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FR2941951B1 - Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. - Google Patents

Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.

Info

Publication number
FR2941951B1
FR2941951B1 FR0900513A FR0900513A FR2941951B1 FR 2941951 B1 FR2941951 B1 FR 2941951B1 FR 0900513 A FR0900513 A FR 0900513A FR 0900513 A FR0900513 A FR 0900513A FR 2941951 B1 FR2941951 B1 FR 2941951B1
Authority
FR
France
Prior art keywords
triazolopyridazine
benzothiazoles
sulfanyl
medicaments
inhibitors
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.)
Expired - Fee Related
Application number
FR0900513A
Other languages
English (en)
Other versions
FR2941951A1 (fr
Inventor
Antonio Ugolini
Conception Nemecek
Sylvie Wentzler
Eric Bacque
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.)
Sanofi Aventis France
Original Assignee
Sanofi Aventis France
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 FR0900513A priority Critical patent/FR2941951B1/fr
Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Priority to BRPI1008188A priority patent/BRPI1008188A2/pt
Priority to SG2011056512A priority patent/SG173562A1/en
Priority to PCT/FR2010/050179 priority patent/WO2010089508A1/fr
Priority to JP2011548752A priority patent/JP2012517409A/ja
Priority to RU2011136855/04A priority patent/RU2011136855A/ru
Priority to AU2010212233A priority patent/AU2010212233A1/en
Priority to US13/147,297 priority patent/US20120040987A1/en
Priority to CA2751539A priority patent/CA2751539A1/fr
Priority to KR1020117020674A priority patent/KR20110126658A/ko
Priority to CN201080015591XA priority patent/CN102369192A/zh
Priority to MX2011008310A priority patent/MX2011008310A/es
Priority to EP10708279A priority patent/EP2393792A1/fr
Priority to TW099103591A priority patent/TW201033214A/zh
Priority to UY0001032421A priority patent/UY32421A/es
Priority to ARP100100318A priority patent/AR075250A1/es
Publication of FR2941951A1 publication Critical patent/FR2941951A1/fr
Application granted granted Critical
Publication of FR2941951B1 publication Critical patent/FR2941951B1/fr
Priority to IL214404A priority patent/IL214404A0/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Neurology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Biomedical Technology (AREA)
  • Emergency Medicine (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
FR0900513A 2009-02-06 2009-02-06 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. Expired - Fee Related FR2941951B1 (fr)

Priority Applications (17)

Application Number Priority Date Filing Date Title
FR0900513A FR2941951B1 (fr) 2009-02-06 2009-02-06 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.
EP10708279A EP2393792A1 (fr) 2009-02-06 2010-02-04 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met
PCT/FR2010/050179 WO2010089508A1 (fr) 2009-02-06 2010-02-04 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met
JP2011548752A JP2012517409A (ja) 2009-02-06 2010-02-04 ６−（６−ｎｈ−置換−トリアゾロピリダジン−スルファニル）ベンゾチアゾールおよびベンゾイミダゾールの誘導体、これらの調製、これらの薬としての使用、ならびにこれらのｍｅｔ阻害剤としての使用
RU2011136855/04A RU2011136855A (ru) 2009-02-06 2010-02-04 Производные бензотиазолов и бензимидазолов, содержащие 6-nh-замещенные триазолопиридазинсульфанил в положении 6: получение, применение в качестве лекарственных средств и применение в качестве ингибиторов мет
AU2010212233A AU2010212233A1 (en) 2009-02-06 2010-02-04 Derivatives of 6-(6-NH-substituted-triazolopyridazine-sulfanyl) benzothiazoles and benzimidazoles, preparation thereof, use thereof as drugs, and use thereof as MET inhibitors
US13/147,297 US20120040987A1 (en) 2009-02-06 2010-02-04 Derivatives of 6-(6-nh-substituted-triazolopyridazine-sulfanyl) benzothiazoles and benzimidazoles, preparation thereof, use thereof as drugs, and use thereof as met inhibitors
CA2751539A CA2751539A1 (fr) 2009-02-06 2010-02-04 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met
BRPI1008188A BRPI1008188A2 (pt) 2009-02-06 2010-02-04 "derivados de 6-(6-nh-subistituído-triazolopiridazina-sulfanil) benzotiazóis e benzimidazóis: preparo, aplicação como medicamentos e utilização como inibidores de met"
CN201080015591XA CN102369192A (zh) 2009-02-06 2010-02-04 6-(6-nh-取代的三唑并哒嗪硫基)苯并噻唑和苯并咪唑的衍生物、其制备方法、其作为药物的用途以及其作为met抑制剂的用途
MX2011008310A MX2011008310A (es) 2009-02-06 2010-02-04 Derivados de 6-(triazolopiridazinsulfanil sustituido en 6 nh) benzotiazoles y bencimidazoles: preparacion, aplicacion como medicamentos y utilizacion como inhibidores de met.
SG2011056512A SG173562A1 (en) 2009-02-06 2010-02-04 Derivatives of 6-(6-nh-substituted-triazolopyridazine-sulfanyl) benzothiazoles and benzimidazoles, preparation thereof, use thereof as drugs, and use thereof as met inhibitors
KR1020117020674A KR20110126658A (ko) 2009-02-06 2010-02-04 6-(6-ｎｈ-치환된-트리아졸로피리다진-술파닐) 벤조티아졸 및 벤즈이미다졸의 유도체, 그의 제조법, 약물로서의 그의 용도, 및 ｍｅｔ 억제제로서의 그의 용도
TW099103591A TW201033214A (en) 2009-02-06 2010-02-05 6-(6-NH-substituted triazolopyridazine sulphanyl) benzothiazole and 6-(6-NH-substituted triazolopyridazine sulphanyl) benzimidazole derivatives: preparation, use as medicaments and use as MET inhibitors
UY0001032421A UY32421A (es) 2009-02-06 2010-02-05 Derivados de 6-(triazolopiridazinsulfanil sustituido en 6-nh) benzotiazoles y bencimidazoles: preparacion, aplicacion como medicamentos y utilizacion como inhibidores de met
ARP100100318A AR075250A1 (es) 2009-02-06 2010-02-05 Derivados de 6-(triazolopiridazinsulfanil sustituido en 6-nh)benzotiazoles y bencimidazoles; preparacion, aplicacion como medicamentos y utilizacion como inhibidores de met.
IL214404A IL214404A0 (en) 2009-02-06 2011-08-02 Derivatives of 6-(6-nh-substituted-triazolopyridazine-sulfanyl)benzothiazoles and benzimidazoles, preparation thereof, use thereof as drugs, and use thereof as met inhibitors

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0900513A FR2941951B1 (fr) 2009-02-06 2009-02-06 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.

Publications (2)

Publication Number Publication Date
FR2941951A1 FR2941951A1 (fr) 2010-08-13
FR2941951B1 true FR2941951B1 (fr) 2011-04-01

Family

ID=40886773

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0900513A Expired - Fee Related FR2941951B1 (fr) 2009-02-06 2009-02-06 Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.

Country Status (17)

Country Link
US (1) US20120040987A1 (fr)
EP (1) EP2393792A1 (fr)
JP (1) JP2012517409A (fr)
KR (1) KR20110126658A (fr)
CN (1) CN102369192A (fr)
AR (1) AR075250A1 (fr)
AU (1) AU2010212233A1 (fr)
BR (1) BRPI1008188A2 (fr)
CA (1) CA2751539A1 (fr)
FR (1) FR2941951B1 (fr)
IL (1) IL214404A0 (fr)
MX (1) MX2011008310A (fr)
RU (1) RU2011136855A (fr)
SG (1) SG173562A1 (fr)
TW (1) TW201033214A (fr)
UY (1) UY32421A (fr)
WO (1) WO2010089508A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2012310168B2 (en) 2011-09-15 2015-07-16 Novartis Ag 6 - substituted 3 - (quinolin- 6 - ylthio) - [1,2,4] triazolo [4, 3 -a] pyradines as tyrosine kinase
CA2878500A1 (fr) * 2012-07-12 2014-01-16 Sanofi Composition antitumorale comprenant le compose 1-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b] pyridazin-3-yl]sulfanyl}-1,3-benzothiazol-2-yl)-3-(2-morpholin-4-ylethyl)uree
AU2020242287A1 (en) 2019-03-21 2021-09-02 INSERM (Institut National de la Santé et de la Recherche Médicale) A Dbait molecule in combination with kinase inhibitor for the treatment of cancer
WO2021089791A1 (fr) 2019-11-08 2021-05-14 INSERM (Institut National de la Santé et de la Recherche Médicale) Méthodes pour le traitement de cancers qui ont acquis une résistance aux inhibiteurs de kinase
WO2021148581A1 (fr) 2020-01-22 2021-07-29 Onxeo Nouvelle molécule dbait et son utilisation

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1298125A1 (fr) 2001-09-26 2003-04-02 Aventis Pharma S.A. Benzimidazoles substitués et leur usage comme traitement du cancer
MX2008007049A (es) * 2005-11-30 2008-10-23 Vertex Pharma Inhibidores de c-met y usos de los mismos.
CN101360748B (zh) * 2005-11-30 2012-05-30 沃泰克斯药物股份有限公司 c-MET抑制剂及其应用
MX2008008277A (es) * 2005-12-21 2009-03-04 Janssen Pharmaceutica Nv Triazolopiridazinas como moduladores de tirosina cinasa.
WO2007138472A2 (fr) * 2006-05-30 2007-12-06 Pfizer Products Inc. Dérivés de la triazolopyridazine
PE20121506A1 (es) * 2006-07-14 2012-11-26 Amgen Inc Compuestos triazolopiridinas como inhibidores de c-met
DK2084162T3 (da) * 2006-10-23 2012-10-01 Sgx Pharmaceuticals Inc Bicykliske triazoler som proteinkinasemodulatorer
PA8792501A1 (es) * 2007-08-09 2009-04-23 Sanofi Aventis Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met.

Also Published As

Publication number Publication date
AR075250A1 (es) 2011-03-16
JP2012517409A (ja) 2012-08-02
UY32421A (es) 2010-09-30
KR20110126658A (ko) 2011-11-23
MX2011008310A (es) 2011-11-02
TW201033214A (en) 2010-09-16
SG173562A1 (en) 2011-09-29
FR2941951A1 (fr) 2010-08-13
EP2393792A1 (fr) 2011-12-14
AU2010212233A1 (en) 2011-08-25
US20120040987A1 (en) 2012-02-16
IL214404A0 (en) 2011-09-27
RU2011136855A (ru) 2013-03-20
BRPI1008188A2 (pt) 2016-03-08
CA2751539A1 (fr) 2010-08-12
WO2010089508A1 (fr) 2010-08-12
CN102369192A (zh) 2012-03-07

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