EP1267813A2 - Utilisation d'inhibiteurs de protease dans les cosmetiques et produits pharmaceutiques - Google Patents

Utilisation d'inhibiteurs de protease dans les cosmetiques et produits pharmaceutiques

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Publication number
EP1267813A2
EP1267813A2 EP01915400A EP01915400A EP1267813A2 EP 1267813 A2 EP1267813 A2 EP 1267813A2 EP 01915400 A EP01915400 A EP 01915400A EP 01915400 A EP01915400 A EP 01915400A EP 1267813 A2 EP1267813 A2 EP 1267813A2
Authority
EP
European Patent Office
Prior art keywords
mmp
preparation
acid
skin
inhibiting substance
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.)
Ceased
Application number
EP01915400A
Other languages
German (de)
English (en)
Inventor
Dirk Petersohn
Günter Schmitt
Klaus Rudolf SCHRÖDER
Thomas Förster
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 DE10020447A external-priority patent/DE10020447A1/de
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1267813A2 publication Critical patent/EP1267813A2/fr
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the invention relates to the use of M P-1 -inhibiting substances in cosmetic preparations, in particular for the prevention of the light and heat-induced aging of human skin.
  • the invention also relates to pharmaceutical preparations containing MMP-1 inhibiting substances.
  • Irradiation of human skin with sunlight is an exogenous stress and leads to changes in the biochemical balance in the skin. This leads to macroscopically visible and cosmetically undesirable phenomena, such as a reduction in skin elasticity, accompanied by wrinkling. In the advanced stage, malignant tissue growth can also occur. Efforts to date to prevent light-induced skin aging have been based on the topical application of light stabilizers and / or substances having an antioxidative effect.
  • MMP matrix metalloproteinases
  • the reduction in the synthesis and / or the activity of these further MMPs is not considered advantageous since these further MMPs perform physiologically important functions.
  • the high-energy solar radiation leads to the generation of reactive oxygen species in the skin, which in turn react with the collagen of the skin and thus destroy the triple-helical structure of the collagen molecule in a non-enzymatic way.
  • This degraded collagen has to be removed from the connective tissue of the skin by collagenases, such as the 92 kDa gelatinase.
  • a UV-A blocker In application WO 98/55075, triple combinations of a UV-A blocker, a UV-B blocker and an MMP inhibitor are claimed, which counteract the aging of the skin by light.
  • the compositions must be applied to the skin 7 to 48 hours before UV exposure.
  • Retinoic acid (tretinoin) and retinol are preferred as MMP inhibitors.
  • retinoic acid has teratogenic properties and may only be used in prescription / gene pharmaceuticals.
  • the use of retinol in cosmetic sunscreen preparations is problematic for several reasons. Retinol, for example, has a relatively high cell toxicity and in particular phototoxicity and can therefore only be used in low concentrations in compositions for use in humans.
  • retinol is easily oxidatively degraded under the influence of heat and / or light and is unstable in formulations, for example in cream formulations.
  • anti-aging skin cosmetics which are understood to mean cosmetic products that are associated with skin aging, in particular sunlight-induced Counteract skin aging.
  • An ideal anti-aging active ingredient inhibits the expression of the collagen-digesting matrix metalloprotease MMP-1 and / or the activity of this enzyme, even in low concentrations and with high selectivity compared to other matrix metalloproteinases, and counteracts, in particular, sunlight-induced skin aging when it is used just before the skin is exposed to light.
  • an active ingredient must have low cell toxicity and must be stable in preparations.
  • the anti-aging active ingredients known from the prior art do not meet these conditions, or do so only to an inadequate extent.
  • the object of the invention was to remedy the shortcomings of the prior art and to provide more suitable agents for the cosmetic treatment of sunlight and / or heat-induced skin aging. Another object of the invention was to provide improved pharmaceutical preparations for the treatment of sunlight and / or heat-induced skin aging.
  • Another aspect of the present invention relates to the use of MMP-1-inhibiting substances in cosmetic products for the treatment of the teeth, the gums and the oral mucosa, in particular for the prevention of inflammation of the gums (gingivitis) and periodontium and for the prevention of periodontitis.
  • the invention further relates to the use of MMP-1-inhibiting substances for producing a pharmaceutical preparation for the treatment of the skin, teeth, gums or oral mucosa.
  • Periodontitis is an inflammatory disease of the tooth bed, which was previously often called periodontitis.
  • the main cause of the disease is dental plaque or "plaque”. This consists of certain components of the saliva, food residues and especially bacteria and their breakdown products.
  • This particular form of an infectious disease is in most cases caused by the bacteria Porphyromonas gingivalis, Bacteroides forsythus and Actinobacillus actinomycetem comitans. These bacteria are components of the "natural" oral flora in the majority of the population of industrialized countries. The presence of the bacteria is therefore a necessary but not sufficient prerequisite for the occurrence of periodontitis. Genetic predispositions ("inheritance”) and environmental influences (e.g. .
  • pro-inflammatory mediators are known to activate the synthesis of matrix-degrading metallo-proteinases in the skin and mucous membrane, which destroy the extracellular matrix of the surrounding connective tissue.
  • bacteria that initially interacted with the gingival margin penetrate deeper into the underlying connective tissue continue inflammatory processes and the synthesis of matrix-degrading metallo-proteinases, and ultimately release the connection between the top layer of the epithelium and the tooth root.
  • a gum pocket forms.
  • the reaction of the body is inflammation of the gingiva and periodontium with damage to the alveolar bone. In the final stage of periodontitis, those affected are at risk of massive tooth loss.
  • the object of this invention was to improve the prior art. Decisive in the process of periodontitis is the degradation of the extracellular matrix and the damage to the alveolar bone by matrix metalloproteases (MMPs). In order to effectively stop this process, damage to the oral mucosa by metallo-proteinases, and here in particular by MMP-1, must be inhibited at a very early stage.
  • the first object of the invention is a cosmetic preparation for topical treatment of the skin, preferably human skin, characterized in that it comprises one or more MMP-1-inhibiting substances.
  • the topical treatment of the skin is preferably to be understood as a preventive treatment against the sunlight-induced aging of human skin or a preventive treatment against the heat-induced aging of human skin.
  • Another object of the invention is a cosmetic preparation for the treatment of teeth, gums and oral mucosa, characterized in that it comprises one or more MMP-1-inhibiting substances.
  • the MMP-1-inhibiting substances contained in the preparations according to the invention are preferably selected from the group formed by
  • 6-Hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran are from the Literature known substances.
  • 3,4-Dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran is commercially available under the name "Lipochroman 6 TM" (Lipotec S.A.).
  • Precocenes are chromium derivatives which occur in plants and are known as hormones (The Merck Index, 12th edition, Merck & Co. 1996).
  • Another object of the invention is the use of one or more MMP-1 inhibiting substances, in particular one or more substances from the group formed by retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl - 1 (2H) -benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and mixtures thereof, for the cosmetic treatment of the skin.
  • the cosmetic treatment of the skin is preferably to be understood as a preventive treatment against the sunlight and / or heat-induced aging of the human skin.
  • Another object of the invention is the use of one or more MMP-1 inhibiting substances, in particular one or more substances from the group formed by retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl - 1 (2H) -benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and their mixtures, for the prevention of inflammation of the gums (gingivitis) and the periodontium and to prevent periodontitis.
  • MMP-1 inhibiting substances in particular one or more substances from the group formed by retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl - 1 (2H) -benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and their mixtures, for the prevention of inflammation of the gums (gingivitis)
  • MMP-1 is predominantly produced by fibroblasts in the UV-irradiated skin. For this reason, photoaging can be prevented particularly effectively by substances which inhibit MMP-1 synthesis in fibroblasts. In the context of the present invention, the effect of the investigated substances was therefore tested and demonstrated on fibroblasts.
  • an MMP-1 inhibitor is to be understood as a substance which
  • the cell toxicity of the investigated substances and their phototoxicity was determined with the help of the MTT test.
  • the MTT test is based on the determination of the metabolic activity of living cells and provides information about cell proliferation and cytotoxicity.
  • the tetrazolium salt 3- [4,5-dimethylthiazol-2-yl] -2,5-diphenyltetrazolium bromide (MTT) is reduced in living cells and thus forms a water-insoluble formazan salt, which is quantified photometrically after extraction ( T. Mosmann, J Immunol. Methods 1983, 65, 55).
  • the results of these measurements showed that the substances claimed according to the invention only have toxic or phototoxic effects in relatively high concentrations. At the concentrations at which the light-induced expression of MMP-1 had already been effectively suppressed, there were no significant toxic or phototoxic effects.
  • MMP-1 inhibitors can advantageously be used anywhere in cosmetics where cosmetically desired effects are associated with MMP-1 inhibition.
  • the substances according to the invention are preferably used for the prevention of sunlight and / or heat-induced aging of human skin and for the prevention of inflammation of the gums (gingivitis) and periodontium and for the prevention of periodontitis.
  • a preferred object of the invention is the use of an MMP-1 inhibiting substance, in particular an MMP-1 inhibiting substance from the group formed by retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2- dimethyl-1 (2H) - benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and their mixtures, for reducing or preventing the increase in MMP-1 - Activity in skin exposed to sunlight or inflamed gums and inflamed oral mucosa.
  • the reduction or prevention of the increase in MMP-1 activity can take place both by a direct inhibition of the MMP-1 and by indirect processes, such as.
  • B. a decrease in MMP-1 formation by inhibiting the transcription factors that control the synthesis of MMP-1.
  • the MMP-1 inhibitors used according to the invention are suitable for the prevention of sunlight-induced skin aging both in the event of sun exposure below the MED (minimum erythemal dose) as well as for an exposure above the MED. They are therefore suitable both for long-term preventive treatment, whereby their daily use protects the skin in the long term even with low sun exposure, as well as for preventing high exposure to sunlight.
  • the MMP-1 inhibitors can be used both before and after exposure to sunlight, ie the effect on the skin desired according to the invention is achieved in both cases.
  • the MMP-1-inhibiting substances according to the invention prevent sunlight-induced skin aging when they are applied topically to the skin only relatively shortly before exposure to sunlight.
  • a relatively short period is understood to mean in particular a period between one and five hours. This rapidly occurring protective effect is particularly advantageous when the skin is exposed to high levels of sunlight and preventive measures can only be taken shortly before the exposure.
  • Another object of the invention is the use of one or more MMP-1 inhibiting substances, in particular one or more substances from the group formed by retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl - 1 (2H) -benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and mixtures thereof, for the manufacture of a cosmetic preparation.
  • This cosmetic preparation is preferably used for the preventive cosmetic treatment against sunlight and / or heat-induced aging of the human skin and for the prevention of gingivitis and periodontitis.
  • Another object of the invention is the use of one or more MMP-1 inhibiting substances, in particular one or more substances from the group formed by retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl - 1 (2H) -benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) -benzopyran and mixtures thereof, for the manufacture of a pharmaceutical preparation.
  • This pharmaceutical preparation is preferably used for the preventive therapeutic treatment against sunlight and / or heat-induced aging of the human skin and for the prevention of gingivitis and periodontitis.
  • the MMP-1-inhibiting substances are preferably used in such a way that the MMP-1-inhibiting substances are contained as a component in a cosmetic or pharmaceutical preparation which additionally comprises a physiologically acceptable carrier.
  • the invention thus furthermore relates to a cosmetic or pharmaceutical preparation in which one or more MMP-1-inhibiting substances are present in the preparation in concentrations of 0.1 to 5 and preferably 0.5 to 2% by weight / are, the concentration information in each case means the total weight of the MMP-1 inhibiting substances based on the total weight of the preparation.
  • the physiologically acceptable carrier comprises one or more adjuvants, such as are commonly used in such preparations, such as. B. thickeners, moisturizing and / or moisturizing substances, surfactants, emulsifiers, fats, oils, waxes, silicones, sequestering agents, anionic, cationic, nonionic or amphoteric polymers, alkalizing or acidifying agents, alcohols, polyols, softeners, adsorbents, electrolytes , organic solvents, preservatives, bactericides, antioxidants, light stabilizers, fragrances, flavors, sweeteners, dyes and pigments.
  • adjuvants such as are commonly used in such preparations, such as. B. thickeners, moisturizing and / or moisturizing substances, surfactants, emulsifiers, fats, oils, waxes, silicones, sequestering agents, anionic, cationic, nonionic or amphoteric polymers, alkalizing or acidifying agents, alcohol
  • Cosmetic preparations are agents for cleaning and / or caring for the body, in particular for the purposes of the invention, for the skin, such as, for example, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat compositions, stick preparations, sprays , Foams, powders, ointments, hair shampoos, hair lotions, hair styling agents, hair fixatives, foam baths and shower baths.
  • the use is aimed at the hair floor or the scalp.
  • the cosmetic preparations contain, in addition to the MMP-1-inhibiting substance, additional emulsifiers and fatty substances as further components.
  • Emulsifiers which can be used according to the invention are, for example
  • alkyl (oligo) glucosides e.g. B. the commercially available product Montanov ® 68,
  • Sterols are understood to be a group of steroids which carry a hydroxyl group on the C atom 3 of the steroid structure and are isolated both from animal tissue (zoosterols) and from vegetable fats (phytosterols). Examples of zoosterols are cholesterol and lanosterol. Examples of suitable phytosterols are beta-sitosterol, stigmasterol, campesterol and ergosterol. Sterols, the so-called mycosterols, are also isolated from fungi and yeasts.
  • glucose phospholipids especially the glucose phospholipids, which, for. B. as lecithins or phosphatidylcholines from z. B. egg yolk or plant seeds (e.g. soybeans) are obtained,
  • Polyglycerols and polyglycerol derivatives preferably polyglyceryl-2-dipolyhydroxystearate (commercial product Dehymuls ® PGPH) and polyglyceryl-3-diisostearate (commercial product Lameform ® TGI),
  • the agents according to the invention preferably contain the emulsifiers in amounts of 0.1 to 25% by weight, in particular 0.5-15% by weight, based on the total agent.
  • At least one nonionic emulsifier with an HLB value of 8 and below is according to the 10th edition, Georg Thieme Verlag Stuttgart, New, in the Rompp-Lexikon Chemie (Eds .: J. Falbe, M. Regitz) York, (1997), Page 1764, listed definitions of the HLB value.
  • a particularly preferred emulsifier of the formula R 1 - O - R 2 is a behen or erucyl derivative in which R 1 represents a linear, terminally substituted alkyl, alkenyl or acyl group having 22 carbon atoms.
  • suitable emulsifiers with an HLB value of 8 and below are the addition products of 1 or 2 moles of ethylene oxide or propylene oxide with behenyl alcohol, erucyl alcohol, arachidyl alcohol or else with behenic acid or erucic acid.
  • the monoesters of C 6 -C 30 fatty acids with polyols such as, for. B. pentaerythritol, trimethylolpropane, diglycerol, sorbitol, glucose or methylglucose. Examples of such products are e.g. B. sorbitan monobehenate or pentaerythritol monoerucate.
  • At least one ionic emulsifier selected from anionic, zwitterionic, ampholytic and cationic emulsifiers is contained.
  • Preferred anionic emulsifiers are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl ester with 8 up to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, monoglyceride sulfates, alkyl and alkenyl ether phosphates and protein fatty acid condensates.
  • Zwitterionic emulsifiers carry at least one quaternary ammonium group and at least one -COO ' or -S0 3 ' group in the molecule.
  • Particularly suitable zwitterionic emulsifiers are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinates, N-acylaminopropyl-N, N-dimethylammonium glycinates and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each have 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • ampholytic emulsifiers contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and can form internal salts.
  • suitable ampholytic emulsifiers are N-alkylglycines, N-alkylaminopropionic acids, N-alkylaminobutyric acids, N-alkyl iminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid, each with about 8 to 24 carbon atoms in the alkyl group.
  • the ionic emulsifiers are present in an amount of 0.01 to 5% by weight, preferably 0.05 to 3% by weight and particularly preferably 0.1 to 1% by weight, based on the total agent ,
  • Suitable as fatty substances according to the invention are vegetable oils, such as sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach seed oil and the liquid fractions of coconut oil, liquid paraffin oils, isoparaffin oils and synthetic hydrocarbons, e.g. B. 1, 3-di- (2-ethyl-hexyl) cyclohexane (Cetiol ® S) or polydecene, di-n-alkyl ether with a total of 12 to 36, in particular 12 to 24, carbon atoms, for. B.
  • vegetable oils such as sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach seed oil and the liquid fractions of coconut oil, liquid paraffin oils, isoparaffin oils and synthetic hydrocarbons, e.g. B. 1, 3-di- (2-ethyl-hexyl) cyclohex
  • di-n-octyl ether (Cetiol ® OE), di-n-n-hexyl-n-octyl ether and n-octyl-n-decyl ether, fatty acids, especially linear and / or branched, saturated and / or unsaturated C 8 . 30 fatty acids. Do-2 2 fatty acids are preferred. Examples are the isostearic acids and isopalmitic acids such as the fatty acids sold under the trade name Edenor ® .
  • fatty acids are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, galeoachidonic acid, galeoachidonic acid and erucic acid and their technical mixtures.
  • the fatty acid cuts that are obtainable from coconut oil or palm oil are usually particularly preferred; the use of stearic acid is particularly preferred.
  • fatty alcohols particularly saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols with 6 to 30, preferably 10 to 22 and very particularly preferably 12 to 22 carbon atoms.
  • 2-ethylhexanol this list is intended to have exemplary and non-limiting character.
  • Esteröle that is, esters of C 6 - 3 o-fatty acids with C.
  • the monoesters of fatty acids with alcohols having 2 to 24 carbon atoms are preferred.
  • the above-mentioned substances can be used as alcohol and acid components of the ester oils.
  • B. are the commercial products Cosmacol ® from EniChem, Augusta Industriale. Also suitable are dicarboxylic acid esters such as di-n-butyl adipate, di- (2-ethylhexyl) adipate, di- (2-ethylhexyl) succinate and di-isotridecylacelate as well as diol esters such as ethylene glycol dioleate, ethylene glycol di-isotridecanoate, propylene glycol di (2-ethylhexanoate) ), Propylene glycol di-isostearate,
  • dicarboxylic acid esters such as di-n-butyl adipate, di- (2-ethylhexyl) adipate, di- (2-ethylhexyl) succinate and di-isotridecylacelate as well as diol esters such as ethylene glycol dioleate, ethylene glycol di-isotri
  • Propylene glycol di-pelargonate, butanediol di-isostearate, neopentyl glycol dicaprylate are also suitable.
  • symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols e.g. B. glycerol carbonate or dicaprylyl carbonate (Cetiol ® CC).
  • mono-, di- and trifatty acid esters of saturated and / or unsaturated linear and / or branched fatty acids with glycerol e.g. B. Monomuls ® 90-O18, Monomuls ® 90-L12 or Cutina ® MD.
  • waxes in particular insect waxes such as beeswax and bumblebee wax, plant waxes such as candelilla wax and carnauba wax, fruit waxes, ozokerite, micro waxes, ceresin, paraffin, triglycerides saturated and optionally hydroxylated C 16 . 3 o-fatty acids, such as B. hardened triglyceride fats (hydrogenated palm oil, hydrogenated coconut oil, hydrogenated castor oil), glyceryl tribehenate or glyceryl tri-12-hydroxystearate, synthetic full esters of fatty acids and glycols (e.g.
  • Syncrowachs ® or polyols with 2 - 6 C atoms, synthetic fatty acid - Fatty alcohol esters, e.g. B. stearyl stearate or cetyl palmitate, ester waxes from natural fatty acids and synthetic C 20 . 4 o-fatty alcohols (INCI name C20-40 alkyl stearate), ozokerite and paraffin.
  • silicone compounds selected from decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane and silicone polymers, which can, if desired, be crosslinked, e.g. B.
  • polydialkylsiloxanes polyalkylarylsiloxanes, ethoxylated polydialkylsiloxanes, preferably the substances with the INCI name Dimethicone Copolyol, and polydialkylsiloxanes containing amine and / or hydroxy groups.
  • Another object of the invention is a preparation for the treatment of the skin, the teeth, the gums or the oral mucosa containing (a) 0.1 to 5, preferably 0.5 to 2% by weight of one or more MMP-1 inhibitors
  • (c) optionally comprises 1 to 90, preferably 5 to 40% by weight of fatty substances, the% by weight relating to the finished preparation.
  • the inventive use of the MMP-1 inhibiting substance is carried out in the presence of at least one antioxidant and / or light stabilizer, and if the cosmetic or pharmaceutical preparations according to the invention are used as a further component (n ) additionally contain at least one antioxidant and / or light stabilizer.
  • Light stabilizers are substances that absorb or reflect UV radiation.
  • the former are also known as light protection factors, light protection filters or UV filters, while the latter include the light protection pigments in particular.
  • Light stabilizers are understood to mean, for example, organic substances which are liquid or crystalline at room temperature and are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again.
  • Light stabilizers can be oil-soluble or water-soluble.
  • the organic UV filters used according to the invention are selected from the derivatives of dibenzoylmethane, cinnamic acid esters, diphenylacrylic acid esters, benzophenone, camphor, p-aminobenzoic acid esters, o-aminobenzoic acid esters, salicylic acid esters, benzimidazoles, 1, 3,5-triazines, monomeric and oligomeric 4,4- Diaryl butadiene carbonate and carboxamides, ketotricyclo (5.2.1.0) decane, benzalmalonic acid esters and any mixtures of the components mentioned.
  • the organic UV filters can be oil-soluble or water-soluble.
  • oil-soluble UV filters are 1 - (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1, 3-dione (Parsol ® 1789), 1-phenyl-3- (4'-isopropylphenyl ) -propane-1, 3-dione, 3- (4 N -methylbenzylidene) -D, L-camphor, 4- (dimethylamino) -benzoic acid-2-ethylhexyl ester, 4- (dimethylamino) benzoic acid-2-octyl ester, 4- (Dimethylamino) benzoic acid amyl ester, 4-methoxycinnamic acid, 2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid, isopentyl ester, 2-cyano-3,3-phenylcinnamic acid, 2-ethyl
  • Preferred water-soluble UV filters are 2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts, sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenon-5 -sulfonic acid and its salts, sulfonic acid derivatives of 3-benzylidene camphor, such as.
  • the preferred inorganic light protection pigments according to the invention are finely dispersed metal oxides and metal salts, for example titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or a shape which differs from the spherical shape in some other way.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobicized. Typical examples are coated titanium dioxide, such as. B.
  • Titanium dioxide T 805 (Degussa) or Eusolex ® T2000 (Merck). Silicones, and in particular trialkoxyoctylsilanes or simethicones, are particularly suitable as hydrophobic coating agents. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide is preferably used.
  • the inventive use of the MMP-1-inhibiting substances is in the form of a sunscreen or after-sun preparation, which can be present, for example, as a cream, milk, lotion, oil, gel or pen preparation.
  • cosmetic or pharmaceutical preparations according to the invention represent sunscreens or after-sun preparations, which are present, for example, as a cream, milk, lotion, oil, gel or also stick preparation.
  • antioxidants are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine) , Carotenoids, carotenes (e.g. ⁇ -carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g.
  • amino acids e.g. glycine, histidine, tyrosine, tryptophan
  • imidazoles e.g. urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine)
  • Carotenoids e.g
  • thiols e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glyco - Syl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters
  • salts dilauryl thiodipropionate , Distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximines homocysteine sulfoximine, butioninsulfones, penta-, hexa-, heptathioninsulfoximines) in very low tolerable dosages e.g. pmol to ⁇ mol / kg
  • metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids e.g.
  • citric acid citric acid, lactic acid, malic acid
  • humic acid bile acid, bile extracts, bi lirubin, bilidverdine, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives eg ascorbyl palmitate, Mg Ascorbyl phosphate, ascorbylacetate
  • tocopherols and derivatives e.g.
  • vitamin E acetate the coniferyl benzoate of benzoin, rutinic acid and its derivatives, glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butylated hydroxytoluene, butylated hydroxyanisoleic acid, nordihydrochloric acid, nordihydrogenated acid Trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, superoxide dismutase, zinc and its derivatives (e.g. ZnO, ZnSO 4 ) selenium and its derivatives (e.g. selenium methionine), stilbenes and their derivatives (e.g.
  • stilbene oxide trans-stilbene oxide
  • derivatives suitable according to the invention salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • Vitamin E is preferred as an antioxidant for the purposes of the invention.
  • the cosmetic or pharmaceutical preparations according to the invention contain, in addition to the MMP-1-inhibiting substance, at least one vitamin, provitamin or vitamin precursor as a further component (s).
  • the vitamins are selected from vitamin groups B, C, E, F and H and are preferably used in amounts of 0.1 to 5% by weight, based on the total composition.
  • the vitamin B group includes a.
  • Vitamin B 1 (thiamine)
  • Vitamin B 2 (riboflavin) • Vitamin B 3 .
  • the compounds nicotinic acid and nicotinamide (niacinamide) are often listed under this name.
  • the following derivatives are preferably used in the agents according to the invention: nicotinyl alcohol, nicotinic acid esters, nicotinyl amino acids, nicotinyl alcohol esters of carboxylic acids, nicotinic acid N-oxide and niacinamide N-oxide.
  • the nicotinic acid esters preferably have a d- 22 alkanol residue and particularly preferably one where the alkanol radicals can be straight-chain or branched, cyclic or acyclic, saturated, unsaturated or aromatic, unsubstituted or substituted.
  • Some of the esters of nicotinic acid have a vasodilatory effect, which is used in certain preparations for non-therapeutic cosmetic skin treatment.
  • Preferred vasodilator nicotinic acid esters are tocopherol nicotinate and inositol hexanicotinate, of which tocopherol nicotinate is particularly preferred according to the invention.
  • niacinamide derivatives result from the substitution of the hydrogen atoms of the amide group, e.g. B. the nicotinyl hydroxamic acid.
  • Preferred nicotinyl alcohol esters are the salicylates, acetates, glycolates and palmitates.
  • panthenol is preferably used.
  • Derivatives of panthenol which can be used according to the invention are, in particular, the esters and ethers of panthenol and cationically derivatized panthenols.
  • Particularly preferred representatives are, for example, panthenol triacetate, panthenol monoethyl ether and its monoacetate and the cationic panthenol derivatives disclosed in WO 92/13829.
  • Pantolactone a precursor of pantothenic acid, can also be used with preference.
  • Vitamin B 6 pyridoxine as well as pyridoxamine and pyridoxal.
  • Vitamin C (ascorbic acid). Ascorbic acid for cosmetic use is preferably used in the form of the palmitic acid ester.
  • Vitamin E tocopherols, especially ⁇ -tocopherol.
  • Tocopherol and its derivatives in particular esters such as acetate, nicotinate, phosphate and succinate, are preferably used in the agents according to the invention.
  • Vitamin F usually means essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H is the compound (3aS, 4S, 6af?) - 2-oxohexahydrothienol [3,4- ⁇ ] - imidazol-4-valeric acid, but for which the trivial name biotin has emerged has prevailed.
  • Biotin is contained in the agents according to the invention preferably in amounts of 0.0001 to 0.1% by weight, in particular in amounts of 0.001 to 0.01% by weight.
  • the cosmetic or pharmaceutical preparations according to the invention are preferably administered topically.
  • they can be in various forms, such as creams, gels or ointments, in particular in anhydrous form such as an oil or a balm, or else in the form of an oil-in-water or water-in-oil emulsion for example a cream or milk, in the form of suspensions, solutions, powders or plasters.
  • the carrier can be a vegetable or animal oil, a mineral oil or else a synthetic oil or mixtures of such oils.
  • Oral and dentifrices in the sense of the invention are mouthwashes and tooth powder, toothpastes, liquid toothpastes and tooth gels containing polishing agents, fluorine compounds, humectants and binders. Toothpastes and liquid tooth cleaning agents are preferred.
  • polishing agent components which are preferably suitable are therefore silicas, aluminum hydroxide, aluminum oxide, sodium aluminum silicates, organic polymers or mixtures of such friction bodies.
  • Calcium-containing polishing components such as Chalk, calcium pyrophosphate, dicalcium phosphate dihydrate can, however, be present in amounts of up to 5% by weight.
  • the total content of polishing agents is preferably in the range of 5-50% by weight of the dentifrice.
  • Toothpastes and liquid tooth cleaning agents which contain silicas as the polishing agent are particularly preferred.
  • Suitable silicas are e.g. Gel silicas, hydrogel silicas and precipitated silicas. Gel silicas are produced by reacting sodium silicate solutions with strong, aqueous mineral acids to form a hydrosol, aging to the hydrogel, washing and drying.
  • a second, preferably suitable group of silicic acid polishing agents are the precipitated silicas. These are obtained by precipitating silica from dilute alkali silicate solutions by adding strong acids under conditions in which the aggregation to the sol and gel cannot occur.
  • a DE OS 31 14 493 produced precipitated silica with a BET surface area of 15-110 m 2 / g, a particle size of 0.5-20 ⁇ m, whereby at least 80% by weight of the primary particles should be less than 5 ⁇ m, and a viscosity in 30 % glycerin-water (1: 1) dispersion of 30 - 60 Pa.s (20 ° C) in an amount of 10 - 20 wt .-% of the toothpaste.
  • Particularly suitable precipitated silicas of this type have rounded corners and edges and are under the tradename ® Sident 12 DS (DEGUSSA).
  • Other precipitated silicas of this type are Sident ® 8 (DEGUSSA) and Sorbosil ® ⁇ C 39 (Crosfield Chemicals).
  • Toothpastes that have a significantly higher viscosity of more than 100 Pas (25 ° C., D 10 s "1 ) require a sufficiently high proportion of silicas with a particle size of less than 5 ⁇ , preferably at least 3% by weight Silica with a particle size of 1 - 3 ⁇ m.So toothpastes are therefore preferably added to the precipitated silicas mentioned, even finer, so-called thickening silicas with a BET surface area of 150-250 m 2 / g, for example the commercial products Sipemat ® 22 LS or Sipemat ® 320 DS.
  • polishing agent component e.g. Alumina in the form of weakly calcined alumina containing ⁇ - and ⁇ -alumina in an amount of about 1 - 5 wt .-%.
  • the dentifrices according to the invention can e.g. Contain sodium fluoride, zinc fluoride, tin (II) fluoride, amine fluoride or sodium monofluorophosphate.
  • An amount of 0.01-0.2% by weight of fluorine should preferably be present in the form of the compounds mentioned.
  • the dentifrices according to the invention preferably contain a mixture of glycerol, sorbitol and polyethylene glycol in a weight ratio of 10: (8-12): (0.1-1) as humectant.
  • Natural and synthetic water-soluble polymers such as carrageenan, tragacanth, guar, cellulose and their non-ionic derivatives such as hydroxyethyl cellulose or methyl hydroxypropyl cellulose are used as binders and consistency regulators.
  • Agar-agar, xanthan gum, pectins, water-soluble carboxyvinyl polymers (eg Carbopol ® types), polyvinyl alcohol, polyvinylpyrrolidone and higher molecular weight polyethylene glycols (with molecular weights of 10 3 - 10 6 D) are also suitable as binders and thickeners.
  • the cosmetic or pharmaceutical preparations can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • Fibroblasts were cultivated on the one hand according to the invention with increasing concentrations of retinyl palmitate, Lipochroman 6 TM, propyl gallate and for comparison with retinol.
  • the toxicity of the substances was measured using an MTT test.
  • the treated cells were irradiated with simulated sunlight, corresponding to a dose of 10 J UV-A / cm2.
  • the phototoxicity of a substance can be recognized from the fact that it has a higher toxicity under irradiation than without irradiation.
  • the MTT test provides information about cell proliferation and cytotoxicity.
  • the metabolic activity of living cells is determined in the test.
  • the tetrazolium salt 3- [4,5-dimethylthiazol-2-ylJ-2,5-diphenyltetrazolium bromide (MTT) is reduced in living cells and converted into a water-insoluble formazan salt.
  • the formazan salt is extracted and quantified photometrically.
  • the amount of formazan salt formed is a measure of the number of living cells in the sample examined.
  • the exact execution of the test is in J. Immunol. Methods 65, 55, 1983 (T. Mosmann), to which explicit reference is made here.
  • the fibroblasts treated or untreated with the MMP-1 inhibitors were transferred to the dish and incubated for 3 hours at 37 ° C. in an atmosphere of CO 2 / air (5% / 95%, v / v) and 90% atmospheric humidity.
  • the fibroblasts were transferred to centrifuge tubes and the formazan salt formed was extracted with 4 ml of extracting agent (292 ml of isopropanol + 8 ml of 1 M HCl) on the shaker for 1.5 hours.
  • the optical density of an aliquot of 200 ⁇ ⁇ was measured in a 96-well plate at a wavelength of 540 nm (Titertek Multiscan MCC 340, from Flow Laboratories).
  • Example 1.1 retinyl palmitate
  • Example 1.2 Lipochroman 6 .TM
  • retinyl palmitate, Lipochroman 6 TM and propyl gallate only show toxic effects in relatively high concentrations. Phototoxic effects have been very mild form only measured with retinyl palmitate. Lipochroman 6 TM and propyl gallate have no phototoxicity. In contrast, the irradiation of retinol-treated cells with simulated sunlight resulted in a vitality reduced by about a power of ten.
  • retinyl palmitate, Lipochroman 6 TM and propyl gallate were tested at concentrations in which the substances are neither toxic nor phototoxic.
  • the RNA of the cells was analyzed in accordance with the method according to RE guitarist et al. (1997), Preparation and Analysis of RNA in "Current Protocols in Molecular Biology", eds. FM Ausubel et al., John Wiley and Sons Inc., Chapter 4.
  • the expression of the MMP-1 gene was analyzed in a Northem blot experiment. A radioactive gene probe specific for the MMP-1 mRNA was used. The production of the mRNA is the first and therefore the most important step in MMP-1 synthesis. Substances that have an effect on mRNA production automatically have an effect on the amount of protein and the enzyme activity of the MMP-1.
  • the tables show the densitometric quantification of the MMP-1 signals of a Northern blot after its normalization.
  • the sunlight-induced expression of MMP-1 in untreated cells was set to 100% and all other values were based on this. pulled.
  • the values of untreated cells that were not irradiated are given as controls.
  • Examples 3.1, 3.4 and 3.7 represent lamellar O / W creams.
  • Examples 3.2, 3.5 and 3.8 represent O / W PIT creams produced by the phase inversion temperature (PIT) method.
  • the examples 3.3, 3.6 and 3.9 represent W / O creams.
  • Examples 3.10, 3.11 and 3.12 represent toothpastes.
  • Lipoxol ® 1550-MED polyethylene glycol with molecular weight 1550 (INC I: PEG-32, Conc

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Abstract

L'invention concerne l'utilisation de substances inhibitrices de métalloprotéase matricielle 1 (MMP-1) dans des préparations cosmétiques, en particulier destinées à prévenir le vieillissement de l'épiderme humain, causé par la lumière et la chaleur, ainsi que la gingivite et la parodontite. Ladite invention concerne également des préparations pharmaceutiques à teneur en substances inhibitrices de MMP-1.
EP01915400A 2000-03-31 2001-03-22 Utilisation d'inhibiteurs de protease dans les cosmetiques et produits pharmaceutiques Ceased EP1267813A2 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10016016 2000-03-31
DE10016016 2000-03-31
DE10020447A DE10020447A1 (de) 2000-03-31 2000-04-26 Verwendung von Protease-Inhibitoren in der Kosmetik und Pharmazie
DE10020447 2000-04-26
PCT/EP2001/003258 WO2001074320A2 (fr) 2000-03-31 2001-03-22 Utilisation d'inhibiteurs de protease dans les cosmetiques et produits pharmaceutiques

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US7217690B2 (en) 2003-10-07 2007-05-15 Kimberly-Clark Worldwide, Inc. Compositions of sunflower trypsin inhibitors
DK2233127T3 (da) 2004-03-17 2020-08-24 Stada Arzneimittel Ag Anvendelse af antioxidanter til fremstilling af en farmaceutisk eller kosmetisk sammensætning for at beskytte huden mod skader som følge af infrarød stråling
EP2100594A1 (fr) 2008-03-14 2009-09-16 Symrise GmbH & Co. KG Mélanges ternaires dotés d'un effet croissant de synthèse du collagène
EP2113242A1 (fr) * 2008-05-02 2009-11-04 Pangaea Laboratories Limited Antioxydant destiné à une utilisation dans des préparations cosmétiques, médicamenteuses et pharmaceutiques
CN108299372B (zh) * 2018-04-09 2022-11-04 青岛新虹锐泽机械科技有限公司 一种用于防治牙龈炎的药物及其制备方法

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