EP2509989A1 - Sucrose octasulfates de zinc, leur preparation et leurs applications pharmaceutiques et cosmetiques - Google Patents

Sucrose octasulfates de zinc, leur preparation et leurs applications pharmaceutiques et cosmetiques

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Publication number
EP2509989A1
EP2509989A1 EP10795975A EP10795975A EP2509989A1 EP 2509989 A1 EP2509989 A1 EP 2509989A1 EP 10795975 A EP10795975 A EP 10795975A EP 10795975 A EP10795975 A EP 10795975A EP 2509989 A1 EP2509989 A1 EP 2509989A1
Authority
EP
European Patent Office
Prior art keywords
zinc
sucrose octasulfate
sucrose
salt
compound 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Withdrawn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
EP10795975A
Other languages
German (de)
English (en)
French (fr)
Inventor
Pierre Fabre
Séverine JEULIN
Marion Kopec
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.)
Pierre Fabre Dermo Cosmetique SA
Original Assignee
Pierre Fabre Dermo Cosmetique 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 Pierre Fabre Dermo Cosmetique SA filed Critical Pierre Fabre Dermo Cosmetique SA
Publication of EP2509989A1 publication Critical patent/EP2509989A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7016—Disaccharides, e.g. lactose, lactulose
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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

  • the present invention relates to a zinc sucrose octasulfate, its method of preparation and its use in the pharmaceutical and / or cosmetic field.
  • Oligosaccharides are carbohydrates whose hydrolysis provides only monosaccharides. These are sugars formed by the union of at least two molecules of simple sugars (or oses). Among the oligosaccharides is sucrose, a double sugar formed by the condensation of 2 oses: a glucose molecule and a fructose molecule.
  • Sulfated oligosaccharides are known in the literature and have multiple biological, cosmetic and / or therapeutic activities.
  • WO2006 / 017752 discloses a method of treating inflammation of the airways by employing oligosaccharides as active substance.
  • oligosaccharides is mentioned, moreover, totally sulphated poligosaccharide resulting from the condensation of glucose and fructose.
  • Sulfated oligosaccharides mainly aluminum sucrose octasulfate, are also used in the treatment of alopecia (US 5,767,104).
  • Sucrose octasulfate is used as an active ingredient in the treatment of gastric ulcers for its repairing / healing properties.
  • FR 2,646,604 describes formulations of sucrose octasulfate of aluminum, or sucralfate, with anti-inflammatory and healing properties for the treatment of wounds or other ulcerative inflammations.
  • WO 94/00476 discloses a method of treating lesions and / or inflammations of the digestive tract by administering a sulfated sucrose salt, more particularly potassium or sodium sucrose octasulfate.
  • FR 1 390 007 describes the topical use of formulation containing sucralfate in combination with copper and zinc sulfate as tissue regenerator, healing and soothing.
  • EP 0 230 023 describes the use of polysulfated oligosaccharides, more particularly potassium sucrose octasulfate, as wound healing agent.
  • the object of the present invention is to provide a novel compound with restorative, antimicrobial and anti-radical properties.
  • a novel compound appears useful in the preparation of pharmaceutical and / or cosmetic compositions for repairing the skin, healing wounds and promoting healing.
  • This type of composition combines the treatment of the skin with antimicrobial protection.
  • the present invention relates to the compounds of general formula I
  • n is an integer
  • Y represents OH, Cl, Br, I, NO 3> CeHsOR, CH 3 CO 2 , CF 3 CO 2 or -OCH 3 .
  • the compound is a compound
  • the compound of formula II corresponds to n equal to 4 in the general formula I.
  • the compound is a compound of formula
  • the compound of formula II corresponds to n equal to 3 in general formula I.
  • the compound is a compound of formula IV
  • the compound of formula II corresponds to n equal to 2 in the general formula I.
  • the compound is a compound of formula
  • the compound of formula II corresponds to n equal to 1 in general formula I.
  • the compound is a compound of formula VI
  • the compound of formula II corresponds to n equal to 0 in the general formula I.
  • the present invention also relates to the process for preparing these compounds.
  • M represents K, Na or H
  • Y represents OH, Cl, Br, I, NO 3 , BF 4 , C 6 H 5 O 7, CH 3 CO 2) CF 3 CO 2 or
  • n is an integer.
  • the compounds of general formula I are obtained starting from potassium sucrose octasulfate (M represents K), sodium sucrose octasulfate (M represents Na) or from the acid form of sucrose octasulfate (M represents H).
  • the starting sucrose octasulphate salt is the sodium or potassium salt
  • a step of exchange of potassium or sodium ions by protons is made by passing on an ion exchange resin.
  • a mineral salt of zinc selected from Zn (OH) 2, ZnC, ZnBr 2, Zn, Zn (NO 3) 2 or Zn (BF 4 ) 2, or an organic salt of zinc, chosen from Zn (CH 3 CO 2 ) 2, Zn (CF 3 CO 2 ) 2, Zn 3 (C 6 H 5 O 7 ) 2 or Zn (CH 3 O) 2 .
  • the zinc salt is added in the proportions necessary to obtain a compound of general formula I having an integer n between 0 and 0 and 4.
  • the invention therefore extends to the following preparation processes.
  • the sucrose octasulfate salt of step 1 is selected from potassium sucrose octasulfate or sodium sucrose octasulfate.
  • the passage over the ion exchange column makes it possible to obtain the acid form of the sucrose octasulfate salt. It is more particularly a cation exchange resin.
  • the cation exchange resin is Amberlite.
  • the zinc salt is chosen from zinc mineral salts such as Zn (OH) 2, ZnO, ZnCk, ZnBr 2 , ZnI 2 , Zn (NO 3) 2 or Zn (BF 4). ) 2, or organic zinc salts such as Zn (CH3C0 2) 2, Zn (CF3C02) 2, ⁇ 3 ( ⁇ 6 ⁇ 7) 2 or Zn (CH 3 O) 2.
  • the zinc salt is, for example, zinc hydroxide Zn (OH) 2 .
  • the precipitation of zinc sucrose octasulftate is carried out by addition of acetone.
  • Process for the preparation of the compounds of general formula I comprising the following steps: 1) dissolution in water of the acid form of sucrose octasulfate;
  • the zinc salt is chosen from zinc mineral salts such as Zn (OH) 2 , ZnO, ZnC, ZnBr 2, Zn, Zn (NO 3) 2 or Zn (BF 4 ) 2 or organic zinc salts such as Zn ( CH 3 CO 2 ) 2, Zn (CF 3 CO 2 ) 2 , Zn 3 (C 6 H 5 O 7) 2 or Zn (CH 3 O) 2 .
  • the precipitation of zinc sucrose octasulftate is carried out by addition of acetone.
  • the compounds of formula I according to the invention may be administered topically or orally.
  • the compound can be administered topically in a suitable formulation.
  • Assays of the compounds of formula I in the compositions of the invention may be adjusted to obtain an amount of active substance that is effective in achieving the desired therapeutic and / or cosmetic response for a particular composition to the method of administration.
  • the chosen level of dosage therefore depends on the desired therapeutic and / or cosmetic effect, the route of administration, the desired duration of treatment and other factors.
  • the invention therefore also relates to a pharmaceutical and / or cosmetic composition
  • a pharmaceutical and / or cosmetic composition comprising at least one compound of general formula I and a pharmaceutically and / or cosmetologically acceptable excipient.
  • the invention also relates to a medical device comprising at least one compound of general formula I and a pharmaceutically or cosmetologically acceptable excipient.
  • pharmaceutically and / or cosmetologically acceptable refers to molecular entities and compositions that do not produce adverse, allergic or other adverse reactions when administered to an animal or a human.
  • the composition according to the invention has a zinc sucrose octasulfate content according to the general formula I of between 0.01 and 30% by weight.
  • the composition comprises the compound of formula II.
  • composition according to the invention is chosen to allow topical or oral administration.
  • the topical form is chosen from the group consisting of a milk, a cream, a balm, an oil, a lotion, a gel, a foaming gel, a ointment, spray, paste, patch, suppository, etc.
  • the oral form is chosen from the group consisting of a gum, a lozenge, a tablet, a boiled sugar, a drinking gel, a dissolving powder, etc. .
  • the topical form includes topical dosage forms for cutaneous application, for oral application (oral mucosa), for genital application (anal mucosa, vaginal) and / or for gastric application.
  • the oral form includes oral dosage forms for oral application (oral mucosa) and / or for gastric application.
  • compositions according to the present invention are intended to promote healing.
  • the antimicrobial properties of zinc are well described.
  • the pharmaceutical and / or cosmetic compositions according to the present invention are therefore also intended to protect microbial infections.
  • compositions according to the present invention promote healing and / or protect against microbial infections.
  • the compounds of the invention can therefore be used in the treatment of the skin, in particular in the process of healing and improving its aesthetic appearance.
  • the compounds of the invention can therefore be used for the preparation of compositions and pharmaceutical and / or cosmetic products to promote healing.
  • Another object of the present invention thus relates to a compound according to the present invention for its use as a medicament.
  • Another object of the present invention also relates to a compound according to the present invention for its use as a cosmetic active ingredient.
  • Another object of the present invention is a compound according to the present invention for use as a medicament and / or cosmetic active ingredient.
  • the compounds of formula I are used for the treatment of the skin.
  • the compounds of Formula I are used to promote healing. More particularly, the invention relates to the healing of acute wounds such as for example abrasions, burns, radiodermites, or chronic such as for example ulcers, pressure ulcers, the foot of the diabetic.
  • acute wounds such as for example abrasions, burns, radiodermites, or chronic such as for example ulcers, pressure ulcers, the foot of the diabetic.
  • the invention relates to the healing of burns (thermal, mechanical, chemical, radiation), radiodermites, various irritations, dermatitis, abrasions, scrapes, scratches, cuts, leg ulcers, pressure sores. , diabetic wounds, gastric ulcers, canker sores, various mouth sores, scarring acne, cryotherapy scars, scars post surgery or post-act of aesthetic dermatology (laser, hair removal, peeling, injection), blisters, cheilitis, eczema, diaper rash, dermatoporosis etc.
  • the compounds of formula I are used to promote healing and / or protect microbial infections.
  • a solution of potassium sucrose octasulfate (1.50 g, 1.16 mmol, 1.00 equiv, 99%) in water (20 ml) is placed in a 100 ml flask.
  • the solution was passed through a column ( ⁇ 40 ⁇ 500 mm) containing 250 g of Amberlite IR 120 H ion exchange resin at a flow rate of 2-3 ml / min at 0 ° C.
  • the resulting mixture, hazy at about pH 6, is stirred overnight (about 12 hours) at room temperature. All these steps were carried out away from light by wrapping the reaction medium with aluminum foil.
  • sucrose octasulfate is determined by an anthrone spectrophotometric assay (Brooks, J., Griffin, VK, Kattan, MW, "A Modified Method for Total Carbohydrate Analysis of Glucose Syrups, Maltodextrins, and Other Starch Hydrolysis Products"; Cereal Chemistry, 63, 5, 465-466, 1986).
  • a standard solution of anthrone is prepared by dissolving 50 mg of anthrone in a mixture of 10 ml of distilled water and 90 ml of concentrated sulfuric acid.
  • sucrose octasulfate zinc is previously dehydrated under vacuum (about 23.5 Pa) at 30 ° C for 6h.
  • Three samples of respective volume 0.3, 0.6 and 0.7 ml of an aqueous solution of sucrose octasulfate zinc (0.4018 mg / ml) are diluted with distilled water to 2 ml.
  • 6.0ml of the standard anthrone solution is added to each solution.
  • the solutions obtained are heated in a water bath for 10 minutes. After returning to room temperature immediately, the absorbance of each solution is measured at 620 nm, using sucrose as reference (Results, see Table 1).
  • Zinc was assayed by EDTA titration.
  • Zinc sucrose octasulfate (0.2009 g) is dissolved in deionized water (250 ml). The salt is titrated with an aqueous solution of EDTA (0.0101 M) with 6 ml of hexamethylenetetramine (20%) as buffer solution and 2 drops of orange xylenol (0.2%) as color indicator (Table 2).
  • the zinc / sucrose octasulfate ratio is 2.86 / 0.737, which is 3.88. d. Search for potassium impurities
  • Ultra Fast Liquid Chromatography (UFLC) was used to detect the presence of potassium from the starting material.
  • sucrose octasulfate of zinc obtained according to Example 1 and two controls were analyzed by UFLC:
  • the migration of epithelial cells is an important step in the development and processes of tissue repair, such as embryogenesis and scarring.
  • keratinocytes are "activated" to undertake the migration process.
  • the cells then see their phenotype influenced by interactions with the extracellular matrix on the one hand and by cell-cell interactions on the other hand (McMillan JR, Akiyama M., Shimizu H. Epidermal Basement Membrane Component Area: Ultrastructural Distribution and molecular interactions J. Derm. Se. 31: 169-177, 2003).
  • the keratinocytes of the basal seat of the banks of a wound migrate on the wound and cover it.
  • keratinocytes are activated in contact with fibronectin, interstitial dermal collagen (type 1), collagen IV and laminin 5 of the basal lamina. They are also regulated by certain polypeptide growth factors such as TGF ⁇ , TGF ⁇ and EGF.
  • cytokines IL1, TNFa
  • chemokines RANTES and PIL-8 also contribute to increase the re-epithelization rate of a wound, following keratinocyte activation (Szabo I., Wetzel MA, Rogers TJ). Cell-Density-Regulated Chemotactic Responsiveness of In Vitro Keratinocytes J. Invest Dermatol 117: 1083-1090, 2001).
  • the objective of this study was to evaluate the effect of zinc sucrose octasulfate on cell migration of HaCAT keratinocyte lines, using the Oris Cell Migration Assay Cell Migration Kit (Platypus Technologies). This study was performed in comparison with sucrose octasulfate potassium, and sucrose octasulfate sodium.
  • the protocol used for the study of cell migration is based on the use of a 96-well kit, Oris Cell Migration Assay (Platypus Technologies - TEBU), allowing the miniaturization and quantification of this cellular process. It is described under the code QRD / TO / 154/107.
  • the principle of this test is to study cell migration to the well center of the 96-well plate. It consists in placing a stopper in wells, to create a detection zone of 2 mm in diameter. Then remove the stoppers once the cells have adhered to the surface around them, and thus allow the cells to migrate to the detection zone. Plates without stoppers and with active ingredients are incubated at 37 ° C for 24 hours in DMEM 0% FCS. The amount of cells located in the area where the stopper was then analyzed for cell migration. A cache is used to view and count only cells in this area. For each condition, the average of 4 to 8 wells is achieved. vs. Products tested
  • the results are expressed in OD (proportional to the amount of cells that migrated).
  • the percentage of activity relative to the negative control is calculated by:
  • the percentage of activity relative to TGFp is calculated by:
  • TGFP at 5 ng / ml induces the migration of the keratinocytes in a reproducible manner
  • zinc sucrose octasulfate (SOS-Zn) also induces cell migration reproducibly at 1 ⁇ . At this concentration it is as active as the TGF positive control;
  • sucrose octasulfate potassium and sucrose octasulfate sodium Unlike sucrose octasulfate potassium and sucrose octasulfate sodium, sucrose octasulfate zinc appears to have very interesting properties on keratinocyte migration and therefore for skin healing.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)
EP10795975A 2009-12-07 2010-12-03 Sucrose octasulfates de zinc, leur preparation et leurs applications pharmaceutiques et cosmetiques Withdrawn EP2509989A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0958689A FR2953522B1 (fr) 2009-12-07 2009-12-07 Sucrose octasulfates de zinc, leur preparation et leurs applications pharmaceutiques et cosmetiques
PCT/EP2010/068873 WO2011069921A1 (fr) 2009-12-07 2010-12-03 Sucrose octasulfates de zinc, leur preparation et leurs applications pharmaceutiques et cosmetiques

Publications (1)

Publication Number Publication Date
EP2509989A1 true EP2509989A1 (fr) 2012-10-17

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EP10795975A Withdrawn EP2509989A1 (fr) 2009-12-07 2010-12-03 Sucrose octasulfates de zinc, leur preparation et leurs applications pharmaceutiques et cosmetiques

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US (1) US20120245120A1 (cg-RX-API-DMAC7.html)
EP (1) EP2509989A1 (cg-RX-API-DMAC7.html)
JP (1) JP2013512938A (cg-RX-API-DMAC7.html)
AR (1) AR079312A1 (cg-RX-API-DMAC7.html)
FR (1) FR2953522B1 (cg-RX-API-DMAC7.html)
TW (1) TW201127388A (cg-RX-API-DMAC7.html)
WO (1) WO2011069921A1 (cg-RX-API-DMAC7.html)

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FR2977798B1 (fr) * 2011-07-13 2016-07-29 Urgo Lab Utilisation de composes oligosaccharidiques pour la prevention et le traitement des cicatrices pathologiques
FR2977797B1 (fr) * 2011-07-13 2014-01-17 Urgo Lab Utilisation cosmetique et/ou dermatologique de composes oligosaccharidiques pour la prevention et le traitement des vergetures
EP2793845A4 (en) * 2011-12-21 2016-02-24 Colgate Palmolive Co METHOD AND PRODUCTS FOR DIAGNOSIS AND TREATMENT OF OVERHEATING
FR2991876B1 (fr) 2012-06-13 2014-11-21 Vivacy Lab Composition, en milieu aqueux, comprenant au moins un acide hyaluronique et au moins un sel hydrosoluble de sucrose octasulfate
FR2993182B1 (fr) 2012-07-13 2014-10-17 Urgo Lab Pansement a liberation prolongee d'actifs
CN103193835B (zh) * 2013-04-18 2015-06-24 安徽赛诺制药有限公司 一种蔗糖八磺酸酯钠合成及纯化的方法
CN114436858A (zh) * 2020-11-03 2022-05-06 江苏开元药业有限公司 一种药用辅料的三乙胺盐的制备方法
CN116063360A (zh) * 2022-09-22 2023-05-05 麦吉丽生物科技有限公司 用于改善皮肤功能的二糖聚硫酸盐及其制备方法和用途

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ZA869530B (en) * 1985-12-24 1987-10-28 Marion Laboratories Inc Use of synthetic sulfated saccharides to enhance wound healing
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US5618798A (en) * 1989-04-20 1997-04-08 Bar-Shalom; Daniel Use of sucralfate to treat baldness
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FR2646604B1 (fr) 1989-05-03 1994-02-04 Fabre Medicament Pierre Composition pour usage externe a base de sucralfate et son procede de preparation
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Also Published As

Publication number Publication date
JP2013512938A (ja) 2013-04-18
FR2953522B1 (fr) 2012-03-09
US20120245120A1 (en) 2012-09-27
AR079312A1 (es) 2012-01-18
WO2011069921A1 (fr) 2011-06-16
WO2011069921A9 (fr) 2011-09-15
FR2953522A1 (fr) 2011-06-10
TW201127388A (en) 2011-08-16

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