ES2559427T3 - Derivados de azaindol - Google Patents
Derivados de azaindol Download PDFInfo
- Publication number
- ES2559427T3 ES2559427T3 ES09778705.5T ES09778705T ES2559427T3 ES 2559427 T3 ES2559427 T3 ES 2559427T3 ES 09778705 T ES09778705 T ES 09778705T ES 2559427 T3 ES2559427 T3 ES 2559427T3
- Authority
- ES
- Spain
- Prior art keywords
- pyridin
- carbonitrile
- pyrrolo
- fluorophenyl
- ridin
- 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.)
- Active
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- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 38
- -1 3,5-dichlorophenyl Chemical group 0.000 claims description 127
- 206010028980 Neoplasm Diseases 0.000 claims description 45
- 238000011282 treatment Methods 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 21
- 201000011510 cancer Diseases 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 6
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 201000008275 breast carcinoma Diseases 0.000 claims description 5
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- 208000037803 restenosis Diseases 0.000 claims description 5
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 5
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- 210000002784 stomach Anatomy 0.000 claims description 4
- YSSSUMUGHHKGCO-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=N1 YSSSUMUGHHKGCO-UHFFFAOYSA-N 0.000 claims description 3
- 206010024305 Leukaemia monocytic Diseases 0.000 claims description 3
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- GNQCLFQBQPEDAE-UHFFFAOYSA-N 2,3-dipyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C12=NC(C#N)=CC=C2NC(C=2C=CN=CC=2)=C1C1=CC=NC=C1 GNQCLFQBQPEDAE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- IPQQKDAYBQMYIE-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=NC(N)=NC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 IPQQKDAYBQMYIE-UHFFFAOYSA-N 0.000 claims description 2
- JSFXKOZDTHPMDK-UHFFFAOYSA-N 3-(2-methylfuran-3-yl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound O1C=CC(C=2C3=NC(=CC=C3NC=2C=2C=CN=CC=2)C#N)=C1C JSFXKOZDTHPMDK-UHFFFAOYSA-N 0.000 claims description 2
- XSWFPAQEENJOFK-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(F)C(F)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 XSWFPAQEENJOFK-UHFFFAOYSA-N 0.000 claims description 2
- VZTBOCWTRFEYTA-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=C(Cl)C(F)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 VZTBOCWTRFEYTA-UHFFFAOYSA-N 0.000 claims description 2
- OXTHCEQMNCQZDC-UHFFFAOYSA-N 3-(4-bromophenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(Br)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 OXTHCEQMNCQZDC-UHFFFAOYSA-N 0.000 claims description 2
- BEOVYRJZUBKQRF-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(1-methylpyrrol-2-yl)-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound CN1C=CC=C1C1=C(C=2C=CC(F)=CC=2)C2=NC(C#N)=CC=C2N1 BEOVYRJZUBKQRF-UHFFFAOYSA-N 0.000 claims description 2
- LQBWYHGAMQUGEW-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-pyridin-3-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=NC=CC=2)NC2=CC=C(C#N)N=C12 LQBWYHGAMQUGEW-UHFFFAOYSA-N 0.000 claims description 2
- ZKWREAZYXJBXGE-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-pyrimidin-5-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=NC=NC=2)NC2=CC=C(C#N)N=C12 ZKWREAZYXJBXGE-UHFFFAOYSA-N 0.000 claims description 2
- VTLMUGWFUKHYEK-UHFFFAOYSA-N 3-phenyl-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C12=NC(C#N)=CC=C2NC(C=2C=CN=CC=2)=C1C1=CC=CC=C1 VTLMUGWFUKHYEK-UHFFFAOYSA-N 0.000 claims description 2
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- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
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- 206010003246 arthritis Diseases 0.000 claims description 2
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- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- ZHGQEIUEYRXNDA-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(1-methyl-1,2,4-triazol-3-yl)-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound FC1=CC=C(C=C1)C1=C(NC=2C1=NC(=CC2)C#N)C2=NN(C=N2)C ZHGQEIUEYRXNDA-UHFFFAOYSA-N 0.000 claims 1
- WFHKUMFOCDWFFL-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-thiophen-2-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2SC=CC=2)NC2=CC=C(C#N)N=C12 WFHKUMFOCDWFFL-UHFFFAOYSA-N 0.000 claims 1
- MCNADUQAZBSKQC-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-2-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CN=CC=2)NC2=CC=C(C#N)N=C12 MCNADUQAZBSKQC-UHFFFAOYSA-N 0.000 claims 1
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008052943 | 2008-10-23 | ||
| DE102008052943A DE102008052943A1 (de) | 2008-10-23 | 2008-10-23 | Azaindolderivate |
| PCT/EP2009/006911 WO2010046013A1 (de) | 2008-10-23 | 2009-09-24 | Azaindolderivate |
Publications (1)
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| ES2559427T3 true ES2559427T3 (es) | 2016-02-12 |
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| WO (1) | WO2010046013A1 (enExample) |
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| JP5596364B2 (ja) * | 2009-02-19 | 2014-09-24 | 住友化学株式会社 | 含窒素有機化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
| WO2011075613A1 (en) * | 2009-12-18 | 2011-06-23 | Sanofi | Azaindole derivatives, their preparation and their therapeutic application |
| DE102010050558A1 (de) * | 2010-11-05 | 2012-05-10 | Merck Patent Gmbh | 1H-Pyrrolo[2,3-b]pyridinderivate |
| EP2701510B1 (en) | 2011-04-25 | 2017-02-15 | Usher III Initiative | Pyrazolopyridazines and methods for treating retinal-degenerative diseases and hearing loss associated with usher syndrome |
| WO2012170867A1 (en) | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| GB201217285D0 (en) * | 2012-09-27 | 2012-11-14 | Univ Central Lancashire | Indole derivatives |
| US9227976B2 (en) | 2012-10-25 | 2016-01-05 | Usher Iii Initiative, Inc. | Pyrazolopyridazines and methods for treating retinal-degenerative diseases and hearing loss associated with usher syndrome |
| EP2968282B1 (en) * | 2013-03-12 | 2018-05-09 | Celgene Quanticel Research, Inc. | Histone dementhylase inhibitors |
| US9499551B2 (en) | 2014-01-24 | 2016-11-22 | Confluence Life Sciences, Inc. | Substituted pyrrolo[2,3-b]pyridines for treating cancer or inflammatory diseases |
| SG11201608708WA (en) | 2014-05-15 | 2016-11-29 | Iteos Therapeutics | Pyrrolidine-2,5-dione derivatives, pharmaceutical compositions and methods for use as ido1 inhibitors |
| AR103232A1 (es) * | 2014-12-22 | 2017-04-26 | Bristol Myers Squibb Co | ANTAGONISTAS DE TGFbR |
| WO2016118951A2 (en) | 2015-01-23 | 2016-07-28 | Confluence Life Sciences, Inc. | Heterocyclic itk inhibitors for treating inflammation and cancer |
| WO2016147144A1 (en) | 2015-03-17 | 2016-09-22 | Pfizer Inc. | Novel 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| CA2994917A1 (en) | 2015-08-10 | 2017-02-16 | Pfizer Inc. | 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| US10590079B2 (en) * | 2016-03-01 | 2020-03-17 | Novartis Ag | Cyano-substituted indoles as LSD1 inhibitors |
| US10513509B2 (en) * | 2016-05-26 | 2019-12-24 | Recurium Ip Holdings, Llc | EGFR inhibitor compounds |
| US20190298715A1 (en) * | 2016-09-30 | 2019-10-03 | Novartis Ag | Immune effector cell therapies with enhanced efficacy |
| WO2018210660A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2018210661A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2018210659A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2018210658A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| WO2019057660A1 (en) | 2017-09-25 | 2019-03-28 | Basf Se | INDOLE AND AZAINDOLE COMPOUNDS HAVING 6-CHANNEL SUBSTITUTED ARYL AND HETEROARYL CYCLES AS AGROCHEMICAL FUNGICIDES |
| EP3730489A1 (en) | 2019-04-25 | 2020-10-28 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
| KR102513463B1 (ko) * | 2020-11-26 | 2023-03-29 | 주식회사 에스앤케이테라퓨틱스 | 엔도솜 톨-유사 수용체를 제어하는 신규 소분자 화합물 및 이를 이용한 자가면역질환 치료제 |
| CN116332940B (zh) * | 2023-02-14 | 2024-09-13 | 广西民族大学 | 一种7-脱氮嘌呤衍生物及其制备方法和应用 |
| WO2024245193A1 (zh) * | 2023-05-26 | 2024-12-05 | 上海艾力斯医药科技股份有限公司 | 杂芳环类化合物、其药物组合物及其应用 |
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| US3022A (en) * | 1843-03-30 | Machine for bending stibrups for paddle-wheels of steam and other | ||
| US7004A (en) * | 1850-01-08 | Connecting ctjttees to shafts of boeing instetjments | ||
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| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| JP4464466B2 (ja) | 1996-03-05 | 2010-05-19 | アストラゼネカ・ユーケイ・リミテッド | ４―アニリノキナゾリン誘導体 |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| DE69728688T2 (de) * | 1996-11-19 | 2004-08-19 | Amgen Inc., Thousand Oaks | Aryl und heteroaryl substituierte kondensierte pyrrole als entzündunghemmende mittel |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| AU745579B2 (en) | 1997-10-20 | 2002-03-21 | F. Hoffmann-La Roche Ag | Bicyclic kinase inhibitors |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
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| DE19951360A1 (de) * | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| JP2001122855A (ja) * | 1999-10-27 | 2001-05-08 | Japan Tobacco Inc | インドール化合物及びその医薬用途 |
| IL152682A0 (en) | 2000-05-31 | 2003-06-24 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| JP2004502766A (ja) | 2000-07-07 | 2004-01-29 | アンギオジェン・ファーマシューティカルズ・リミテッド | 血管損傷剤としてのコルヒノール誘導体 |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| AUPR283801A0 (en) * | 2001-02-01 | 2001-03-01 | Australian National University, The | Chemical compounds and methods |
| SE0202463D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel compounds |
| CN1713910A (zh) | 2002-10-09 | 2005-12-28 | 西奥斯股份有限公司 | 作为p38激酶抑制剂的氮杂吲哚衍生物 |
| JP4787150B2 (ja) | 2003-03-06 | 2011-10-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Ｊｎｋ阻害剤 |
| CN1925855B (zh) | 2003-12-19 | 2010-06-16 | 普莱希科公司 | 开发Ret调节剂的化合物和方法 |
| GB0405055D0 (en) | 2004-03-05 | 2004-04-07 | Eisai London Res Lab Ltd | JNK inhibitors |
| CA2560454C (en) | 2004-03-30 | 2013-05-21 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of jak and other protein kinases |
| EP2325184A1 (en) | 2004-06-30 | 2011-05-25 | Vertex Pharmceuticals Incorporated | Azaindoles useful as inhibitors of protein kinases |
| WO2006017443A2 (en) | 2004-08-02 | 2006-02-16 | Osi Pharmaceuticals, Inc. | Aryl-amino substituted pyrrolopyrimidine multi-kinase inhibiting compounds |
| WO2006112828A1 (en) | 2005-04-15 | 2006-10-26 | Scios, Inc. | Azaindole derivatives as inhibitors of p38 kinase |
| FR2884821B1 (fr) | 2005-04-26 | 2007-07-06 | Aventis Pharma Sa | Pyrrolopyridines substitues, compositions les contenant, procede de fabrication et utilisation |
| ES2380795T3 (es) | 2005-05-20 | 2012-05-18 | Vertex Pharmaceuticals, Inc. | Pirrolopiridinas útiles como inhibidores de proteínas quinasas |
| DK2395004T3 (en) | 2005-06-22 | 2016-03-21 | Plexxikon Inc | Pyrrolo [2,3-b] pyridine derivatives as protein kinase inhibitors |
| CA2615291A1 (en) | 2005-07-14 | 2007-01-18 | Astellas Pharma Inc. | Heterocyclic janus kinase 3 inhibitors |
| CN102127078A (zh) | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1963320A1 (en) | 2005-12-07 | 2008-09-03 | OSI Pharmaceuticals, Inc. | Pyrrolopyridine kinase inhibiting compounds |
| EP1962851A2 (en) | 2005-12-22 | 2008-09-03 | SmithKline Beecham Corporation | Compounds |
| KR20080083680A (ko) | 2005-12-23 | 2008-09-18 | 스미스클라인 비참 코포레이션 | 오로라 키나제의 아자인돌 억제제 |
| US20090306126A1 (en) | 2006-05-22 | 2009-12-10 | Astrazeneca Ab | Indole Derivatives |
| WO2008014249A2 (en) | 2006-07-24 | 2008-01-31 | Sanofi-Aventis | Improved preparations of 2 -substituted pyrrolo [2, 3-b] pyrazine ( 4, 7 -diazaindole ) compounds |
| GB0708141D0 (en) * | 2007-04-26 | 2007-06-06 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
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| JP5662325B2 (ja) | 2015-01-28 |
| CA2741428C (en) | 2017-05-09 |
| IL212285A0 (en) | 2011-06-30 |
| EP2342202A1 (de) | 2011-07-13 |
| AU2009306795B2 (en) | 2015-07-16 |
| AU2009306795A1 (en) | 2010-04-29 |
| JP2012506389A (ja) | 2012-03-15 |
| CA2741428A1 (en) | 2010-04-29 |
| DE102008052943A1 (de) | 2010-04-29 |
| WO2010046013A1 (de) | 2010-04-29 |
| EP2342202B1 (de) | 2015-11-11 |
| US20110207732A1 (en) | 2011-08-25 |
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