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WO2007082864A2 - Utilisation du chavicol comme antiseptique - Google Patents

Utilisation du chavicol comme antiseptique Download PDF

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Publication number
WO2007082864A2
WO2007082864A2 PCT/EP2007/050345 EP2007050345W WO2007082864A2 WO 2007082864 A2 WO2007082864 A2 WO 2007082864A2 EP 2007050345 W EP2007050345 W EP 2007050345W WO 2007082864 A2 WO2007082864 A2 WO 2007082864A2
Authority
WO
WIPO (PCT)
Prior art keywords
chavicol
use according
composition
skin
agents
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/EP2007/050345
Other languages
English (en)
Other versions
WO2007082864A3 (fr
Inventor
Carlo Ghisalberti
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.)
Polichem SA
Original Assignee
Polichem 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 Polichem SA filed Critical Polichem SA
Publication of WO2007082864A2 publication Critical patent/WO2007082864A2/fr
Publication of WO2007082864A3 publication Critical patent/WO2007082864A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • 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
    • A61P17/08—Antiseborrheics
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the invention relates to the use of chavicol (p-allylpenol) as an antiseptic and, in particular, for the manufacture of a composition indicated for the treatment of infected skin and scalp.
  • the invention also relates to a regimen or a method for the treatment of infected skin and scalp which comprises topically applying a composition comprising chavicol.
  • chavicol p-allylpenol
  • the body normally hosts a variety of micro-organisms including bacteria and fungi. Skin and scalp are in fact a good growth medium of lipophilic, generally nonpathogenic ubiquitous anaerobic micro-organisms. Some of these are even useful to the body, some produce no harm or benefits, while others may cause harmful infections.
  • Propionibacterium acnes infects oily skin and provokes acne, a common disorder characterized by follicular papules or comedones either in inflammatory or non inflammatory conditions.
  • Acne vulgaris affects the areas of skin with the densest population of sebaceous follicles including face, the upper chest, and the back.
  • other key factors in acne are the follicular epidermal hyperproliferation and an excessive sebum production.
  • Yeasts specifically Malassezia furfur or Pityrosporum ovale are the pathogenic agents linked to several skin diseases including: dandruff, seborrheic dermatitis, folliculitis, pityriasis versicolor, and atopic dermatitis.
  • Pseudomonas folliculitis is a recognized, community-acquired skin infection resulting from the bacterial colonization of hair follicles after exposure to contained, contaminated water.
  • infection caused by strains of P. aeruginosa was acquired secondary to skin contamination.
  • P. putida is another common cause of skin and scalp infection.
  • pathogens may gain entrance to the dermis to cause high-impact disorders.
  • cellulites in skin and appendages is, in vast majority of cases, caused by Streptococcus pyogenes or Staphylococcus aureus.
  • Further aggressive pathogen such as Salmonella typhimurium is a proved skin tumor initiating and promoting bacteria.
  • An object of this invention is the use of chavicol to manufacture an antiseptic composition to kill or eradicate certain pathogenic micro-organisms in skin and scalp.
  • Another object of this invention the use of chavicol for the manufacture of a topically administrable, cosmetic/dermatologic composition for the treatment of infected skin and/or scalp.
  • Another object of this invention the use of chavicol in conjunction with other active ingredients for the manufacture of a topically administrable, cosmetic/dermatologic composition for the treatment of infected skin and/or scalp.
  • a further object of this invention is a cosmetic or regimen for the cosmetic/dermatologic treatment of infected skin and/or scalp in mammalian subjects, preferably human, in need of such a treatment.
  • chavicol is defined to include derivatives or prodrugs thereof.
  • derivative or prodrug means any pharmaceutically acceptable salt, ester, salt of an ester, or other derivatives which capable of releasing chavicol.
  • Particularly favoured derivatives and prodrugs are those that increase the bioavailability of chavicol when administered to a subject in need thereof, e.g. enhance the delivery of chavicol into the skin layers or allow the orally administered compound to be more readily absorbed into the blood.
  • infected skin and scalp means an skin or scalp with over-growth infection of micro-organism.
  • chavicol is suitable for the treatment of infections caused by susceptible strains of the designated micro-organisms in the complicated skin and skin structure infections caused by such as, for example, yeast/fungi of genus Malassezia (or Pityrosporum) or Candida, and bacteria of genus
  • Propionibacterium Pseudomonas, Salmonella, Staphylococcus, Streptococcus, as well as Escherichia coli, Enterococcus faecalis, and Bacteroides fragilis.
  • Chavicol alias 4-(2-propenyl)-phenol, or p-hydroxy-allylbenzene, or 4-allylphenol, with MW 134.18 (CAS 501-92-8) is a colourless liquid product with m.p. 16 0 C.
  • chavicol is used to manufacture an antiseptic topically administrable composition to kill or eradicate pathogenic micro- organisms in skin and scalp
  • chavicol is used to manufacture a cosmetic/dermatologic composition for the treatment of infected skin and/or scalp.
  • the present invention refers to the use of chavicol as active ingredient in the manufacture of a topically administrable composition suitable for the treatment of infected skin and scalp to kill superinfecting anaerobic microorganisms;
  • chavicol is used in association with other active principles which have auxiliary action in the treatment and/or the disinfection of infected skin and scalp or may provide skin benefits.
  • active principles are, for instance, other antibiotics such as erythromycin, clindamycin, tetracyclines, chlorexidine, benzoylperoxide, cedrene, caryophyllene, longifolene, and thujoene; comedolytic agents such as tretinoin, adapalene, tazarotene, salicylic acid, benzoic acid, and derivatives thereof; antinfiammatory agents such as NSAID (i.e.
  • chavicol can be incorporated into a variety of formulations suitable for topical delivery of active ingredients.
  • the topical formulations suitable for topical treatment of treat superinfected oily skin and scalp are creams, lotions, mousses, sprays, emulsions, shampoos, gels and the like, which are manufactured according to methods commonly known in the art (see, for instance: Topical Formulations: Design and Development-Bozena Michniak/Paperback/CRC Press, LLC/February 1999; Remington: The Science and Practice of Pharmacy 20 th - Alfonso L.
  • Gennaro Alfonso R. (Ed. ) Gennaro; Publisher: Lippincott Williams & Wilkins, December 2000,20th Ed.; Encyclopedia of Pharmaceutical Technology- James Swarbrick (Editor), James C. Boylan (Editor)/Hardcover/Marcel Dekker/May 1997).
  • the amount of chavicol that may be used according to the invention obviously depends on the desired effect.
  • the amount of chavicol in the topical composition for treating and/or disinfecting skin and/or scalp according to this invention may range from about 0.1% (w/w) to about 10% (w/w).
  • the topical compositions useful for delivering chavicol may contain the usual acceptable excipients, including carriers and vehicles, preservative agents, surfactants, moisturizing agents, thickeners, perfumes, chelating agents, water, alcohols, antioxidants, antiseptics, colorants and adsorbents.
  • One embodiment of the invention thus features a regimen or method to treat infected skin and scalp comprising topically applying chavicol in association with a cosmetically/dermatologically acceptable excipients.
  • the method of the present invention can be performed for a period ranging from several days to several months, e.g. between 1 week and 6 months, or even longer if necessary.
  • the dosage levels can be kept constant over the treatment period.
  • the treatment can start at relatively high dosages, e.g. between the levels indicated above and twice these levels for a first period of e.g. between 1 and 6 weeks, followed by relatively low dosages of e.g. half the levels indicated above, for a second period of e.g. between 4 weeks and 1 year or even longer.
  • the treatment can be given to any subject suffering or liable to suffering from infected skin, for example acne.
  • the treatment can also be given as a means to inhibit further expansion of acne.
  • the anti-septic treatment can also suitably be given during the menstrual period.
  • An important aspect of the present invention is that chavicol, although it kills superinfecting anaerobic micro-organisms, it possesses no significant estrogenic potential and no significant sensitizing potential.
  • Chavicol suitable for purpose of the invention can be obtained from chavicol- containing plant distillates, or by chemical synthesis with know methods, provided that the final purity of the material is not less than 95% w/w of the active ingredient.
  • Estragole l-methoxy-4-(2- propenyl)benzene
  • chavicol by demethylation (methyl-ether cleavage), e.g. with EtMgBr, MeMgI, HBr/AcOH, EtSNa/DMF, TMSI, pyridine.HCl, BBr 3 and the like.
  • chavicol suitable for the inventive purpose may be from any natural source and/or synthetic method, a convenient process for manufacturing chavicol is herein provided.
  • the process entails the demethylation of Estragole with a Lewis acid followed a 2-step extractions in alkaline and acid-neutral media.
  • this reaction is carried out under mild conditions with a Lewis acid such as boron alogenide (BX 3 ) associated with a quaternarium ammonium-iodine salt, preferably the former is BCl 3 and the latter 77-Bu 4 NI, preferably in 1 : 1 ratio at around 1.5 eq., wherein the reaction is followed by at least two solvent-water extractions to afford pure chavicol.
  • a Lewis acid such as boron alogenide (BX 3 ) associated with a quaternarium ammonium-iodine salt
  • Samples are taken from the patients' scalp are isolated, purified on agar and stored in peptone/dextrose slant agar tubes. The strains were applied, undiluted or diluted 1:100, to an RPMI 1640 agar (Gibco/BRL, Life Technologies GmbH, Eggenstein, D) containing about 1.0 [mu]g/ml Pityrosporum ovale strains. The activity of chavicol was determined by the microtiter dilution technique in RPMI 1640 medium. The growth medium RPMI 1640 buffered with 0.165 M morpholinopropanesulfonic acid pH 7.0 is introduced into 96-well microtiter plates.
  • a single colony of C. albicans has been incubated at 30 0 C for 48 hours in a 5 ml growth medium Yeast Peptone-Dextrose ("YPD") containing lOg/1 yeast extract, 20 g/1 peptone and 20 g/1 dextrose.
  • YPD Yeast Peptone-Dextrose
  • At day 3.5 ⁇ l of saturated culture in 2 ml in YPD was incubated at 30 0 C for 65 hours in the presence of different concentration of chavicol prepared in serial dilutions by a factor of 10 in ethanol.
  • plates have been visually analyzed, wherein the absence of turbidity indicates no growth. Chavicol MIC50 on C. albicans results ⁇ 2 mmol.
  • Example 3 Antiseptic activity on Pseudomonas yutida
  • KT2440 Pseudomonas putida
  • LB rich medium LePoivre
  • 20 ⁇ l of the saturated colony has been inoculated in 2 ml of LP medium in the presence of different concentration of chavicol, prepared in serial dilutions by a factor of 10 in ethanol.
  • plates have been analyzed for optical density at 600nm (OD 600) by triplicate samples. Chavicol MIC50 on Pseudomonas putida results ⁇ 2 mmol.
  • a single colony of E. coli 71/18 has been inoculated in 2 ml a poor medium named "M9" prepared with Na 2 HPO 4 (7.526 g/1), KH 2 PO 4 (3.0 g/1), NH 4 Cl (l.Og/1), NaCl (0.5 g/1), MgSO 4 (1 mM), CaCl 2 (0.1 mM), vitamin Bl (5 ⁇ g/ml), and glucose (0.2%), then incubated at 37°C under slow stirring.
  • M9 prepared with Na 2 HPO 4 (7.526 g/1), KH 2 PO 4 (3.0 g/1), NH 4 Cl (l.Og/1), NaCl (0.5 g/1), MgSO 4 (1 mM), CaCl 2 (0.1 mM), vitamin Bl (5 ⁇ g/ml), and glucose (0.2%), then incubated at 37°C under slow stirring.
  • Example 5-6 Antiseptic activity on Salmonella Typhimurium and Propionibacterium acnes
  • Example 4 The method of Example 4 has been applied with Salmonella Typhimurium (ATCC 14028) and Propionibacterium acnes, wherein Chavicol MIC50 results 2 and 2.5 mmol, respectively.
  • Chavicol Determination of the efficacy of Chavicol on strains of Propionibacterium acnes and Pityrosporum ovale.
  • samples are taken from the patients' skin or scalp are isolated, purified on agar and stored in peptone/dextrose slant agar tubes.
  • the strains were applied, undiluted or diluted 1:100, to an RPMI 1640 agar (Gibco/BRL, Life Technologies GmbH, Eggenstein, Germany) containing about 1.0 [mu]g/ml Propionibacterium acnes and Pityrosporum ovale strains.
  • the activity of Chavicol is determined by the microtiter dilution technique in RPMI 1640 medium.
  • the growth medium RPMI 1640 buffered with 0.165 M morpholinopropanesulfonic acid pH 7.0 is introduced into 96-well microtiter plates. Serial dilutions by a factor of 2 are prepared to result in final concentrations of 256 to 0.002 [mu]g/ml of Chavicol.
  • the microtiter plates prepared in this way are incubated with the test strains. The initial cell count is 1-5x10 3 colony- forming units per ml of growth medium.
  • the microtiter plates are incubated at 35 0 C for 48 hours. As determined by photometry at 510 nm, Chavicol MIC50 is ⁇ 2.5 mmol on Propionibacterium acnes, and ⁇ 0.5 mmol on Pityrosporum ovale.
  • a 2% cream is made by melting 2 g of Chavicol at 75 0 C in 10 g EmulvamaTM AGC (premix of: glyceril stearate, cetearyl alcohol, stearic acid, sodium cocoyl glutamate) from VaMa Farmacosmetica (Zibido (MI), Italy) in water at 75 0 C under high stirring.
  • EmulvamaTM AGC premix of: glyceril stearate, cetearyl alcohol, stearic acid, sodium cocoyl glutamate
  • Influence of Chavicol 2% on sebum excretion rate is expressed as % area occupied by sebum spots.
  • Each line represents an individual study volunteer (Skin Oiliness Reference: Low: 4%>; Normal: 4-6.5%; Oily: 6.5-9%; Very Oily: >9%).
  • Safety evaluations are based on detection of potential skin irritation or other signs of adverse reaction to the treatment.
  • Example 9 Emulsion 100 g of emulsion contains
  • Azelaic acid 1.5 g perfume, additives, preservatives q.b.
  • Example 10 - Shampoo 100 g of detergent contains:
  • Triethanolamine laurylsulfate 5.O g
  • Example 11 - Gel 100 g of gel contains:
  • Example 12 Cream-Gel 100 g of cream-gel contains:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des compositions topiques contenant du chavicol (p-allylphénol), utilisées de manière efficace dans le traitement de la peau et du cuir chevelu infectés par des microorganismes pathogènes tels que les levures, les champignons ou les bactéries. Le chavicol peut être présent en une quantité variant de 0,1 à 10% en poids de la composition qui peut se présenter sous forme de crème, de lotion, de mousse, de spray, d'émulsion, de shampoing ou de gel. La composition peut également contenir un principe actif supplémentaire, avec les excipients habituels acceptables d'un point de vue topique.
PCT/EP2007/050345 2006-01-20 2007-01-15 Utilisation du chavicol comme antiseptique Ceased WO2007082864A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IB2006000087 2006-01-20
IBPCT/IB2006/000087 2006-01-20

Publications (2)

Publication Number Publication Date
WO2007082864A2 true WO2007082864A2 (fr) 2007-07-26
WO2007082864A3 WO2007082864A3 (fr) 2008-02-07

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Application Number Title Priority Date Filing Date
PCT/EP2007/050345 Ceased WO2007082864A2 (fr) 2006-01-20 2007-01-15 Utilisation du chavicol comme antiseptique
PCT/EP2007/050348 Ceased WO2007082866A2 (fr) 2006-01-20 2007-01-15 Utilisation du chavicol dans le traitement d'une peau et d'un cuir chevelu gras surinfectes

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/050348 Ceased WO2007082866A2 (fr) 2006-01-20 2007-01-15 Utilisation du chavicol dans le traitement d'une peau et d'un cuir chevelu gras surinfectes

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2606725A1 (fr) * 2011-12-20 2013-06-26 Symrise AG Dérivés de phénol en tant quýagents antimicrobiens
US8586008B2 (en) 2003-01-24 2013-11-19 Stiefel West Coast, Llc Pharmaceutical foam
US8808716B2 (en) 2009-02-25 2014-08-19 Stiefel Research Australia Pty Ltd Topical foam composition
KR101935904B1 (ko) * 2017-07-27 2019-01-07 주식회사 엑티브온 피부 외용제용 보존제, 이를 포함하는 화장료 조성물 및 약학 조성물

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016125344A1 (de) * 2016-12-22 2018-06-28 Peter Jürgensen Zubereitung zur Verwendung bei der Behandlung des erblich bedingten Haarausfalls

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20020693A1 (it) * 2002-04-03 2003-10-03 Carlo Ghisalberti Sostanze composizioni e metodi per il trattamento dell'alopecia androgenetica e dell'ipersecrezione sebacea

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8586008B2 (en) 2003-01-24 2013-11-19 Stiefel West Coast, Llc Pharmaceutical foam
US9486394B2 (en) 2003-01-24 2016-11-08 Stiefel West Coast, Llc Pharmaceutical foam
US8808716B2 (en) 2009-02-25 2014-08-19 Stiefel Research Australia Pty Ltd Topical foam composition
US10568859B2 (en) 2009-02-25 2020-02-25 Mayne Pharma Llc Topical foam composition
US10688071B2 (en) 2009-02-25 2020-06-23 Mayne Pharma Llc Topical foam composition
EP2606725A1 (fr) * 2011-12-20 2013-06-26 Symrise AG Dérivés de phénol en tant quýagents antimicrobiens
KR101935904B1 (ko) * 2017-07-27 2019-01-07 주식회사 엑티브온 피부 외용제용 보존제, 이를 포함하는 화장료 조성물 및 약학 조성물

Also Published As

Publication number Publication date
WO2007082864A3 (fr) 2008-02-07
WO2007082866A3 (fr) 2008-03-13
WO2007082866A2 (fr) 2007-07-26

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