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WO1998040082A1 - UTILISATION DE β-GLUCANES SOLUBLES DANS L'EAU COMME PRINCIPES ACTIFS POUR PREPARER DES AGENTS THERAPEUTIQUES UTILISES DANS LE TRAITEMENT DE LA PEAU - Google Patents

UTILISATION DE β-GLUCANES SOLUBLES DANS L'EAU COMME PRINCIPES ACTIFS POUR PREPARER DES AGENTS THERAPEUTIQUES UTILISES DANS LE TRAITEMENT DE LA PEAU Download PDF

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Publication number
WO1998040082A1
WO1998040082A1 PCT/EP1998/001202 EP9801202W WO9840082A1 WO 1998040082 A1 WO1998040082 A1 WO 1998040082A1 EP 9801202 W EP9801202 W EP 9801202W WO 9840082 A1 WO9840082 A1 WO 9840082A1
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WO
WIPO (PCT)
Prior art keywords
glucans
water
soluble
production
use according
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
PCT/EP1998/001202
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German (de)
English (en)
Inventor
Ute Griesbach
Elke Wiemann
Heinz Eggensperger
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1998040082A1 publication Critical patent/WO1998040082A1/fr
Anticipated expiration legal-status Critical
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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • 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
    • A61K8/73—Polysaccharides
    • 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

Definitions

  • the invention relates to the use of water-soluble ß-glucans as active ingredients for combating wrinkles in the skin and skin diseases such as psoriasis, psoriasis or UV erythema.
  • Age-related wrinkling is caused by the breakdown of various macromolecules such as elastin and collagen, for which elastases in the stratum corneum are responsible.
  • a variety of inflammatory skin diseases, such as psoriasis or UV erythema, can also be linked to an increased concentration of elastase in the upper layers of the skin [cf. R. Voegeli et al. in Cosm.Toil. _____, 51 (1996)].
  • cytostatic active ingredients such as selenium sulfide, cadmium sulfide, zinc pyrithione or corticosteroids, are used to combat psoriasis, the medical effect of which is based, for example, on a reduction in mitotic activity in the basal membrane.
  • these substances should not be used for extended periods.
  • psoriasis can be reduced by antiseptic agents, such as selenium oxide, salicylic acid, pyrithione derivatives, hexachlorophene or quaternary ammonium compounds or by cell-dissolving and degreasing agents such as benzoyl peroxide or tar extracts, but do not cure them.
  • antiseptic agents such as selenium oxide, salicylic acid, pyrithione derivatives, hexachlorophene or quaternary ammonium compounds
  • cell-dissolving and degreasing agents such as benzoyl peroxide or tar extracts
  • glucan-containing preparations as antitumor agents is known from German published application DE-OS 2604481 (Ajinomoto).
  • European patent application EP-A1 0463540 (Taito) reports on the use of glucans against viruses. According to the teaching of the two documents DE-A1 3744345 (Lomapharm) and EP-B1 0175667 (noise), glucans are suitable for stimulating macrophage activity.
  • the pharmaceutical effect of various glucans is also known from the two European patent applications EP-A1 0045338 (Debat) and EP-A1 0561408 (Kaken). Finally, soluble phosphorylated glucans are the subject of the European patent EP-B1 0232405 (Tulane Educational Fund).
  • the complex object of the invention was therefore to provide active ingredients which can be used at the same time against wrinkling in the skin (cosmetic effect) and skin diseases (medical effect) and which have a high dermatological and toxicological compatibility.
  • the invention relates to the use of water-soluble ß-glucans as active ingredients for the production of therapeutic agents for skin treatment, in particular for the preparation of agents which simultaneously counteract skin aging and wrinkling and erythema. Thanks to their significant contribution to UV protection, the ß-glucans are particularly suitable for use in sunscreens.
  • water-soluble ⁇ -glucans preferably those obtained by extraction of Basidiomycetes and / or Ascomyceten, in the Langerhans cells of the cause deeper skin layers to have an immune modulation that produces special cytokines.
  • ß-Glucans are also toxicologically safe.
  • glucans is understood to mean homopolysaccharides based on glucose. Depending on the steric linkage, a distinction is made between ß-1, 3-, ß-1,4- and ß-1,6-glucans.
  • ⁇ -1,3-glucans usually have a helical structure, while glucans with a 1,4-linkage generally have a linear structure.
  • the ⁇ -glucans of the invention can be obtained, for example, by extracting higher fungi, such as, for example, the Basidiomycete Schizophyllum Commune or Conolosus versicolor, or by extracting tubular fungi, such as e.g. Prepare ascomycetes of the type Scleroticum glucanium.
  • ⁇ -glucans or their technical mixtures which have a proportion of at least 50, preferably 60 to 100 and in particular 70 to 90% by weight of a ⁇ -1,3 basic structure. It is also advantageous if the glucans have a triple helix fine structure and Molecular weights in the range above 50,000, preferably 100,000 to 1,000,000 daltons. It can also be advantageous to use glucans which have a branch at C-6, preferably with a further saccharide such as, for example, glucose, arabinose or xylose.
  • CM-glucan aqueous or aqueous-alcoholic solutions with an active substance content in the range from 0.1 to 5, preferably 0.5 to 3.
  • the water-soluble ⁇ -glucans can be used as active ingredients for the production of cosmetic and / or pharmaceutical preparations.
  • Typical examples of such agents are skin care products such as anti-wrinkle creams, anti-cellulite creams or sunscreen lotions and ointments for the treatment of skin diseases such as cradle cap, psoriasis, seborrheic dermatitis, seborrhea sicca, seborrhoe oleosa, psoriasis vulgaris, ichthyosis or UV erythema.
  • skin care products such as anti-wrinkle creams, anti-cellulite creams or sunscreen lotions and ointments for the treatment of skin diseases such as cradle cap, psoriasis, seborrheic dermatitis, seborrhea sicca, seborrhoe oleosa, psoriasis vulgaris, ichthyosis or UV erythem
  • the preparations can contain minor amounts of anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants that are compatible with the other ingredients.
  • anionic surfactants are soaps, alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerin ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether sulfates, fatty ether sulfate monates dialkyl sulfosuccinates, mono- and Dialkylsulfo- succinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts thereof, fatty acid
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, alk (en) yl oligo glycosides, fatty acid N-alkylglucamides, protein hydrolyzates (especially vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides.
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
  • the agents can contain, as further auxiliaries and additives, oil bodies, emulsifiers, superfatting agents, stabilizers, waxes, consistency agents, thickeners, cation polymers, silicone compounds, biogenic active ingredients, antidandruff agents, film formers, preservatives, hydrotropes, solubilizers, UV light protection filters, colorants and fragrances .
  • Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C2o fatty acids with linear C6-C20 fatty alcohols, esters of branched C6-Ci3-carboxylic acids with linear C6-C20- Fe.talkol.olen, esters of linear C6-Ci8 fatty acids with branched alcohols, especially 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C ⁇ -Cio fatty acids, vegetable oils, branched primary alcohols, substituted cyclo-hexanes, Guerbet carbonates, dialkyl ethers, silicone oils and / or aliphatic or naphthenic hydrocarbons.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • polystyrene resin e.g. Polyglycerol polyricin oleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of substance of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C12 /. . -Fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • C8 / i8 alkyl mono- and oligoglycosides their preparation and their use as surface-active substances are known, for example, from US 3,839,318, US 3,707,535, US 3,547,828, DE-OS 1943689, DE-OS 2036472 and DE-A1 3001064 and EP-A 0077167. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • the glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N- dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylamino-propyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each with 8 to 18 C-atoms or acyl group in the C-atom group as well as the cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • betaines such as the N-alkyl-N, N- dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylamino-propyl-N, N-dimethylammonium g
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a Cs-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / ⁇ s-acylsarcosine.
  • quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Substances such as lanolin and lecithin as well as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • As consistency agents primarily fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms come into consideration. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methyl glucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as, for example ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as table salt and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as, for example, Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, and quaternized hydroxylated collagen polypeptides hydrolyzed collagen (Lamequat ⁇ L, Grünau GmbH), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as Amidomethicone or Dow Corning, Dow Corning Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Cartaretine®, Sandoz / CH), polyaminopolyamides as described for example in FR-A 22 52 840 and their crosslinked water-soluble polymers, cationic chitin
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine- and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides, waxes include Beeswax, paraffin wax or micro waxes, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol in question.
  • Mono and difatty acid esters of polyalkylene glycols, partial glycerides or esters of fatty alcohols with polyvalent carboxylic acids or hydroxycarboxylic acids can be used in particular as pearlescent waxes.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate can be used.
  • Biogenic active substances are understood to mean, for example, bisabolol, allantoin, phytantriol, panthenol, AHA acids, plant extracts and vitamin complexes.
  • Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Hydrotropes such as ethanol, isopropyl alcohol, propylene glycol or glucose can also be used to improve the flow behavior.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • UV light protection filters are 4-aminobenzoic acid and its esters and derivatives (e.g. 2-ethylhexyl p-dimethylaminobenzoate or p-dimethylaminobenzoic acid octyl ester), methoxycinnamic acid and its derivatives (e.g. 4-methoxycinnamic acid 2-ethylhexyl ester), benzophenones (e.g.
  • Finely dispersed metal oxides or salts such as titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc) and barium sulfate, are also suitable.
  • secondary light stabilizers of the antioxidant type can also be used, such as superoxide dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C).
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • O / W skin creams of the following composition were prepared by mixing phases I and II at 95 ° C:
  • Phase I cetylstearyl alcohol 8.0% by weight
  • Phase II glycerin 6.0% by weight ceteareth-12 1.5% by weight glucan * 20.0% by weight ceteareth-20 1.5% by weight %
  • the number, depth and length of the skin folds were determined every 7 days using profilometry of a selected area of skin, namely a vertical stripe 2 cm wide and 5 cm long, the upper left and right boundaries of which result when one draws a horizontal line from the root of the nose, removes 2 or 4 cm from this towards the right eye and extends the two resulting points at an angle of 270 ° each 2 cm.

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  • Gerontology & Geriatric Medicine (AREA)
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  • Pharmacology & Pharmacy (AREA)
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Abstract

L'invention concerne l'utilisation de beta -glucanes solubles dans l'eau comme principes actifs pour préparer des agents thérapeutiques utilisés dans le traitement de la peau. Ces agents renforcent le système immunitaire de la peau, préviennent la formation de rides et peuvent également s'utiliser pour lutter contre le psoriasis. L'invention concerne également un autre domaine d'application, savoir leur utilisation pour préparer des agents de protection solaire.
PCT/EP1998/001202 1997-03-13 1998-03-04 UTILISATION DE β-GLUCANES SOLUBLES DANS L'EAU COMME PRINCIPES ACTIFS POUR PREPARER DES AGENTS THERAPEUTIQUES UTILISES DANS LE TRAITEMENT DE LA PEAU Ceased WO1998040082A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19710368.5 1997-03-13
DE1997110368 DE19710368A1 (de) 1997-03-13 1997-03-13 Verwendung von wasserlöslichen beta-Glucanen als Wirkstoffe zur Herstellung von therapeutischen Mitteln zur Hautbehandlung

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WO1998040082A1 true WO1998040082A1 (fr) 1998-09-17

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Cited By (11)

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WO2000054738A1 (fr) * 1999-03-12 2000-09-21 Biotec Asa Preparations cosmetiques
WO2000054742A1 (fr) * 1999-03-12 2000-09-21 Biotec Asa UTILISATION DE β-(1,3)-GLUCANES SOLUBLES DANS L'EAU COMME AGENTS ACTIFS POUR LA PREPARATION D'AGENTS THERAPEUTIQUES POUR LES SOINS DE PEAU
DE19911052A1 (de) * 1999-03-12 2000-09-21 Cognis Deutschland Gmbh Sonnenschutzmittel
DE19911058A1 (de) * 1999-03-12 2000-09-21 Cognis Deutschland Gmbh Verwendung von nanoskaligen wasserlöslichen beta-(1,3)-Glucanen
DE19911053A1 (de) * 1999-03-12 2000-09-21 Cognis Deutschland Gmbh Kosmetische und/oder pharmazeutische Zubereitungen
US6251877B1 (en) * 1998-03-24 2001-06-26 Pacific Corporation Composition for external application containing a β-1,6-branched-β-1,3-glucan
US6342486B1 (en) * 1996-07-19 2002-01-29 Mibelle Ag Cosmetics Polymer glucan ether derivatives, their manufacturing as well as their use
WO2003086421A1 (fr) * 2002-04-16 2003-10-23 Cac Corporation Preparations a usage externe renforcant l'activite cellulaire
WO2003101460A1 (fr) 2002-06-03 2003-12-11 Cac Corporation Preparations a usage externe pour le traitement de la dermatite
KR100543124B1 (ko) * 1998-12-30 2006-04-28 주식회사 태평양 약물에 의한 피부 자극 또는 감작화의 경감 또는 방지용 약학적 조성물
CN112079938A (zh) * 2020-08-18 2020-12-15 周银根 一种青稞多糖的提取方法、青稞多糖提取物及其应用

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DE19911057C2 (de) * 1999-03-12 2001-01-25 Cognis Deutschland Gmbh Haarkosmetische Zubereitungen
DE10145008A1 (de) * 2001-09-12 2003-03-27 Odenco Kosmetik Gmbh Kosmetische Wirkstoffzubereitung
WO2007001904A2 (fr) * 2005-06-21 2007-01-04 The Procter & Gamble Company Compositions cosmetiques contenant des alpha-glucanes et/ou des beta-glucanes
CN103735566A (zh) * 2013-12-26 2014-04-23 南京理工大学 索拉胶在抑制紫外线对皮肤损伤中的应用
CN105106032A (zh) * 2015-09-10 2015-12-02 南京理工大学 索拉胶在洗发、护发方面的应用

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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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US6251877B1 (en) * 1998-03-24 2001-06-26 Pacific Corporation Composition for external application containing a β-1,6-branched-β-1,3-glucan
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