EP1401393A2 - No-synthase-inhibitor und seine anwendung - Google Patents

No-synthase-inhibitor und seine anwendung

Info

Publication number
EP1401393A2
EP1401393A2 EP02758511A EP02758511A EP1401393A2 EP 1401393 A2 EP1401393 A2 EP 1401393A2 EP 02758511 A EP02758511 A EP 02758511A EP 02758511 A EP02758511 A EP 02758511A EP 1401393 A2 EP1401393 A2 EP 1401393A2
Authority
EP
European Patent Office
Prior art keywords
bis
composition
ethylenediamine
pyridyl
methyl
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Withdrawn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
EP02758511A
Other languages
English (en)
French (fr)
Inventor
Marie-Madeleine Cals-Grierson
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.)
LOreal SA
Original Assignee
LOreal SA
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 LOreal SA filed Critical LOreal SA
Publication of EP1401393A2 publication Critical patent/EP1401393A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/14Drugs for dermatological disorders for baldness or alopecia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/16Emollients or protectives, e.g. against radiation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00Preparations for affecting hair growth
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74Biological properties of particular ingredients
    • A61K2800/75Anti-irritant
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74Biological properties of particular ingredients
    • A61K2800/78Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention relates to the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to inhibit NO-synthase.
  • NO-synthase covers a family of enzymes which ensure the enzymatic transformation of L-arginine into citrulline, a reaction during which a gaseous mediator with multiple functions is produced, nitrogen monoxide or NO.
  • NO-synthases exist in three forms, two constitutive forms, nomenclature grouping together neuronal NO-synthase (or NOS 1) and endothelial NO-synthase (or NOS 3), and the inducible form (or NOS 2) (Medicine / Sciences , 1992, 8, pp. 843-845).
  • NO-synthase covers all of the isoforms of the enzyme.
  • NO-synthase inhibitors means any product which ultimately leads, notwithstanding the isoform of NO-synthase, to the reduction of the concentration of NO.
  • Nitric oxide has, by its structure, an additional electron making it extremely chemically reactive. It is well known that such compounds are harmful and we seek to limit their production as much as possible. Thus, in the case of nitric oxide, the NO-synthase inhibitors have been widely studied.
  • NO is a multifunctional signal molecule active in a wide variety of body systems and tissues.
  • a speaker particularly in the cardiovascular system (regulator of blood pressure with vasodilator, inhibitor of platelet aggregation with anticoagulant effect), in the nervous system (memory, modulation of neurotransmitter release), in the immunological system (modulation of immune defenses, inflammation, involvement in autoimmune pathologies).
  • NO plays a predominant role in the skin. NO can be synthesized by all varieties of cells constituting the skin and as such it intervenes in multiple and complex regulatory processes such as the regulation of cell differentiation and / or proliferation, vasodilation, melanogenesis , response to environmental variations (homeostasis). Its involvement in cell differentiation and proliferation (stimulating effect), particularly in keratinocytes, associates it with the growth of the epidermis and scarring as well as hyperproliferative disorders (psoriasis). Due to its electronic hyperreactivity which can lead to degradation or even destruction of cells, NO is involved in apoptotic processes and in intrinsic and / or extrinsic aging of the skin.
  • NO plays a role in contact hypersensitivity reactions, in allergic skin manifestations, in the skin's immune response.
  • CGRP Calcitonin Gene Related Peptide
  • NO is also involved in the reduction of the barrier effect of the skin, as well as in the reduction of skin hydration.
  • NO is recognized as an intermediary in melanogenesis induced by type B ultraviolet radiation (UVB). It is also one of the factors involved in hypermelanosis-like disorders.
  • UVB type B ultraviolet radiation
  • NMMA N G -monomethyl-L-arginine
  • NAME the methyl ester of N G -nitro-L-arginine
  • NNA N G -nitro-L-arginine
  • NAA N G - amino-L-arginine
  • ADMA diphenyleneiodonium chloride
  • 2- (4-carboxyphenyl) -4,4,5 5-tetramethylimidazoline-1-oxy-3-oxide
  • the object of the present invention is to provide a new inhibitor of NO-synthase which is moreover a natural inhibitor of NO-synthase.
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine has the property of being a NO-synthase inhibitor, particularly of inducible NO-synthase (NOS 2) which makes it a good candidate for uses in applications where it turns out to be advantageous to use a NO-synthase inhibitor, particularly in cosmetics .
  • NOS 2 inducible NO-synthase
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine is described for its use in pharmaceutical and cosmetic compositions in order to protect the body against oxidative stress (EP0755925)
  • a primary object of the invention is therefore the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to inhibit NO-synthase.
  • physiologically acceptable medium a medium compatible with the skin, mucous membranes, nails, hair.
  • a second object of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended for application in all areas in which inhibition of NO synthases is necessary, particularly in the skin and / or hair area.
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition containing it can be used to slow down or even inhibit differentiation and / or cell proliferation, and / or vasodilation, and / or melanogenesis, and / or response to environmental variations (homeostasis).
  • the third object of the invention is the use of an effective amount of N, N'- bis-pyridyl-2-yl-methyl-N, N , -bis- (3,4,5-trimethoxybenzyl) ethylenediamine , in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl ) ethylenediamine or the composition being intended to slow down or even inhibit cell differentiation and / or proliferation, in particular to regulate the growth of the epidermis and / or to treat hyperproliferative disorders such as for example psoriasis.
  • a fourth object of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N , -bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to inhibit the degradation and / or destruction of cells and to inhibit apoptotic processes, particularly of skin cells, very particularly of keratinocytes and / or to treat intrinsic and / or extrinsic aging of cells, particularly skin cells.
  • a fifth object of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N , -bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to inhibit or even eliminate symptoms linked to immunological and or inflammatory phenomena linked to the synthesis of NO, such as for example contact hypersensitivity reactions and / or allergic manifestations and / or the immune response, particularly in the skin.
  • the N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition are intended to reduce or even inhibit irritation skin, caused by external agents.
  • the skin irritant effect is a response of the skin most often resulting in redness, pain or tingling, this response being caused by chemicals of natural or synthetic origin applied topically to the skin.
  • This irritation is accompanied by an alteration in the function and or in the epithelial structure, directly linked to the effect of the irritant product. They are therefore particularly suitable in the case of skin reactions linked to processes of neurogenic origin such as certain skin rashes, and therefore to treat, reduce or eliminate the manifestations of so-called sensitive skin.
  • dysesthesic sensations is meant more or less painful sensations felt in a skin area such as tingling, tingling, itching or itching, heating, discomfort, tightness, etc.
  • Sensitive skin can be divided into two main clinical forms, irritable and / or reactive skin, and intolerant skin. Irritable and / or reactive skin is skin that reacts with pruritus, that is, itching or tingling, to various factors such as the environment, emotions, food, wind, friction, razor, soap, surfactants, hard water with a high concentration of limestone, temperature variations or wool.
  • these signs are associated with dry skin with or without sores or with skin that presents with erythema, which is non-inflammatory.
  • Intolerant skin is skin that reacts with sensations of heating, tightness, tingling and / or redness, to various factors such as the environment, emotions, food and certain cosmetic products. In general, these signs are associated with hyperseborrheic or acne-prone skin with or without sores and erythema.
  • “Sensitive” scalps have a more unequivocal clinical semiology: the sensations of pruritus and or tingling and or heating are essentially triggered by local factors such as friction, soap, surfactants, hard water with a high concentration of lime, shampoos or lotions. These sensations are also sometimes triggered by factors such as the environment, emotions and / or food. Erythema and hyperseborrhea of the scalp and dandruff are frequently associated with the above signs.
  • the sixth object of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N , -bis-pyridyl-2-yl-methyl-N, N , -bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to increase the barrier effect of the skin or the skin hydration. .
  • a seventh subject of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N , -bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to treat rosacea and / or skin erythemas, particularly erythemas induced by ultraviolet radiation and / or localized or diffuse erythematous rashes of the skin such as those caused by drugs toxins and / or viral or bacterial infections.
  • the eighth object of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to inhibit melanogenesis induced by ultraviolet radiation of type A and or B and / or to treat disorders of hypermelanosis type.
  • the ninth object of the invention is the use of an effective amount of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine, in a physiologically acceptable medium, in a composition or for the preparation of a composition, N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition being intended to control sweating and / or to stimulate lipolysis or to decrease or inhibit hair loss.
  • the composition comprising N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine can be a cosmetic or dermatological composition.
  • the composition is a cosmetic composition.
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine or the composition comprising it is applied to the skin of topically.
  • the amount of extract N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine used in the composition is of course a function of the desired effect and can therefore vary to a large extent.
  • N, N'-bis-pyridyl-2-yl-methyl- N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine can be used in a amount representing from 10 "4 % to 20% of the total weight of the composition and preferably in an amount representing from 5.10 " 3 % to 10% of the total weight of the composition.
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine can be combined with other NO inhibitors - synthases such as plant extracts such as for example an extract of at least one plant of the species Olea europaea or an extract of Ginkgo biloba or an extract of V / ' f / s vinifera or also an extract of green tea or cocoa.
  • plant extracts such as for example an extract of at least one plant of the species Olea europaea or an extract of Ginkgo biloba or an extract of V / ' f / s vinifera or also an extract of green tea or cocoa.
  • the tenth subject of the invention is a cosmetic treatment process with a view to treating disorders linked to the synthesis of NO, characterized in that it is used by application on the skin, on the hair, and / or on the mucous membranes , a cosmetic composition comprising at least N, N'-bis-pyridyl-2-yl-methyl-N, N'- bis- (3,4,5-trimethoxybenzyl) ethylenediamine in a physiologically acceptable medium.
  • the cosmetic treatment method of the invention aims to improve the appearance of the individual affected by the disorders due to the synthesis of NO.
  • the cosmetic treatment process of the invention can be implemented in particular by applying the cosmetic compositions as defined above, according to the usual technique for using these compositions. So, for example, it is possible to apply creams, gels, serums, lotions, cleansing milks or anti-sun compositions on the skin or on dry hair, applications of a hair lotion on wet hair, shampoos, or even applications of toothpaste on the gums.
  • composition according to the invention in which N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine is used, that -this can be ingested, injected or applied to the skin (on any cutaneous area of the body), the hair, the nails or the mucous membranes (buccal, jugale, gingival, genital, conjunctiva).
  • the composition according to the invention can be in all the dosage forms normally used.
  • the composition may take the form in particular of an aqueous or oily solution or of a dispersion of the lotion or serum type, of emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersion of a phase fatty in an aqueous phase (O / W) or vice versa (W / O), or of suspensions or emulsions of soft consistency of the aqueous or anhydrous cream or gel type, or of microcapsules or microparticles, or of vesicular dispersions of the ionic type and / or non-ionic.
  • These compositions are prepared according to the usual methods.
  • They can also be used for the hair in the form of aqueous, alcoholic or hydroalcoholic solutions, or in the form of creams, gels, emulsions, foams or also in the form of aerosol compositions also comprising a propellant under pressure.
  • the composition may be in the form of an aqueous, oily lotion or in the form of a serum.
  • the eyes it can be in the form of drops and for ingestion, it can be in the form of capsules, granules of syrups or tablets.
  • compositions according to the invention are those conventionally used in the fields considered.
  • compositions constitute in particular cleansing, protective, treatment or care creams for the face, for the hands, for the feet, for large anatomical folds or for the body (for example day creams, night, make-up removing creams, foundation creams, sunscreen creams), fluid foundations, make-up removal milks, body protection or care milks, anti-sun milks, lotions, gels or foams for skin care, such as cleansing lotions, sunscreen lotions, artificial tanning lotions, bath compositions, deodorant compositions comprising a bactericidal agent, aftershave gels or lotions, depilatory creams, compositions against insect bites, pain relieving compositions, compositions for treating certain skin diseases such as eczema, rosacea, psoriasis, lichens, severe pruritus.
  • compositions according to the invention may also consist of solid preparations constituting soaps or cleaning bars.
  • compositions can also be packaged in the form of an aerosol composition also comprising a propellant under pressure.
  • the composition according to the invention may also be a composition for hair care, and in particular a shampoo, a styling lotion, a treating lotion, a styling cream or gel, a composition of dyes (in particular oxidation dyes) in the form of coloring shampoos, restructuring hair lotions, a perm composition (in particular a composition for the first time of a perm), a fall prevention lotion or gel, an antiparasitic shampoo, etc.
  • a composition for hair care and in particular a shampoo, a styling lotion, a treating lotion, a styling cream or gel, a composition of dyes (in particular oxidation dyes) in the form of coloring shampoos, restructuring hair lotions, a perm composition (in particular a composition for the first time of a perm), a fall prevention lotion or gel, an antiparasitic shampoo, etc.
  • the composition can also be for oral use, for example a toothpaste.
  • the composition may contain adjuvants and additives customary for compositions for oral use and in particular surfactants, thickening agents, humectants, polishing agents such as silica, various active ingredients such as fluorides, in particular particularly sodium fluoride, and optionally sweetening agents such as sodium saccharinate.
  • the proportion of the fatty phase can range from 5% to 80% by weight, and preferably from 5% to 50% by weight relative to the total weight of the composition.
  • the oils, waxes, emulsifiers and coemulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the cosmetic field.
  • the emulsifier and the coemulsifier are present in the composition in a proportion ranging from 0.3% to 30% by weight, and preferably from 0.5 to 20% by weight relative to the weight total of the composition.
  • the emulsion may, in addition, contain lipid vesicles.
  • the fatty phase can represent more than 90% of the total weight of the composition.
  • the cosmetic composition may also contain adjuvants customary in the cosmetic field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters.
  • adjuvants customary in the cosmetic field such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters.
  • the amounts of these various adjuvants are those conventionally used in the cosmetic field, and for example from 0.01% to 10% of the total weight of the composition.
  • These adjuvants depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid spherules.
  • emulsifiers which can be used in the invention, there may be mentioned for example glycerol stearate, polysorbate 60 and the mixture of PEG-6 / PEG-32 / Glycol Stearate sold under the name Tefose R 63 by the company Gattefosse.
  • solvents which can be used in the invention mention may be made of lower alcohols, in particular ethanol and isopropanol, propylene glycol.
  • hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica, ethylcellulose, polyethylene.
  • carboxyvinyl polymers carboxyvinyl polymers
  • acrylic copolymers such as acrylate / alkylacrylate copolymers
  • polyacrylamides polysaccharides
  • polysaccharides such as hydroxypropylcellulose
  • natural gums and clays and, as lipophilic gelling agents
  • modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica,
  • composition may contain other hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.
  • hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.
  • retinol and its derivatives
  • tocopherol vitamin E
  • essential fatty acids ceramides
  • essential oils ceramides
  • the composition can combine at least one N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine extract with other active agents.
  • active agents there may be mentioned by way of example:
  • agents modulating differentiation and / or proliferation and / or skin pigmentation such as retinoic acid and its isomers, retinol and its esters, vitamin D and its derivatives, kojic acid or hydroquinone;
  • - antibacterials such as clindamycin phosphate, erythromycin or antibiotics of the tetracycline class
  • - antiparasitics in particular metronidazole, crotamiton or pyrethroids
  • - antifungals in particular compounds belonging to the class of imidazoles such as econazole, ketoconazole or miconazole or their salts, polyene compounds, such as amphotericin B, compounds of the allylamine family, such as terbinafine, or octopirox;
  • non-steroidal anti-inflammatory agents such as ibuprofen and its salts, diclofenac and its salts, acetylsalicylic acid, acetaminophen or glycyrrhetinic acid;
  • - anesthetic agents such as lidocaine hydrochloride and its derivatives
  • - antipruritic agents such as thenaldine, trimeprazine or cyproheptadine
  • - keratolytic agents such as alpha- and beta-hydroxycarboxylic or beta-ketocarboxylic acids, their salts, amides or esters and more particularly hydroxy acids such as glycolic acid, lactic acid, salicylic acid, acid citric and generally fruit acids, and n-octanoyl-5-salicylic acid
  • - anti-free radical agents such as alpha-tocopherol or its esters, superoxide dismutases, certain metal chelators or ascorbic acid and its esters
  • - anti-seborrheic drugs such as progesterone
  • - anti-dandruff agents such as octopirox or zinc pyrithione
  • - anti-acne drugs such as retinoic acid or benzoyl peroxide
  • compositions illustrate the invention without limiting it in any way.
  • proportions indicated are percentages by weight.
  • Example 1 Biological activity of N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine:
  • A positive control (induction of the enzyme): mixtures of interferon- ⁇ (1000u / ml) and interleukin 1 - ⁇ (100 u / ml);
  • the quantity of stable NO reaction products is measured using the “nitric colorimetric assay” kit sold by the company Boehringer under the reference 1756.28.
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine was tested at concentrations of 10 ⁇ M, 50 ⁇ M and 100 ⁇ M in the ethanol.
  • N, N'-bis-pyridyl-2-yl-methyl-N, N'-bis- (3,4,5-trimethoxybenzyl) ethylenediamine has an inducible NO-synthase inhibiting effect.
  • Composition 1 Compound face gel * 0.1%
  • Composition 2 Lotion
  • Composition 3 Gel for care
  • composition 4 Care cream (oil in water emulsion)
  • Composition 5 Shampoo
  • Composition 6 Care cream (oil / water emulsion)
  • Composition 8 Sun erythema care cream (oil-in-water emulsion)
  • Composition 9 Gel for the treatment of acne
  • Composition 10 Lotion to remove scars due to acne Compound * 5.00%

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
EP02758511A 2001-06-15 2002-06-14 No-synthase-inhibitor und seine anwendung Withdrawn EP1401393A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0107878A FR2825921B1 (fr) 2001-06-15 2001-06-15 Inhibiteur de no-synthase et utilisations
FR0107878 2001-06-15
PCT/FR2002/002064 WO2002102344A2 (fr) 2001-06-15 2002-06-14 Inhibiteur de no-synthase et utilisations

Publications (1)

Publication Number Publication Date
EP1401393A2 true EP1401393A2 (de) 2004-03-31

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Family Applications (1)

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EP02758511A Withdrawn EP1401393A2 (de) 2001-06-15 2002-06-14 No-synthase-inhibitor und seine anwendung

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US (1) US20040152735A1 (de)
EP (1) EP1401393A2 (de)
JP (1) JP2004534069A (de)
FR (1) FR2825921B1 (de)
WO (1) WO2002102344A2 (de)

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CA2456035A1 (fr) * 2003-02-03 2004-08-03 L'oreal Utilisation de n-arylmethylene ethylenediaminetriacetates, n-arylmethyleneiminodiacetates ou n,n'-diarylmethylene ethylenediamineacetates comme donneurs de no
FR2850578B1 (fr) * 2003-02-03 2006-07-28 Oreal Utilisation de n-arylmethylene ethylenediaminetriacetates, n-arylmethyleneiminodiacetates ou n,n'-diarylmethylene ethylenediamineacetates comme donneurs de no

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US4959551A (en) * 1989-02-27 1990-09-25 Gte Products Corporation Cosmetic tanning lamp and system having adjustable UVB proportion
ES2136723T3 (es) * 1992-11-13 1999-12-01 Oreal Utilizacion de n-aril-metilen-etilen-diamino-triacetatos, n-aril-metilen-imino-diacetatos o n,n'-diaril-metilen-etilen-diamino-acetatos contra el estres oxidante.
WO1996030012A1 (en) * 1995-03-24 1996-10-03 Defeudis Francis V Methods for treating conditions associated with excess nitric oxide
FR2737205B1 (fr) * 1995-07-26 1997-09-12 Oreal Nouveaux derives de n,n'-di(aralkyl) n,n'-di(2-azaaralkyl) alkylene diamine et leur utilisation dans des compositions pharmaceutiques et cosmetiques
FR2740339B1 (fr) * 1995-10-26 1997-12-05 Oreal Utilisation d'au moins un inhibiteur de no-synthase dans le traitement des peaux sensibles
DE19711565A1 (de) * 1997-02-21 1998-08-27 Beiersdorf Ag Zubereitungen für die Behandlung von Rosacea
FR2786694B1 (fr) * 1998-12-03 2002-09-27 Serobiologiques Lab Sa Utilisation d'extraits de plantes notamment a action anti-radicalaire et composition cosmetique ou dermopharmaceutique comportant de tels extraits
US6828460B2 (en) * 1999-03-22 2004-12-07 Pfizer Inc. Resorcinol derivatives

Non-Patent Citations (1)

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Title
See references of WO02102344A2 *

Also Published As

Publication number Publication date
FR2825921B1 (fr) 2005-02-11
WO2002102344A3 (fr) 2003-03-20
FR2825921A1 (fr) 2002-12-20
US20040152735A1 (en) 2004-08-05
WO2002102344A2 (fr) 2002-12-27
JP2004534069A (ja) 2004-11-11

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