US20100159013A1 - flavored clay-based therapeutic composition - Google Patents

flavored clay-based therapeutic composition Download PDF

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Publication number
US20100159013A1
US20100159013A1 US12/733,172 US73317208A US2010159013A1 US 20100159013 A1 US20100159013 A1 US 20100159013A1 US 73317208 A US73317208 A US 73317208A US 2010159013 A1 US2010159013 A1 US 2010159013A1
Authority
US
United States
Prior art keywords
composition according
flavor
composition
weight
encapsulated
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.)
Abandoned
Application number
US12/733,172
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English (en)
Inventor
Jerome Barra
Denis Le Hazie
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.)
Firmenich SA
Ipsen Pharma SAS
Original Assignee
Individual
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 Individual filed Critical Individual
Assigned to IPSEN PHARMA S.A.S., FIRMENICH S.A. reassignment IPSEN PHARMA S.A.S. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LE HAZIF, DENIS, BARRA, JEROME
Publication of US20100159013A1 publication Critical patent/US20100159013A1/en
Assigned to FIRMENICH S.A., IPSEN PHARMA S.A.S. reassignment FIRMENICH S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LE HAZIF, DENIS, BARRA, JEROME
Abandoned legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4816—Wall or shell material
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
    • A61K33/12—Magnesium silicate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/02—Medicinal preparations containing materials or reaction products thereof with undetermined constitution from inanimate materials
    • 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
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61P1/04—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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • 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
    • A61P1/12—Antidiarrhoeals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present Application relates to a flavored pharmaceutical composition containing a smectite as active ingredient.
  • the subject of the present invention is therefore a flavored therapeutic composition containing a clay as active ingredient, and characterized in that
  • a composition according to the present invention can be used for the prevention and/or treatment of certain pathologies such as the symptomatic treatment of pain associated with oesogastroduodenal and colic conditions, acute and chronic diarrhoeas, coeliac disease.
  • Smectites represent a particular family of clay in which dioctaedral species such as montmorillonite and beidellite, and trioctaedral species such as hectorite and saponite are found.
  • the clay used according to the invention is a dioctahedral smectite.
  • the dioctahedral smectite is a montmorillonite or a beidellite or a crystallographic structure intermediate between the two crystal-chemical poles: montmorillonite and beidellite.
  • This intermediate crystallographic structure can be close to the montmorillonite pole and even very close to the montmorillonite pole; it can also be close to the beidellite pole and even very close to the beidellite pole.
  • a smectite according to the invention is a montmorillonite or an intermediate structure close to the montmorillonite pole, and very preferably very close to the montmorillonite pole.
  • the clay used is the smectite known as “diosmectite” and sold under the trade-mark Smecta®.
  • the therapeutic composition according to the present invention comprises “a flavoring ingredient or composition”, called “flavor”.
  • flavor as used in the present Application covers the flavoring ingredients or compositions usually used in the food industry, whether of natural or synthetic origin. It comprises single compounds or mixtures.
  • the flavor is a hydrophobic liquid, soluble in organic solvents but only very weakly soluble in water.
  • the flavor is characterized by a Hildebrand solubility parameter 8 less than 30 MPa 1/2 .
  • the incompatibility with water of most of the flavors and perfumes can in fact be expressed by means of the Hildebrand solubility parameter which is in general less than 25 MPa 1/2 while the same parameter for water is 48 MPa 1/2 and for alkanes, 15-16 MPa 1/2 .
  • This parameter gives a useful polarity scale correlated with a cohesive energy density of the molecules. For mixing to take place spontaneously, the difference in solubility of the molecules to be mixed must be kept to a minimum.
  • the handbook of solubility parameters (Handbook of Solubility Parameters, A. F. M. Barton, CRC Press, Bocca Raton, 1991) gives a list of 8 values for a large number of chemical products but also recommended group-contribution methods allowing the 8 values for complex chemical structures to be calculated.
  • the flavor is in a liquid, volatile or labile form, with a log P comprised within the range ⁇ 2 to 7, and very preferably, from 2 to 6.
  • composition according to the present invention comprises, as flavor, natural extracts, essential oils or a mixture thereof.
  • traditional flavors can be mentioned such as liquorice, exotic fruits, red fruits, extracts of citrus fruits such as lime, lemon, orange, grapefruit, or mandarin oils or coffee, tea, mint, cocoa, vanilla/caramel or essential oils from herbs and spices, or also flavors known as “modern” such as coca-cola, green tea, caramel custard.
  • a composition according to the invention comprises at least one encapsulated flavor different from vanilla.
  • the flavors are preferably chosen from the traditional flavors such as liquorice, exotic fruits, red fruits, extracts of citrus fruits, vanilla/caramel/chocolate but also flavors known as “modern” such coca-cola, green tea, caramel custard.
  • the flavor is chosen from vanilla/caramel/chocolate flavors and extracts of citrus fruits and very preferably, vanilla/caramel/chocolate and orange, lemon, grapefruit or clementine.
  • the flavor is a mixture of flavors, and very preferably, a mixture of vanilla and orange flavors.
  • the flavor can be mixed with solvents, adjuvants, additives and/or other substances, for example those usually used in the flavor and/or food industry.
  • the flavor according to the present invention is preferably encapsulated in a glassy matrix (encapsulation matrix) of carbohydrate(s).
  • Any sugar or sugar derivative which can be processed by extrusion techniques can be used as constituent(s) of the encapsulation matrix, in order to form a dry extruded solid.
  • suitable constituents can be chosen from the following products: sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, pentatol, arabinose, pentose, xylose, galactose, hydrogenated starch hydrolysates, maltodextrin, Stabilite (trade name; origin: SPI Polyols, USA), agar, carrageenan, other gums, polydextrose and the derivatives and mixtures thereof.
  • maltodextrin or mixtures of maltodextrin and at least one product chosen from: sucrose, glucose, lactose, levulose, maltose, fructose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol and hydrogenated starch hydrolysates are used.
  • the matrix is constituted by maltodextrin or a mixture of maltodextrin and at least one product chosen from: sucrose, maltose, isomalt, maltitol and hydrogenated starch hydrolysates.
  • the matrix is constituted by maltodextrin and sucrose.
  • the maltodextrin has a dextrose equivalent (DE) greater than 5 and less than 20.
  • DE dextrose equivalent
  • An emulsifier such as lecithin, and/or a plasticizer, typically water, can be added to the mixture if necessary.
  • the flavored product or the flavored composition according to the invention, which are extruded, can be prepared by any standard method.
  • the methods described in U.S. Pat. Nos. 4,610,890 and 4,707,367, the content of which is incorporated by way of reference, are suitable for supplying encapsulated flavors as used in the present invention.
  • the flavor is present in a proportion of at least 10% by weight expressed as dry matter, with respect to the total weight (expressed as dry matter) of the encapsulation matrix, and preferably in a proportion comprised between 15 and 35%.
  • a composition according to the invention comprises preferably 70 to 90% by weight of active ingredient, and very preferably from 75 to 85%, with respect to the total weight of the composition.
  • a composition according to the invention comprises 0.1 to 3% by weight of encapsulated flavor with respect to the total weight of the composition, and very preferably 0.3 to 2.5%. Also very preferably, a composition according to the invention comprises 0.5 to 2% by weight of encapsulated flavour with respect to the total weight of the composition.
  • a therapeutic composition according to the present invention can be presented in different solid forms such as for example powders, granules, tablets or capsules.
  • Appropriate solid supports can be, for example, talc, sugars, lactose, dextrin, gelatin, cellulose and its esters.
  • composition according to the present invention there can also be also other additives such as colouring agents, sweetening agents, lubricants, glidants.
  • a composition according to the present invention can also contain minerals.
  • the colouring agent(s) used according to the present invention can be any type of colouring agents usually used in the food and/or the pharmaceutical industries.
  • sweetening agents the following can be mentioned: saccharin, aspartame, maltodextrin, monosaccharides such as fructose or glucose, disaccharides such as saccharose.
  • talc can be mentioned for example.
  • glidant agents saccharose can be mentioned.
  • the mineral contribution can for example consist of the addition of metal salts such as aluminium or magnesium salts such as aluminium hydroxide, magnesium carbonate.
  • compositions according to the invention are chosen, among others, according to its pharmaceutical form and the pathology to be treated.
  • composition as defined above is administered by the oral route.
  • the daily administration dose is the usual recommended dose for this product.
  • the smectite known as “diosmectite”
  • it can be administered at a maximum daily dose of 18 g/day.
  • a syrup is prepared from maltodextrin, sucrose, water and flavor.
  • the mixture is then heated to 123° C. in order to reduce the moisture content of the syrup.
  • the emulsifier is mixed with the concentrated syrup under high shear conditions in order to form a uniform melt.
  • the melt is then extruded under a pressure of 2 ⁇ 10 5 Pa through an extrusion die plate with holes of 0.8 mm diameter in a cold solvent for chilling and breaking of the extrudates.
  • Example 1 is reproduced by using a vanilla extract (ex Firmenich) instead of the orange flavor.
  • Example 1 is reproduced by using a caramel flavor (ex Firmenich) instead of the orange flavor.
  • compositions below are prepared by gently mixing all the substances together in the proportions indicated, until they are dispersed in a homogenous fashion. In the table below, all the quantities are expressed in mg.
  • Example Example Example Example Ingredients 4a 4b 4c Diosmectite 3000 3000 3000 Encapsulated orange flavor — — 10 (flavor prepared according to Example 1) 1 Encapsulated vanilla flavor 50 50 (flavor prepared according to Example 2) 2 Encapsulated caramel ® flavor 10 — — (flavor prepared according to Example 3) 3 Soluble saccharine + hydrated 700 710 700 glucose Water 100 100 100 1 ex Firmenich, ref. 501289 TD 0990B; 2 ex Firmenich, ref. 501465 TD1591; 3 ex Firmenich, ref. 501403 TD 1094
  • composition according to the invention is measured both as regards the organoleptic characteristics of the flavor and for its inertia vis-à-vis the clay.
  • the stability of the organoleptic characteristics of the flavor is established by testers (panel of 7 experts) on the basis of a number of criteria (sugary, fruity, acidic, bitterness, etc.) over a period of at least 6 months.
  • the flavor shows no deterioration in the presence of the clay over this same period.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (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)
  • Inorganic Chemistry (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Medicinal Preparation (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Cosmetics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Confectionery (AREA)
US12/733,172 2007-08-13 2008-08-12 flavored clay-based therapeutic composition Abandoned US20100159013A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07291005A EP2025332A1 (fr) 2007-08-13 2007-08-13 Composition thérapeutique aromatisée à base d'argile
EP07291005.2 2007-08-13
PCT/FR2008/001185 WO2009056703A1 (fr) 2007-08-13 2008-08-12 Composition thérapeutique aromatisée à base d'argile

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2008/001185 A-371-Of-International WO2009056703A1 (fr) 2007-08-13 2008-08-12 Composition thérapeutique aromatisée à base d'argile

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/178,445 Continuation US9056055B2 (en) 2007-08-13 2014-02-12 Flavoured clay-based therapeutic composition

Publications (1)

Publication Number Publication Date
US20100159013A1 true US20100159013A1 (en) 2010-06-24

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Family Applications (2)

Application Number Title Priority Date Filing Date
US12/733,172 Abandoned US20100159013A1 (en) 2007-08-13 2008-08-12 flavored clay-based therapeutic composition
US14/178,445 Expired - Fee Related US9056055B2 (en) 2007-08-13 2014-02-12 Flavoured clay-based therapeutic composition

Family Applications After (1)

Application Number Title Priority Date Filing Date
US14/178,445 Expired - Fee Related US9056055B2 (en) 2007-08-13 2014-02-12 Flavoured clay-based therapeutic composition

Country Status (27)

Country Link
US (2) US20100159013A1 (ja)
EP (3) EP2025332A1 (ja)
JP (2) JP5670189B2 (ja)
KR (2) KR101503957B1 (ja)
CN (2) CN101778622A (ja)
AR (2) AR067929A1 (ja)
BR (1) BRPI0814979A2 (ja)
CA (1) CA2696062C (ja)
CL (1) CL2008002366A1 (ja)
DK (1) DK2194968T3 (ja)
EA (1) EA017118B1 (ja)
ES (2) ES2582871T3 (ja)
GE (1) GEP20125539B (ja)
HK (2) HK1143956A1 (ja)
HU (1) HUE029713T2 (ja)
MA (1) MA31678B1 (ja)
ME (1) ME00975B (ja)
MX (1) MX2010001533A (ja)
NO (1) NO20100114L (ja)
PE (1) PE20090939A1 (ja)
PL (2) PL2710998T3 (ja)
PT (2) PT2194968E (ja)
SA (1) SA08290496B1 (ja)
TN (1) TN2010000058A1 (ja)
TW (2) TWI519303B (ja)
UA (1) UA97408C2 (ja)
WO (1) WO2009056703A1 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITUA20162277A1 (it) * 2016-04-04 2017-10-04 Chemists Res Srl Composizione comprendente diosmectite

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2025332A1 (fr) * 2007-08-13 2009-02-18 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Composition thérapeutique aromatisée à base d'argile
FR2952814B1 (fr) * 2009-11-23 2013-07-19 Ephyla Sas Composition comprenant un complexe de phyllosilicates organiquement modifies generer des emulsions huile dans eau eventuellement a froid
JP2014503552A (ja) 2011-01-12 2014-02-13 ソーフト イタリア エスピーエー 円錐角膜の処置のためのイオン導入による架橋剤の角膜送達および関連眼科組成物
CN105902625A (zh) * 2016-05-26 2016-08-31 朱胜利 一种小儿止泻药的服用方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4610890A (en) * 1984-07-16 1986-09-09 Sunkist Growers, Inc. Preparation of solid essential oil flavor composition
US4707367A (en) * 1984-07-16 1987-11-17 Sunkist Growers, Inc. Solid essential oil flavor composition
US6187351B1 (en) * 1993-04-16 2001-02-13 Mccormick & Company, Inc. Encapsulation compositions

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JPH064530B2 (ja) * 1985-02-23 1994-01-19 日本化薬株式会社 親水性基剤
US5288497A (en) * 1985-05-01 1994-02-22 The University Of Utah Compositions of oral dissolvable medicaments
FR2770778B1 (fr) * 1997-11-12 2000-05-26 Investigations Therapeutiques Composition pour le traitement des gastro-enterites aigues, procede de fabrication de cette composition et solution de traitement obtenue a partir de cette composition
KR20030050958A (ko) * 2001-12-20 2003-06-25 송우영 디옥타헤드랄 스멕타이트를 유효성분으로 함유하는 항균성외용조성물
US8334007B2 (en) * 2003-03-19 2012-12-18 Firmenich Sa Continuous process for the incorporation of a flavor or fragrance ingredient or composition into a carbohydrate matrix
CN100340235C (zh) * 2004-05-21 2007-10-03 山东绿叶制药有限公司 蒙脱石分散片及其制备工艺
EP1627573A1 (en) * 2004-08-20 2006-02-22 Firmenich Sa A process for the incorporation of a flavor or fragrance ingredient or composition into a carbohydrate matrix
JP2006083071A (ja) * 2004-09-14 2006-03-30 Takasago Internatl Corp 香粧品用固形製剤
WO2007051427A1 (fr) * 2005-11-04 2007-05-10 Zhejiang Hailisheng Pharmaceutical Limited Co. Montmorillonite modifiee, son procede de preparation et ses utilisations
FR2901360A1 (fr) 2006-05-16 2007-11-23 Horiba Abx Sas Soc Par Actions Dispositif de conditionnement pour analyse biologique
EP2025332A1 (fr) * 2007-08-13 2009-02-18 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Composition thérapeutique aromatisée à base d'argile

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4610890A (en) * 1984-07-16 1986-09-09 Sunkist Growers, Inc. Preparation of solid essential oil flavor composition
US4707367A (en) * 1984-07-16 1987-11-17 Sunkist Growers, Inc. Solid essential oil flavor composition
US6187351B1 (en) * 1993-04-16 2001-02-13 Mccormick & Company, Inc. Encapsulation compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITUA20162277A1 (it) * 2016-04-04 2017-10-04 Chemists Res Srl Composizione comprendente diosmectite
EP3228318A1 (en) * 2016-04-04 2017-10-11 Chemist's Research S.r.l. Composition comprising diosmectite

Also Published As

Publication number Publication date
BRPI0814979A2 (pt) 2015-02-03
TW201509424A (zh) 2015-03-16
WO2009056703A8 (fr) 2010-03-04
TWI519303B (zh) 2016-02-01
US9056055B2 (en) 2015-06-16
MA31678B1 (fr) 2010-09-01
AR114148A2 (es) 2020-07-29
CL2008002366A1 (es) 2009-05-29
PT2194968E (pt) 2013-07-25
CN104173371A (zh) 2014-12-03
TW200914034A (en) 2009-04-01
CN101778622A (zh) 2010-07-14
CA2696062C (fr) 2017-09-05
KR101503957B1 (ko) 2015-03-18
ES2421379T3 (es) 2013-09-02
UA97408C2 (ru) 2012-02-10
CA2696062A1 (fr) 2009-05-07
EP2710998B1 (fr) 2016-04-20
ME00975B (me) 2012-06-20
TWI511734B (zh) 2015-12-11
ES2582871T3 (es) 2016-09-15
KR20140133617A (ko) 2014-11-19
KR20100055460A (ko) 2010-05-26
NO20100114L (no) 2010-03-10
PL2194968T3 (pl) 2013-10-31
SA08290496B1 (ar) 2012-11-03
JP5670189B2 (ja) 2015-02-18
EA017118B1 (ru) 2012-09-28
EP2025332A1 (fr) 2009-02-18
PT2710998T (pt) 2016-07-28
JP2010535852A (ja) 2010-11-25
US20140377354A1 (en) 2014-12-25
HK1143956A1 (en) 2011-01-21
MX2010001533A (es) 2010-03-15
HK1196271A1 (zh) 2014-12-12
EP2194968B1 (fr) 2013-06-19
AR067929A1 (es) 2009-10-28
EA201070257A1 (ru) 2010-06-30
DK2194968T3 (da) 2013-09-02
HUE029713T2 (en) 2017-03-28
WO2009056703A1 (fr) 2009-05-07
GEP20125539B (en) 2012-05-25
EP2194968A1 (fr) 2010-06-16
PE20090939A1 (es) 2009-07-27
EP2710998A1 (fr) 2014-03-26
TN2010000058A1 (fr) 2011-09-26
JP2014208715A (ja) 2014-11-06
PL2710998T3 (pl) 2016-11-30

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