WO1997009975A1 - Preparations topiques efficaces contre le cancer de la peau - Google Patents

Preparations topiques efficaces contre le cancer de la peau Download PDF

Info

Publication number
WO1997009975A1
WO1997009975A1 PCT/EP1996/003945 EP9603945W WO9709975A1 WO 1997009975 A1 WO1997009975 A1 WO 1997009975A1 EP 9603945 W EP9603945 W EP 9603945W WO 9709975 A1 WO9709975 A1 WO 9709975A1
Authority
WO
WIPO (PCT)
Prior art keywords
sphingosine
salts
preparations
skin
arginine
Prior art date
Application number
PCT/EP1996/003945
Other languages
German (de)
English (en)
Inventor
Gerhard Sauermann
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
Priority to EP96931055A priority Critical patent/EP0850056A1/fr
Priority to JP9511642A priority patent/JPH11512410A/ja
Publication of WO1997009975A1 publication Critical patent/WO1997009975A1/fr

Links

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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • UV radiation is mutagenic, i.e. it changes the DNA of skin cells.
  • UV-related mutations have been detected in the basal cells of the epidermis, in melanocytes and in the fibroblasts of the dermis.
  • a gene, called P53 has become the focus of attention in recent years when the relationships between cancer risk and mutation frequency are considered: the greater the number of mutations, the greater the risk of degeneration. Proteins, for which the DNA of the P53 gene serves as a blueprint, are increasingly produced with increasing frequency of mutations in terms of their natural function.
  • ceramides and the other active compounds according to the invention administered topically, trigger apoptosis and / or growth inhibition and are suitable for the prophylaxis and treatment of skin cancer.
  • the invention relates to the use of cosmetic or dermatological topical preparations containing one or more active substances, selected from the group of the compounds arginine, citrulline, ornithine or their salts, acid addition salts, esters or amides, folic acid or salts thereof , Cysteine, N-acetylcysteine, homocysteine, glutamine, the flavins and ceramides, for the treatment of keratoses or skin cancer and for the prophylactic treatment of the skin against these diseases.
  • one or more active substances selected from the group of the compounds arginine, citrulline, ornithine or their salts, acid addition salts, esters or amides, folic acid or salts thereof , Cysteine, N-acetylcysteine, homocysteine, glutamine, the flavins and ceramides, for the treatment of keratoses or skin cancer and for the prophylactic treatment of the skin against these diseases.
  • Derivatives of the active compounds according to the invention are also the subject of the invention.
  • the invention also relates to the topical use of the active compounds according to the invention for the prophylaxis and treatment of the skin and of the diseases mentioned.
  • photokeratoses UV-induced forms of cancer, basal cell carcinomas or spinaliomas can be treated or combated prophylactically.
  • the active substances and preparations according to the invention can be used particularly advantageously on photo-aged skin and the skin of children and adolescents.
  • the active compounds according to the invention are known or can be obtained by known analog processes.
  • arginine citrulline and ornithine are preferred.
  • Arginine and L-arginine and their salts, acid addition salts, esters or amides are particularly preferred.
  • Ceramides are also particularly preferred.
  • the invention also relates to the use of cosmetic or dermatological topical preparations, characterized by a content of a combination of active compounds according to the invention, comprising one or more active compounds selected from group (A) of the compounds arginine, its salts, acid addition salts, esters or Amides in combination with one or more active substances, selected from group (B) of ceramides, for the treatment of keratoses or skin cancer and for the prophylactic treatment of the skin against these diseases.
  • A active compounds selected from group (A) of the compounds arginine, its salts, acid addition salts, esters or Amides in combination with one or more active substances, selected from group (B) of ceramides
  • the weight ratio of the compounds of group (A) to the compounds of group (B) can preferably be 10: 1 to 1:10, particularly preferably 5: 1 to 1: 5, but in particular 1: 1.
  • Preferred salts of arginine, ornithine and citrulline are water-soluble salts, for example sodium, potassium and ammonium salts. This also applies to the acid addition salts. Suitable acid addition salts are obtained with inorganic and organic acids. The hydrochlorides, sulfates, acetates, caprylates or citrates are preferred. Physiologically acceptable salts and addition salts are preferred. Suitable esters of these compounds are, for example, those which are formed with short-chain and medium-chain alcohols, preferably mono-alcohols, but especially methanol, ethanol or propanol. Ethyl esters are preferred.
  • Preferred amides are short and medium chain mono- and di-alkylamides.
  • Alkyls of the above substituents contain e.g. up to 12, preferably up to 6 carbon atoms.
  • Particularly suitable salts of folic acid are water-soluble salts, in particular sodium, potassium and ammonium salts.
  • Preferred compounds from the group of flavins are flavin adenine dinucleotide (FAD), flavin mononucleotide (FMN).
  • FAD flavin adenine dinucleotide
  • FMN flavin mononucleotide
  • the skin ceramides are preferred, in particular ceramide 1, ceramide 2, ceramide 3, ceramide 4/5, ceramide 6 I and ceramide 6 II. They are described in the literature under these names.
  • Alkyl chain lengths e.g. Alkyl chain lengths, varied ceramides and skin ceramides are the subject of the invention.
  • R 1 is an alkyl radical having 1 to 24, preferably 1 to 10 carbon atoms and R 2 is an alkyl radical having 1 to 22, preferably 1 to 13 carbon atoms.
  • ceramides are N-acyl-sphingosines and acyl-phytosphinosines, for example those with 1 to 19, in particular with 1 to 9 carbon atoms in the alkyl radical of the acyl groups. Be particularly preferred
  • N-octanoyl sphingosine and the corresponding phyto-sphingosine N-octanoyl sphingosine and the corresponding phyto-sphingosine.
  • N-acetyl-D-sphingosine N-hexanoyl-D-sphingosine, N-palmitoyl-sphingosine,
  • N-nervonoyl sphingosine (cis-15).
  • the D and DL forms are particularly preferred.
  • Particularly preferred ceramides are N-acyl-sphingosine, N-acetyl-sphingosine, N-octanoyl-sphingosine, N-oleoyl-sphingosine.
  • Combination Natio ⁇ particularly preferred nen contain arginine and N-acetyl-sphingosine or N-octanoyl-sphingosine.
  • the cosmetic or dermatological topical preparations according to the invention can be based on conventional formulation bases and can be used to treat the skin and diseased skin in the sense of a dermatological treatment or a prophylactic treatment, in particular with cosmetic preparations according to the invention.
  • the active ingredients are administered, e.g. to prevent the diseases or manifestations of the diseases or to reduce their frequency and strength.
  • the cosmetic or dermatological preparations or formulations according to the invention can be composed as usual and can be used to treat the skin. They contain e.g. B. 0.0001 to 30 wt .-% preferably 0.01 wt .-% to 10 wt .-%, but in particular 0.1 wt .-% to 5 wt .-%, each based on the total weight of the preparations the active ingredients according to the invention.
  • the cosmetic and dermatological preparations according to the invention are applied in a customary manner to the skin or diseased areas of the skin in a sufficient amount.
  • the invention also relates to the use of the active compounds mentioned for the production of topical preparations for the stated uses.
  • amino acids according to the invention and / or their derivatives are preferably present in amounts of 0.01 to 30% by weight, particularly preferably 0.01 to 10% by weight, in particular 0.1 to 7.5% by weight on the entire preparation, contained in the cosmetic and dermatological preparations according to the invention.
  • Arginine, ornithine and citrulline and the derivatives can be used individually or in combination, but preparations then particularly preferably contain I-arginine in amounts of 1 to 10% by weight, based on the preparation as a whole.
  • Folic acid or its salts and / or flavins are preferably contained in the preparations according to the invention in each case in amounts of 0.0001 to 5% by weight, in particular 0.01 to 1.5% by weight, in each case based on the total weight of the Preparation.
  • Ceramides are preferably present in the preparations according to the invention in quantities of 0.01 to 10% by weight, but in particular 0.1 to 2% by weight, in each case based on the total weight of the preparations.
  • Cosmetic and dermatological preparations according to the invention can be in the known various forms. So you can e.g. a solution, a cream, a lotion, an anhydrous preparation, an emulsion or microemulsion e.g. of the water-in-oil (W / O) or oil-in-water (O / W) type, a multiple emulsion, for example of the water-in-oil-in-water (W / O / W) type, represent a gel, a powder, an oil, a solid stick, an ointment or an aerosol. It is also advantageous to present the active compounds according to the invention in encapsulated form in a manner known per se. Particularly preferred preparations are sun protection products and apresun products. Such preparations can contain IR, UVA and / or UVB filters and / or pigments.
  • the cosmetic and dermatological preparations according to the invention can contain cosmetic auxiliaries, as are usually used in such preparations, e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary substances
  • cosmetic auxiliaries e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary substances
  • Components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • the preparations preferably also contain antioxidants, for example in amounts of 0.001 to 20% by weight, based on the total weight of the preparations.
  • Emulsions according to the invention are advantageous and contain, for example, the fats, oils, waxes and other fat bodies mentioned, as well as water and an emulsifier, as is customarily used for such a type of formulation.
  • the lipid phase can advantageously be selected from the following group of substances: natural, synthetic and / or partially synthetic oils, such as triglycerides of capric or caprylic acid, but preferably castor oil;
  • Fats, waxes and other natural synthetic and / or partially synthetic fat bodies preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • saturated compounds such as hydrocarbons of natural or synthetic origin (petroleum jelly, squalane)
  • the aqueous phase of the preparations according to the invention advantageously contains alcohols, diols or polyols with a low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and similar products, furthermore alcohols of low C number, for example ethanol, isopropanol, 1,2-propanediol, glycerol and in particular one or more thickeners, which one or more can advantageously be selected from the group Silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called
  • 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 low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener which, in the case of oily-alcoholic gels, preferably silicon dioxide or an aluminum silicate, in the case of aqueous-alcoholic or alcoholic gels, preferably a poly is acrylate.
  • a thickener which, in the case of oily-alcoholic gels, preferably silicon dioxide or an aluminum silicate, in the case of aqueous-alcoholic or alcoholic gels, preferably a poly is acrylate.
  • Suitable propellants for preparations according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air is also advantageous to use.
  • hydrocarbons propane, butane, isobutane
  • Preparations according to the invention can also advantageously contain substances which absorb UV radiation in the UVB range, the total amount of filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight. , in particular 1.0 to 6.0% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens for the skin.
  • the emulsions according to the invention contain UVB filter substances, they can be oil-soluble or water-soluble.
  • Oil-soluble UVB filters which are advantageous according to the invention are, for example:
  • 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
  • Esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycinnamic acid isopentyl ester;
  • esters of salicylic acid preferably salicylic acid (2-ethylhexyl) ester, salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomethyl ester,
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably 4-methoxybenzalmalonic acid di (2-ethylhexyl) ester, 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) - 1,3,5-triazine.
  • Salts of 2-phenylbenzimidazole-5-suffonic acid such as its sodium, potassium or triethanolammonium salt, and also the sulfonic acid itself;
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
  • the invention also relates to the use of the active compounds according to the invention with at least one UVB filter in a cosmetic or dermatological preparation.
  • UVA filters can also be advantageous to combine active ingredients according to the invention with UVA filters.
  • suitable are those which have hitherto usually been contained in cosmetic preparations.
  • These 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.
  • These combinations or preparations which contain these combinations are also the subject of the invention.
  • the quantities used for the UVB combination can be used.
  • the invention also relates to the use of a combination of the active compounds according to the invention with at least one UVA filter in a cosmetic or dermatological preparation.
  • the invention also relates to the use of a combination of the active compounds according to the invention with at least one UVA filter in a cosmetic or dermatological preparation.
  • Cosmetic and dermatological preparations with an effective content of active ingredients according to the invention can also contain inorganic pigments in the usual amounts which are usually used in cosmetics to protect the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum, cerium and mixtures thereof, as well as modifications in which the oxides are the active agents. It is particularly preferred to use pigments based on titanium dioxide. Preferred amounts are 0.001-20% by weight.
  • UVA filter and / or UVB filter and pigment or preparations which contain these combinations are also the subject of the invention. dung. The amounts given for the above combinations can be used.
  • the active substances according to the invention can be used individually or as a mixture of several active substances and can also be contained individually or as a mixture in the preparations.
  • the invention also relates to the process for the preparation of the preparations according to the invention, which is characterized in that active ingredients according to the invention are incorporated into cosmetic and dermatological formulations in a manner known per se. This can e.g. done by stirring or emulsifying.
  • the production takes place in a manner known per se, e.g. by mixing or emulsifying the substances, advantageously after separate fat phases and water phases have been produced, possibly also with heating.
  • the preparations show a good activity against the diseases according to the invention and a good prophylactic effect.
  • Vitamin E acetate 2.00
  • Titanium dioxide 1.00

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne l'utilisation de préparations topiques cosmétiques ou dermatologiques contenant au moins une substance active, sélectionnée dans le groupe des composés arginine, citrulline, ornithine ou leurs sels, sels d'addition d'acide, esters ou amides, l'acide folique ou ses sels, cystéine, n-acétylcystéine, homocystéine, glutamine, des flavines et des céramides, pour le traitement de la kératose ou du cancer de la peau et pour le traitement prophylactique de la peau contre ces affections.
PCT/EP1996/003945 1995-09-11 1996-09-09 Preparations topiques efficaces contre le cancer de la peau WO1997009975A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP96931055A EP0850056A1 (fr) 1995-09-11 1996-09-09 Preparations topiques efficaces contre le cancer de la peau
JP9511642A JPH11512410A (ja) 1995-09-11 1996-09-09 局所用抗皮膚癌調製物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19533330.6 1995-09-11
DE19533330A DE19533330A1 (de) 1995-09-11 1995-09-11 Gegen Hautkrebs wirksame topische Zubereitungen

Publications (1)

Publication Number Publication Date
WO1997009975A1 true WO1997009975A1 (fr) 1997-03-20

Family

ID=7771680

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/003945 WO1997009975A1 (fr) 1995-09-11 1996-09-09 Preparations topiques efficaces contre le cancer de la peau

Country Status (4)

Country Link
EP (1) EP0850056A1 (fr)
JP (1) JPH11512410A (fr)
DE (1) DE19533330A1 (fr)
WO (1) WO1997009975A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2760972A1 (fr) * 1997-02-27 1998-09-25 William H Waugh Utilisation de l-citrulline en medecine orthomoleculaire pour la vasoprotection, le tonus relaxatif des muscles lisses et la protection cellulaires
JPH11193212A (ja) * 1997-12-26 1999-07-21 Shiseido Co Ltd 皮膚ｐＨ緩衝能維持強化用皮膚外用剤
WO2002064129A2 (fr) * 2001-02-14 2002-08-22 Rath, Matthias Compositions de composes biochimiques impliques dans le metabolisme bioenergetique cellulaire et procede d'utilisation
WO2004078168A1 (fr) * 2003-03-07 2004-09-16 Korea Atomic Energy Research Institute Composition contenant une phytosphingosine ou un derive de celle-ci
EP1572093A2 (fr) * 2002-08-01 2005-09-14 Aesgen, Inc. Traitement ameliore du cancer avec la glutamine
CN109198648A (zh) * 2018-08-20 2019-01-15 苟春虎 金虫癌症救星基酶肽

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10032964B4 (de) * 2000-07-06 2017-10-12 Beiersdorf Ag Verwendung von Kreatin in kosmetischen oder dermatologischen Zubereitungen
DE10036797A1 (de) * 2000-07-28 2002-02-07 Beiersdorf Ag Verwendung von Kombinationen mit einem Gehalt an Carnitinen
DE10062401A1 (de) * 2000-12-14 2002-06-20 Beiersdorf Ag Verwendung von Folsäure und/oder deren Derivaten zur Herstellung kosmetischer oder dermatologischer Zubereitungen zur Prophylaxe von Schäden an der hauteigenen DNA und/oder zur Reparatur bereits eingetretener Schäden an der hauteigenen DNA
DE10133202A1 (de) * 2001-07-07 2003-01-16 Beiersdorf Ag Osmolyte enthaltende kosmetische und dermatologische Zubereitungen zur Behandlung und aktiven Prävention trockener Haut und anderer negativer Veränderungen der physiologischen Homöostase der gesunden Haut
DE10133201A1 (de) * 2001-07-07 2003-01-23 Beiersdorf Ag Elektrolythaltige kosmetische und dermatologische Zubereitungen zur Behandlung und aktiven Prävention trockener Haut und anderer negativer Veränderungen der physiologischen Homöostase der Haut
EP1291340B1 (fr) * 2001-09-05 2006-03-15 Charmzone Co., Ltd Dérivés de phytosphingosine avec une activité antitumorale
WO2003075903A2 (fr) * 2002-03-08 2003-09-18 Universiteit Leiden Utilisations de proline et d'equivalents fonctionnels de celle-ci et compositions contenant lesdits composes
DE102004002602A1 (de) * 2004-01-15 2005-08-04 Beiersdorf Ag Visualisierung von Sonnenschutzmitteln auf der Haut
FR2970414B1 (fr) * 2011-01-14 2013-03-22 Univ Paris Descartes Action preventive de la citrulline sur le developpement spontane des tumeurs
US8642655B2 (en) * 2011-03-09 2014-02-04 Benjamin Johnson Systems and methods for preventing cancer and treating skin lesions

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4207315A (en) * 1976-10-20 1980-06-10 University Patents, Inc. Process for treating proliferative skin diseases using certain diamino compounds

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE325667B (fr) * 1968-03-06 1970-07-06 Medisan Ab
BE790592A (fr) * 1971-10-28 1973-04-26 Oreal
FR2381558A1 (fr) * 1977-02-23 1978-09-22 Oreal Nouvelles emulsions du type " eau-dans-l'huile " ou " huile-dans-l'eau " et produits cosmetiques obtenus a l'aide de ces emulsions
DE3118882C2 (de) * 1981-05-13 1985-11-14 Rudolf V. Dr.rer.nat Dipl.-Chem. 5024 Pulheim Noronha Mittel gegen Haarausfall und zur Förderung des Haarwuchs
DE3210669A1 (de) * 1982-03-23 1983-09-29 Hrvoje Dr. Zagreb Krnjević Pharmazeutisches mittel zur behandlung von hautkrankheiten, schleimhauterkrankungen und nagelwuchsstoerungen
DE3440090A1 (de) * 1984-11-02 1986-05-07 Novo-Med AG, Appenzell Aminosaeureloesungen enthaltendes arzneimittel zur therapie von krebserkrankungen und verfahren zu seiner herstellung
FR2658076B1 (fr) * 1990-02-12 1992-06-12 Sanofi Sa Composition cosmetique contenant des copolymeres d'aminoacides, utile comme agent hydratant.
JP3091270B2 (ja) * 1990-09-28 2000-09-25 協和醗酵工業株式会社 美白化粧料
DE4127790A1 (de) * 1991-08-22 1993-02-25 Wank Anna Verwendung von oligopeptiden mit 2 bis 5 peptidbindungen fuer kosmetische zwecke und einige neue oligopeptid-metallkomplexe
TW222591B (fr) * 1991-08-30 1994-04-21 Procter & Gamble
BR9306564A (pt) * 1992-06-19 1999-01-12 Univ California Processo para o tratamento da epiderme de um mamífero terrestre sofrendo de uma condição constitída por uma função de barreira epidérmica perturbada
DE4307976A1 (de) * 1993-03-15 1994-09-22 Beiersdorf Ag Neue Verwendung von Aknemitteln
DE4328871A1 (de) * 1993-08-27 1995-03-02 Beiersdorf Ag Mittel gegen empfindliche, hyperreaktive Hautzustände, atopische Dermatiden, Pruritus, Psoriasis Prurigo, Photodermatosen und Ichthyosis
FR2711138B1 (fr) * 1993-10-12 1995-11-24 Oreal Céramides, leur procédé de préparation et leurs applications en cosmétique et en dermopharmacie.
DE4341001A1 (de) * 1993-12-02 1995-06-08 Beiersdorf Ag Topische Zubereitungen mit einem Gehalt an L-Arginin
DE4341000A1 (de) * 1993-12-02 1995-06-08 Beiersdorf Ag Verwendung von L-Arginin, L-Ornithin oder L-Citrullin und topischen Zubereitungen mit diesen Stoffen
FR2714829B1 (fr) * 1994-01-10 1996-02-02 Oreal Composition cosmétique et/ou dermatologique pour le traitement du vieillissement contenant des céramides, son utilisation.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4207315A (en) * 1976-10-20 1980-06-10 University Patents, Inc. Process for treating proliferative skin diseases using certain diamino compounds

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
A. ZIEGLER ET AL.: "Sunburn and p53 in the onset of skin cancer.", NATURE, vol. 372, no. 6508, 1994, pages 773 - 776, XP000616666 *
H. WEFERS ET AL.: "Influence of UV irradiation on the composition of human stratum corneum lipids.", J.INVEST. DERMATOL., vol. 96, no. 6, 1991, pages 959 - 962, XP000617947 *
H.L. GENSLER: "prevention by alpha difluoromethylornithine of skin cancer and immunosuppression induced by UV radiation.", PROC. AM. ASSOC. CANCER RES. ANNU. MEET., vol. 32, 1991, pages 125, XP000614049 *
W.E. PIERCEALL ET AL.: "Mutations in the p53 tumor suppressor gene in human cutaneous squamous cell carcinomas.", MOL. CARCINOG., vol. 4, no. 6, 1991, pages 445 - 449, XP000614050 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2760972A1 (fr) * 1997-02-27 1998-09-25 William H Waugh Utilisation de l-citrulline en medecine orthomoleculaire pour la vasoprotection, le tonus relaxatif des muscles lisses et la protection cellulaires
JPH11193212A (ja) * 1997-12-26 1999-07-21 Shiseido Co Ltd 皮膚ｐＨ緩衝能維持強化用皮膚外用剤
WO2002064129A2 (fr) * 2001-02-14 2002-08-22 Rath, Matthias Compositions de composes biochimiques impliques dans le metabolisme bioenergetique cellulaire et procede d'utilisation
WO2002064129A3 (fr) * 2001-02-14 2003-05-08 Rath Matthias Compositions de composes biochimiques impliques dans le metabolisme bioenergetique cellulaire et procede d'utilisation
US7056950B2 (en) 2001-02-14 2006-06-06 Matthias Rath Compositions of biochemical compounds involved in bioenergy metabolism of cells
EP1572093A2 (fr) * 2002-08-01 2005-09-14 Aesgen, Inc. Traitement ameliore du cancer avec la glutamine
EP1572093A4 (fr) * 2002-08-01 2008-04-09 Aesgen Inc Traitement ameliore du cancer avec la glutamine
WO2004078168A1 (fr) * 2003-03-07 2004-09-16 Korea Atomic Energy Research Institute Composition contenant une phytosphingosine ou un derive de celle-ci
CN109198648A (zh) * 2018-08-20 2019-01-15 苟春虎 金虫癌症救星基酶肽

Also Published As

Publication number Publication date
DE19533330A1 (de) 1997-03-13
EP0850056A1 (fr) 1998-07-01
JPH11512410A (ja) 1999-10-26

Similar Documents

Publication Publication Date Title
EP0802783B1 (fr) Preparations a teneur en l-arginine a usage local
EP1296642B1 (fr) Utilisation de creatine et/ou de derives de creatine dans des preparations dermatologues
EP0731686A1 (fr) Utilisation de l-arginine, de l-ornithine ou de l-citrulline et preparations topiques realisees a l'aide de ces substances
EP0674505A1 (fr) Combinaisons synergiques de principes actifs pour les soins cosmetiques ou dermatologiques de la peau ou des elements tegumentaires
WO1997009975A1 (fr) Preparations topiques efficaces contre le cancer de la peau
EP0716847A1 (fr) Compositions cosmétiques ou dermatologiques contenant des dérivés d'acide cinnamique et des flavonoides
EP1194115A1 (fr) Agent pour usage topique a action protectrice et regeneratrice, comprenant de l'idebenone
WO2002009652A2 (fr) Utilisation d'associations contenant des carnitines
EP0969790A2 (fr) Compositions de traitement de l'acne rosacee
DE10136077A1 (de) Kosmetische oder dermatologische Zubereitungen mit einer Kombination von Kreatinin und/oder Kreatininderivaten mit Kreatin und/oder seinen Derivaten
EP1324745A1 (fr) Preparations cosmetiques et dermatologiques contenant de l'aminoguanidine
DE10128910A1 (de) Verwendung von Wirkstoffkombinationen aus Arginin und Ascorbinsäure zur Hautstraffung
DE19720339A1 (de) Wirkstoffe und Zubereitungen für die Hautaufhellung und zur Verhinderung der Hautbräunung
EP1084701A1 (fr) Emulsion H/E contenant un ou plusieurs bioquinones et un teneur de glycerine élevée
DE10136076A1 (de) Verwendung von Kreatinin und/oder Kreatininderivaten in kosmetischen oder dermatologischen Zubereitungen
DE19711565A1 (de) Zubereitungen für die Behandlung von Rosacea
DE19806946A1 (de) Kosmetische oder dermatologische Wirkstoffkombinationen aus mindestens einer Substanz gewählt aus der Gruppe, bestehend aus Carnitin und den Acylcarnitinen, und mindestens einem Retinoid sowie Zubereitungen mit einem Gehalt an solchen Wirkstoffkombinationen
WO2002098386A2 (fr) Utilisation de polystyrene sulfonate de sodium pour raffermir la peau
DE19806889A1 (de) Verwendung von Acyl-Carnitin
DE29924371U1 (de) O/W-Emulsionen mit einem Gehalt an einem oder mehreren Biochinonen und einem erhöhten Gehalt an Glycerin
EP0706786A2 (fr) Utilisation de l'acide chlorogénique comme antioxydant en compositions cosmétiques notamment compositions cosmétiques pour les cheveux et compositions contenant de l'acide chlorogénique
DE10316666B4 (de) Kosmetische oder dermatologische Zubereitungen mit einer Kombination von Kreatinin mit Kreatin und Coenzym Q10
WO2002078686A1 (fr) Carbonates de retinyle utilises dans des preparations cosmetiques et dermatologiques
WO2002102371A9 (fr) Utilisation d'acide ascorbique pour produire des preparations topiques a action angiogenique

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
ENP Entry into the national phase

Ref country code: JP

Ref document number: 1997 511642

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 1996931055

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1996931055

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1996931055

Country of ref document: EP