DK2025661T3 - Fluoralkyloxyholdige combretastatinderivater, fremstilling og anvendelse heraf - Google Patents
Fluoralkyloxyholdige combretastatinderivater, fremstilling og anvendelse herafInfo
- Publication number
- DK2025661T3 DK2025661T3 DK06817879.7T DK06817879T DK2025661T3 DK 2025661 T3 DK2025661 T3 DK 2025661T3 DK 06817879 T DK06817879 T DK 06817879T DK 2025661 T3 DK2025661 T3 DK 2025661T3
- Authority
- DK
- Denmark
- Prior art keywords
- combretastatin
- fluoroalkyloxy
- preparation
- compounds
- combretastatin derivatives
- Prior art date
Links
- 150000004814 combretastatins Chemical class 0.000 title abstract 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 abstract 1
- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 abstract 1
- 102000029749 Microtubule Human genes 0.000 abstract 1
- 108091022875 Microtubule Proteins 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 102000004243 Tubulin Human genes 0.000 abstract 1
- 108090000704 Tubulin Proteins 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 239000004037 angiogenesis inhibitor Substances 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 210000004688 microtubule Anatomy 0.000 abstract 1
- 229930014626 natural product Natural products 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006257 total synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P37/02—Immunomodulators
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Biotechnology (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006100273076A CN101085743B (zh) | 2006-06-06 | 2006-06-06 | 含氟烷氧基康普立停衍生物及制法和用途 |
| PCT/CN2006/003149 WO2007140662A1 (fr) | 2006-06-06 | 2006-11-22 | Dérivés combrétastatine contenant une fonction fluoroalkyloxy, leur préparation et leur utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2025661T3 true DK2025661T3 (da) | 2011-06-14 |
Family
ID=38801042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK06817879.7T DK2025661T3 (da) | 2006-06-06 | 2006-11-22 | Fluoralkyloxyholdige combretastatinderivater, fremstilling og anvendelse heraf |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7786098B2 (da) |
| EP (1) | EP2025661B1 (da) |
| JP (1) | JP5100749B2 (da) |
| KR (1) | KR101321960B1 (da) |
| CN (1) | CN101085743B (da) |
| AT (1) | ATE501999T1 (da) |
| AU (1) | AU2006344313B8 (da) |
| CA (1) | CA2660760C (da) |
| DE (1) | DE602006020787D1 (da) |
| DK (1) | DK2025661T3 (da) |
| ES (1) | ES2363716T3 (da) |
| RU (1) | RU2417216C2 (da) |
| WO (1) | WO2007140662A1 (da) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8003627B2 (en) * | 2005-10-21 | 2011-08-23 | Universiteit Antwerpen | Urokinase inhibitors |
| CN101723813A (zh) * | 2008-10-15 | 2010-06-09 | 上海华理生物医药有限公司 | 一种乙氧基二苯乙烷衍生物及其制备方法和用途 |
| CN103012248B (zh) * | 2013-01-11 | 2014-11-05 | 浙江大德药业集团有限公司 | 氨基康普立停衍生物的合成及其作为口服抗肿瘤药物的应用 |
| RU2594281C2 (ru) * | 2013-04-03 | 2016-08-10 | Чайна Медикал Юнивёсити | Стильбеноидные соединения в качестве ингибиторов плоскоклеточной карциномы и гепатомы и их применения |
| CN103214422B (zh) * | 2013-05-07 | 2015-07-15 | 南通大学 | 一类新型取代胺基咪唑酮衍生物的制备方法及抗癌作用 |
| CN104447598B (zh) * | 2013-09-18 | 2017-09-22 | 浙江大德药业集团有限公司 | Ca‑4的大环多胺衍生物及其抗肿瘤特性 |
| AU2016256470B2 (en) | 2015-04-29 | 2020-10-15 | Radius Pharmaceuticals, Inc. | Methods of treating cancer |
| CN107365248A (zh) * | 2017-07-25 | 2017-11-21 | 上海应用技术大学 | 二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 |
| CN107311846B (zh) * | 2017-07-25 | 2022-05-13 | 上海华理生物医药股份有限公司 | 偕二氟乙基取代的二苯乙烯和二苯乙烷类衍生物及其制备方法和应用 |
| CN108129325A (zh) * | 2018-02-07 | 2018-06-08 | 上海应用技术大学 | 一种氟代含氮二苯乙烯衍生物及其制备方法和应用 |
| CN108606970A (zh) * | 2018-04-20 | 2018-10-02 | 浙江大德药业集团有限公司 | 含有ca-4p的药物组合物及其制备方法和在肝癌血管性介入治疗中的应用 |
| CN108675918B (zh) * | 2018-05-29 | 2020-06-26 | 常州大学 | 一种白皮杉醇的合成方法 |
| CN110240539B (zh) * | 2019-06-11 | 2021-12-07 | 上海应用技术大学 | 一种氟取代二苯乙烷类化合物及制备方法和应用 |
| CN110642885A (zh) * | 2019-09-23 | 2020-01-03 | 上海应用技术大学 | 一种多取代苯酚磷酸酯盐及其制备方法和应用 |
| CN111362837A (zh) * | 2020-03-23 | 2020-07-03 | 新乡医学院 | 一种NQO1激活型Combretastatin A4前药及其合成方法和应用 |
| CN112225673B (zh) | 2020-11-13 | 2022-08-02 | 义乌市华耀医药科技有限公司 | 氨基康普立停衍生物及其应用 |
| CN113511962A (zh) * | 2021-06-30 | 2021-10-19 | 上海应用技术大学 | 一种氟代乙氧基毛兰素及其制备方法与应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5561122A (en) | 1994-12-22 | 1996-10-01 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Combretastatin A-4 prodrug |
| JP3163391B2 (ja) * | 1995-03-07 | 2001-05-08 | 味の素株式会社 | スチルベン誘導体及びそれを含有する制癌剤 |
| JP2002500227A (ja) * | 1998-01-09 | 2002-01-08 | アリゾナ ボード オブ リーゼンツ | コンブレタスタチンａ−４プロドラッグとそのトランス異性体 |
| GB9918912D0 (en) * | 1999-08-12 | 1999-10-13 | Angiogene Pharm Ltd | New stilbenes with vascular damaging activity |
| GB0019944D0 (en) * | 2000-08-15 | 2000-09-27 | Angiogene Pharm Ltd | Compositions with vascular damaging activity |
| AU2002216228A1 (en) * | 2000-12-21 | 2002-07-01 | Cancer Research Ventures Limited | Substituted stilbenes, their reactions and anticancer activity |
| GB0031263D0 (en) * | 2000-12-21 | 2001-01-31 | Paterson Inst For Cancer Res | Materials and methods for synthesizing stilbenes |
| US6773702B2 (en) | 2000-12-26 | 2004-08-10 | Oxigene, Inc. | Use of combretastatin A4 and its prodrugs as an immune enhancing therapy |
| CA2463902A1 (en) * | 2001-10-26 | 2003-05-01 | Oxigene, Inc. | Functionalized stilbene derivatives as improved vascular targeting agents |
| GB2403949A (en) | 2003-07-18 | 2005-01-19 | Sigma Tau Ind Farmaceuti | Combretastatin derivatives |
| AU2005289773A1 (en) * | 2004-09-24 | 2006-04-06 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona Acting For And On Behalf Of Arizona State University | Halocombstatins and methods of synthesis thereof |
| WO2006074192A2 (en) * | 2005-01-03 | 2006-07-13 | Bionaut Pharmaceuticals, Inc. | Treatment of inflammatory disorders |
-
2006
- 2006-06-06 CN CN2006100273076A patent/CN101085743B/zh active Active
- 2006-11-22 JP JP2009513532A patent/JP5100749B2/ja not_active Expired - Fee Related
- 2006-11-22 DE DE602006020787T patent/DE602006020787D1/de active Active
- 2006-11-22 AU AU2006344313A patent/AU2006344313B8/en not_active Ceased
- 2006-11-22 EP EP06817879A patent/EP2025661B1/en active Active
- 2006-11-22 ES ES06817879T patent/ES2363716T3/es active Active
- 2006-11-22 KR KR1020097000209A patent/KR101321960B1/ko active IP Right Grant
- 2006-11-22 RU RU2008153041/04A patent/RU2417216C2/ru not_active IP Right Cessation
- 2006-11-22 WO PCT/CN2006/003149 patent/WO2007140662A1/zh active Application Filing
- 2006-11-22 AT AT06817879T patent/ATE501999T1/de not_active IP Right Cessation
- 2006-11-22 DK DK06817879.7T patent/DK2025661T3/da active
- 2006-11-22 CA CA2660760A patent/CA2660760C/en not_active Expired - Fee Related
- 2006-11-22 US US12/088,984 patent/US7786098B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| RU2417216C2 (ru) | 2011-04-27 |
| JP2009539779A (ja) | 2009-11-19 |
| CA2660760A1 (en) | 2007-12-13 |
| RU2008153041A (ru) | 2010-07-20 |
| US7786098B2 (en) | 2010-08-31 |
| AU2006344313A1 (en) | 2007-12-13 |
| CN101085743B (zh) | 2012-02-15 |
| KR101321960B1 (ko) | 2013-10-25 |
| US20080306027A1 (en) | 2008-12-11 |
| AU2006344313B8 (en) | 2012-12-06 |
| JP5100749B2 (ja) | 2012-12-19 |
| ATE501999T1 (de) | 2011-04-15 |
| EP2025661B1 (en) | 2011-03-16 |
| EP2025661A4 (en) | 2010-07-28 |
| KR20090023465A (ko) | 2009-03-04 |
| EP2025661A1 (en) | 2009-02-18 |
| DE602006020787D1 (de) | 2011-04-28 |
| WO2007140662A1 (fr) | 2007-12-13 |
| CA2660760C (en) | 2013-01-08 |
| ES2363716T3 (es) | 2011-08-12 |
| CN101085743A (zh) | 2007-12-12 |
| AU2006344313B2 (en) | 2012-07-26 |
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