WO2008119428A1 (en) * 2007-04-03 2008-10-09 Merck Patent Gmbh Photostable compositions
DE102007038097A1 (de) 2007-08-13 2009-02-19 Merck Patent Gmbh Tyrosinaseinhibitoren
DE102007038098A1 (de) 2007-08-13 2009-02-19 Merck Patent Gmbh Tyrosinaseinhibitoren
MX2010008065A (es) * 2008-01-25 2010-10-20 Schering Plough Healthcare Metodo de selección de antioxidantes para su uso en composiciones de aplicación topica.
FR2928370B1 (fr) * 2008-03-07 2017-07-14 Catalys Preparation de composes hydroquinone-amide a proprietes anti-oxydantes
JP2010248150A (ja) * 2009-04-17 2010-11-04 Rohto Pharmaceut Co Ltd アドバンスド・グリケーション・エンド・プロダクツの蓄積による肌老化の予防、抑制、又は改善剤
WO2011006566A2 (de) 2009-07-14 2011-01-20 Merck Patent Gmbh Monomethoxy-hydroxy-benzylmalonate
KR20110012148A (ko) * 2009-07-30 2011-02-09 서울대학교산학협력단 펩타이드가 결합된 하이드록시 시나믹산 유도체, 이의 제조 방법 및 이를 포함하는 화장품 조성물
WO2011023287A1 (en) 2009-08-27 2011-03-03 Merck Patent Gmbh Use of faa and its derivatives in cosmetics and dermatology
DE102010001905A1 (de) * 2010-02-12 2011-08-18 ROVI Cosmetics International GmbH, 36381 UV-Schutzmittel für die Haut oder die Haare mit einer in einem vesikulären Trägersystem verkapselten UV-Filtersubstanz
DE102010045890A1 (de) 2010-09-17 2012-03-22 Merck Patent Gmbh 2,2'-Furoin-Derivte und deren Verwendung zur Hautaufhellung
US8481591B2 (en) * 2010-11-01 2013-07-09 Stiefel Research Australia Pty. Ltd. Polymeric topical compositions
DE102010051689A1 (de) 2010-11-17 2012-05-24 Merck Patent Gmbh Dihydroxyfumarsäure-Derivate und deren Verwendung zur Hautaufhellung
DE102011102824A1 (de) 2011-05-30 2012-12-06 Merck Patent Gmbh Extrakte aus Eugenia uniflora
DE102011117364A1 (de) 2011-10-29 2013-05-02 Merck Patent Gmbh Hautaufheller in der Phototherapie
CN103385516A (zh) * 2013-07-29 2013-11-13 安徽燕之坊食品有限公司 一种液体补充物
WO2017147718A1 (en) 2016-03-03 2017-09-08 Universite De Moncton Modulators of lipoxygenase and cyclooxygenase enzyme activity
US20180221426A1 (en) 2017-02-06 2018-08-09 William Van Dover Stoecker Compositions and Methods for Treating and Removing Seborrheic Keratoses
WO2018162368A1 (en) 2017-03-06 2018-09-13 Merck Patent Gmbh Use of compatible solutes
CN107157788A (zh) * 2017-05-05 2017-09-15 海南京润珍珠生物技术股份有限公司 一种添加甲氧基肉桂酸乙基己酯脂质体包裹物的防晒霜
WO2019197368A1 (de) * 2018-04-13 2019-10-17 Merck Patent Gmbh Verwendung spezieller benzylidenmalonate zum schutz der haut vor chemisch induziertem stress
CN109010101A (zh) * 2018-09-17 2018-12-18 天津大学 一种广谱化学防晒剂和广谱防晒霜及其制备方法
CN114206300A (zh) 2019-08-01 2022-03-18 默克专利股份有限公司 预防和减少角质化障碍及相关美容剂
CN111603396B (zh) * 2020-06-12 2021-07-20 四川大学 一种聚天然多酚型防晒凝胶及其制备方法
US11547645B2 (en) * 2021-01-05 2023-01-10 L'oreal Organic UVA filter-stabilized antioxidant composition
CN115819239A (zh) * 2021-09-17 2023-03-21 无锡和誉生物医药科技有限公司 一种成纤维细胞生长因子受体抑制剂的中间体及其制备方法和用途

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2415624A (en) * 1945-01-17 1947-02-11 Eastman Kodak Co Light-sensitive layers having ultraviolet light filters
US3830828A (en) * 1967-08-17 1974-08-20 Ciba Geigy Corp Stabilizer for organic compounds
US3856911A (en) 1969-07-21 1974-12-24 Takeda Chemical Industries Ltd Cholagogic composition containing pentanedione derivatives
JPS4910664B1 (enrdf_load_stackoverflow) 1969-07-21 1974-03-12
DE2240609A1 (de) * 1972-08-18 1974-02-28 Hoechst Ag Stoffwechselwirksame derivate der 4-hydroxy-3,5-di-alkylphenyl-propionsaeure
US4069340A (en) * 1976-01-30 1978-01-17 Hooker Chemicals & Plastics Corporation Immonium salts and derivatives thereof
DE3047106A1 (de) * 1980-12-13 1982-07-29 Henkel Kgaa Topische kosmetische zubereitungen zur behandlung von stark fettendem haar und seborrhoeischer haut
EP0100651A1 (en) * 1982-08-03 1984-02-15 VAN DYK & COMPANY, INC. Dialkyl malonates as organic suncreen adjuvants
DE3521558A1 (de) * 1985-06-15 1986-12-18 Basf Ag, 6700 Ludwigshafen 3-t-butyl-4-hydroxiphenylpropionsaeureaminoalkylamidderivate und damit stabilisiertes organisches material
DE3673113D1 (de) * 1985-10-11 1990-09-06 Ciba Geigy Ag Substituierte p-hydroxyphenylverbindungen.
JPS63227542A (ja) * 1987-03-17 1988-09-21 Yoshitomi Pharmaceut Ind Ltd ４−ヒドロキシフエニルプロピオン酸化合物またはそのエステルの製法
JP2552297B2 (ja) * 1987-07-03 1996-11-06 ポーラ化成工業株式会社 美肌化粧料
US4888444A (en) * 1987-10-26 1989-12-19 Ciba-Geigy Corporation Substituted hydroxylamine ester stabilizers
IT1216687B (it) * 1988-04-01 1990-03-08 Boehringer Biochemia Srl Complessi di platino (ii), loro preparazione e impiego come antitumorali.
US5051531A (en) * 1988-05-31 1991-09-24 Atochem North America, Inc. Antioxidant-peroxides
LU87271A1 (fr) * 1988-07-08 1990-02-07 Oreal Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique
FR2636338B1 (fr) * 1988-09-09 1990-11-23 Rhone Poulenc Chimie Diorganopolysiloxane a fonction benzalmalonate
AU630631B2 (en) * 1988-10-25 1992-11-05 Ciba-Geigy Ag Phenol group-containing compounds as anti-oxidants in organic materials
EP0474589A1 (de) * 1990-08-02 1992-03-11 Ciba-Geigy Ag Orthophenolacetamide
JP2555830B2 (ja) * 1991-04-30 1996-11-20 株式会社ツムラ 多環性化合物の製造法
EP0511666A1 (en) 1991-04-30 1992-11-04 TSUMURA & CO. Process for the preparation of polycyclic compounds
FR2679133B1 (fr) * 1991-07-17 1993-10-15 Oreal Utilisation de derives d'acides (2,5-dihydroxyphenyl)carboxyliques, leurs homologues et leurs sels dans la preparation d'une composition cosmetique ou dermatologique a action depigmentante.
US5453514A (en) 1992-12-25 1995-09-26 Yamanouchi Pharmaceutical Co., Ltd. Pyrazole derivatives and compositions and methods of use as maillard reaction inhibitors
PL183812B1 (pl) * 1996-12-17 2002-07-31 Politechnika Wroclawska Nowe chlorki alkoksymetyloamoniowe pochodne aminoestrów kwasu p-(3,5-di-t-butylo-4-hydroksy)- fenylopropionowego
BE1014162A3 (fr) * 1997-05-26 2003-06-03 Ciba Sc Holding Ag Produits stabilisants, compositions et concentres les contenant, et leur procede d'utilisation.
US5834544A (en) * 1997-10-20 1998-11-10 Uniroyal Chemical Company, Inc. Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities
AUPP616498A0 (en) * 1998-09-25 1998-10-15 University Of Queensland, The Synthesis of cyclic peptides
ATE283252T1 (de) 1999-03-26 2004-12-15 Firmenich & Cie Cyklische verbindungen sowie deren verwendung als vorstufen von duftalkoholen
DE10000209A1 (de) * 2000-01-05 2001-07-12 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen vom Typ Öl-in-Wasser
PL196298B1 (pl) * 2000-02-29 2007-12-31 Politechnika Wroclawska Nowe sole dietyloamoniowe pochodne aminoestru kwasu b-(3,5-di-t-butylo-4-hydroksy)fenylopropionowego
JP2001261654A (ja) 2000-03-21 2001-09-26 Mitsui Chemicals Inc キノリン誘導体およびそれを有効成分として含有する核内レセプター作動薬
DE10124914A1 (de) 2001-05-22 2002-11-28 Henkel Kgaa Lipoprotein-Cremes mit UV-Filtern
DE60215656T2 (de) 2001-07-16 2007-08-23 Merck Patent Gmbh Photostabile organische sonnenschutzmittel mit antioxidativen eigenschaften und zusammensetzungen damit
ITRM20020016A1 (it) 2002-01-15 2003-07-15 Sigma Tau Ind Farmaceuti Derivati di acidi fenil(alchil)carbossilici e derivati fenilalchileterociclici dionici, loro uso come medicamenti ad attivita' ipoglicemizza
JP2004307460A (ja) * 2002-07-22 2004-11-04 Sankyo Co Ltd マロン酸誘導体
EP1604643A1 (en) 2004-06-03 2005-12-14 Cognis France, S.A.S. Cosmetic use of derivatives of 3-Phenylpropionic acid
EP1871339A1 (de) * 2005-04-19 2008-01-02 Merck Patent GmbH Uv schutz

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006111234A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7058874B2 (en) * 2002-05-24 2006-06-06 Lucent Technologies Inc. Interleaver address generator and method of generating an interleaver address

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WO2006111233A1 (de) 2006-10-26
CN101203278A (zh) 2008-06-18
JP5415755B2 (ja) 2014-02-12
US8106233B2 (en) 2012-01-31
US8268293B2 (en) 2012-09-18
US20080171004A1 (en) 2008-07-17
EP1871735B1 (de) 2015-12-23
JP2008538381A (ja) 2008-10-23
CN101163659A (zh) 2008-04-16
JP2008539167A (ja) 2008-11-13
ES2568516T3 (es) 2016-04-29

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