EP0869797A2 - Utilisation des derives des glucides comme substances actives antimicrobiennes, antimycosiques et/ou antivirales - Google Patents

Utilisation des derives des glucides comme substances actives antimicrobiennes, antimycosiques et/ou antivirales

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Publication number
EP0869797A2
EP0869797A2 EP96942332A EP96942332A EP0869797A2 EP 0869797 A2 EP0869797 A2 EP 0869797A2 EP 96942332 A EP96942332 A EP 96942332A EP 96942332 A EP96942332 A EP 96942332A EP 0869797 A2 EP0869797 A2 EP 0869797A2
Authority
EP
European Patent Office
Prior art keywords
cosmetic
alkylated
substances
acid
acylated
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Withdrawn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
EP96942332A
Other languages
German (de)
English (en)
Inventor
Joachim BÜNGER
Günther Schneider
Jörg SCHREIBER
Stefan Teichmann
Florian Wolf
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP0869797A2 publication Critical patent/EP0869797A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/001—Preparations for care of the lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • sugar derivatives as antimicrobial, antifungal and / or antiviral
  • the present invention relates to the use of substances known per se as substances effective against bacteria, mycota and viruses.
  • the present invention relates to cosmetic and dermatological preparations containing such substances.
  • the healthy warm-blooded organism especially the healthy human skin, is populated with a large number of non-pathogenic microorganisms.
  • This so-called microflora of the skin is not only harmless, it is an important protection for the defense against opportunistic or pathogenic germs.
  • Bacteria are prokaryotic unicellular organisms. They can be roughly differentiated according to their shape (ball, cylinder, curved cylinder) and the structure of their cell wall (gram-positive, gram-negative). Finer subdivisions also take into account the physiology of the organisms. So there are aerobic, anaerobic and facultative anaerobic bacteria. Some individuals are of medical importance as pathogenic germs, while others are completely harmless.
  • Antibiotics which is not applicable to all antimicrobial substances, can be dated to 1941, although the first findings on penicillin were found as early as 1929.
  • Antibiotics in today's sense are not for all medical purposes, least of all non-cosmetic applications are suitable, since the warm-blooded organism, that is to say the sick patient, is frequently impaired in some way in its metabolic functions when used.
  • An object of the present invention was therefore to enrich the prior art in this direction, in particular to provide substances which are effective against gram-positive and / or gram-negative bacteria without the use of the substances having an unacceptable impairment of the Ge ⁇ health of the user would be connected.
  • Gram-negative germs are, for example, Escherichia coli, Pseudomonas species and Enterobacteriaceen, such as Citrobacter freundii.
  • Gram-positive germs also play a role in cosmetics and dermatology.
  • bacterial secondary infections are of etiological importance in addition to other influences.
  • One of the main microorganisms associated with blemished skin is Propionibacterium acnes.
  • Impure skin and / or comedones affect the well-being of those affected, even in mild cases. Since practically every or every young person is affected by impure skin of any kind, there is a need for many people to remedy this condition.
  • a particular object of the present invention was therefore to find a substance or combination of substances which is effective against impure skin or Propionibacterium acnes.
  • the present invention relates to cosmetic deodorants.
  • Such formulations serve to eliminate body odor that arises when the odorless fresh sweat is decomposed by microorganisms.
  • the usual cosmetic deodorants are based on different active principles.
  • liquid deodorants for example aerosol sprays, roll-ons and the like
  • solid preparations for example deodorant sticks, powders, powder sprays, intimate cleansers, etc.
  • antiperspirants the formation of sweat can be prevented by astringents - predominantly aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate).
  • aluminum hydroxychloride aluminum hydroxychloride
  • body odor can also be masked by fragrances, a method that least meets the aesthetic needs of the consumer, since the mixture of body odor and perfume smells rather unpleasant.
  • Deodorants should meet the following conditions: 1) They should cause reliable deodorization.
  • a further object of the present invention was therefore to develop cosmetic detergents which do not have the disadvantages of the prior art.
  • the deodorants should largely protect the microflora of the skin, but selectively reduce the number of microorganisms that are responsible for body odor.
  • a further task was to develop cosmetic deodorants which harmonize with the largest possible number of customary cosmetic auxiliaries and additives, in particular with the perfume components which are particularly important in formulations having a deodorant or antiperspirant effect.
  • Yet another object of the invention was to provide cosmetic deodorants which are effective over a relatively long period of time, on the order of at least half a day, without their action noticeably diminishing.
  • mycobionts include, for example, yeast (Protoascomycetes), mold (Plectomycetes), powdery mildew (Pyrenomycetes), downy mildew (Phycomycetes) and the stand tip (Basidiomycetes).
  • Fungi are not plant organisms, but like them, they have a cell wall, vacuoles filled with cell sap, and a microscopically visible plasma flow. They contain no photosynthetic pigments and are C-heterotrophic. They grow under aerobic conditions and gain energy through the oxidation of organic substances. However, some representatives, such as yeasts, are optional anaerobes and are capable of generating energy through fermentation processes.
  • Dermatomycoses are diseases in which certain types of fungi, especially dermatophytes, penetrate the skin and hair follicles.
  • the symptoms of dermatomycoses include blisters, exfoliation, rhagades and erosion, usually associated with itching or allergic eczema.
  • Dermatomycoses can essentially be divided into the following four groups: dermatophytia (e.g. epidermophytia, favus, microsporie, trichophytia), yeast mycoses (e.g. pityriasis and other pityrosporum-related mycoses, Candida infections, blastomycosis, Busse-Buschke's disease, torbaulosis, Piedophysia) , Torulopsidosis, trichosporosis), mold mycoses (eg aspergillosis, cephalosporidosis, phycomycosis and scopulariopsidosis), system mycoses (eg chromomycosis, coccidiomycosis, histoplasmosis).
  • dermatophytia e.g. epidermophytia, favus, microsporie, trichophytia
  • yeast mycoses e.g.
  • Pathogenic and facultatively pathogenic germs include, for example, from the group of yeasts Candida species (for example Candida albicans) and those of the Pityrosporum family.
  • the participation of Pityrosporum ovale in the development of psoriasis is being discussed by experts.
  • Dermatophytia almost exclusively affect skin, hair and nails. Hefemycoses can also affect mucous membranes and internal organs, system mycoses regularly extend to entire organ systems.
  • the areas of the body where clothing, jewelry or footwear can accumulate moisture and heat are particularly often affected.
  • the athlete's foot is one of the best known and most widespread dermatomycoses. Fungal diseases of the finger and toenail areas (onychomycoses) are particularly unpleasant.
  • Superinfections of the type described above are, for example, secondary diseases which frequently occur in the full screen of AIDS. In itself - at least in low germ densities - harmless, but possibly also extremely pathogenic germs in this way promote the healthy skin flora. With AIDS, however, other body organs are also affected by superinfections.
  • Such superinfections are also used in a variety of dermatological diseases, e.g. Atopic eczema, eczema, acne, seborrheic dermatitis or psoriasis are observed. Also promote many medical and therapeutic measures, such as radio or chemotherapy for tumor diseases, drug-induced immunosuppression as a side effect or systemic antibiotic treatment, as well as external chemical or physical influences (e.g. pollution, smog, extreme UV light exposure) the appearance of superinfections of the external and internal organs, especially the skin and mucous membranes.
  • dermatological diseases e.g. Atopic eczema, eczema, acne, seborrheic dermatitis or psoriasis are observed.
  • medical and therapeutic measures such as radio or chemotherapy for tumor diseases, drug-induced immunosuppression as a side effect or systemic antibiotic treatment, as well as external chemical or physical influences (e.g. pollution, smog, extreme UV light exposure) the appearance of superin
  • topically administered antibiotics have the disadvantage that they not only free the skin flora from the secondary pathogen, but also severely impair the physiological skin flora and the natural healing process is slowed down again in this way.
  • the object of the present invention was to eliminate the disadvantages of the prior art and to make available substances and preparations containing such substances, the use of which can cure superinfections, the physiological skin flora not suffering any appreciable losses.
  • viruses are biological structures that require a host cell for biosynthesis.
  • Extracellular viruses also called “virions” consist of a single- or double-stranded nucleic acid sequence (DNA or RNA) and a protein coat (called dapsid), optionally an additional lipid-like envelope (envelope).
  • the entirety of nucleic acid and capsid is also Nucleocapsid, classifying viruses according to the clinical class Criteria, but today mostly according to their structure, their morphology, but especially according to the nucleic acid sequence.
  • Medically important virus types are, for example, infusion viruses (family of the Orthomyxoviridae), lyssaviruses (e.g. rabies, family of the rhabdoviruses) enteroviruses (e.g. hepatitis A, family of the Picornaviridae), hepadnaviruses (e.g. hepatitis B, family of the Hepadnaviridae).
  • infusion viruses family of the Orthomyxoviridae
  • lyssaviruses e.g. rabies, family of the rhabdoviruses
  • enteroviruses e.g. hepatitis A, family of the Picornaviridae
  • hepadnaviruses e.g. hepatitis B, family of the Hepadnaviridae
  • viruses-killing substances there are no virucides, that is to say viruses-killing substances in the actual sense, since viruses do not have their own metabolism. For this reason, it was also discussed whether viruses should be classified as living beings. In any case, pharmacological interventions without damage to the unaffected cells is difficult. Possible mechanisms of action in the fight against the viruses are primarily the disruption of their replication, e.g. by blocking the enzymes important for replication that are present in the host cell. Furthermore, the release of the viral nucleic acids into the host cell can be prevented.
  • antivira!” Or “effective against viruses”, “virucidal” or similar means the property of a substance, be it a single-cell or multicellular organism against harmful consequences of a virus infection, be it prophylactically or therapeutically to protect, regardless of what the actual mechanism of action of the substance in individual cases.
  • the active ingredients used according to the invention are capable of preventing the growth of yeasts, in particular of the Pityrosporum species, namely Pityrospoum rum oval.
  • the active substances used according to the invention prevent the formation of seborrheic phenomena, in particular dandruff, and eliminate existing seborrheic phenomena, in particular dandruff.
  • the active ingredients used according to the invention are furthermore well suited for use as a deodorant active ingredient in cosmetic deodorants and against blemished skin, mild forms of acne or propionibacterium acnes.
  • the active compounds used according to the invention can prevent the spoilage of organic substances, in particular cosmetic and dermatological preparations, by infestation with gram-positive and gram-negative bacteria, mycobionts and viruses if they are added to these preparations.
  • alkylated and / or acylated monosaccharides and / or oligosaccharides used according to the invention are also referred to as alkyl or acyl monoglycosides or oligoglycosides, since the alkyl or acyl group is glycosidically linked to the saccharide group.
  • the active compounds used according to the invention are brought into contact with the area contaminated by mycobionts, if appropriate in a suitable cosmetic or dermatological carrier, and a process for protecting organic products from the Infestation with mycobionts, characterized in that the active ingredients used according to the invention are added in effective amounts to these organic products.
  • a preferred embodiment of the present invention are therefore formulations to be used against dandruff, for example antidandruff shampoos.
  • alkylated and / or acylated monosaccharides and / or oligosaccharides used according to the invention are preferably encompassed by the generic structure Glyc-R, where Glyc comprises a monosaccharide group, a disaccharide group or a trisaccharide group and the radical R, which is a branched or includes unbranched saturated alkyl group or acyl group with 1-25 carbon atoms, which is glycosidically bonded to the group Glyc.
  • the hexoses advantageously underlying the alkyl or acyl monoglycosides used according to the invention are preferably selected from the group of aldohexoses, usually in their pyranoside form, that is to say allo (pyrano) se, alto (pyrano) se, gluco (pyrano) se, Manno (pyrano) se, gulo (pyrano) se, ldo (pyrano) se, galacto (pyrano) se and talo (pyrano) se, but also the aldohexosyl derivatives present in furanoside form can optionally be used advantageously according to the invention.
  • (Hexosyl) hexoses on which disaccharides are used according to the invention are advantageous and can preferably be selected from the group of pyranosylpyranoses and furanosylpyranoses having a 1,4-glycosidic or 1,6-glycosidic bond. They are preferably selected from the group of maltose, leucrose, lactose and sucrose.
  • alkyl or acyl monoglycosides preferably used according to the invention can be represented by the general structural formulas respectively
  • Ri - Re comprise branched or unbranched saturated alkyl groups or acyl groups with 1-25 carbon atoms.
  • D-glycosides it is advantageous to use D-glycosides, but L-glycosides or mixed D / L-glycosides can also be used advantageously for the purposes of the present invention.
  • Hexosylglycosides which are based on D- or L-ketohexoses, ie psicose, fructose, sorbose or tagatose, usually present in their furanoside form, can optionally be used advantageously for the purposes of the present invention.
  • Alkyl or acylglycosides which are used particularly advantageously according to the invention are selected from the group ⁇ -D-octylglucopyranoside, ⁇ -D-nonylglucopyranoside, ⁇ -D-decylglucopyranoside, ⁇ -D-undecylgiucopyranoside, ⁇ -D-dodecylglucopyranoside Tetradecylglucopyranoside and ⁇ -D-hexadecylglucopyranoside.
  • ⁇ -D-octylglucopyranoside, ⁇ -D-nonylglucopyranoside and ⁇ -D-dodecylglucopyranoside are particularly preferred, which are particularly notable for their very good activity against Corynebacterium xerosis. It is also advantageous to use natural or synthetic raw materials and auxiliaries or mixtures which are distinguished by an effective content of the active compounds used according to the invention, for example Plantar ⁇ n® 1200 (Hankel KGaA), Oramix® NS 10 (Seppic)
  • the active ingredients used according to the invention are capable of preventing the growth of yeasts, in particular of the Pityrosporum species, namely Pityrospoum rum oval
  • the active ingredients used according to the invention are furthermore well suited for use as a deodorant active ingredient in cosmetic deodorants and against blemished skin, light forms of acne or propionibactum acnes
  • the active compounds used according to the invention can prevent the spoilage of organic substances, in particular cosmetic and dermatological preparations, by infestation with gram-positive and gram-negative bacteria, mycobionts and viruses if they are added to these preparations
  • the active compounds used according to the invention are brought into contact with the area contaminated by mycobionts, if appropriate in a suitable cosmetic or dermatological carrier, and a process for protecting organic products from the Infestation with mycobionts, characterized in that the active ingredients used according to the invention are added in effective amounts to these organic products.
  • a preferred embodiment of the present invention are therefore formulations to be used against dandruff, for example antidandruff shampoos.
  • the active compounds are preferably used in cosmetic or dermatological compositions with a content of 0.005-50.0% by weight, in particular 0.01-20.0% by weight, based on the total weight of the composition, are preferred.
  • the compositions advantageously contain 0.02-10.0% by weight, particularly preferably 0.02-5.0% by weight of the active compounds used according to the invention, very particularly advantageously 0.5-3.0% by weight. , each based on the total weight of the composition.
  • the active ingredients used according to the invention can be incorporated into conventional cosmetic or dermatological formulations without difficulty, advantageously in pump sprays, aerosol sprays, creams, ointments, tinctures, lotions, nail care products (e.g. nail polishes, nail polish remover, nail balms) and the like.
  • nail care products e.g. nail polishes, nail polish remover, nail balms
  • active substances used according to the invention with other active substances, for example with other antimicrobial, antimycotic or antiviral substances.
  • a pH range from 3.5 to 7.5 is advantageous. It is particularly favorable to choose the pH in a range from 4.0 to 6.5.
  • the cosmetic and / or dermatological formulations according to the invention can be composed as usual and for the treatment of the skin and / or the Hair in the sense of a dermatological treatment or a treatment in the sense of nourishing cosmetics. But they can also be used in make-up products in decorative cosmetics.
  • the cosmetic and / or dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics and dermatics.
  • Cosmetic and dermatological preparations which are in the form of a sunscreen are advantageous. These advantageously additionally contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment.
  • Cosmetic preparations according to the invention for protecting the skin from UV rays can be in various forms, e.g. are usually used for this type of preparation. So you can e.g. a solution, an emulsion of the type water-in-oil (W / O) or of the type oil-in-water (O / W), or a multiple emulsions, for example of the type water-in-oil-in-water (W / O / W), a gel, a hydrodispersion, a solid stick or an aerosol.
  • the cosmetic preparations according to the invention can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, antioxidants, perfumes, anti-foaming agents, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening substances, moisturizing and / or moisturizing substances, fats, oils, waxes or other conventional components of a cosmetic formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries e.g. Preservatives, bactericides, antioxidants, perfumes, anti-foaming agents, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening substances, moisturizing and / or moisturizing substances, fats, oils, waxes or other conventional components of a cosmetic formulation such as alcohols, polyols, polymers,
  • the cosmetic or dermatological preparation is a solution or lotion
  • the following can be used as solvents: water or aqueous solutions;
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols with a low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids;
  • Alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerin, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and ana ⁇ loge products.
  • Water can also be a component of alcoholic solvents.
  • antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • the antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L- Carosin and its derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, lipoic acid and their derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin , Glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oley
  • buthioninsulfoximines homocysteine sulfoximine, buthioninsulfoxin, heptathione sulfox, penta-, hexa-, hexa-, hexa- Very low tolerable doses (e.g. pmol to ⁇ mol / kg), further (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, bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated Fatty acids and their derivatives e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives e.g. ascorbyl palmitate, Mg - ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g.
  • vitamin E - acetate vitamin A and derivatives (vitamin A - palmitate) as well as konyferylbenzoate of benzoin, rutinic acid and its derivatives, ferulic acid and its derivatives, butylhydroxytoluene, butylhydroxyanisole, nordihydroguajak resin acid, nordihydroguajaretic acid, trihydroxybutyrophenose and their derivatives, har Derivatives, zinc and its derivatives (e.g. ZnO, ZnSÜ4) selenium and its derivatives (e.g. selenium methionine), stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides) , Peptides and lipids) of these active ingredients.
  • konyferylbenzoate of benzoin rutinic acid and its derivatives, ferulic
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the additives ⁇ preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to have their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation tion to choose.
  • Emulsions according to the invention are advantageous and contain e.g. the fats, oils, waxes and other fat bodies mentioned, as well as water and an emulsifier, as is usually used for such a type of formulation.
  • Gels according to the invention usually contain alcohols of low C number, for example ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener, which is used in oily alcoholic gels preferably silicon dioxide or an aluminum silicate, preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • alcohols of low C number for example ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener, which is used in oily alcoholic gels preferably silicon dioxide or an aluminum silicate, preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • Fixed pins according to the invention contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters. Lip care sticks and deodorant sticks (“deodorant sticks”) are preferred.
  • Suitable blowing agents for cosmetic or dermatological preparations according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied blowing agents, e.g. Suitable hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with each other. Compressed air can also be used advantageously.
  • Suitable hydrocarbons propane, butane, isobutane
  • the preparations according to the invention can preferably also contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances e.g. 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1 to 6% by weight, based on the total weight of the preparation, in order to provide cosmetic preparations, that protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens.
  • the UVB filters can be oil-soluble or water-soluble.
  • oil-soluble substances e.g. to call:
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid
  • esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-
  • esters of salicylic acid preferably salicylic acid (2-ethylhexyl) ester, salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomethyl ester;
  • Esters of benzalmalonic acid preferably 4-methoxybenzalmalonic acid di (2-ethylhexyl) ester;
  • 2-phenylbenzimidazole-5-sulfonic acid and its salts e.g. Sodium, potassium or triethanolammonium salts
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
  • Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidenemethyl) sulfonic acid and their salts.
  • UVB filters which can be used according to the invention, is of course not intended to be limiting.
  • UVA filters in the preparations according to the invention, which are usually contained in cosmetic and / or dermatological preparations.
  • Such substances are preferably derivatives of dibenzoylmethane, in particular 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione and 1-phenyl- 3- (4'-isopropylphenyl) propane-1,3-dione.
  • Preparations containing these combinations are also the subject of the invention.
  • the same amounts of UVA filter substances that were mentioned for UVB filter substances can be used.
  • Cosmetic and / or dermatological preparations according to the invention can also contain inorganic pigments which are usually used in cosmetics to protect the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum. Cers and mixtures thereof, as well as modifications in which the oxides are the active ones Are agents. It is particularly preferred to use pigments based on titanium dioxide. The amounts given for the above combinations can be used.
  • Cosmetic preparations for the care of the hair are, for example, shampooing agents, preparations which are used when rinsing the hair before or after the shampooing, before or after the permanent wave treatment, before or after the coloring or discoloration of the hair, to formulations for blow drying or Laying in the hair, preparations for dyeing or decoloring, a styling and treatment lotion, a hair lacquer or permanent waving agents.
  • the cosmetic preparations contain active substances and auxiliaries of the kind normally used for this type of preparation for hair care and hair treatment.
  • Preservatives surface-active substances, substances to prevent foaming, emulsifiers, thickeners, fats, oils, waxes, organic solvents, bactericides, perfumes, dyes or pigments, the purpose of which is to dye the hair or the preparation itself, serve as auxiliaries , Electrolytes, preparations for greasing hair.
  • Cosmetic preparations which are a shampooing agent or a washing, showering or bathing preparation preferably contain at least one anionic, nonionic or amphoteric surface-active substance or mixtures thereof, active substances and auxiliaries according to the invention, as are usually used therefor.
  • Examples of surface-active substances which can advantageously be used according to the invention are conventional soaps, e.g. Fatty acid salts of sodium, alkyl sulfates, alkyl ether sulfates, alkane and alkyl benzene sulfonates, sulfoacetates, sulfobetaines, sarcosinates, amidosulfobetaines, sulfosuccinates,
  • soaps e.g. Fatty acid salts of sodium, alkyl sulfates, alkyl ether sulfates, alkane and alkyl benzene sulfonates, sulfoacetates, sulfobetaines, sarcosinates, amidosulfobetaines, sulfosuccinates,
  • Sulfosuccinic acid semiesters alkyl ether carboxylates, protein fatty acid condensates, alkyl betaines and amido betaines, fatty acid alkanolamides, polyglycol ether derivatives.
  • the surface-active substance can be present in a concentration between 1% by weight and 50% by weight in the shampooing agent, or in the washing, showering or bathing preparation.
  • This cosmetic or dermatological preparation can also be an aerosol with the auxiliaries usually used for it.
  • a cosmetic preparation in the form of a lotion that is not rinsed out, in particular a lotion for inlaying the hair, a lotion that is used for blow-drying the hair, a styling and treatment lotion is generally an aqueous, alcoholic or represents aqueous-alcoholic solution and contains at least one cationic, anionic, non-ionic or amphoteric polymer or mixtures thereof, as well as active substances according to the invention.
  • the amount of active ingredients according to the invention used is e.g. between 0.1 and 10% by weight, preferably between 0.1 and 3% by weight.
  • Cosmetic and dermatological preparations for the treatment and care of the hair which contain the active substances used according to the invention, can be present as emulsions which are of the non-ionic or anionic type.
  • non-ionic emulsions contain oils or fatty alcohols, which can be polyethoxylated or polypropoxylated, for example, or also mixtures of the two organic components.
  • These emulsions may contain cationic surface-active substances.
  • Cosmetic and dermatological preparations for the treatment and care of the hair can be in the form of gels which, in addition to the active substances used according to the invention and the solvents usually used for them, also include organic thickeners, for example gum arabic, xanthan gum, sodium alginate, cellulose Derivatives, preferably methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic thickeners, for example aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • the thickener is contained in the gel, for example, in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
  • the amount of the active ingredients used according to the invention in an agent intended for the hair is preferably 0.01% by weight to 10% by weight, in particular 0.5% by weight to 5% by weight, based on the total weight of the preparations .
  • the liquid phase obtained by mixing the respective components together is filled into aerosol containers together with a propane-butane mixture (2: 7) in a ratio of 39:61.

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  • Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
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  • Birds (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
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  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Utilisation de monosaccharides et/ou d'oligosaccharides alkylés et/ou acylés comme substances actives antimicrobiennes, antimycosiques et/ou antivirales.
EP96942332A 1995-12-16 1996-12-04 Utilisation des derives des glucides comme substances actives antimicrobiennes, antimycosiques et/ou antivirales Withdrawn EP0869797A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19547160 1995-12-16
DE19547160A DE19547160A1 (de) 1995-12-16 1995-12-16 Verwendung von Zuckerderivaten als antimikrobiell, antimykotisch und/oder antivirale Wirkstoffe
PCT/EP1996/005400 WO1997022346A2 (fr) 1995-12-16 1996-12-04 Utilisation des derives des glucides comme substances actives antimicrobiennes, antimycosiques et/ou antivirales

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EP0869797A2 true EP0869797A2 (fr) 1998-10-14

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US (1) US20020165168A1 (fr)
EP (1) EP0869797A2 (fr)
JP (1) JP2000506499A (fr)
DE (1) DE19547160A1 (fr)
WO (1) WO1997022346A2 (fr)

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JP2000506499A (ja) 2000-05-30
US20020165168A1 (en) 2002-11-07
WO1997022346A2 (fr) 1997-06-26
DE19547160A1 (de) 1997-06-19
WO1997022346A3 (fr) 1997-08-28

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