CA2589136C - Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry - Google Patents
Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry Download PDFInfo
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- CA2589136C CA2589136C CA2589136A CA2589136A CA2589136C CA 2589136 C CA2589136 C CA 2589136C CA 2589136 A CA2589136 A CA 2589136A CA 2589136 A CA2589136 A CA 2589136A CA 2589136 C CA2589136 C CA 2589136C
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- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
- 229940075620 somatostatin analogue Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/082—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being a RGD-containing peptide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/10—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody
- A61K51/1045—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody against animal or human tumor cells or tumor cell determinants
- A61K51/1051—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody against animal or human tumor cells or tumor cell determinants the tumor cell being from breast, e.g. the antibody being herceptin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Optics & Photonics (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Cell Biology (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2817636A CA2817636A1 (en) | 2004-12-22 | 2005-12-09 | Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0428012.9A GB0428012D0 (en) | 2004-12-22 | 2004-12-22 | Radiolabelling methods |
| GB0428012.9 | 2004-12-22 | ||
| PCT/GB2005/004729 WO2006067376A2 (en) | 2004-12-22 | 2005-12-09 | Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2817636A Division CA2817636A1 (en) | 2004-12-22 | 2005-12-09 | Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2589136A1 CA2589136A1 (en) | 2006-06-29 |
| CA2589136C true CA2589136C (en) | 2015-10-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2589136A Expired - Fee Related CA2589136C (en) | 2004-12-22 | 2005-12-09 | Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry |
| CA2817636A Abandoned CA2817636A1 (en) | 2004-12-22 | 2005-12-09 | Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2817636A Abandoned CA2817636A1 (en) | 2004-12-22 | 2005-12-09 | Radiolabelled conjugates of rgd-containing peptides and methods for their preparation via click-chemistry |
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| EP (4) | EP2275145A1 (enExample) |
| JP (2) | JP5743372B2 (enExample) |
| KR (1) | KR101314460B1 (enExample) |
| CN (2) | CN101084020A (enExample) |
| AU (1) | AU2005317903C1 (enExample) |
| BR (1) | BRPI0519317A2 (enExample) |
| CA (2) | CA2589136C (enExample) |
| GB (1) | GB0428012D0 (enExample) |
| MX (1) | MX2007007560A (enExample) |
| NO (1) | NO341638B1 (enExample) |
| RU (1) | RU2419627C2 (enExample) |
| WO (1) | WO2006067376A2 (enExample) |
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| US8071718B2 (en) | 2004-12-22 | 2011-12-06 | General Electric Company | Selective radiolabeling of biomolecules |
| GB0428012D0 (en) * | 2004-12-22 | 2005-01-26 | Hammersmith Imanet Ltd | Radiolabelling methods |
| EP2029616A1 (en) * | 2006-06-21 | 2009-03-04 | Hammersmith Imanet Limited | Chemical methods and apparatus |
| EP2029179A2 (en) | 2006-06-21 | 2009-03-04 | Hammersmith Imanet, Ltd | Radiolabelling methods |
| JP2010502585A (ja) * | 2006-08-28 | 2010-01-28 | ジーイー・ヘルスケア・リミテッド | ６８Ｇａ標識ペプチド系放射性医薬品 |
| WO2008025886A1 (en) * | 2006-09-01 | 2008-03-06 | Wallac Oy | Metal chelates and chelating agents containing triazolyl subunits |
| US8652440B2 (en) * | 2007-05-10 | 2014-02-18 | The Trustees Of Columbia University In The City Of New York | Methods for diagnosing diseases and evaluating treatments therefor using PET |
| CN101903047B (zh) * | 2007-12-20 | 2015-10-21 | 通用电气公司 | 生物分子的选择性放射性标记 |
| EP2147684A1 (en) * | 2008-07-22 | 2010-01-27 | Bracco Imaging S.p.A | Diagnostic Agents Selective Against Metalloproteases |
| GB0815831D0 (en) * | 2008-09-01 | 2008-10-08 | Imp Innovations Ltd | Compounds |
| US8961930B2 (en) | 2008-09-05 | 2015-02-24 | Imperial Innovations Limited | Isatin derivatives for use as in vivo imaging agents |
| PL2346870T3 (pl) * | 2008-10-10 | 2016-01-29 | Merck & Cie | Foliany znakowane fluorem-18 jako radioznaczniki pet |
| US20120165650A1 (en) | 2010-12-22 | 2012-06-28 | General Electric Company | Her2 binders |
| EP2210882A1 (en) * | 2009-01-16 | 2010-07-28 | Commissariat à l'Énergie Atomique et aux Énergies Alternatives | Synthesis of new protected azahistidine, their processes and their use in synthesises |
| WO2010099273A1 (en) * | 2009-02-27 | 2010-09-02 | Genentech, Inc. | Methods and compositions for protein labelling |
| US8722014B2 (en) * | 2009-05-01 | 2014-05-13 | Washington University | 1 H-[1, 2, 3] triazole substituted amino acids and uses thereof |
| GB0914543D0 (en) | 2009-08-20 | 2009-09-30 | Ge Healthcare Ltd | Radioiodination method |
| EP2498826A1 (en) * | 2009-11-11 | 2012-09-19 | NeuroSearch AS | Labelled pyrrolyl-oxadiazolyl-diazabicyclononane derivatives and their use in diagnostic methods |
| GB0921573D0 (en) * | 2009-12-10 | 2010-01-27 | Ge Healthcare Ltd | Iodine radiolabelling method |
| GB0922304D0 (en) | 2009-12-22 | 2010-02-03 | Ge Healthcare Ltd | Radioiodinated compounds |
| AU2010336357B2 (en) * | 2009-12-23 | 2015-04-16 | Board Of Regents Of The University Of Nebraska | Targeted radiolabeled compounds and their use for the treatment and diagnosis of cancer |
| US9517279B2 (en) * | 2010-04-14 | 2016-12-13 | The Mclean Hospital Corporation | 2-alkoxy-11-hydroxyaporphine derivatives and uses thereof |
| US9770515B2 (en) | 2010-06-01 | 2017-09-26 | Advanced Proteome Therapeutics Inc. | Crosslinking of proteins and other entities via conjugates of α-haloacetophenones, benzyl halides, quinones, and their derivatives |
| EP2595967B1 (en) * | 2010-07-23 | 2016-03-23 | University Of Delaware | Tetrazine-trans-cyclooctene ligation for the rapid construction of radionuclide labeled probes |
| GB201014023D0 (en) * | 2010-08-20 | 2010-10-06 | Ucl Business Plc | Process for producing bioconjugates and products thereof |
| WO2012074840A2 (en) | 2010-11-22 | 2012-06-07 | The General Hospital Corporation | Compositions and methods for in vivo imaging |
| GB201019824D0 (en) | 2010-11-23 | 2011-01-05 | Ge Healthcare Ltd | Radioiodination method |
| GB201021369D0 (en) | 2010-12-16 | 2011-01-26 | Ge Healthcare Ltd | Radioiodinated fatty acids |
| GB201021517D0 (en) * | 2010-12-20 | 2011-02-02 | Ge Healthcare Ltd | Radioiodinated guanidines |
| CN103402550B (zh) | 2010-12-22 | 2015-12-09 | 通用电气健康护理有限公司 | 用含有18f的有机硅化合物标记的her2结合肽 |
| SG191292A1 (en) | 2010-12-22 | 2013-07-31 | Gen Electric | Radiolabled her2 binding peptides |
| CA2828810A1 (en) | 2011-03-01 | 2012-09-07 | Ge Healthcare Limited | Radiolabelled octreotate analogues as pet tracers |
| US20120251448A1 (en) * | 2011-03-03 | 2012-10-04 | Hefti Franz F | Compounds for Use in the Detection of Neurodegenerative Diseases |
| US9023318B2 (en) * | 2011-06-08 | 2015-05-05 | Siemens Medical Solutions Usa, Inc. | Compounds with matrix-metalloproteinase inhibitory activity and imaging agents thereof |
| WO2013048832A1 (en) | 2011-09-29 | 2013-04-04 | Ge Healthcare Limited | 18 f - labelled 6 - ( 2 - fluoroethoxy) - 2 - naphthaldehyde for detecting cancer stem cells |
| WO2013048811A1 (en) | 2011-09-30 | 2013-04-04 | Ge Healthcare Limited | Imaging and radiotherapy methods for tumour stem cells |
| WO2013082508A1 (en) * | 2011-12-02 | 2013-06-06 | The Regents Of The University Of Michigan | Compositions and methods for the treatment and analysis of neurological disorders |
| GB201121911D0 (en) | 2011-12-20 | 2012-02-01 | Ge Healthcare Ltd | Radiofluorination method |
| WO2013113680A1 (en) * | 2012-02-03 | 2013-08-08 | Aarhus Universitet | Radiolabeled bile acids and bile acid derivatives |
| EP2657213A1 (en) * | 2012-04-24 | 2013-10-30 | Institut National de la Santé et de la Recherche Medicale | Labelled quinoxaline derivatives as multimodal radiopharmaceuticals and their precursors |
| US20140065070A1 (en) * | 2012-08-28 | 2014-03-06 | Mcmaster University | Methods of preparing triazole-containing radioiodinated compounds |
| WO2014065413A1 (ja) * | 2012-10-26 | 2014-05-01 | 日本たばこ産業株式会社 | トリアゾール・イソオキサゾール化合物およびその医薬用途 |
| US20150023877A1 (en) * | 2013-07-18 | 2015-01-22 | The Board Of Trustees Of The Leland Stanford Junior University | Methods of parkinsons disease diagnosis and monitoring treatment |
| ES2700348T3 (es) * | 2014-01-05 | 2019-02-15 | Univ Washington | Trazadores radioetiquetados para poli (ADP-ribosa) polimerasa-1 (PARP-1), métodos y usos para estos |
| US20160022846A1 (en) * | 2014-07-22 | 2016-01-28 | Ge Healthcare Limited | Iodine radiolabelling method |
| MD3310816T2 (ro) * | 2015-06-19 | 2021-01-31 | Eisai R&D Man Co Ltd | Imunoglobuline conjugate Cys80 |
| WO2017023999A1 (en) * | 2015-08-03 | 2017-02-09 | Emory University | Methylsulfonamide derivatives and uses related thereto |
| WO2019227490A1 (en) | 2018-06-01 | 2019-12-05 | Tayu Huaxia Biotech Medical Group Co., Ltd. | Compositions and methods for imaging |
| JP7554178B2 (ja) * | 2018-07-26 | 2024-09-19 | タユー ファシャ バイオテック メディカル グループ カンパニー， リミテッド | イメージングのための組成物および方法 |
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| US4913891A (en) * | 1986-04-17 | 1990-04-03 | The United States Of America As Represented By The United States Department Of Energy | Positron emitter labeled enzyme inhibitors |
| WO2001072714A2 (en) * | 2000-03-24 | 2001-10-04 | Euro-Celtique S.A. | Aryl substituted pyrazoles, triazoles and tetrazoles as sodium channel blocker |
| US6350360B1 (en) | 2000-04-07 | 2002-02-26 | Sandia Coroporation | Method of fabricating a 3-dimensional tool master |
| NZ521735A (en) * | 2000-04-12 | 2004-12-24 | Amersham Health As | Peptide-based compounds, their use as targeting vectors that bind to receptors associated with antiogenesis such as integrin receptors |
| GB0115927D0 (en) * | 2001-06-29 | 2001-08-22 | Nycomed Amersham Plc | Solid-phase nucleophilic fluorination |
| JP4510444B2 (ja) * | 2001-07-10 | 2010-07-21 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | ペプチドベースの化合物 |
| ATE469135T1 (de) | 2002-05-30 | 2010-06-15 | Scripps Research Inst | Kupferkatalysierte ligierung von aziden und acetylenen |
| AU2003297859A1 (en) * | 2002-12-13 | 2004-07-09 | The Trustees Of Columbia University In The City Of New York | Biomolecular coupling methods using 1,3-dipolar cycloaddition chemistry |
| MXPA05011127A (es) * | 2003-04-17 | 2006-03-10 | Scripps Research Inst | Expansion del codigo genetico eucariontico. |
| JP5275566B2 (ja) * | 2003-06-18 | 2013-08-28 | ザ スクリプス リサーチ インスティチュート | 反応性非天然アミノ酸遺伝コード付加 |
| NO20033115D0 (no) | 2003-07-08 | 2003-07-08 | Amersham Health As | Peptid-baserte forbindelser |
| CN101035565A (zh) * | 2004-10-07 | 2007-09-12 | 皇家飞利浦电子股份有限公司 | 用于医学显像的化合物、试剂盒和方法 |
| GB0428012D0 (en) * | 2004-12-22 | 2005-01-26 | Hammersmith Imanet Ltd | Radiolabelling methods |
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2004
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2005
- 2005-12-09 RU RU2007122804/04A patent/RU2419627C2/ru not_active IP Right Cessation
- 2005-12-09 EP EP20100179449 patent/EP2275145A1/en not_active Withdrawn
- 2005-12-09 US US11/721,694 patent/US7972588B2/en active Active
- 2005-12-09 CN CNA2005800441130A patent/CN101084020A/zh active Pending
- 2005-12-09 KR KR1020077014048A patent/KR101314460B1/ko not_active Expired - Fee Related
- 2005-12-09 CA CA2589136A patent/CA2589136C/en not_active Expired - Fee Related
- 2005-12-09 EP EP10179446.9A patent/EP2266629B1/en not_active Expired - Lifetime
- 2005-12-09 BR BRPI0519317-6A patent/BRPI0519317A2/pt not_active Application Discontinuation
- 2005-12-09 AU AU2005317903A patent/AU2005317903C1/en not_active Ceased
- 2005-12-09 MX MX2007007560A patent/MX2007007560A/es active IP Right Grant
- 2005-12-09 EP EP20100179459 patent/EP2258403A1/en not_active Withdrawn
- 2005-12-09 CN CN201510494983.3A patent/CN105012972A/zh active Pending
- 2005-12-09 JP JP2007547612A patent/JP5743372B2/ja not_active Expired - Lifetime
- 2005-12-09 EP EP05818037A patent/EP1830890A2/en not_active Withdrawn
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- 2005-12-09 WO PCT/GB2005/004729 patent/WO2006067376A2/en not_active Ceased
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2011
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2007122804A (ru) | 2009-01-27 |
| CA2817636A1 (en) | 2006-06-29 |
| US8679455B2 (en) | 2014-03-25 |
| CN105012972A (zh) | 2015-11-04 |
| US7972588B2 (en) | 2011-07-05 |
| JP2012254998A (ja) | 2012-12-27 |
| RU2419627C2 (ru) | 2011-05-27 |
| CA2589136A1 (en) | 2006-06-29 |
| EP2275145A1 (en) | 2011-01-19 |
| JP5743372B2 (ja) | 2015-07-01 |
| AU2005317903B8 (en) | 2012-01-19 |
| EP1830890A2 (en) | 2007-09-12 |
| JP2008528445A (ja) | 2008-07-31 |
| AU2005317903B2 (en) | 2011-12-01 |
| KR20070091626A (ko) | 2007-09-11 |
| WO2006067376A3 (en) | 2007-07-26 |
| BRPI0519317A2 (pt) | 2009-01-13 |
| KR101314460B1 (ko) | 2013-10-10 |
| AU2005317903A1 (en) | 2006-06-29 |
| US20090311177A1 (en) | 2009-12-17 |
| EP2266629B1 (en) | 2015-12-09 |
| MX2007007560A (es) | 2007-11-21 |
| CN101084020A (zh) | 2007-12-05 |
| NO341638B1 (no) | 2017-12-18 |
| WO2006067376A2 (en) | 2006-06-29 |
| NO20073157L (no) | 2007-06-20 |
| GB0428012D0 (en) | 2005-01-26 |
| US20110236311A1 (en) | 2011-09-29 |
| AU2005317903C1 (en) | 2012-05-10 |
| EP2266629A1 (en) | 2010-12-29 |
| EP2258403A1 (en) | 2010-12-08 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20161209 |