EP0969790A2 - Compositions de traitement de l'acne rosacee - Google Patents

Compositions de traitement de l'acne rosacee

Info

Publication number
EP0969790A2
EP0969790A2 EP98913571A EP98913571A EP0969790A2 EP 0969790 A2 EP0969790 A2 EP 0969790A2 EP 98913571 A EP98913571 A EP 98913571A EP 98913571 A EP98913571 A EP 98913571A EP 0969790 A2 EP0969790 A2 EP 0969790A2
Authority
EP
European Patent Office
Prior art keywords
arginine
derivatives
preparations
group
cosmetic
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Withdrawn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
EP98913571A
Other languages
German (de)
English (en)
Inventor
Walter Diembeck
Udo Hoppe
Birgit Salzer
Gerhard Sauermann
Volker Steinkraus
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
Priority claimed from DE19711565A external-priority patent/DE19711565A1/de
Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP0969790A2 publication Critical patent/EP0969790A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the invention relates to topical cosmetic or dermatological preparations which are suitable for the treatment of rosacea. Rosacea also includes the manifestations of cuperose.
  • Rosacea is an inflammatory disease, preferably of the face, which is accompanied by pronounced erythema, papules and pustules of varying duration. Telangiectasias and elastosis are common, and intrafollicular accumulation of neutrophils can also be observed. Rosacea patients have exceptionally sensitive skin to chemical toxins and physical stress factors (UV light). The pathogenesis is unclear.
  • Rosacea is not curable, but can be treated with antibiotics, isotretinoin, fungal agents such as metronidazole or beta blockers.
  • the object of the invention was therefore to remedy this and in particular to provide active substances and preparations with which rosacea, in particular the early forms of this disease, can be treated safely and free of side effects.
  • the invention relates to the use, in particular topical use, of one or more compounds selected from the group of NO synthase inhibitors and their derivatives for the prophylaxis and / or treatment of rosacea and cuperose.
  • the invention also relates to the use of cosmetic or dermatological topical preparations containing one or more compounds selected from the group of NO synthase inhibitors and their derivatives for the prophylaxis and / or treatment of rosacea and cuperose.
  • the invention furthermore relates to cosmetic or dermatological topical preparations containing one or more compounds selected from the group of NO synthase inhibitors and their derivatives.
  • Suitable NO synthase inhibitors are, for example, 2-iminobiotin,
  • SMT S-methylisothiourea sulfate
  • L-thiocitruliin (2-thioureido-L-norvaline) and their derivatives and in particular the arginine derivatives.
  • NO synthase inhibitors which contain a guanidine group are preferred.
  • Suitable derivatives are, for example, the compounds of the invention monoalkylated or dialkylated on the imino groups or amino groups.
  • the alkyl radicals of the monoalkyl groups or dialkyl groups can have 1 to 10, preferably 1 to 6, but in particular 1, 2 or 3, carbon atoms and can be straight-chain or branched.
  • Derivatives especially arginine, whose amino groups are fully or partially acylated are also very suitable. These are in particular the amino groups of the amino acid residue and in particular the amino groups bound to the alpha-C atom.
  • The are preferred mono-acyl compounds of the active ingredient according to the invention, in particular an arginine derivative.
  • the preferred acyl radical is alkylcarbonyl, which is used in acylations with carboxylic acids or their derivatives, e.g. Acid chlorides or anhydrides is obtained.
  • the acyl radical or alkylcarbonyl radical can have 2-12, in particular 2-6, carbon atoms and is particularly preferably acetyl.
  • L-NAME in which the amino group of the alpha-C atom of the amino acid function is mono-acetylated, is particularly preferred.
  • acyl derivatives are notable for their storage stability and their stability in the preparations.
  • Suitable derivatives of the compounds according to the invention are in particular the salts and acid addition salts. Esters of carboxylic acid groups of the compounds according to the invention with alcohols are also preferred.
  • Preferred salts are water soluble salts, e.g. Sodium, potassium and ammonium salts. This also applies to the acid addition salts. Suitable acid addition salts are e.g. obtained with inorganic and organic acids. The hydrochlorides, phosphates, sulfates, acetates, caprylates, citrates, lactates, malates or tartrates are preferred.
  • Suitable esters are, for example, those which are formed with short-chain or medium-chain alcohols, preferably with mono-alcohols. They can be straight-chain or branched and have, for example, 1 to 12, preferably 1 to 6, carbon atoms. Methanol, ethanol, n-propanol and iso-propanol are preferred. The esters are particularly preferred derivatives. They are also characterized by better penetration.
  • the compounds according to the invention are known per se, are commercially available or can be obtained by known processes. Their action as NO synthase inhibitors is described in the literature.
  • the acylated compounds can be obtained by the known acylation process.
  • NO synthase inhibitors according to the invention which contain an arginine residue and their derivatives, in particular as described below, are particularly preferred.
  • the invention therefore relates in particular to the use, in particular topical use, of one or more compounds
  • the invention also relates in particular to the use of cosmetic or dermatological topical preparations containing one or more compounds selected from the
  • the invention furthermore relates to cosmetic or dermatological topical preparations containing one or more compounds C c *
  • the alkyl radicals of the monoalkyl groups or dialkyl groups can have 1 to 10, preferably 1 to 6, but in particular 1, 2 or 3, carbon atoms and can be straight-chain or branched.
  • Suitable derivatives of the compounds according to the invention are in particular the salts and acid addition salts. Esters of the carboxylic acid group of arginine with alcohols are also particularly preferred.
  • Preferred salts are water soluble salts, e.g. Sodium, potassium and ammonium salts. This also applies to the acid addition salts. Suitable acid addition salts are e.g. obtained with inorganic and organic acids. The hydrochlorides, phosphates, sulfates, acetates, caprylates, citrates, lactates, malates or tartrates are preferred.
  • Suitable esters are e.g. those formed with short-chain or medium-chain alcohols, preferably with mono-alcohols. They can be straight or branched and e.g. 1 to 12, preferably 1 to 6 carbon atoms. Methanol, ethanol, n-propanol and iso-propanol are preferred.
  • esters are particularly preferred derivatives. They are also characterized by better penetration.
  • N -monomethyl-L-arginine monoacetate (L-NMMA), N -monoethyl-L-arginine monoacetate (L-MEA),
  • N -Nitro-L-arginine methyl ester or L-NAME is very particularly preferred.
  • the dermatological and cosmetic topical preparations according to the invention can contain, as active ingredient, one or more NO synthase inhibitors, for example one, two or three compounds. If preparations contain two or more of the active compounds according to the invention, those preparations are particularly preferred which contain at least one NO synthase inhibitor with an arginine residue, in particular one of the above-mentioned active compounds with an arginine residue.
  • Active ingredient combinations and preparations containing L-NAME and / or L-NMMA are particularly preferred.
  • the active ingredients containing an arginine residue can be used in the combinations e.g. in amounts of 10-90% by weight, in particular 30-70% by weight, based in each case on the total weight of the active ingredients.
  • the compounds according to the invention and the dermatological and cosmetic topical preparations therewith are outstandingly suitable for the treatment and prophylactic treatment of cuprose and rosacea, in particular stages I or II.
  • the active substances and preparations according to the invention have a long-lasting, continuous action during use. Even after the end of treatment, the skin remains symptom-free or significantly improved for a long time, such as several weeks.
  • 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 in the sense of a dermatological treatment or a treatment in the sense of cosmetics.
  • the use, in particular topical, of the NO synthase inhibitors according to the invention surprisingly leads to a reduction in the cutaneous blood flow and thus the erythema.
  • the resulting increased infiltration of leukocytes and other immune cells leads to better healing of the inflamed tissue.
  • the active compounds according to the invention and / or their derivatives are preferably in amounts of 0.001 to 20% by weight, particularly preferably 0.01 to 10% by weight, but in particular 0.1 to 5% by weight, in each case based on the total Preparation, contained in the topical cosmetic and dermatological preparations according to the invention.
  • rosacea in particular erythema
  • erythema The symptoms of rosacea, in particular erythema, are surprisingly alleviated or avoided.
  • the antioxidants according to the invention can advantageously be selected from the group of customary cosmetic and dermatological antioxidants, in particular from the group consisting of tocopherols and their derivatives, in particular tocopherol or ⁇ -tocopheryl esters, in particular ⁇ -tocopheryl acetate, furthermore sesamol, bile acid derivatives such as methyl, Ethyl, propyl, amyl, butyl and lauryl gallate, the konyferyl benzoate of benzoic resin, nordihydroguajakarzarzäure, nordihydroguajaretic acid, butylhydroxy-anisole, butylhydroxytoluene, ascorbic acid, citric acid, phosphoric acid, lecithin, tri-hydroxynate, trihydonroxybenxin, trihydonroxy in particular retinyl palmitate, ascorbic acid, ascorbyl palmitate, dilauryl thiodipropionate, distearyl thio
  • Flavonoids e.g. 4-alpha-glucopyranosyl-rutin.
  • the cosmetic or dermatological preparations according to the invention preferably contain 0.01 to 10% by weight, but in particular 0.1 to 6% by weight, based on the total weight of the preparations, on one or more substances from the group of antioxidants.
  • antioxidants according to the invention from the group of flavonoids or tocopherols and their derivatives.
  • the preparations are applied to the skin in a sufficient amount once or more times a day in the manner customary for cosmetics or dermatics.
  • Dermatological and cosmetic preparations according to the invention can be in various forms.
  • aqueous, alcoholic or aqueous-alcoholic solutions oil-in-water (O / W) type emulsions, water-in-oil (W / O) type emulsions, multiple emulsions e.g. of the type water-in-oil-in-water (W / O / W), gels, hydrodispersions, solid sticks or aerosols the above Combinations of active ingredients included.
  • Low-water or water-free ointments and preparations are also preferred.
  • the topical preparations according to the invention can contain the customary auxiliaries such as emulsifiers and preservatives.
  • Those cosmetic and dermatological preparations which are in the form of a sunscreen are also preferred. These advantageously additionally contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment. Preparations with one or more UVA filters are particularly preferred. UVA filters with strong absorption at 340 nm are particularly preferred.
  • compositions according to the invention for protecting the skin from UV rays can be in various forms, such as are usually used for this type of preparation.
  • they can be an aqueous, alcoholic or aqueous alcoholic solution, an emulsion of the water-in-oil (W / O) or oil-in-water (O / W) type, or multiple emulsions, for example of the water type in oil-in-water (w / o / w), a gel, a hydrodispersion, an oil, a solid stick or an aerosol.
  • W / O water-in-oil
  • O / W oil-in-water
  • multiple emulsions for example of the water type in oil-in-water (w / o / w), a gel, a hydrodispersion, an oil, a solid stick or an aerosol.
  • the topical preparations according to the invention can contain dermatological and cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, 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.
  • dermatological and cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, 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
  • the cosmetic or dermatological preparation is a solution or lotion, the following can be used as solvents:
  • 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 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;
  • 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 analog products.
  • Water can also be a component of alcoholic solvents.
  • Oils or emulsions according to the invention e.g. in the form of a sunscreen cream, a sunscreen lotion or a sunscreen milk 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.
  • Cosmetic and dermatological preparations for the treatment and care of the skin can be in the form of gels which, in addition to the active ingredients and the solvents usually used for them, also contain organic thickeners, e.g. Gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic thickeners, e.g. B. aluminum silicates such as bentonite, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • the thickener is in the gel e.g. in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
  • 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 is preferably silicon dioxide or an aluminum silicate in the case of oleo-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oleo-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • Hydrodispersions are dispersions of a liquid, semi-solid or solid inner (discontinuous) lipid phase in an outer aqueous (continuous) phase.
  • hydrodispersions are essentially free of emulsifiers.
  • Hydrodispersions like the rest of emulsions, are metastable systems and tend to transition into a state of two interrelated discrete phases. In emulsions, the choice of a suitable emulsifier prevents phase separation.
  • the stability of such a system can be ensured, for example, by building a gel structure in the aqueous phase in which the lipid droplets are stably suspended.
  • Fixed pins according to the invention can e.g. contain natural or synthetic waxes, fatty alcohols or fatty acid esters. Lip care 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, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
  • 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 being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, is in particular 1 to 6% by weight, based on the total weight of the preparation, in order to provide preparations which 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. Examples of oil-soluble substances are:
  • 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;
  • the invention also relates to the combination of active ingredients according to the invention with one or more UVA and / or UVB filters or cosmetic or dermatological preparations according to the invention which also contain one or more UVA and / or UVB filters.
  • UVA filters which are also usually contained in cosmetic and / or dermatological 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.
  • Combinations of the active compounds according to the invention with one or more antioxidants and one or more UVA filters and / or one or more UVB filters are also particularly advantageous according to the invention.
  • the cosmetic or dermatological preparations 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, 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.
  • the invention also relates to the process for the preparation of the topical preparations according to the invention, which is characterized in that the active ingredients are incorporated into cosmetic or dermatological formulations in a manner known per se.
  • Carbomer (Carbopol 981) 1.0
  • H-NMR spectrum 1, 60, multiple, 4 H; 1, 90, singlet, 3 H; 3.15, triplet, 2 H; 3.60, singlet, 3 H of the Acetyl-Me group; 4.35, triplet, 1 H.
  • alpha-N-acetyl-N-monomethyl-L-arginine monoacetate alpha-N-acetyl-L-NMMA
  • alpha-N-acetyl-N-monoethyl-L-arginine monoacetate alpha-N-acetyl-L-MEA
  • N-acyl compounds according to the invention of the NO synthase inhibitors which optionally carry one or more amino groups or a guanidine group are new, in particular the acetyl compounds e.g. the mono-acetyl compounds, especially those acyl compounds or acetyl compounds of amino groups or alpha-C-amino groups of amino acids.
  • Further preferred acyl radicals are aromatically substituted carbonyl, for example benzoyl.
  • Acyl compounds according to the invention are obtained by the customary acylation processes, for example by reaction with acid halides or acid anhydrides, if appropriate with the addition of solvents and bases, for example triethylamine or Alcoholates.
  • solvents and bases for example triethylamine or Alcoholates.
  • mono-acyl compounds equivalent amounts of NO synthase inhibitors and acylating agents are preferred.
  • multiple acylated compounds for multiple acylated compounds

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Toxicology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne l'utilisation, notamment l'utilisation topique, d'un ou plusieurs composés sélectionnés dans le groupe des inhibiteurs de la NO-synthase et de leurs dérivés pour la prophylaxie et/ou le traitement de l'acné rosacée et de la couperose.
EP98913571A 1997-02-21 1998-02-20 Compositions de traitement de l'acne rosacee Withdrawn EP0969790A2 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19706581 1997-02-21
DE19706581 1997-02-21
DE19711565A DE19711565A1 (de) 1997-02-21 1997-03-20 Zubereitungen für die Behandlung von Rosacea
DE19711565 1997-03-20
PCT/EP1998/000991 WO1998036730A2 (fr) 1997-02-21 1998-02-20 Compositions de traitement de l'acne rosacee

Publications (1)

Publication Number Publication Date
EP0969790A2 true EP0969790A2 (fr) 2000-01-12

Family

ID=26034114

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98913571A Withdrawn EP0969790A2 (fr) 1997-02-21 1998-02-20 Compositions de traitement de l'acne rosacee

Country Status (3)

Country Link
EP (1) EP0969790A2 (fr)
JP (1) JP2001512471A (fr)
WO (1) WO1998036730A2 (fr)

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See references of WO9836730A2 *

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WO1998036730A2 (fr) 1998-08-27
JP2001512471A (ja) 2001-08-21
WO1998036730A3 (fr) 1998-10-22

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