WO2011070380A1 - Nouveau procédé de préparation de la dronédarone - Google Patents

Nouveau procédé de préparation de la dronédarone Download PDF

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Publication number
WO2011070380A1
WO2011070380A1 PCT/HU2010/000128 HU2010000128W WO2011070380A1 WO 2011070380 A1 WO2011070380 A1 WO 2011070380A1 HU 2010000128 W HU2010000128 W HU 2010000128W WO 2011070380 A1 WO2011070380 A1 WO 2011070380A1
Authority
WO
WIPO (PCT)
Prior art keywords
process according
general formula
reaction
carried out
compound
Prior art date
Application number
PCT/HU2010/000128
Other languages
English (en)
Inventor
Antal Friesz
Zsolt DOMBRÁDY
Marianna CSATÁRINĖ NAGY
Original Assignee
Sanofi-Aventis
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
Priority to EP10809325A priority Critical patent/EP2509971A1/fr
Application filed by Sanofi-Aventis filed Critical Sanofi-Aventis
Priority to BR112012013753A priority patent/BR112012013753A2/pt
Priority to JP2012542624A priority patent/JP2013512944A/ja
Priority to RU2012128568/04A priority patent/RU2012128568A/ru
Priority to AU2010329655A priority patent/AU2010329655B2/en
Priority to CN2010800629901A priority patent/CN102741238A/zh
Priority to SG2012041927A priority patent/SG181562A1/en
Priority to CA2781647A priority patent/CA2781647A1/fr
Priority to MX2012006654A priority patent/MX2012006654A/es
Publication of WO2011070380A1 publication Critical patent/WO2011070380A1/fr
Priority to US13/479,615 priority patent/US8501971B2/en
Priority to IL220170A priority patent/IL220170A0/en
Priority to US13/905,624 priority patent/US8889734B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Definitions

  • the present invention relates to novel process for the preparation of the N- [2- «-butyl-3- ⁇ 4-[(3-dibutylamin0)-propoxy]benzoyl ⁇ -l-benzofuran-5-yl]methane- sulfonamide (dronedarone) of formula I and its pharmaceutically acceptable salts, and to the new intermediates of the reparation process.
  • Dronedarone of formula I is used in the treatment of certain pathological changes of the cardiovascular system, especially in the treatment of angina pectoris, high blood pressure, arrhythmia and insufficient cerebral blood circulation (EP 0471609 B l).
  • One reactant is dibutylamine, which is volatile and thus can be removed from the system and reused after workup, the other is a compound of the general formula (II) -where the meaning of X is as defined above- which can be treated well under the applied reaction conditions.
  • dronedarone of formula (I) is obtained in appropriate purity and yield, no byproduct is formed, only a few percent of the unreacted starting material may remain in the reaction mixture, and this can be reused.
  • the reaction of the compound of the general formula (II) -wherein X stands for chloro-, bromo- or iodo atom, hydroxyl- or activated hydroxyl group- with dibutylamine is carried out using equivalent amount or excess of dibutylamine.
  • the reaction is performed in an organic solvent or in a mixture of organic solvents.
  • organic solvent ketones (acetone, methyl ethyl ketone), for mixture of organic solvents, mixtures of ketones and aromatic hydrocarbons (xylene, toluene) are used.
  • other organic solvents and their mixtures can also be used. .
  • the compound of the general formula (II) -where the meaning of X is as defined above- is reacted with dibutylamine, optionally in the presence of a catalyst. If in the general formula (II) the meaning of X is chloro- or bromo atom, then iodides (as for example sodium iodide or potassium iodide) are used as catalyst.
  • the hydroxyl group may be activated with methylsulfonyl or substituted benzenesulfonyl group.
  • the substituent of the benzenesulfonyl group may be C 1 . 4 -alkyl group, halogen atom or nitro group.
  • Y stands for chloro- or bromo atom
  • X represents halogen atom or protected hydroxy 1 group
  • the thus obtained compound of formula (II) -where the meanings of X are defined above- is reacted with dibutylamine in a manner as described above, to obtain dronedarone of formula (I).
  • reaction of the benzofuran derivative of formula (III) with the acid halide of the general formula (IV) - where the meanings of X and Y are as defined above- is carried out in the presence of Friedel-Crafts catalyst in a halogenated organic solvent or in nitrobenzene.
  • reaction of the compounds (III) and (IV) is carried out in a temperature range of 10-80 °C.
  • the hydrogenation reaction of the compound of formula (VI) is carried out in the presence of a catalyst.
  • a catalyst In one version of the method palladium catalyst is used. In another version of the method platinum catalyst is applied.
  • the hydrogenation reaction of the compound of formula (VI) is performed in an organic solvent, in a temperature range of 10-80 °C.
  • the mesylation of the compound of formula (V) is carried out with methanesulfonyl chloride or with methanesulfonic anhydride.
  • the mesylation of the compound of formula (V) is performed in an inert solvent.
  • ether or a halogenated solvent is used.
  • the mesylation of the compound of formula (V) is carried out in a temperature range of 5-80 °C.
  • the mesylation of the compound of formula (V) is carried out in the presence of a base.
  • an amine pyridine, triethylamine
  • X stands for chloro-, bromo- or iodo atom, hydroxyl- or activated hydroxyl group; .
  • X stands for chloro-, bromo- or iodo atom, hydroxyl- or activated hydroxyl group are new compounds, not known from the literature.
  • the compounds of the general formula (II), where the meanings of X are defined above are prepared by reacting the compounds of formula (III) with the compounds of the general formula (IV) - wherein Y stands for chloro- or bromp atom, and X represents a halogen atom or a protected hydroxyl group.
  • the compound of formula (III) is known, its preparation by mesylation of 5-amino-2- «-butyl-benzofuran is described in patent application WO 02/048132.
  • the compounds of the general formula (IV) wherein the meanings of X and Y are defined above, are also known from the literature, their preparation is disclosed in patent EP 0471609 Bl.
  • the compounds of the general formula (II) - where the meaning of X is defined above - are prepared by mesylation of a compound of the general formula (V) - wherein X means chloro-, bromo- or iodo atom, hydroxyl- or activated hydroxyl group.
  • the compound of the general formula (V) - where the meaning of X is defined above - is prepared by catalytic hydrogenation of the benzofuran derivative of the general formula (VI) - where the meaning of X is defined above.
  • the compound of the general formula (VI), wherein X represents bromo atom is known from the literature.
  • Example 2 The process as described in Example 2. was followed, starting from (2- «-but l-5-nitro-l-benzofuran-3-yl)-[4-(3-bromopropoxy)phenyl]methanone -the compound of the general formula (VI) where X is bromo atom.
  • the product is identical with the product prepared in Example 4.
  • Example 10 The product is identical with the product prepared in Example 5. Example 10.
  • the product is purified through its oxalate salt (90%).
  • the product is identical with the product prepared in Example 12. -
  • the product is identical with the product prepared according to Example 12.
  • Example 20 Example 20.
  • dronedarone base 5 g was dissolved in 24 ml isopropanol and 0.98 g 37% hydrochloric acid was added to it. The mixture was cooled to 0°C and kept at that temperature for 5 hours. The precipitated white crystals were collected, washed with 3.5 ml isopropanol. The product was dried at 50°C under vacuum.

Abstract

La présente invention concerne un nouveau procédé de préparation de N- [2-n-butyl-3-{4-[(3-dibutylamino)propoxy]benzoyl}-1-benzofuran-5- yl] méthanesulfonamide de la formule (I), et les nouveaux intermédiaires de ce procédé de préparation.
PCT/HU2010/000128 2009-12-08 2010-11-23 Nouveau procédé de préparation de la dronédarone WO2011070380A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
CN2010800629901A CN102741238A (zh) 2009-12-08 2010-11-23 制备决奈达隆的新方法
BR112012013753A BR112012013753A2 (pt) 2009-12-08 2010-11-23 "processo para a preparação de dronedarona"
JP2012542624A JP2013512944A (ja) 2009-12-08 2010-11-23 ドロネダロンの新規な調製方法
RU2012128568/04A RU2012128568A (ru) 2009-12-08 2010-11-23 Новый способ получения дронедарона
AU2010329655A AU2010329655B2 (en) 2009-12-08 2010-11-23 New process for the preparation of dronedarone
EP10809325A EP2509971A1 (fr) 2009-12-08 2010-11-23 Nouveau procédé de préparation de la dronédarone
SG2012041927A SG181562A1 (en) 2009-12-08 2010-11-23 New process for the preparation of dronedarone
CA2781647A CA2781647A1 (fr) 2009-12-08 2010-11-23 Nouveau procede de preparation de la dronedarone
MX2012006654A MX2012006654A (es) 2009-12-08 2010-11-23 Nuevo proceso para la preparacion de dronedarona.
US13/479,615 US8501971B2 (en) 2009-12-08 2012-05-24 Process for the preparation of dronedarone
IL220170A IL220170A0 (en) 2009-12-08 2012-06-04 New process for the preparation of dronedarone
US13/905,624 US8889734B2 (en) 2009-12-08 2013-05-30 Process for the preparation of dronedarone

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU0900759A HUP0900759A2 (en) 2009-12-08 2009-12-08 Novel process for producing dronedarone
HUP0900759 2009-12-08

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/479,615 Continuation US8501971B2 (en) 2009-12-08 2012-05-24 Process for the preparation of dronedarone

Publications (1)

Publication Number Publication Date
WO2011070380A1 true WO2011070380A1 (fr) 2011-06-16

Family

ID=89989418

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2010/000128 WO2011070380A1 (fr) 2009-12-08 2010-11-23 Nouveau procédé de préparation de la dronédarone

Country Status (16)

Country Link
US (2) US8501971B2 (fr)
EP (1) EP2509971A1 (fr)
JP (1) JP2013512944A (fr)
CN (1) CN102741238A (fr)
AR (1) AR079269A1 (fr)
AU (1) AU2010329655B2 (fr)
BR (1) BR112012013753A2 (fr)
CA (1) CA2781647A1 (fr)
HU (1) HUP0900759A2 (fr)
IL (1) IL220170A0 (fr)
MX (1) MX2012006654A (fr)
RU (1) RU2012128568A (fr)
SG (1) SG181562A1 (fr)
TW (1) TW201144291A (fr)
UY (1) UY33094A (fr)
WO (1) WO2011070380A1 (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012032545A1 (fr) 2010-09-08 2012-03-15 Cadila Healthcare Limited Procédé pour préparer un dérivé de benzofurane et des produits intermédiaires de celui-ci
WO2012004658A3 (fr) * 2010-07-09 2012-05-18 Frichem Private Limited Procédé de préparation du n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-5-benzofuranyl]méthanesulfonamide, sels d'addition acide et produit de celui-ci
WO2013014479A1 (fr) * 2011-07-26 2013-01-31 Sanofi Procédé d'amination réductrice pour la préparation de dronédarone, utilisant un composé intermédiaire aldéhyde
WO2013014478A1 (fr) * 2011-07-26 2013-01-31 Sanofi Procédé d'amination réductrice pour la préparation de dronédarone, utilisant un composé intermédiaire carboxyle
FR2983198A1 (fr) * 2011-11-29 2013-05-31 Sanofi Sa Procede de preparation de derives de 5-amino-benzoyl-benzofurane
EP2539331B1 (fr) * 2010-02-23 2014-10-08 Laboratorio Chimico Internazionale S.p.A. Nouveau procédé pour la fabrication de dronédarone
US9174959B2 (en) 2011-03-29 2015-11-03 Sanofi Process for preparation of dronedarone by N-butylation
US9174958B2 (en) 2010-06-18 2015-11-03 Sanofi Process for the preparation of dronedarone
US9193703B2 (en) 2011-03-29 2015-11-24 Sanofi Process for preparation of dronedarone by mesylation
US9221777B2 (en) 2012-01-20 2015-12-29 Sanofi Process for preparation of dronedarone by the use of dibutylaminopropanol reagent
US9221778B2 (en) 2012-02-13 2015-12-29 Sanofi Process for preparation of dronedarone by removal of hydroxyl group
US9238636B2 (en) 2012-05-31 2016-01-19 Sanofi Process for preparation of dronedarone by Grignard reaction
US9249119B2 (en) 2012-02-14 2016-02-02 Sanofi Process for the preparation of dronedarone by oxidation of a sulphenyl group
US9334254B2 (en) 2010-03-30 2016-05-10 Sanofi Process for preparing sulfonamidobenzofuran derivatives
US9382223B2 (en) 2012-02-22 2016-07-05 Sanofi Process for preparation of dronedarone by oxidation of a hydroxyl group

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0900759A2 (en) * 2009-12-08 2011-11-28 Sanofi Aventis Novel process for producing dronedarone
FR2957079B1 (fr) 2010-03-02 2012-07-27 Sanofi Aventis Procede de synthese de derives de cetobenzofurane
FR2958291B1 (fr) 2010-04-01 2013-07-05 Sanofi Aventis Procede de preparation de derives d'amino-benzofurane
FR2962731B1 (fr) 2010-07-19 2012-08-17 Sanofi Aventis Procede de preparation de derives d'amino-benzoyl-benzofurane
FR2963006B1 (fr) 2010-07-21 2013-03-15 Sanofi Aventis Procede de preparation de derives de nitro-benzofurane
HUP1000386A2 (en) 2010-07-22 2012-05-29 Sanofi Sa Novel process for producing dronedarone
CN102653530A (zh) * 2011-03-04 2012-09-05 浙江省医学科学院 一种苯并呋喃衍生物的制备方法及其应用

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EP0471609A1 (fr) * 1990-08-06 1992-02-19 Sanofi Dérivés de Benzofuranne, Benzothiophène, Indole ou Indolizine, leur procédé de préparation ainsi que les compositions les contenant
WO2002048132A1 (fr) 2000-12-11 2002-06-20 Sanofi-Synthelabo Derive de methanesulfonamido-benzofurane, son procede de preparation et son utilisation comme intermediaire de synthese
WO2002048078A1 (fr) 2000-12-11 2002-06-20 Sanofi-Synthelabo Chlorhydrate du 2-butyl-3-(4-'3-(dibutylamino)propoxy!benzoyl)-5-nitro-benzofurane et sa preparation
WO2003040120A1 (fr) * 2001-11-08 2003-05-15 Isp Investments Inc. Procede de preparation de dronedarone

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FR2833262A1 (fr) 2001-12-06 2003-06-13 Rhodia Chimie Sa Procede de monosulfonylation d'un compose de type aminobenzofuranne ou aminobenzothiophene
DE10237819A1 (de) 2002-08-19 2004-03-04 Bayer Ag 5-Nitrobenzofurane
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TW201107303A (en) 2009-05-27 2011-03-01 Sanofi Aventis Process for the production of benzofurans
HUP0900759A2 (en) * 2009-12-08 2011-11-28 Sanofi Aventis Novel process for producing dronedarone
HUP1000010A2 (en) 2010-01-08 2011-11-28 Sanofi Sa Process for producing dronedarone
FR2957079B1 (fr) 2010-03-02 2012-07-27 Sanofi Aventis Procede de synthese de derives de cetobenzofurane
FR2958290B1 (fr) 2010-03-30 2012-10-19 Sanofi Aventis Procede de preparation de derives de sulfonamido-benzofurane
FR2958291B1 (fr) 2010-04-01 2013-07-05 Sanofi Aventis Procede de preparation de derives d'amino-benzofurane
HUP1000330A2 (en) 2010-06-18 2011-12-28 Sanofi Sa Process for the preparation of dronedarone and the novel intermediates
FR2962731B1 (fr) 2010-07-19 2012-08-17 Sanofi Aventis Procede de preparation de derives d'amino-benzoyl-benzofurane
FR2963006B1 (fr) 2010-07-21 2013-03-15 Sanofi Aventis Procede de preparation de derives de nitro-benzofurane
HUP1000386A2 (en) 2010-07-22 2012-05-29 Sanofi Sa Novel process for producing dronedarone
FR2973027A1 (fr) 2011-03-24 2012-09-28 Sanofi Aventis Procede de synthese de derives de cetobenzofurane
HUP1100166A2 (en) 2011-03-29 2012-12-28 Sanofi Sa Reductive amination process for preparation of dronedarone using amine intermediary compound
HUP1100165A2 (en) 2011-03-29 2012-12-28 Sanofi Sa Process for preparation of dronedarone by n-butylation
HUP1100167A2 (en) 2011-03-29 2012-11-28 Sanofi Sa Process for preparation of dronedarone by mesylation

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EP0471609A1 (fr) * 1990-08-06 1992-02-19 Sanofi Dérivés de Benzofuranne, Benzothiophène, Indole ou Indolizine, leur procédé de préparation ainsi que les compositions les contenant
EP0471609B1 (fr) 1990-08-06 1996-11-27 Sanofi Dérivés de Benzofuranne, Benzothiophène, Indole ou Indolizine, leur procédé de préparation ainsi que les compositions les contenant
WO2002048132A1 (fr) 2000-12-11 2002-06-20 Sanofi-Synthelabo Derive de methanesulfonamido-benzofurane, son procede de preparation et son utilisation comme intermediaire de synthese
WO2002048078A1 (fr) 2000-12-11 2002-06-20 Sanofi-Synthelabo Chlorhydrate du 2-butyl-3-(4-'3-(dibutylamino)propoxy!benzoyl)-5-nitro-benzofurane et sa preparation
WO2003040120A1 (fr) * 2001-11-08 2003-05-15 Isp Investments Inc. Procede de preparation de dronedarone

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Title
See also references of EP2509971A1

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2539331B1 (fr) * 2010-02-23 2014-10-08 Laboratorio Chimico Internazionale S.p.A. Nouveau procédé pour la fabrication de dronédarone
US9334254B2 (en) 2010-03-30 2016-05-10 Sanofi Process for preparing sulfonamidobenzofuran derivatives
US9174958B2 (en) 2010-06-18 2015-11-03 Sanofi Process for the preparation of dronedarone
WO2012004658A3 (fr) * 2010-07-09 2012-05-18 Frichem Private Limited Procédé de préparation du n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-5-benzofuranyl]méthanesulfonamide, sels d'addition acide et produit de celui-ci
WO2012032545A1 (fr) 2010-09-08 2012-03-15 Cadila Healthcare Limited Procédé pour préparer un dérivé de benzofurane et des produits intermédiaires de celui-ci
US9193703B2 (en) 2011-03-29 2015-11-24 Sanofi Process for preparation of dronedarone by mesylation
US9174959B2 (en) 2011-03-29 2015-11-03 Sanofi Process for preparation of dronedarone by N-butylation
US9611242B2 (en) 2011-03-29 2017-04-04 Sanofi Process for preparation of dronedarone by N-butylation
WO2013014478A1 (fr) * 2011-07-26 2013-01-31 Sanofi Procédé d'amination réductrice pour la préparation de dronédarone, utilisant un composé intermédiaire carboxyle
WO2013014479A1 (fr) * 2011-07-26 2013-01-31 Sanofi Procédé d'amination réductrice pour la préparation de dronédarone, utilisant un composé intermédiaire aldéhyde
WO2013079866A1 (fr) * 2011-11-29 2013-06-06 Sanofi Procede de preparation de derives de 5-amino-benzoyl-benzofurane
FR2983198A1 (fr) * 2011-11-29 2013-05-31 Sanofi Sa Procede de preparation de derives de 5-amino-benzoyl-benzofurane
US9499507B2 (en) 2011-11-29 2016-11-22 Sanofi Method for preparing 5-amino-benzoyl-benzofuran derivatives
US9221777B2 (en) 2012-01-20 2015-12-29 Sanofi Process for preparation of dronedarone by the use of dibutylaminopropanol reagent
US9708281B2 (en) 2012-01-20 2017-07-18 Sanofi Process for preparation of dronedarone by the use of dibutylaminopropanol reagent
US9221778B2 (en) 2012-02-13 2015-12-29 Sanofi Process for preparation of dronedarone by removal of hydroxyl group
US9701654B2 (en) 2012-02-13 2017-07-11 Sanofi Process for preparation of dronedarone by removal of hydroxyl group
US9249119B2 (en) 2012-02-14 2016-02-02 Sanofi Process for the preparation of dronedarone by oxidation of a sulphenyl group
US9382223B2 (en) 2012-02-22 2016-07-05 Sanofi Process for preparation of dronedarone by oxidation of a hydroxyl group
US9238636B2 (en) 2012-05-31 2016-01-19 Sanofi Process for preparation of dronedarone by Grignard reaction

Also Published As

Publication number Publication date
US8501971B2 (en) 2013-08-06
CA2781647A1 (fr) 2011-06-16
TW201144291A (en) 2011-12-16
AU2010329655B2 (en) 2014-01-16
IL220170A0 (en) 2012-07-31
HUP0900759A2 (en) 2011-11-28
US8889734B2 (en) 2014-11-18
RU2012128568A (ru) 2014-01-20
SG181562A1 (en) 2012-07-30
EP2509971A1 (fr) 2012-10-17
MX2012006654A (es) 2012-06-25
BR112012013753A2 (pt) 2015-09-15
AR079269A1 (es) 2012-01-04
HU0900759D0 (en) 2010-01-28
AU2010329655A1 (en) 2012-06-21
JP2013512944A (ja) 2013-04-18
UY33094A (es) 2011-07-29
CN102741238A (zh) 2012-10-17
US20120289717A1 (en) 2012-11-15
US20130261321A1 (en) 2013-10-03

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