WO2005105149A1 - Nouveaux excipients pharmaceutiques ou cosmetiques a base d'acetals cycliques - Google Patents
Nouveaux excipients pharmaceutiques ou cosmetiques a base d'acetals cycliques Download PDFInfo
- Publication number
- WO2005105149A1 WO2005105149A1 PCT/FR2005/050181 FR2005050181W WO2005105149A1 WO 2005105149 A1 WO2005105149 A1 WO 2005105149A1 FR 2005050181 W FR2005050181 W FR 2005050181W WO 2005105149 A1 WO2005105149 A1 WO 2005105149A1
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- WO
- WIPO (PCT)
- Prior art keywords
- reaction
- edm
- glycerol
- cosmetic
- use according
- Prior art date
Links
- YVNCJCSIDJAGMD-UHFFFAOYSA-N CCC(OC1)OCC1O Chemical compound CCC(OC1)OCC1O YVNCJCSIDJAGMD-UHFFFAOYSA-N 0.000 description 1
- KZODGPRCEZYZRW-UHFFFAOYSA-N CCC1OC(CO)CO1 Chemical compound CCC1OC(CO)CO1 KZODGPRCEZYZRW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Definitions
- the invention relates to new pharmaceutical or cosmetic excipients based on cyclic acetals. It also relates to pharmaceutical or cosmetic compositions incorporating said excipients.
- excipient means a neutral substance of variable nature into which are introduced the elements called “active and preservatives”, optionally dyes and perfumes, the whole constituting a cosmetic composition or pharmaceutical.
- Cyclic acetals result in known manner from the reaction between an aldehyde and a polyol having at least two hydroxyl functions, thus leading to the formation of acetal rings comprising five or six atoms.
- Document US-A-4031 112 describes emulsifiers used in industry, in particular in the field of printing.
- these emulsifiers are obtained by an oxyalkylation reaction carried out on cyclic acetals.
- the latter are obtained from aldehyde advantageously comprising from 5 to 20 carbon atoms, although formaldehyde, acetaldehyde, propionaldehyde or butyraldehyde are not expressly excluded.
- the polyols used are generally polyols comprising from 3 to 6 carbon atoms and in particular glycerol or even pentaerythritol.
- the oxyalkylation reaction is then carried out in two stages by bringing together the cyclic acetal obtained with, advantageously, propylene oxide.
- Document GB-A-5 49213 describes the use of cyclic acetals as an anti-inflammatory in cosmetic compositions, in particular in sunscreen compositions.
- cyclic acetals are obtained by reaction of an aldehyde on a diol.
- the aldehydes and diols used for the manufacture of anti-i-iflammatory are listed exhaustively and only certain combinations are exemplified.
- acetaldehyde, propionaldehyde and butyraldehyde are especially mentioned.
- the emo properties of the product thus obtained are then compared with other products obtained from the same oxoaldehyde, but having reacted on different polyols, such as for example ethylene glycol, 1,2-propylene glycol and pentaerythritol. .
- polyols such as for example ethylene glycol, 1,2-propylene glycol and pentaerythritol.
- the emollient properties of the cyclic acetals obtained from glycerol and pentaerythritol are much lower than those obtained with ethylene glycol or even 1,2-propylene glycol.
- Document US-A-5 175 143 describes new perfumes based on cyclic acetals which can be used in different presentations, such as toilet soaps, deodorants, etc.
- the cyclic acetals described are obtained from cyclic aldehydes and 1- 3 diol.
- Document US-A-5,917,059 relates exclusively to a process for the preparation of cyclic acetal, without particular application.
- the improved process consists in reacting an aldehyde having from 1 to 6 carbon atoms with a polyol having at least 2 hydroxyls.
- Advantageously cited are diols and triols having 2 to 12 carbon atoms, in particular glycerol and trimethylol propane.
- Document EP-A-268460 describes a therapeutic composition comprising, as a penetration promoter, a dioxolane and / or a dioxane substituted with at least one R group, at least one of which is a C4 to C8 alkyl or alkenyl group.
- This molecule has the following formula:
- R is C4 alkyl or alkenyl.
- these molecules are obtained by reacting a C5 aldehyde (pentanal or valeraldehyde) on glycerol.
- a mixture of 2-butyl-1,3-dioxolane-4-hydroxymethyl and 2-butyl-1,3-dioxan-5-ol is obtained.
- the main drawback of these molecules is that they are not miscible in water, which limits their use as a pharmaceutical or cosmetic excipient. This product is subsequently referred to as BDM.
- Document GB-A-2075833 describes an injectable solution containing, as active ingredient, a mixture of trimethoprim and sulfamethoxypyridazine in a solvent itself resulting from a mixture of 4-hydroxymethyl-1,3 dioxolane and 5 hydroxy- 1.3 dioxane obtained from formaldehyde.
- Document FR-A-2 789 586 describes the use of certain cyclic acetals, in particular solketa 11, as an absorption promoter.
- the invention relates to new pharmaceutical or cosmetic excipients based on cyclic acetal.
- These excipients are characterized in that the cyclic acetal is the product of the reaction between an aliphatic aldehyde comprising from 2 to 4 carbon atoms and a polyol comprising from 3 to 6 carbon atoms and at least three hydroxyl functions, of which two at fewer are located on vicinal carbons or separated by a carbon.
- the excipient may contain the cyclic acetals described above alone or as a mixture between them.
- cyclic acetals obtained by reaction of saturated, linear or branched aldehydes, having a low number of carbon atoms, in practice between 2 and 4, for example, a polyol comprising in practice from 3 to 6 carbon atoms and advantageously having 3 to 6 OH functions, at least two of which are located on the vicinal carbons or separated by a carbon, were interesting for the desired application.
- cyclic acetals of the invention had the following properties or better miscibility as close molecules, such as for example solketal ® or the molecules described in EP-A-268460. More generally, it has been demonstrated that the cyclic acetals of the invention were soluble in many oils and alcohols used in pharmacy and cosmetics and in water, and were capable of dissolving many active ingredients which are soluble or insoluble in water. In addition, they are compatible with gelling agents and can be incorporated into emulsions, microemulsions, etc. Finally, they are also endowed with an activity promoting effect of active molecules, cosmetic or pharmaceutical.
- the cyclic acetal results from the reaction between propanai (propionaldehyde) and glycerol. Because of the possible cyclization between the hydroxyl functions of glycerol located in positions 1 and 3 (functions separated by a carbon) or in positions 1 and 2 (vicinals) with the carbonyl function of propionaldehyde, the reaction leads to a mixture of two molecules, respectively 2-ethyl-4-hydroxymethyl-1,3-dioxolane and 2-ethyl-1,3-dioxan-5-ol of formula:
- a mixture of the same type also showing satisfactory results for the envisaged application is that corresponding to 2-propyl-4-hydroxyrnéthy ⁇ -l, 3-dioxolane with 2-propyl-l, 3-dioxan-5-ol obtained by reaction between butyraldehyde and glycerol.
- the invention naturally relates to a pharmaceutical or cosmetic composition incorporating the excipient described above.
- the cyclic acetals forming part of the invention can be used for their solubilizing properties of active principles which are sparingly or not soluble in water or in oil, and as activity promoter probably resulting from a promoter effect. 'absorption.
- composition containing the cyclic acetals of the invention can be in all the galenical forms normally used for topical application to the skin or the hair, in particular in the form of an aqueous solution, of an oil-in-water emulsion or water-in-oil or multiple, a silicone emulsion, a microemulsion or nanoemulsion, an aqueous gel.
- This composition can be more or less fluid and have the appearance of, among other things, a white or colored cream, an ointment, a milk, a lotion, a serum, a gel.
- the composition can contain the usual adjuvants in the cosmetic and dermatological fields, such as fatty phases, emulsifiers and co-emulsifiers, hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, perfumes , fillers, hydrophilic and lipophilic filters, dyes, neutralizers, penetrating agents, and polymers.
- these various adjuvants are those conventionally used in the fields considered, and for example from 0.01 to 30% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase or into the aqueous phase.
- emulsifiers and coemulsifiers which can be used, mention may, for example, be made of polyglycerol and fatty acid esters, sucrose and fatty acid esters, sorbitan and fatty acid esters, fatty acid and sorbitane esters oxyethylenated, fatty alcohol and PEG ethers, glycerol and fatty acid esters, alkyl sulfates, alkyl ether sulfates, alkyl phosphates, alkyl polyglucosides, silicone emulsifiers.
- polyglycerol and fatty acid esters sucrose and fatty acid esters, sorbitan and fatty acid esters, fatty acid and sorbitane esters oxyethylenated, fatty alcohol and PEG ethers, glycerol and fatty acid esters, alkyl sulfates, alkyl ether sulfates, alkyl phosphates, alkyl polyglu
- hydrophilic gelling agents mention may in particular be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides such as xanthan gum, guar gum, natural gums such as cellulose gum and derivatives, and clays.
- lipophilic gelling agents mention may be made of modified clays such as bentones, metal salts of fatty acids, hydrophobic silica and ethylcellulose.
- depigmentants As active agents, depigmentants, emollients, moisturizers, anti-seborrheics, anti-acne, keratolytic and / or desquamating agents, anti-wrinkle and tightening agents, draining agents, anti-aging agents can be used in particular.
- irritants irritants, soothing agents, slimming agents such as xanthic bases (caffeine), vitamins and their mixtures, matifying agents, anti-aging active agents such as retinol, anti-wrinkle agents, essential oils.
- the active agents indicated above can be incorporated into spherules, in particular ionic or non-ionic vesicles and / or nanoparticles (nanocapsules and / or nanospheres), so as to isolate them from each other others in the composition.
- preservatives which can be used, mention may be made of benzoic acid, its salts and its esters; sorbic acid and its salts; parabens, their salts and esters; triclosan; imidazoHdinyl urea; phenoxyethanol; DMDM hydantoin; diazohdinyl urea; chlorphenesin.
- antioxidants which can be used, mention may be made of BHA, BHT, TBHQ, propyl gallate, tocopherols and their esters, tocotrienols, ascorbyl palmitate, rosemary extracts, green tea extract, chlorogenic acid, beta-carotene, flavonoids, chelating agents such as 1 ⁇ DTA and its salts, citric acid.
- useful solvents mention may be made of water, ethanol, glycerin, propylene glycol, butylene glycol, sorbitol.
- fillers which may be used, mention may be made of talc, kaolin, mica, serecite, magnesium carbonate, aluminum silicate, magnesium silicate, organic powders such as nylon.
- UVA and UNB filters which can be used
- UVA and UNB filters conventionally used such as benzophenone-3, butyl methoxydibenzoyl methane, octocrylene, octyl methoxycinnamate, 4-methylbenzylidene camphor, octyl salycylate, titanium dioxide and zinc oxide in their micrometric and nanometric forms.
- neutralizers which can be used, mention may be made of sodium hydroxide, triethanolamine, raminomethyl propanol and potassium hydroxide.
- penetrating agents there may be mentioned alcohols and glycols (ethanol, propylene glycol), Fethoxydigrycol, alcohols and fatty acids (oleic acid), esters of fatty acids, dimethyl isosorbide.
- composition containing an excipient from the invention can be used as a care product, as a cleaning product, and / or as a skin makeup product, as a sun protection product, or as a hair product, for example as a shampoo or hair conditioner.
- the cyclohexane is evaporated under reduced pressure and the reaction product (EDM) purified by distillation under reduced pressure using a vigorous column.
- the mass yield of the reaction is 70% and the product has a purity greater than 99%.
- NMR and gas chromatographic analyzes coupled to a mass spectrometer (GC-MS) confirm that the product obtained is a mixture of 2-ethyl-1,3-dioxolane-4-hydroxymethyl and 2-ethyl-1,3-dioxan -5-ol.
- the BDM molecule is produced according to the same process as that of Example 1 (without solvent), from pentanal and glycerol.
- the product obtained is confirmed by GC-MS analysis. Its solubility in water is around 2 g in 100g of water. Beyond that we see a disturbance appear.
- EDM is very soluble in many esters, in hydrophilic solvents and in vegetable oils. 4 / Solubilization of filters by FTE. SHS. PDM The solubility of two organic UV filters (benzophenone-3 and 1,2-butyl methoxydibenzoylmethane) is evaluated in 1 ⁇ TP, EDM and PDM.
- Protocol Homogenize the mixture 30 seconds using a Nortex, - spend 15 minutes with ultrasound (to be renewed if the filter is immiscible up to 60 minutes maximum), - for the following percentages, add always an identical amount of UV filter in a fixed starting quantity of solvent.
- the solubility is expressed in g of filter soluble in 100 g of final solution.
- the molecules tested are better filter solubilizers than
- hydrophobic active agents Five hydrophobic active agents were dissolved in water, using EDM. In the following table, it is indicated which mass of solvent (g) must be added to dissolve lg of a mixture consisting of 98% water and 2% active. The lower the amount of solvent to be added, the greater its solubilizing power.
- EDM has the power to dissolve hydrophobic active ingredients in water. It performs better than Arlasolve DMI (Dimethyl Isosorbide), another solvent on the cosmetic market.
- Arlasolve DMI Dimethyl Isosorbide
- EXAMPLE 4 Stability of the pH of an EDM solution The stability of solutions at different pH, after the introduction of 5% EDM is studied.
- Buffer solutions The different solutions are prepared: - for pH 3 to 7 using citric acid and Na 2 HPO, - for pH 8 to 10 using boric acid, KC1 and of NaOH.
- EDM has good compatibility with the gaffers from different families tested. Indeed, none of the formulated gels is broken by the addition of EDM. 2. Emulsion compatibility 2.1 - O / W emulsion
- Bi-gel is a surfactant-free emulsion.
- EDM can be formulated in microemulsions.
- Emulsion reference ALE 1833 / A excipient formula, without kojic acid - ALE 1833 / B: formula with 2% kojic acid - ALE 1833 / C: formula with 2% acid Kojique and 5%
- the depigmenting activity of the various formulas is evaluated by measuring the level of melanin produced by a suspension of cells.
- the melanin level is determined by measuring the optical density at 405 nm of cell extracts obtained from the epidermis treated with the test products.
- the depigmenting activity of the products under study is evaluated in the following manner "Application, on D0, Dl, D2, D3, and D6, of the ALE 1833 / A, B, C and MelanexDuo® Cream formulas , at a rate of 2.5 mg / cm 2 on the stratum corneum of pigmented human epidermis. Incubation of the epidermis at 37 ° C. in an air-CO 2 oven. "Determination of the melanin level on D7, 24 hours after the last application.
- FIG. 1 is a diagram representing the cytotoxicity of the formulas containing ALE 1833 A, B and C.
- FIG. 2 is a diagram representing the depigmenting activity of the ALE 1833 B and C formulas. As this figure shows, without EDM, the formula ALE1833 / B containing kojic acid has no depigmenting activity. With EDM, the same formula has depigmenting activity.
- EDM makes it possible to increase the activity of certain active cosmetic molecules probably by a promoter effect of cutaneous absorption.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0509994-3A BRPI0509994A (pt) | 2004-04-21 | 2005-03-21 | utilização de acetal cìclico e composição farmacêutica ou cosmética |
EP05739633A EP1737495A1 (fr) | 2004-04-21 | 2005-03-21 | Nouveaux excipients pharmaceutiques ou cosmetiques a base d'acetals cycliques |
US11/568,008 US20080280997A1 (en) | 2004-04-21 | 2005-03-21 | Novel Pharmaceutical or Cosmetic Carriers Containing Cyclic Acetals |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0404198 | 2004-04-21 | ||
FR0404198A FR2869232B1 (fr) | 2004-04-21 | 2004-04-21 | Nouveaux excipients pharmaceutiques ou cosmetiques a base d'acetals cyliques |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005105149A1 true WO2005105149A1 (fr) | 2005-11-10 |
Family
ID=34944666
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2005/050181 WO2005105149A1 (fr) | 2004-04-21 | 2005-03-21 | Nouveaux excipients pharmaceutiques ou cosmetiques a base d'acetals cycliques |
Country Status (5)
Country | Link |
---|---|
US (1) | US20080280997A1 (fr) |
EP (1) | EP1737495A1 (fr) |
BR (1) | BRPI0509994A (fr) |
FR (1) | FR2869232B1 (fr) |
WO (1) | WO2005105149A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2974113A1 (fr) * | 2011-04-18 | 2012-10-19 | Rhodia Poliamida E Especialidades Ltda | Preparations pour compositions nettoyantes tout usage |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE602007010986D1 (de) * | 2006-12-13 | 2011-01-13 | Roche Diagnostics Gmbh | Verwendung von acetalen zur isolation von nukleinsäuren |
DE102009027420A1 (de) | 2009-07-02 | 2011-01-05 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Acrolein |
US8475774B2 (en) * | 2010-02-08 | 2013-07-02 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions comprising an ultraviolet radiation-absorbing polymer |
CN110215413B (zh) * | 2018-03-02 | 2023-04-28 | 广州华狮化妆品科技有限公司 | 一种双凝胶体系的眼唇卸妆凝露化妆品及制备方法 |
WO2024145888A1 (fr) * | 2023-01-06 | 2024-07-11 | Beiersdorf Ag | Émulsion cosmétique contenant de l'adipate de diisopropyle et du polyglycérylester |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2075833A (en) * | 1980-05-20 | 1981-11-25 | Farmos Oy | Injectable solution of sulfamethoxypyridazine and trimethoprim |
US5917059A (en) * | 1996-11-15 | 1999-06-29 | Basf Aktiengesellschaft | Preparation of cyclic acetals or ketals |
FR2789586A1 (fr) * | 1999-02-16 | 2000-08-18 | Synthelabo | Composition pharmaceutique pour administration transmucosale balanique d'alfuzosine |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2510636A1 (de) * | 1975-03-12 | 1976-09-23 | Basf Ag | Cyclische acetale |
US4861764A (en) * | 1986-11-17 | 1989-08-29 | Macro Chem. Corp. | Percutaneous absorption enhancers, compositions containing same and method of use |
US5175143A (en) * | 1987-01-29 | 1992-12-29 | Unilever Patent Holdings B.V. | Perfumery materials |
DE4309830C1 (de) * | 1993-03-26 | 1994-05-05 | Lohmann Therapie Syst Lts | Wirkstoffpflaster für die Abgabe von Estradiol an die Haut |
-
2004
- 2004-04-21 FR FR0404198A patent/FR2869232B1/fr not_active Expired - Fee Related
-
2005
- 2005-03-21 BR BRPI0509994-3A patent/BRPI0509994A/pt not_active Application Discontinuation
- 2005-03-21 WO PCT/FR2005/050181 patent/WO2005105149A1/fr not_active Application Discontinuation
- 2005-03-21 US US11/568,008 patent/US20080280997A1/en not_active Abandoned
- 2005-03-21 EP EP05739633A patent/EP1737495A1/fr not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2075833A (en) * | 1980-05-20 | 1981-11-25 | Farmos Oy | Injectable solution of sulfamethoxypyridazine and trimethoprim |
US5917059A (en) * | 1996-11-15 | 1999-06-29 | Basf Aktiengesellschaft | Preparation of cyclic acetals or ketals |
FR2789586A1 (fr) * | 1999-02-16 | 2000-08-18 | Synthelabo | Composition pharmaceutique pour administration transmucosale balanique d'alfuzosine |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2974113A1 (fr) * | 2011-04-18 | 2012-10-19 | Rhodia Poliamida E Especialidades Ltda | Preparations pour compositions nettoyantes tout usage |
WO2012143769A1 (fr) * | 2011-04-18 | 2012-10-26 | Rhodia Poliamida E Especialidades Ltda | Préparations pour compositions nettoyantes tout usage |
CN103492546A (zh) * | 2011-04-18 | 2014-01-01 | 罗狄亚聚酰胺特殊品有限公司 | 多用途清洁组合物的制备 |
US8821648B2 (en) | 2011-04-18 | 2014-09-02 | Rhodia Poliamida E Especialidades Ltda | Preparations for all-purpose cleaning compositions |
KR101522129B1 (ko) * | 2011-04-18 | 2015-05-20 | 로디아 폴리아미다 이 에스페시아리다데스 엘티디에이 | 다용도 세정 조성물을 위한 제제 |
Also Published As
Publication number | Publication date |
---|---|
BRPI0509994A (pt) | 2007-10-16 |
FR2869232A1 (fr) | 2005-10-28 |
EP1737495A1 (fr) | 2007-01-03 |
FR2869232B1 (fr) | 2007-09-21 |
US20080280997A1 (en) | 2008-11-13 |
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