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WO2008050173A1 - Composition topique de soin de la peau contenant un ester d'acide tranexamique - Google Patents

Composition topique de soin de la peau contenant un ester d'acide tranexamique Download PDF

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Publication number
WO2008050173A1
WO2008050173A1 PCT/IB2006/003008 IB2006003008W WO2008050173A1 WO 2008050173 A1 WO2008050173 A1 WO 2008050173A1 IB 2006003008 W IB2006003008 W IB 2006003008W WO 2008050173 A1 WO2008050173 A1 WO 2008050173A1
Authority
WO
WIPO (PCT)
Prior art keywords
tranexamic acid
component
topical composition
skin
ester
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.)
Ceased
Application number
PCT/IB2006/003008
Other languages
English (en)
Inventor
Hitoshi Masaki
Nobuhiro Ando
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.)
Chanel Parfums Beaute SAS
Nikko Chemicals Co Ltd
Original Assignee
Chanel Parfums Beaute SAS
Nikko Chemicals Co Ltd
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 Chanel Parfums Beaute SAS, Nikko Chemicals Co Ltd filed Critical Chanel Parfums Beaute SAS
Priority to PCT/IB2006/003008 priority Critical patent/WO2008050173A1/fr
Publication of WO2008050173A1 publication Critical patent/WO2008050173A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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

Definitions

  • Tranexamic acid is known to have the effect of decreasing the activity of plasminolytic or fibrinolytic enzyme (antiplasmin activity) , and such effects as antiallergic, antiedematous and anti-inflammatory effects are anticipated.
  • plasmin activity plasmin activity
  • tranexamic acid is administered clinically by oral administration, intravenous injection and intramuscular injection, with the objective of inhibiting erythema, itching and the like of the skin and mucous membrane.
  • internal administration of tranexamic acid is known to be effective for skin disease.
  • tranexamic acid such as, for instance, anti-pigmentation agent and skin roughness improvement agent
  • percutaneous administration being common when used in such applications.
  • an anti-pigmentation agent for external use with tranexamic acid ester and salt thereof as an active ingredient is disclosed in Japanese Patent Application Laid-open No. H04-46144.
  • a dermatological topical composition containing a stress handling agent containing tranexamic acid and/or a derivative thereof is disclosed in Japanese Patent Application Laid-open No. 2002-234836.
  • the present invention was devised in view of such a situation, and it is an object of the invention to provide a dermatological or cosmetic topical composition allowing stability of application onto the skin and an improved percutaneous penetrability (and thus better efficacy) of tranexamic acid ester and a derivative thereof.
  • the present inventors found a component having excellent compatibility with tranexamic acid ester and/or a derivative thereof, and at the same time, discovered that when a tranexamic acid ester composition wherein that component is admixed is used, the effect of tranexamic acid ester persisted over a long time period, leading to completion of the present invention.
  • a dermatological or cosmetic topical composition according to the present invention contains tranexamic acid ester and/or a salt thereof (Component A) and silicone oil having a viscosity of at least 100,000 cSt at 25 0 C (Component B), which is not a crosslinked organopolysiloxane, provided that the composition does not contain 4 wt . % of tranexamic acid cetyl ester hydrochloride in combination with 0.3 wt . % of polydimethylsiloxane having a viscosity of 1,000,000 cSt at
  • the above-mentioned Component (A) is preferably a compound having the following Formula (1) and/or a salt thereof.
  • R represents a saturated or unsaturated aliphatic hydrocarbon group having a linear chain or a branched chain with 1 to 22 carbons, wherein one or several hydrogen atoms in R may be independently replaced by a hydroxyl group or an amino group.
  • topical composition according to the present invention is particularly useful if used as cosmetics .
  • FIG. 1 Graph showing the measurement results of the amount of moisture on the skin surface.
  • FIG. 2 Graph showing the measurement results of transepidermal water loss (TEWL) .
  • FIG. 3 Graph showing the measurement results of skin color.
  • FIG. 4 Graph showing the measurement results of skin elasticity.
  • FIG. 5 Graph showing the measurement results of cell area (stratum corneum cell area) .
  • FIG. 6 Graph showing the measurement results of degree of multi-layer peeling.
  • FIG. 7 Graph showing the measurement results of nucleated cell ratio.
  • the topical composition according to the present invention contains a Component A and a Component B .
  • Component A is tranexamic acid ester and/or a salt thereof and is not limited to a particular component / however, a compound represented by the following Formula (1) or a derivative thereof is preferred.
  • R represents a saturated or unsaturated aliphatic hydrocarbon group having a linear chain or a branched chain with 1 to 22, preferably 8 to 20, and more preferably 12 to 18 carbon atoms.
  • one or several hydrogen atoms in R may be independently replaced by a hydroxyl group or an amino group.
  • tranexamic acid esters include, for instance, tranexamic acid lauryl ester, tranexamic acid myristyl ester, tranexamic acid cetyl ester, tranexamic acid stearyl ester and the like and their mixtures.
  • tranexamic acid cetyl ester, tranexamic acid stearyl ester and their mixtures are particularly preferred from the view point of higher effect of the present invention.
  • salts of tranexamic acid ester are not limited in particular as long as they are salts that are physiologically acceptable, more specifically pharmaceutically and/or cosmetically acceptable, and examples include, for instance, inorganic salts such as phosphate, hydrochloride, hydrobromide and sulphate, and salts with organic acids such as ⁇ -hydroxy acids (glycolic acid, lactic acid, malic acid, citric acid and the like) , acidic amino acids, long-chain fatty acids (palmitic acid, stearic acid, linoleic acid and the like) . These may be used singly, or used by combining two species or more.
  • silicone oils used in general for make-up preparations and agents for external use may be used as Component B.
  • Examples include, for instance :
  • linear polydimethylsiloxanes (dimethicones) , which may be chosen from the group consisting of polydimethylsiloxanes such as those sold by GOLDSCHMIDT under the trade name ABIL or those sold by CLEARCO under product codes PSF, whose viscosities range from 100,000 to 2,500,000 cSt at 25°C or those sold by DOW CORNING under trade name DC 200 100,000 or those sold by RHODIA such as RHODORSIL 47V 100,000 or those sold by SHIN ETSU under the trade name KF-96H; linear polydimethylsiloxanes containing trimethylsilyl end groups such as some silicon oils sold by GENERAL ELECTRIC under the Viscasil series or containing trihydroxysilyl end groups ; silicone gums (polydiorganosiloxanes) with a high molecular mass used alone or as a mixture in a solvent chosen from volatile silicones, polydimethylsiloxane oils (PDMS) , polyphenylmethylsilox
  • Polydimethylsiloxanes (dimethicones) are preferably used in this invention.
  • the silicon oils have a viscosity of at least 100,000 cSt at 25°C, for example of at least 500,000 cSt at 25°C or even of at least 1,000,000 cSt at 25°C. Their viscosity is generally less than 2,000,000 cSt at 25 0 C. Mixtures of silicon oils having different viscosities within the above ranges may also be used. For instance, a silicon oil having a viscosity of about 100,000 cSt at 25°C may be used together with another silicon oil having a viscosity of about 1,000,000 cSt at 25°C.
  • silicon oils may be used singly, or two species or more may be combined for use. Among these, for instance, when using dimethicones, adhesiveness is inhibited, and the "sticky" feeling or the oily feeling (oiliness) of the skin can be attenuated. Note that these silicone oils can be used by selecting one species, two species, or more.
  • the mixing ratio of the Component A to the Component B is preferably from 0.01:100 to 100:0.01, more preferably from 1:10 to 10:1 and even more preferably from 5:1 to 10:1, by weight.
  • a cosmetic or dermatological topical composition is a collective name for a composition that is administered to the skin by external use.
  • a composition can be used as, for instance, medicine or skin- care for epicutaneous use, such as whitening preparation, cleansing preparation, bath agent, disinfectant for epicutaneous use, bactericide for epicutaneous use and the like, and can preferably be used in particular as a whitening preparation.
  • the topical composition of the present invention can be in the form of an ointment, cream, fluid, milky lotion, cosmetic water, lotion, serum, gel, facial mask such as a sheet mask, watery or anhydrous stick, lipstick, powder, and the like.
  • this composition includes water. More preferably, it is in the form of a gel or of an oil-in-water or water-in-silicon emulsion.
  • Oil-in-water emulsions may preferably be produced according to a process involving : adding Component A blended with a solvent at high temperature into the heated oil phase of the emulsion, mixing the heated water phase therewith, homogenizing the mixture thus obtained and cooling it. This process might prevent unwanted crystallization of Component A.
  • Various additives can be provided in this topical composition and in particular, any type of agent used in a common medicinal product, quasi drug, cosmetic and the like.
  • examples of carrier materials included in the topical composition include well known raw materials such as animal and plant oils, mineral oils, synthetic oils, ester oils, waxes, linear higher alcohols, fatty acids, surfactants, phospholipids, gelling and/or thickening agents (including taurate homopolymers and copolymers, either crosslinked or not, which may be hydrophobized, including Simulgel NS from SEPPIC, and Aristoflex AVC and HMB from CLARIANT ; and polyacrylamide homo- and copolymers, including Sepigel 305 from SEPPIC) ) , alcohols such as ethanol, polyols (including glycerine and propylene glycol) , fillers such as clay minerals, soft-focus powders, preservatives, fragrances, pigments and purified water.
  • raw materials such as animal and plant oils, mineral oils, synthetic oils, ester oils, waxes, linear higher alcohols, fatty acids, surfactants, phospholipids, gelling and/or thickening agents (including tau
  • topical composition of the present invention may include one or more silicon oils, volatile or non volatile, or organic solutions containing organosiloxane resin, having a viscosity of less than
  • polyorganosiloxanes such as polydimethylsiloxanes (dimethicones) , which may be chosen from the group consisting of tetramethyldisiloxane, hexamethyltri- siloxane, octamethyltetrasiloxane and their mixtures ; polyalkylcyclosiloxanes, such as polydimethyl- cyclosiloxanes (cyclomethicones) , which may be chosen from the group consisting of : octamethylcyclotetra- siloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane, such as those sold by DOW CORNING under the trade names DC 200, DC 244, DC 245, DC 344 et DC 345 or by GENERAL ELECTRIC under the trade names SF-1204, SF-1202, GE 7207 and GE 7158 or by S
  • silicones o polyether-modified polysiloxanes such as a dimethylsiloxane and methyl (polyoxyethylene) siloxane copolymer or methyl (polyoxyethylene and polyoxypropylene) siloxane copolymer.
  • Preferred non- emulsifying organopolysiloxane elastomers are dimethicone/vinyl dimethicone crosspolymers .
  • dimethicone/vinyl dimethicone crosspolymers are supplied by a variety of suppliers including DOW
  • SHIN ETSU KSG-15, 16, 18 [dimethicone/phenyl vinyl dimethicone crosspolymer]
  • GRANT INDUSTRIES KSG-15, 16, 18 [dimethicone/phenyl vinyl dimethicone crosspolymer]
  • lauryl dimethicone/vinyl dimethicone crosspolymers supplied by SHIN ETSU e.g., KSG-31, KSG-32, KSG-41, KSG-42,
  • KSG-43, and KSG-44) organopolysiloxane resins such as the product sold under the name DOW CORNING 593 or those sold under the names Silicone Fluid SS 4230 and SS 4267 by GENRAL ELECTRIC and which are dimethyl/trimethylpolysiloxane; and - their mixtures.
  • topical composition of the present invention may suitably contain various active agents which may be chosen from the group consisting of:
  • antioxidants such as ascorbic acid and its derivatives, including ascorbyl palmitate, ascorbyl tetraisopalmitate, ascorbyl glucoside, magnesium ascorbyl phosphate, sodium ascorbyl phosphate and ascorbyl sorbate ; tocopherol and its derivatives, such as tocopheryl acetate, tocopheryl sorbate and others esters of tocopherol ; BHT and BHA ; and plant extracts, for instance from Chondrus cripsus, Rhodiola, Thermus thermophilus, mate leaf, oak wood, kayu rapet bark, sakura leaves and ylang ylang leaves ;
  • acyl aminoacids for instance Maxilip, Matrixyl 3000 or Biopeptide CL from SEDERMA or Sepilift from SEPPIC
  • Pisum sativum extracts hydrolyzed soy proteins, methylsilanol derivatives such as methylsilanol mannuronate, hydrolyzed cucurbita pepo seedcake, Scenedesmus extract
  • anti-pollution agents such as Moringa pterygosperma seed extracts
  • keratolytic agents such as ⁇ -hydroxyacids (for instance, glycolic, lactic, citric, malic, mandelic or tartaric acid) and ⁇ -hydroxyacids (for instance, salicylic acid)
  • esters including C 12 - 13 alkyl lactate, and plant extracts containing these hydroxyacids, such as Hibiscus sabdriffa extracts ; astringents such as hamamelis extracts
  • the topical composition can also include organic and/or inorganic sunscreens.
  • organic sunscreens mention can be made of dibenzoylmethane derivatives such as butyl methoxydibenzoylmethane (Parsol 1789 from HOFFMANN LA ROCHE) , cinnamic acid derivatives such as ethylhexyl methoxycinnamate (Parsol MCX from HOFFMANN LA ROCHE) , salicylates, para-aminobenzoic acids, ⁇ - ⁇ '- diphenylacrylate derivatives, benzophenone derivatives, benzylidenecamphor derivatives such as terephtalylidene dicamphor sulphonic acid, phenylbenzimidazole derivatives, triazine derivatives, phenylbenzotriazole derivatives, anthranilic derivatives, all of which may be coated or encapsulated.
  • dibenzoylmethane derivatives such as butyl me
  • pigments or alternatively nanopigments formed from coated or uncoated metal oxides such as, for example, titanium oxide, iron oxide, zinc oxide, zirconium oxide or cerium oxide nanopigments; which are all UV photoprotective agents well known per se.
  • the mixing ratio of Component A and Component B in the topical composition is not restricted in particular. However, from the view point of higher whitening, anti- aging, and skin roughness prevention effects, preferably 0.01:100 to 100:0.01, more preferably from 1:10 to 10:1 and even more preferably from 5:1 to 10:1, by weight are desirable. If this mixing ratio is less than the lower limit value (that is to say, with respect to 100 mass parts of Component B, Component A is less than 0.01 mass parts), whitening, anti-aging, and skin roughness prevention effects tend to not improve enough.
  • this mixing ratio exceeds the upper limit value (that is to say, with respect to 0.01 mass parts of Component B, Component A exceeds 100 mass parts) , dispersing and mixing Component A homogeneously in the topical composition tend to be difficult. Note that, such mixing ratio is particularly useful when using the composition for epicutaneous use according to the present invention as an anti-aging agent.
  • Component B a mixing ratio of cyclic silicone oil and linear silicone oil of preferably 0.01:100 to 100:0.01 and more preferably 1:100 to 100:1 by mass criteria is optimum. If this mixing ratio is less than the lower limit value
  • Component A is preferably mixed in the topical composition in an amount of from 0.5 to 10%, more preferably from 1 to 6% by weight, and even more preferably from 2 to 4% by weight, such as 3% by weight, when the total of all the components of the topical composition is taken as 100%.
  • Component B is preferably mixed in the topical composition in an amount of from 0.01 to 50%, more preferably from 0.1 to 30%, even more preferably from 0.1 to 10% by weight, when the total of all the components of the topical composition is taken as 100%. If this mixing proportion is less than 0.01 weight % and no low-viscosity silicon oil is provided, depending on the circumstance, the desired effect of improving the feeling upon use sometimes cannot be obtained; in addition, if 50 weight % is exceeded, depending on the circumstance, a "sticky" feeling can sometimes occur.
  • the desirable pH of the topical composition of the present invention is 4 to 8, and preferably 4.5 to 7, from the view point of obtaining a sufficient effectiveness at the same time as increasing safety.
  • Example 1 Evaluation of skin penetration ⁇ Compositions 1 and 2 and Comparative Compositions 1 and 2> Creams whose compositions are shown in the following Table 1 were prepared as a topical composition according to established methods well known from the skilled artisan.
  • the test samples remained in contact with the skin model on the donor side for 24 hours at 32°C.
  • the receptor was filled with isotonic phosphate buffer (pH 4.5).
  • TXC within the skin model was extracted with 2.0 ml of the mobile phase (Table 2) for 15 minutes supersonic treatment at below 0 0 C. Each 1.0 ml of the extracted solution was filtrated by a filter (0.45 ⁇ m, for HPLC grade, SUN Sri Co. Ltd. ) . The determination of TXC concentration in the extract was carried out by HPLC analysis.
  • TXC penetrated into a fluid through the skin model was determined by a following procedure. Each 1.0 ml of the receptor fluid was also filtrated to prepare the test solution by the same filter described above. The determination of TXC concentration in the fluid was carried out by HPLC analysis.
  • TXC total amount of TXC from the compositions 1 and 2 according to this invention were much higher than for comparative compositions 1 and 2 in both 3D skin model and penetration into a fluid. Therefore, it was demonstrated that the skin absorption ability of TXC could be improved clearly with the addition of silicon oils having a viscosity of a hundred thousand centistokes and over.
  • Creams whose compositions are shown in the following Table 4 were prepared as a topical composition according to established methods well known from the skilled artisan.
  • compositions topical compositions
  • Comparative Compositions 3 to 7 For the creams (topical compositions) of Composition 3 and Comparative Compositions 3 to 7, the effects of action exerted on the skin such as amelioration of skin condition and amelioration of wrinkles, were measured and evaluated by the test indicated below.
  • test sample was applied over the face of the test subjects of each group in suitable amounts, twice daily, in the morning and at night.
  • the test was performed continuously for 8 weeks, and the following items were measured as skin conditions immediately before the beginning of the test, 4 weeks after and 8 weeks after.
  • test subjects were placed in a room with constant temperature and humidity (22°C; relative humidity: 45%), acclimatized to the environment by resting for 15 minutes, whereafter the measurements were carried out according to the procedures shown in (1) to (6) below. Note that in all cases mentioned below in (1) to (6), a significant difference test was performed for each measurement value by the Student t test or the Wilcoxson test, to evaluate the difference between the blank non-application group and the group with the topical compositions- applied.
  • Composition 3 are shown in black filled squares, and black filled circles. In addition, measurement data of each
  • Comparative Composition are shown in white empty circles.
  • solid line B, solid line El, and broken lines Cl to C5 represent respectively the blank, Composition 3 and Comparative
  • compositions 3 to 7 (hereinafter, same for Fig. 2 to 9) .
  • Transepidermal water loss was measured using the dual channel transepidermal water loss meter AS-TW2 (manufactured by ASAHI BIOMED) . The measurement was carried out 3 times, and the mean value thereof was taken as TEWL (g/cm 2 /h) . Note that a decrease in the TEWL value is one indication representing an improvement of the skin condition. The measurement results are shown in Fig. 2.
  • stratum corneum cells were peeled using a commercially available adhesive tape (30 ⁇ 24 mm) .
  • the peeled stratum corneum cells were transferred onto a slide glass and were used as samples for brilliant green/gentian violet
  • BG BG staining
  • DAM N- (7-dimethylamino-4-methyl-3-coumarinyl) maleimide staining.
  • Stratum corneum cell area, stratum corneum cell peeling pattern (degree of multi-layer peeling) , nucleated cell ratio, and the degree of SH staining due to free SH groups were used as assessment parameters. Note that a decrease in the stratum corneum cell area is one indication representing the acceleration of the speed of epidermis turnover. In addition, a diminution of the stratum corneum cell peeling pattern, a diminution of nucleated cell ratio, and a diminution of the degree of SH staining are all one indication representing normal keratinization. Each of the measurement results is shown in Fig. 5 to Fig. 8.
  • a template (replica) of the wrinkles present at the eye corners was obtained using a replica agent. Thereafter, against this template, the shadows of the wrinkles were generated by hitting with a light from a direction that is orthogonal to the direction in which the wrinkles predominantly run and 30° above. In addition, analyses were performed on the images thereof, to measure the depth of the shadows of the wrinkles that arose. Note that SILFLO (manufactured by Flexico. England) was used as the replica agent, which allows a form to be transferred finely, and has numerous performance reports for taking replica. The results are shown in Fig. 9.
  • Figs. 1 to 9 reveal that the cream of Composition 3 shows higher improvement effects than the creams of Comparative Compositions 3 to 7 for all the measurement items described above.
  • the composition for epicutaneous use of the present invention significantly improves wrinkle and skin condition and can sufficiently accelerate whitening of the skin.
  • the composition for epicutaneous use pertaining to the present invention can maintain high improvement effect even after a prescribed time period. This demonstrates that stability of application onto the skin, percutaneous penetrability, and continuity of long term release from skin, of tranexamic acid ester, are improved.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition cosmétique ou dermatologique topique contenant un ester d'acide tranexamique et/ou un sel de celui-ci (composant A) et de l'huile de silicone présentant une viscosité d'au moins 100 000 cSt à 25°C (composant B), qui n'est pas un organopolysiloxane réticulé, à condition que la composition ne contienne pas 4% en poids d'hydrochlorure d'ester cétylique d'acide tranexamique, en combinaison avec 0,3% en poids de polydiméthylsiloxane présentant une viscosité de 1 000 000 cSt à 25°C.
PCT/IB2006/003008 2006-10-26 2006-10-26 Composition topique de soin de la peau contenant un ester d'acide tranexamique Ceased WO2008050173A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011069915A1 (fr) * 2009-12-11 2011-06-16 Chanel Parfums Beaute Composition à usage externe et procédé de production associé
WO2012101102A3 (fr) * 2011-01-24 2013-05-02 Chanel Parfums Beaute Composition se présentant sous la forme d'une émulsion huile dans eau et son procédé de production
WO2021101508A1 (fr) * 2019-11-18 2021-05-27 Actera Ingredients, Inc. Sels d'esters de l'acide tranexamique
US11642324B1 (en) 2022-03-01 2023-05-09 Bio 54, Llc Topical tranexamic acid compositions and methods of use thereof

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Publication number Priority date Publication date Assignee Title
JPH07215839A (ja) * 1994-02-04 1995-08-15 Shiseido Co Ltd 皮膚外用剤
WO2000037071A1 (fr) * 1998-12-21 2000-06-29 Aps Kbus 8 Nr. 4788 Traitement local de dermatoses
EP1180371A1 (fr) * 2000-03-27 2002-02-20 Shiseido Company Limited Agents favorisant la formation d'une membrane de base de la peau, agents favorisant la formation d'une peau artificielle et procede de production de peau artificielle
JP2002234836A (ja) * 2001-02-13 2002-08-23 Kinji Ishida ストレス対応皮膚外用剤
EP1369101A1 (fr) * 2001-03-16 2003-12-10 Shiseido Company Limited Preparation cosmetique en emulsion eau-huile-eau
EP1543811A1 (fr) * 2002-07-16 2005-06-22 Shiseido Company Limited Composition emulsion huile dans eau contenant des particules
WO2006114338A1 (fr) * 2005-04-26 2006-11-02 Chanel Parfums Beaute Composition topique pour le soin de la peau

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07215839A (ja) * 1994-02-04 1995-08-15 Shiseido Co Ltd 皮膚外用剤
WO2000037071A1 (fr) * 1998-12-21 2000-06-29 Aps Kbus 8 Nr. 4788 Traitement local de dermatoses
EP1180371A1 (fr) * 2000-03-27 2002-02-20 Shiseido Company Limited Agents favorisant la formation d'une membrane de base de la peau, agents favorisant la formation d'une peau artificielle et procede de production de peau artificielle
JP2002234836A (ja) * 2001-02-13 2002-08-23 Kinji Ishida ストレス対応皮膚外用剤
EP1369101A1 (fr) * 2001-03-16 2003-12-10 Shiseido Company Limited Preparation cosmetique en emulsion eau-huile-eau
EP1543811A1 (fr) * 2002-07-16 2005-06-22 Shiseido Company Limited Composition emulsion huile dans eau contenant des particules
WO2006114338A1 (fr) * 2005-04-26 2006-11-02 Chanel Parfums Beaute Composition topique pour le soin de la peau

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8647650B2 (en) 2009-12-11 2014-02-11 Chanel Parfums Beaute Composition for external use and method for producing the same
JP2011140487A (ja) * 2009-12-11 2011-07-21 Chanel Keshohin Gijutsu Kaihatsu Kenkyusho:Kk 外用組成物及びその製造方法
US20120244204A1 (en) * 2009-12-11 2012-09-27 Chanel Parfums Beaute Composition for external use and method for producing the same
WO2011069915A1 (fr) * 2009-12-11 2011-06-16 Chanel Parfums Beaute Composition à usage externe et procédé de production associé
US8758785B2 (en) 2009-12-11 2014-06-24 Chanel Parfums Beaute Composition for external use and method for producing the same
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