EP2173198A2 - Utilisation d'au moins un dérivé oxime de la cholest-4-èn-3-one comme antioxydants - Google Patents

Utilisation d'au moins un dérivé oxime de la cholest-4-èn-3-one comme antioxydants

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Publication number
EP2173198A2
EP2173198A2 EP08836563A EP08836563A EP2173198A2 EP 2173198 A2 EP2173198 A2 EP 2173198A2 EP 08836563 A EP08836563 A EP 08836563A EP 08836563 A EP08836563 A EP 08836563A EP 2173198 A2 EP2173198 A2 EP 2173198A2
Authority
EP
European Patent Office
Prior art keywords
carbon
oxime
hydrogen atom
cholest
use according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08836563A
Other languages
German (de)
English (en)
French (fr)
Inventor
Rebecca Pruss
Cyrille Drouot
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.)
Trophos SA
Original Assignee
Trophos 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 Trophos SA filed Critical Trophos SA
Publication of EP2173198A2 publication Critical patent/EP2173198A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/742—Organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/762—Organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B70/00—Preservation of non-alcoholic beverages
    • A23B70/10—Preservation of non-alcoholic beverages by addition of preservatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • Oxidative stress is one of the biological consequences of the body's use of oxygen. It results in the formation of free radicals in the cells. Free radicals, if uncontrolled, can quickly react with molecules in their surroundings, giving rise to toxic compounds that can interfere with normal physiological processes. These substances can lead to cellular damage if the antiradical defenses are not sufficient. More and more studies show that reactive oxygen species play an important role in multiple biological processes and in particular in the development of multiple human pathologies, and in aging.
  • Preventing or treating skin aging, whether intrinsic or extrinsic, and the clinical signs described above, is to maintain or improve the appearance of the skin or scalp.
  • Antioxidants also have a beneficial effect when they are applied to the skin, they are indeed used in cosmetics.
  • antioxidants as preservatives in various types of oxidation-sensitive products.
  • antioxidants are sometimes inadequate or have insufficient action. It is known, for example, that tocopherol, which is a reference product in this field, is sensitive to light and requires particular preservation means. There is therefore a real need for antioxidant compounds, and it would be interesting to have new antioxidants with a powerful antioxidant activity and which would have a beneficial effect in the cosmetic field, in the food field, and also an effect on the preservation of products.
  • the present invention responds to this demand for potent antioxidant compounds since it relates to the use of cholest-4-en-3-one derivatives as antioxidants, which are potent antioxidants.
  • antioxidant refers to the ability of a compound to reduce the damage caused by free radicals:
  • a first aspect of the invention is the use of at least one oxime derivative of cholest-4-en-3-one to protect the skin.
  • the skin is especially the place of aggression of extrinsic and intrinsic toxic factors.
  • Extrinsic factors include, for example, ultraviolet radiation, wind, low humidity, abrasives and strong surfactants.
  • Intrinsic factors include chronological aging and biochemical changes in the skin.
  • the compounds of the present invention are capable of providing effective protection against factors that cause the appearance of wrinkles and other histological changes associated with aging of the skin.
  • UV that is, skin damage that appears as a result of repeated exposure to the sun to prevent, erase and treat wrinkles, fine lines in the skin, and / or fight against skin and / or subcutaneous looseness; and / or improve the texture of the skin and revive the radiance of the skin; and / or decrease the pore sizes of the skin.
  • Another aspect of the invention consists in the use of the compounds of the invention in cleansing and / or make-up removing products, as well as in products for protecting the skin and / or the hair against the side effects of UV radiation. .
  • the antioxidant properties of at least one oxime derivative of cholest-4-en-3-one also recommend their use in the food field as a dietary supplement. It is therefore within the scope of the invention to use the compounds of the invention as antioxidants in the food field.
  • antioxidant in the food field is meant in the present invention, a compound which, in pure form or in admixture with various carriers and / or other acceptable food additives, may be in powder form, in the form of capsules, tablet or other solid form that may optionally comprise a lipid phase, aqueous or be in solution or oral suspension.
  • the compound can be consumed alone, between meals, or during meals.
  • it can be consumed during meals, as a dietary supplement, associated with other foods.
  • it will be incorporated or sprinkled on a food.
  • foods can be simple or compound foods, and can be presented under any usual forms known in human nutrition.
  • the term "food” means any food which may be ingested, alone or accompanied, raw or cooked, whether or not prepared in any way, such as, for example, meat and meat products, seafood and freshwater products, milk and milk products, including infant formula, eggs and egg products, fruits and vegetables, cereals and cereal products, starchy foods such as pasta and rice, oils, vinegars and condiments, edible sauces and fats, sweet products, jams, jellies, compotes, spreads, confectionery, canned and semi-preserved foods, soups, coffee , tea, beverages, pastry, cocoa, chocolate, ice cream, meal replacements, fresh and frozen ready-to-eat meals and caterers, bread and bakery products.
  • meat and meat products seafood and freshwater products
  • milk and milk products including infant formula, eggs and egg products, fruits and vegetables, cereals and cereal products, starchy foods such as pasta and rice, oils, vinegars and condiments, edible sauces and fats, sweet products, jams, jellies, compotes, spreads, confectionery, canned and semi
  • the compound can accompany any food without disturbing the taste and does not constitute a constraint for the consumer. His catch is assimilated to a culinary gesture. He does not remember taking medications or meal replacements.
  • the compounds according to the invention can be frozen or, on the contrary, heated without losing their properties.
  • the invention also relates to the use of the compounds according to the invention as antioxidant preservatives in various products, in particular cosmetic, food and pharmaceutical products.
  • preservative is meant a compound which preserves a product of any physico-chemical alteration.
  • the compounds of the invention as antioxidants for the preservation of cosmetic, dermatological, pharmaceutical, detergent and perfuming products.
  • food products degrade under the action of air oxidation, which causes changes in texture, color and taste, and can render a food unfit for consumption.
  • the compounds of the invention make it possible to ensure a better preservation of the cosmetic or dermatological compositions comprising a fatty phase while avoiding the rancidity of unsaturated lipids contained therein, which they could also make it possible to avoid the degradation.
  • oxidative active compounds contained in these compositions such as vitamin A or carotenoids.
  • the compounds according to the invention having strong antioxidant capacities, they can be used as antioxidant preservatives of any preparation based on lipids, including food products, cosmetics, dermatological, perfumes, detergents or pharmaceuticals.
  • the subject of the present invention is therefore the use of compounds according to the invention as preserving agents in products, in particular cosmetic or dermatological, and food products. This is why the subject of the present invention is the use of at least one oxime derivative of cholest-4-en-3-one or one of its addition salts with acceptable acids, or one of of its esters or one of the addition salts of said esters with the acceptable acids, as antioxidants.
  • At least one compound of formula I is used. in which
  • A represents a hydrogen atom or together with B a carbon-carbon bond
  • B represents a hydrogen atom, a hydroxyl group or together with a carbon-carbon bond
  • E represents a hydrogen atom or together with F a carbon-carbon bond
  • F represents a hydrogen atom or together with E a carbon-carbon bond, or one of its addition salts with the acceptable acids, or one of its esters or one of the addition salts with them; acceptable acids of said esters, as an antioxidant.
  • the compounds of formula I as defined above are described in the international application published on September 30, 2004 under the number WO 2004/082581, as well as in the French application published on 22/06/2007 under the number FR2894968.
  • E represents together with F a double bond
  • C, D, A, B represent a hydrogen atom and R has the meaning R1, or one of its addition salts with acceptable acids, or one of its esters or one of the addition salts with the acceptable acids of said esters.
  • cholestan-3-one oxime, cholest-4-en-3-one oxime and cholest-1,4-dien-3-one oxime are used.
  • the oxime group represents the two isomers syn and anti in mixture or isolated.
  • the oxime derivative of cholest-4-en-3-one alone or in admixture with at least one other oxime derivative of cholest-4-en-3-one.
  • other compounds known for their antioxidant properties include compounds derived from the families of thiols and phenols and polyphenols, for example flavonoids (which are very common in plants), phenolic acids (in cereals, fruits and vegetables), tannins (in cocoa, coffee, tea, grapes, etc.), anthocyanins (especially in red fruits, ⁇ -carotene (provitamins A), tocopherols (vitamin E ) or its esters such as alpha-tocopherol, gamma-tocopherol, delta-tocopherol, certain metal chelators or ascorbic acid and its esters such as sodium or calcium ascorbate, diacetyl acid 5-6 -1-ascorbic acid, palmityl 6-1 -ascorbic acid, citric acid and citrates such as those of sodium, potassium and calcium, tartaric acid and tartrates such as sodium, potassium, butylhydroxyanisol and butylhydroxytoluol, octyl gallates
  • the antioxidants that can be used in the composition of the invention may be natural or synthetic.
  • one of the aspects of the invention is therefore to provide an antioxidant cosmetic composition comprising at least in a cosmetically acceptable medium an effective amount of at least one oxime derivative of cholest-4-en-3-one.
  • the invention also relates to a cosmetic composition for combating chronobiological and / or photoinduced aging comprising in a cosmetically acceptable medium an effective amount of at least one oxime derivative of cholest-4-en-3-one.
  • the amount of cholest-4-en-3-one or one of its derivatives that can be used according to the invention obviously depends on the desired effect and must be in an amount effective to produce the desired antioxidant effect.
  • the amount of at least one oxime derivative of cholest-4-en-3-one or of its derivatives that can be used according to the invention can range, for example, from 0.01% to 30% and preferably from 0.1% to at 10% of the total weight of the composition.
  • the composition of the invention may also contain the usual adjuvants in the cosmetic and dermatological fields, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, solvents, perfumes, fillers, filters, pigments, chelating agents, odor absorbers and dyestuffs.
  • the amounts of these various adjuvants are those conventionally used in the fields under consideration, and for example from 0.01% to 20% of the total weight of the composition.
  • These adjuvants depending on their nature, can be introduced into the fatty phase, into the aqueous phase, into the lipid vesicles and / or into the nanoparticles.
  • the proportion of the fatty phase can range from 5% to 80% by weight, and preferably from 5% to 50% of the total weight of the composition.
  • the oils, emulsifiers and coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in the field under consideration.
  • 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% of the total weight of the composition.
  • emulsifiers and coemulsifiers that can be used in the invention, mention may be made, for example, of fatty acid and polyethylene glycol esters such as PEG-40 stearate, PEG-100 stearate, fatty acid and polyol esters. such as glyceryl stearate and sorbitan tristearate.
  • hydrophilic gelling agents mention may in particular be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as copolymers of acrylates / alkylacrylates, polyacrylamides, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids, hydrophobic silica and polyethylenes .
  • the composition may contain other hydrophilic active agents such as protein or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and the like. hydroxy acids.
  • auxins - plant hormones
  • antibacterial agents such as macrolides, pyranosides and tetracyclines, and in particular erythromycin;
  • calcium antagonists such as verapamil and diltiazem
  • OH radical scavengers such as dimethylsulfoxide
  • Extracts of plants such as Iridaceae or soybean extracts, which may then contain isoflavones or not;
  • extracts of micro-organisms in particular bacterial extracts such as those of non-photosynthetic filamentous bacteria.
  • potassium channel openers such as diazoxide and minoxidil, spiroxazone, phospholipids such as lecithin, linoleic and linolenic acids, and the like.
  • salicylic acid and its derivatives described in French Patent FR 2,581,542 such as salicylic acid derivatives bearing an alkanoyl group having from 2 to 12 carbon atoms at the 5-position of the benzene ring, hydroxycarboxylic or ketocarboxylic acids and its esters, lactones and its corresponding salts, anthralin, carotenoids, eicosatetraenoic and eicosatrienoic acids or its esters and amides, vitamin D and its derivatives.
  • agents that modulate skin differentiation and / or proliferation and / or pigmentation such as retinoic acid and its isomers, retinol and its esters, vitamin D and its derivatives, estrogens such as estradiol, kojic acid or hydroquinone;
  • agents that modulate bacterial adhesion to the skin and / or mucous membranes such as honey, especially acacia honey and certain sugar derivatives;
  • antiparasitics in particular metronidazole, crotamiton or pyrethrinoids
  • antifungals in particular compounds belonging to the class of imidazoles such as econazole, ketoconazole or miconazole or its salts, polyene compounds, such as amphotericin B, compounds of the allylamine family, such as terbinafine or octopirox
  • antiviral agents such as acyclovir
  • keratolytic agents such as alpha- and beta-hydroxycarboxylic acids or beta-ketocarboxylic acids, its 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;
  • antiseborrhoeics such as progesterone
  • anti-dandruff such as octopirox or zinc pyrithione
  • - anti-acne drugs such as retinoic acid or benzoyl peroxide
  • substances such as substance P, CGRP or bradykinin antagonists or NO synthase inhibitors, compounds described as being active in the treatment of sensitive skin and having anti-irritant effects, in particular vis-à-vis of irritating compounds that may be present in the compositions.
  • compositions comprising an effective amount of at least one oxime of cholest-4-en-3-one and at least one agent chosen from antibacterial, antiparasitic, antifungal and antiviral agents, anti-inflammatory, antipruritic, anesthetic, keratolytic, anti-seborrhoeic, anti-dandruff, anti-acne, agents modulating differentiation and / or proliferation and / or skin pigmentation, substance P, CGRP or bradykinin antagonists or inhibitors of NO synthase.
  • agent chosen from antibacterial, antiparasitic, antifungal and antiviral agents, anti-inflammatory, antipruritic, anesthetic, keratolytic, anti-seborrhoeic, anti-dandruff, anti-acne, agents modulating differentiation and / or proliferation and / or skin pigmentation, substance P, CGRP or bradykinin antagonists or inhibitors of NO synthase.
  • moisturizers such as polyols (for example glycerine), vitamins (for example D-panthenol), anti-inflammatory agents, soothing agents (allantoin, cornflower water), filters UVA and UVB, matting agents (eg partially crosslinked polydimethylorganosiloxanes sold under the name KSG® by Shin Etsu), and mixtures thereof.
  • polyols for example glycerine
  • vitamins for example D-panthenol
  • anti-inflammatory agents for example D-panthenol
  • soothing agents allantoin, cornflower water
  • filters UVA and UVB filters UVA and UVB
  • matting agents eg partially crosslinked polydimethylorganosiloxanes sold under the name KSG® by Shin Etsu
  • anti-wrinkle active agents and especially tensor products such as vegetable proteins and their hydrolysates, in particular the soy protein extract sold under the name Eleseryl® by the company LSN or the oat derivative sold under the name Reductine® by the company Silab.
  • Example 1 Competition of oxime of cholest-4-en-3-one with 5,5-dimethyl-1-pyrroline-1-oxide in the presence of free radicals.
  • the antiradical properties of the claimed products are demonstrated by conducting a competition study with a reference product belonging to the family of nitrones.
  • Nitrones such as DMPO (5,5-dimethyl-1-pyrroline-1-oxide) are widely described as compounds having a very high reactivity with respect to free radicals (Novelli GP et al., Free Radical Res. Commun., 1986,1, 321). Nitrones trap radical species (R-; RO) and allow their observation in electron paramagnetic resonance (EPR) (Degray J.
  • the oxime of cholest-4-en-3-one inhibits on the order of 50% the level of the DMPO-tBuO signal radical and this with rapid kinetics, less than 10 minutes.
  • the intensity of the trapping of the tBuO radical and its kinetics demonstrate the anti-radical and therefore antioxidant property of the claimed compounds.
  • EXAMPLE 2 Antioxidant effect of the oxime of cholest-4-en-3-one in the oxidation model of cumene by activated oxygen.
  • the technique used made it possible to compare the appearance of cumene hydroperoxide in the presence of an antioxidant agent such as the claimed products and the vitamin E used as reference product.
  • oxime cholest-4-en-3-one reduces the oxidation of cumene by oxygen by about 40% and has a similar activity to vitamin E under these conditions at the same concentrations.
  • Example 3 Toxicology Study with Cholesterol-4-en-3-one Oxime A general toxicity study in Beagle dogs receiving cholest-4-en-3-one oxime suspended in corn oil by oral administration once daily for 39 weeks was performed. The detailed toxicological analysis of this study described a no observed effect level (NOEL) at 50 mg / kg. This result demonstrates the very high security of this product.
  • NOEL no observed effect level
  • a pharmacokinetic study with oral administration suspended in corn oil and intravenously in solution in cremophor / ethanol / water (5%, 10%, 85%) made it possible to calculate the bioavailability of product.
  • the determination of the product in the plasma is carried out by a method of high pressure liquid chromatography coupled with mass spectrometry.
  • the bioavailability was calculated at 6%.
  • the circulating level of cholest-4-en-3-one oxime is therefore quantifiable and demonstrates a real absorption of the product.
  • Example 5 Chemical stability of cholest-4-en-3-one oxime
  • ICH International Conference on Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human Use
  • These analyzes were performed using a high pressure liquid chromatography method coupled to a UV detector. This method makes it possible to quantify the impurities at a rate of 0.05%.
  • the results (Sum of impurities as a function of time) are presented in the following table.

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EP08836563A 2007-07-25 2008-07-24 Utilisation d'au moins un dérivé oxime de la cholest-4-èn-3-one comme antioxydants Withdrawn EP2173198A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0705426A FR2919180B1 (fr) 2007-07-25 2007-07-25 Utilisation d'au moins un derive oxime de la cholest-4-en-3-one comme antioxydants
PCT/FR2008/001101 WO2009044010A2 (fr) 2007-07-25 2008-07-24 Utilisation d'au moins un dérivé oxime de la cholest-4-èn-3-one comme antioxydants

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EP2173198A2 true EP2173198A2 (fr) 2010-04-14

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MX2010000915A (es) 2010-03-01
WO2009044010A2 (fr) 2009-04-09
ZA201000192B (en) 2011-05-25
NZ582646A (en) 2012-11-30
JP2010534227A (ja) 2010-11-04
WO2009044010A3 (fr) 2009-11-05
RU2475052C2 (ru) 2013-02-20
FR2919180A1 (fr) 2009-01-30
BRPI0814580A2 (pt) 2014-10-07
RU2010106614A (ru) 2011-08-27
US20100267680A1 (en) 2010-10-21
CA2697125A1 (fr) 2009-04-09
FR2919180B1 (fr) 2009-11-27
AU2008306838A1 (en) 2009-04-09

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