AU2008240153B2 - SMAC mimetic dimers and trimers useful as anti-cancer agents - Google Patents

SMAC mimetic dimers and trimers useful as anti-cancer agents Download PDF

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Publication number
AU2008240153B2
AU2008240153B2 AU2008240153A AU2008240153A AU2008240153B2 AU 2008240153 B2 AU2008240153 B2 AU 2008240153B2 AU 2008240153 A AU2008240153 A AU 2008240153A AU 2008240153 A AU2008240153 A AU 2008240153A AU 2008240153 B2 AU2008240153 B2 AU 2008240153B2
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optionally substituted
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alkyl
independently
formula
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AU2008240153A
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AU2008240153A1 (en
Inventor
Gunnar Hanson
Haizhou Sun
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Joyant Pharmaceuticals Inc
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Joyant Pharmaceuticals Inc
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Publication of AU2008240153B2 publication Critical patent/AU2008240153B2/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/04Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/06Tripeptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D207/16Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/04Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05Dipeptides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
AU2008240153A 2007-04-12 2008-04-11 SMAC mimetic dimers and trimers useful as anti-cancer agents Ceased AU2008240153B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US91147207P 2007-04-12 2007-04-12
US60/911,472 2007-04-12
US95249307P 2007-07-27 2007-07-27
US60/952,493 2007-07-27
PCT/US2008/060140 WO2008128121A1 (en) 2007-04-12 2008-04-11 Smac mimetic dimers and trimers useful as anti-cancer agents

Publications (2)

Publication Number Publication Date
AU2008240153A1 AU2008240153A1 (en) 2008-10-23
AU2008240153B2 true AU2008240153B2 (en) 2013-01-31

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
AU2008240153A Ceased AU2008240153B2 (en) 2007-04-12 2008-04-11 SMAC mimetic dimers and trimers useful as anti-cancer agents

Country Status (10)

Country Link
US (2) US8642554B2 (https=)
EP (1) EP2079309B1 (https=)
JP (1) JP5454943B2 (https=)
CN (1) CN101668426B (https=)
AU (1) AU2008240153B2 (https=)
BR (1) BRPI0810178A2 (https=)
CA (1) CA2684169C (https=)
MX (1) MX2009010667A (https=)
NZ (1) NZ580313A (https=)
WO (1) WO2008128121A1 (https=)

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2475207T3 (es) 2004-07-15 2014-07-10 Tetralogic Pharmaceuticals Corporation Compuestos de unión a IAP
MX2007010371A (es) * 2005-02-25 2008-01-11 Tetralogic Pharmaceuticals Inhibidores dimericos iap.
JP4954983B2 (ja) 2005-05-18 2012-06-20 ファーマサイエンス・インコーポレイテッド Birドメイン結合化合物
US20100256046A1 (en) * 2009-04-03 2010-10-07 Tetralogic Pharmaceuticals Corporation Treatment of proliferative disorders
WO2007048224A1 (en) 2005-10-25 2007-05-03 Aegera Therapeutics Inc. Iap bir domain binding compounds
TWI504597B (zh) 2006-03-16 2015-10-21 Pharmascience Inc 結合於細胞凋亡抑制蛋白(iap)之桿狀病毒iap重複序列(bir)區域之化合物
KR20090024834A (ko) 2006-07-05 2009-03-09 인터뮨, 인크. C형 간염 바이러스 복제의 신규 억제제
US20100143499A1 (en) * 2006-07-24 2010-06-10 Tetralogic Pharmaceuticals Corporation Dimeric iap inhibitors
WO2008014240A2 (en) * 2006-07-24 2008-01-31 Tetralogic Pharmaceuticals Corporation Dimeric iap inhibitors
JP5452223B2 (ja) * 2006-07-24 2014-03-26 テトラロジック ファーマシューティカルズ コーポレーション Iap阻害剤
MX2009000824A (es) * 2006-07-24 2009-02-04 Tetralogic Pharmaceuticals Cor Antagonistas dimericos de las proteinas inhibidoras de la apoptosis.
US20100056495A1 (en) * 2006-07-24 2010-03-04 Tetralogic Pharmaceuticals Corporation Dimeric iap inhibitors
WO2008014229A2 (en) * 2006-07-24 2008-01-31 Tetralogic Pharmaceuticals Corporation Dimeric iap inhibitors
JP2010528587A (ja) * 2007-05-07 2010-08-26 テトラロジック ファーマシューティカルズ コーポレーション アポトーシス阻害タンパク質のアンタゴニストに対する感受性のバイオマーカーとしてTNFα遺伝子の発現を用いる方法
WO2008141227A1 (en) 2007-05-10 2008-11-20 Intermune, Inc. Novel peptide inhibitors of hepatitis c virus replication
US20110177060A1 (en) * 2008-09-19 2011-07-21 Aegera Therapeutics, Inc. Iap bir domain binding compounds
SG172352A1 (en) 2008-12-23 2011-07-28 Abbott Lab Anti-viral compounds
US8546405B2 (en) 2008-12-23 2013-10-01 Abbott Laboratories Anti-viral compounds
US9278922B2 (en) 2009-04-15 2016-03-08 Abbvie Inc. Anti-viral compounds
US8937150B2 (en) 2009-06-11 2015-01-20 Abbvie Inc. Anti-viral compounds
US9394279B2 (en) 2009-06-11 2016-07-19 Abbvie Inc. Anti-viral compounds
EA020031B1 (ru) 2009-06-11 2014-08-29 Эббви Бахамаз Лтд. Противовирусные соединения
US8716454B2 (en) 2009-06-11 2014-05-06 Abbvie Inc. Solid compositions
US8283372B2 (en) 2009-07-02 2012-10-09 Tetralogic Pharmaceuticals Corp. 2-(1H-indol-3-ylmethyl)-pyrrolidine dimer as a SMAC mimetic
US8551955B2 (en) * 2009-10-28 2013-10-08 Joyant Pharmaceuticals, Inc. Dimeric Smac mimetics
US9284350B2 (en) 2010-02-12 2016-03-15 Pharmascience Inc. IAP BIR domain binding compounds
UY33236A (es) * 2010-02-25 2011-09-30 Novartis Ag Inhibidores dimericos de las iap
NZ605440A (en) 2010-06-10 2014-05-30 Abbvie Bahamas Ltd Solid compositions comprising an hcv inhibitor
UY33794A (es) 2010-12-13 2012-07-31 Novartis Ag Inhibidores diméricos de las iap
US10201584B1 (en) 2011-05-17 2019-02-12 Abbvie Inc. Compositions and methods for treating HCV
US9034832B2 (en) 2011-12-29 2015-05-19 Abbvie Inc. Solid compositions
US9603889B2 (en) * 2012-10-02 2017-03-28 Bristol-Myers Squibb Company IAP antagonists
US11484534B2 (en) 2013-03-14 2022-11-01 Abbvie Inc. Methods for treating HCV
GB201311891D0 (en) 2013-07-03 2013-08-14 Glaxosmithkline Ip Dev Ltd Novel compound
GB201311888D0 (en) 2013-07-03 2013-08-14 Glaxosmithkline Ip Dev Ltd Novel compounds
CN104710510A (zh) * 2013-12-12 2015-06-17 深圳先进技术研究院 Smac蛋白二聚拟合物及其鉴定方法
WO2015103490A1 (en) 2014-01-03 2015-07-09 Abbvie, Inc. Solid antiviral dosage forms
US20180228907A1 (en) 2014-04-14 2018-08-16 Arvinas, Inc. Cereblon ligands and bifunctional compounds comprising the same
JP6768522B2 (ja) 2014-06-04 2020-10-14 サンフォード−バーンハム メディカル リサーチ インスティテュート Hiv治療におけるアポトーシスタンパク質阻害剤(iap)のアンタゴニストの使用
US12312316B2 (en) 2015-01-20 2025-05-27 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of androgen receptor
JP6817962B2 (ja) 2015-01-20 2021-01-20 アルビナス・オペレーションズ・インコーポレイテッドArvinas Operations, Inc. ターゲティングされたアンドロゲン受容体分解のための化合物および方法
WO2016197114A1 (en) 2015-06-05 2016-12-08 Arvinas, Inc. Tank-binding kinase-1 protacs and associated methods of use
US10772962B2 (en) 2015-08-19 2020-09-15 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of bromodomain-containing proteins
WO2017194390A1 (en) * 2016-05-09 2017-11-16 F. Hoffmann-La Roche Ag Dimeric compounds
MX2019005007A (es) 2016-11-01 2019-07-18 Arvinas Inc Protac dirigidos a la proteína tau y métodos asociados de uso.
BR112019011200B1 (pt) 2016-12-01 2021-12-28 Arvinas Operations, Inc Derivados de tetrahidronaftaleno e tetrahidroisoquinolina como degradadores do receptor de estrogênio
US10806737B2 (en) 2016-12-23 2020-10-20 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of fetal liver kinase polypeptides
JP2020505327A (ja) 2016-12-23 2020-02-20 アルビナス・オペレーションズ・インコーポレイテッドArvinas Operations, Inc. Egfrタンパク質分解標的化キメラ分子およびその関連する使用方法
US11173211B2 (en) 2016-12-23 2021-11-16 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of rapidly accelerated Fibrosarcoma polypeptides
KR20250117470A (ko) 2016-12-23 2025-08-04 아비나스 오퍼레이션스, 인코포레이티드 급속 진행성 섬유육종 폴리펩티드의 표적화 분해를 위한 화합물 및 방법
US11191741B2 (en) 2016-12-24 2021-12-07 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of enhancer of zeste homolog 2 polypeptide
BR112019015312A2 (pt) 2017-01-26 2020-03-10 Arvinas Operations, Inc. Moduladores da proteólise pelo receptor de estrogênio e métodos de uso associados
EP3710443A1 (en) 2017-11-17 2020-09-23 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of interleukin-1 receptor-associated kinase 4 polypeptides
WO2019195609A2 (en) 2018-04-04 2019-10-10 Arvinas Operations, Inc. Modulators of proteolysis and associated methods of use
JP7297053B2 (ja) 2018-08-20 2023-06-23 アルビナス・オペレーションズ・インコーポレイテッド 神経変性疾患を治療するためのe3ユビキチンリガーゼ結合活性を有するキメラ(protac)化合物を標的とし、アルファ-シヌクレインタンパク質を標的とするタンパク質分解
CN113677399B (zh) * 2019-04-05 2024-10-11 和博医药有限公司 凋亡蛋白抑制剂的二价拮抗剂
EP3999182A1 (en) 2019-07-17 2022-05-25 Arvinas Operations, Inc. Tau-protein targeting compounds and associated methods of use
KR20220054347A (ko) 2019-08-26 2022-05-02 아비나스 오퍼레이션스, 인코포레이티드 에스트로겐 수용체 분해제로서의 테트라히드로나프탈렌 유도체로 유방암을 치료하는 방법
WO2021148396A1 (en) 2020-01-20 2021-07-29 Astrazeneca Ab Epidermal growth factor receptor tyrosine kinase inhibitors for the treatment of cancer
WO2022047145A1 (en) 2020-08-28 2022-03-03 Arvinas Operations, Inc. Rapidly accelerating fibrosarcoma protein degrading compounds and associated methods of use
US12503475B2 (en) 2020-09-03 2025-12-23 Centessa Pharmaceuticals (Uk) Limited Bicyclic-heterocycle derivatives and their uses as orexin-2 receptor agonists
WO2022056368A1 (en) 2020-09-14 2022-03-17 Arvinas Operations, Inc. Crystalline forms of a compound for the targeted degradation of estrogen receptor
US20240309557A1 (en) * 2021-01-27 2024-09-19 Unm Rainforest Innovations Pyrazole and pyrazoline-containing peptides, high throughput click libraries, and methods
AU2022239717A1 (en) 2021-03-15 2023-11-02 Maze Therapeutics, Inc. Inhibitors of glycogen synthase 1 (gys1) and methods of use thereof
MX2024004848A (es) 2021-10-22 2024-07-15 Univ Houston System Metodos y composiciones para el tratamiento de lesiones inflamatorias cronicas, metaplasias, displasia y canceres de tejidos epiteliales.
WO2024054591A1 (en) 2022-09-07 2024-03-14 Arvinas Operations, Inc. Rapidly accelerated fibrosarcoma (raf) degrading compounds and associated methods of use
US12448399B2 (en) 2023-01-26 2025-10-21 Arvinas Operations, Inc. Cereblon-based KRAS degrading PROTACs and uses related thereto
CN120957983A (zh) * 2023-04-17 2025-11-14 亚飞络思制药公司 取代的乙炔化合物衍生物及其药物用途

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007104162A1 (en) * 2006-03-16 2007-09-20 Aegera Therapeutics, Inc. Iap bir domain binding compounds

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4261989A (en) * 1979-02-19 1981-04-14 Kaken Chemical Co. Ltd. Geldanamycin derivatives and antitumor drug
US5387584A (en) * 1993-04-07 1995-02-07 Pfizer Inc. Bicyclic ansamycins
US5932566A (en) * 1994-06-16 1999-08-03 Pfizer Inc. Ansamycin derivatives as antioncogene and anticancer agents
US5624677A (en) * 1995-06-13 1997-04-29 Pentech Pharmaceuticals, Inc. Controlled release of drugs delivered by sublingual or buccal administration
SE9603466D0 (sv) * 1996-09-23 1996-09-23 Astra Ab New compounds
US6916846B2 (en) * 2000-05-12 2005-07-12 Merck & Co. Inc. Coumermycin analogs as chemical dimerizers of chimeric proteins
US7439359B2 (en) 2000-11-02 2008-10-21 Sloan-Kettering Institute For Cancer Research Small molecule compositions for binding to hsp90
EP1495124A2 (en) 2002-04-17 2005-01-12 Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts Smac-peptides as therapeutics against cancer and autoimmune diseases
WO2004005248A1 (en) * 2002-07-02 2004-01-15 Novartis Ag Peptide inhibitors of smac protein binding to inhibitor of apoptosis proteins (iap)
MXPA06002997A (es) 2003-09-18 2007-02-08 Conforma Therapeutics Corp Novedosos compuestos heterociclicos como inhibidores- hsp90.
WO2005084317A2 (en) * 2004-03-01 2005-09-15 Board Of Regents, The University Of Texas System Dimeric small molecule potentiators of apoptosis
AU2005228950B2 (en) 2004-03-23 2012-02-02 Genentech, Inc. Azabicyclo-octane inhibitors of IAP
DK2253614T3 (da) 2004-04-07 2013-01-07 Novartis Ag IAP-inhibitorer
KR100984459B1 (ko) * 2004-07-02 2010-09-29 제넨테크, 인크. Iap의 억제제
ES2475207T3 (es) * 2004-07-15 2014-07-10 Tetralogic Pharmaceuticals Corporation Compuestos de unión a IAP
DK1836201T4 (da) 2004-12-20 2013-11-11 Genentech Inc Pyrrolidininhibitorer af IAP.
MX2007010371A (es) * 2005-02-25 2008-01-11 Tetralogic Pharmaceuticals Inhibidores dimericos iap.
JP4954983B2 (ja) * 2005-05-18 2012-06-20 ファーマサイエンス・インコーポレイテッド Birドメイン結合化合物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007104162A1 (en) * 2006-03-16 2007-09-20 Aegera Therapeutics, Inc. Iap bir domain binding compounds

Also Published As

Publication number Publication date
US8642554B2 (en) 2014-02-04
EP2079309A1 (en) 2009-07-22
JP5454943B2 (ja) 2014-03-26
AU2008240153A1 (en) 2008-10-23
CA2684169A1 (en) 2008-10-23
EP2079309A4 (en) 2011-07-06
EP2079309B1 (en) 2015-11-11
CA2684169C (en) 2012-06-19
US20090104151A1 (en) 2009-04-23
JP2010523717A (ja) 2010-07-15
BRPI0810178A2 (pt) 2014-09-23
WO2008128121A1 (en) 2008-10-23
NZ580313A (en) 2011-11-25
CN101668426B (zh) 2014-01-15
MX2009010667A (es) 2010-02-24
US20140127155A1 (en) 2014-05-08
CN101668426A (zh) 2010-03-10

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