NO20076349L - Stereoselektiv syntese av aminosyreanaloger for tumorbilleddannelse - Google Patents
Stereoselektiv syntese av aminosyreanaloger for tumorbilleddannelseInfo
- Publication number
- NO20076349L NO20076349L NO20076349A NO20076349A NO20076349L NO 20076349 L NO20076349 L NO 20076349L NO 20076349 A NO20076349 A NO 20076349A NO 20076349 A NO20076349 A NO 20076349A NO 20076349 L NO20076349 L NO 20076349L
- Authority
- NO
- Norway
- Prior art keywords
- syn
- amino
- acbc
- analogs
- carboxylic acid
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- 206010028980 Neoplasm Diseases 0.000 title abstract 2
- 230000000707 stereoselective effect Effects 0.000 title abstract 2
- 150000001413 amino acids Chemical class 0.000 title 1
- 238000003384 imaging method Methods 0.000 title 1
- FVTVMQPGKVHSEY-UHFFFAOYSA-N 1-AMINOCYCLOBUTANE CARBOXYLIC ACID Chemical compound OC(=O)C1(N)CCC1 FVTVMQPGKVHSEY-UHFFFAOYSA-N 0.000 abstract 2
- NTEDWGYJNHZKQW-DGMDOPGDSA-N fluciclovine ((18)F) Chemical compound OC(=O)[C@]1(N)C[C@H]([18F])C1 NTEDWGYJNHZKQW-DGMDOPGDSA-N 0.000 abstract 1
- 229940027541 fluciclovine f-18 Drugs 0.000 abstract 1
- 239000012216 imaging agent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002600 positron emission tomography Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000002603 single-photon emission computed tomography Methods 0.000 abstract 1
- 210000004881 tumor cell Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
- A61K51/0402—Organic compounds carboxylic acid carriers, fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
- C07C227/20—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/84—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/04—Saturated compounds having a carboxyl group bound to a three or four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69338505P | 2005-06-23 | 2005-06-23 | |
| PCT/US2006/023740 WO2007001958A2 (fr) | 2005-06-23 | 2006-06-19 | Synthèse stéréo-sélective d'analogues d'acides aminés pour l'imagerie des tumeurs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO20076349L true NO20076349L (no) | 2008-02-15 |
Family
ID=37595707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20076349A NO20076349L (no) | 2005-06-23 | 2007-12-11 | Stereoselektiv syntese av aminosyreanaloger for tumorbilleddannelse |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060292073A1 (fr) |
| EP (1) | EP1893246A4 (fr) |
| JP (1) | JP5349960B2 (fr) |
| AU (1) | AU2006262425C1 (fr) |
| CA (1) | CA2612187C (fr) |
| NO (1) | NO20076349L (fr) |
| RU (1) | RU2376282C2 (fr) |
| WO (1) | WO2007001958A2 (fr) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009505947A (ja) * | 2005-06-23 | 2009-02-12 | エモリー・ユニバーシティ | 画像化剤 |
| CA2629227C (fr) | 2005-11-29 | 2014-02-25 | Nihon Medi-Physics Co., Ltd. | Compose precurseur de compose organique marque a l'halogene radioactif |
| JPWO2008056481A1 (ja) * | 2006-11-09 | 2010-02-25 | 日本メジフィジックス株式会社 | 放射性画像診断剤 |
| EP2106808B1 (fr) * | 2006-12-21 | 2018-02-21 | Nihon Medi-Physics Co., Ltd. | Agent d'imagerie de diagnostic radioactif comprenant de l'acid 1-amino-3-[18f]fluorocyclobutane carboxylique |
| JP5518337B2 (ja) * | 2006-12-27 | 2014-06-11 | 日本メジフィジックス株式会社 | 放射性ハロゲン標識有機化合物の前駆体化合物の製造方法 |
| KR101485445B1 (ko) | 2007-02-13 | 2015-01-22 | 니혼 메디피직스 가부시키가이샤 | 방사성 화상진단제의 제조 방법 |
| US7910583B2 (en) | 2007-05-04 | 2011-03-22 | Bristol-Myers Squibb Company | [6,6] and [6,7]-bicyclic GPR119 G protein-coupled receptor agonists |
| JP2010526146A (ja) | 2007-05-04 | 2010-07-29 | ブリストル−マイヤーズ スクイブ カンパニー | ［６，５］−二環式ｇｐｒ１１９ｇタンパク質結合受容体アゴニスト |
| US7928230B2 (en) * | 2007-07-17 | 2011-04-19 | Bristol-Myers Squibb Company | Method for modulating GPR119 G protein-coupled receptor and selected compounds |
| US8258313B2 (en) * | 2007-07-19 | 2012-09-04 | Tokuyama Corporation | Compound having hydantoin ring and method of producing the same |
| SI2230229T1 (sl) * | 2007-12-19 | 2017-03-31 | Nihon Medi-Physics,Ltd. | Postopek za proizvodnjo z radioaktivnim fluorom markirane organske spojine |
| US8246752B2 (en) | 2008-01-25 | 2012-08-21 | Clear Catheter Systems, Inc. | Methods and devices to clear obstructions from medical tubes |
| EP2271372A4 (fr) * | 2008-04-14 | 2012-12-19 | Univ Emory | Agent d'imagerie |
| TW201006821A (en) | 2008-07-16 | 2010-02-16 | Bristol Myers Squibb Co | Pyridone and pyridazone analogues as GPR119 modulators |
| JP2012532834A (ja) | 2009-07-11 | 2012-12-20 | バイエル ファーマ アクチエンゲゼルシャフト | シクロアルキル基を用いる放射性標識方法 |
| JPWO2011040574A1 (ja) * | 2009-09-30 | 2013-02-28 | 国立大学法人京都大学 | アゼチジニルメトキシピリジン誘導体の製造方法及びその使用 |
| JP2013523822A (ja) | 2010-04-08 | 2013-06-17 | ブリストル−マイヤーズ スクイブ カンパニー | Ｇｐｒ１１９修飾因子としてのピリミジニルピペリジニルオキシピリジノ類似体 |
| EP2392568A1 (fr) | 2010-06-04 | 2011-12-07 | Bayer Pharma Aktiengesellschaft | Acides aminés hétérocycliques pour imagerie du cancer de la prostate |
| GB201021530D0 (en) * | 2010-12-20 | 2011-02-02 | Ge Healthcare Ltd | Purification of precursor compound by crystallisation |
| BR112013021021A2 (pt) * | 2011-02-17 | 2016-08-02 | Bayer Ip Gmbh | 3- (bifenil - 3 - il) - 8, 8 - difluoro - 4 - hidroxi - 1 - azaspiro [4, 5] dec - 3 - eno - 2 - onas substituídas para terapia e cetoenóis espirocíclicos substituídos com halogéneo |
| MX339188B (es) * | 2011-03-11 | 2016-05-13 | Bayer Ip Gmbh | Derivados de 1h-pirrolidina -2,4-diona espirociclicos cis-alcoxi-sustituidos. |
| EP2734494B1 (fr) * | 2011-07-21 | 2019-01-02 | GE Healthcare Limited | Composés précurseurs et leurs procédés de fabrication |
| US11534494B2 (en) | 2011-12-21 | 2022-12-27 | Ge Healthcare Limited | Formulation and method of synthesis |
| GB201411569D0 (en) * | 2014-06-30 | 2014-08-13 | Ge Healthcare Ltd | Novel formulation and method of synthesis |
| GB201305687D0 (en) * | 2013-03-28 | 2013-05-15 | Ge Healthcare Ltd | Radiolabelling process |
| CN105431428A (zh) | 2013-06-03 | 2016-03-23 | 拜耳制药股份公司 | 取代的苯并噁唑 |
| UY35592A (es) | 2013-06-03 | 2014-12-31 | Bayer Pharma AG | Benzoxazoles sustituidos |
| TWI868065B (zh) * | 2018-04-10 | 2025-01-01 | 德商拜耳廠股份有限公司 | 用於製備經取代之環己烷胺基酸酯和經螺縮酮取代之環狀酮烯醇之方法 |
| WO2021225147A1 (fr) * | 2020-05-07 | 2021-11-11 | 国立大学法人東京工業大学 | Méthode de concentration d'astate simple |
| CN111574389B (zh) * | 2020-05-14 | 2023-08-18 | 河北威远生物化工有限公司 | 1-氨基-4-取代环己基羧酸及其盐的顺式异构体的制备方法 |
| CN114031652B (zh) * | 2021-11-04 | 2023-05-26 | 北京师范大学 | 一种含环己烷的葡萄糖衍生物及其应用 |
| CN118955332A (zh) * | 2024-07-31 | 2024-11-15 | 德阳悦合生物医药科技有限公司 | 一种作为医药中间体的化合物叔丁基甲基(3-酮环丁基)氨基甲酸酯的制备方法 |
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| US3855208A (en) * | 1971-05-24 | 1974-12-17 | Becton Dickinson Co | Derivatives of digoxigenin |
| US4695588A (en) * | 1977-06-01 | 1987-09-22 | Merck & Co., Inc. | Fluorinated amino acids |
| US4325961A (en) * | 1977-06-01 | 1982-04-20 | Merck & Co., Inc. | Fluorinated amino acids |
| US4743691A (en) * | 1977-07-11 | 1988-05-10 | Merrell Dow France Et Cie | 2-halomethyl derivatives of 2-amino acids |
| US4483870A (en) * | 1978-07-24 | 1984-11-20 | Merck & Co., Inc. | α-Difluoromethyl amino acids and hypertension treating compositions thereof |
| US4358434A (en) * | 1979-12-19 | 1982-11-09 | New England Nuclear Corporation | Method, composition and kit for stabilizing radiolabeled compounds |
| US4390517A (en) * | 1979-12-19 | 1983-06-28 | New England Nuclear Corporation | Method, composition and kit for stabilizing radiolabeled compounds |
| US4942231A (en) * | 1984-05-24 | 1990-07-17 | Mallinckrodt, Inc. | Method of preparing a chlorinated, brominated, radio-brominated, iodinated and/or radioiodinated aromatic or heteroaromatic compound |
| US4760091A (en) * | 1985-10-01 | 1988-07-26 | The Dow Chemical Company | Method of controlling phytopathogenic fungus |
| US5227467A (en) * | 1987-08-03 | 1993-07-13 | Merck & Co., Inc. | Immunosuppressive fluorinated cyclosporin analogs |
| US5116599A (en) * | 1989-07-31 | 1992-05-26 | Johns Hopkins Univ. | Perfluoro-t-butyl-containing compounds for use in fluorine-19 nmr and/or mri |
| ZA907743B (en) * | 1989-10-03 | 1991-07-31 | Merrell Dow Pharma | Radiolabeled anticoagulant peptides |
| US5128118A (en) * | 1990-08-09 | 1992-07-07 | Research Triangle Institute | Cocaine receptor binding ligands |
| US6096874A (en) * | 1990-10-01 | 2000-08-01 | Board Of Regents, The University Of Texas System | High affinity tamoxifen derivatives |
| US5698179A (en) * | 1992-02-25 | 1997-12-16 | Neuro Imaging Technologies, Llc | Iodinated neuroprobe for mapping monoamine reuptake sites |
| US5310912A (en) * | 1992-02-25 | 1994-05-10 | Research Biochemicals Limited Partnership | Iodinated neuroprobe for mapping monoamine reuptake sites |
| US5637759A (en) * | 1992-07-30 | 1997-06-10 | The Regents Of The University Of California | Metal-ligating amino acid derivatives for MRI and for peptide synthesis |
| US5493026A (en) * | 1993-10-25 | 1996-02-20 | Organix, Inc. | Substituted 2-carboxyalkyl-3-(fluorophenyl)-8-(3-halopropen-2-yl) nortropanes and their use as imaging for agents for neurodegenerative disorders |
| US6043271A (en) * | 1994-08-03 | 2000-03-28 | Sarawak Medichem Pharmaceuticals, Inc. | Method for the preparation of (±)-calanolide A and intermediates thereof |
| IL117574A0 (en) * | 1995-04-03 | 1996-07-23 | Bristol Myers Squibb Co | Processes for the preparation of cyclobutanone derivatives |
| US5808146A (en) * | 1995-11-09 | 1998-09-15 | Emory University | Amino acid analogs for tumor imaging |
| AUPO763197A0 (en) * | 1997-06-30 | 1997-07-24 | Sigma Pharmaceuticals Pty Ltd | Health supplement |
| RU2123701C1 (ru) * | 1998-05-26 | 1998-12-20 | Общество с ограниченной ответственностью "Импакт" | Набор для ферментного анализа и способ его получения |
| AU4974700A (en) * | 1999-04-22 | 2000-11-10 | Emory University | Fluoroalkenyl nortropanes |
| US6399042B1 (en) * | 1999-04-26 | 2002-06-04 | Emory University | 4-fluoroalkyl-3-halophenyl nortropanes |
| US6843979B2 (en) * | 1999-04-26 | 2005-01-18 | Emory University | 4-haloethenylphenyl tropane:serotonin transporter imaging agents |
| US7146209B2 (en) * | 2000-05-08 | 2006-12-05 | Brainsgate, Ltd. | Stimulation for treating eye pathologies |
| GB0121439D0 (en) * | 2001-09-05 | 2001-10-24 | Univ St Andrews | An enzymatic process for the generation of organo-fluorine compounds |
| GB0206117D0 (en) * | 2002-03-15 | 2002-04-24 | Imaging Res Solutions Ltd | Use of microfabricated devices |
| CN101041674A (zh) * | 2002-04-30 | 2007-09-26 | 埃默里大学 | 肿瘤成像化合物 |
| GB0229695D0 (en) * | 2002-12-20 | 2003-01-29 | Amersham Plc | Solid-phase preparation of 18F-labelled amino acids |
| US20050197350A1 (en) * | 2003-03-31 | 2005-09-08 | Taisho Pharmaceutical Co., Ltd. | Novel quinoline, tetrahydroquinazoline, and pyrimidine derivatives and methods of treatment related to the use thereof |
| BRPI0413880A (pt) * | 2003-08-27 | 2006-10-24 | Boehringer Ingelheim Int | compostos cicloalquilaminoácidos, processo para a obtenção dos mesmos |
| AU2006250594B2 (en) * | 2005-05-23 | 2011-06-16 | Nihon Medi-Physics Co., Ltd. | Novel organic compound and method for producing radioactive halogen-labeled organic compound using the same |
| JP2009505947A (ja) * | 2005-06-23 | 2009-02-12 | エモリー・ユニバーシティ | 画像化剤 |
-
2006
- 2006-06-19 WO PCT/US2006/023740 patent/WO2007001958A2/fr not_active Ceased
- 2006-06-19 RU RU2008100844/04A patent/RU2376282C2/ru not_active IP Right Cessation
- 2006-06-19 JP JP2008518271A patent/JP5349960B2/ja not_active Expired - Fee Related
- 2006-06-19 US US11/425,051 patent/US20060292073A1/en not_active Abandoned
- 2006-06-19 AU AU2006262425A patent/AU2006262425C1/en not_active Ceased
- 2006-06-19 CA CA2612187A patent/CA2612187C/fr not_active Expired - Fee Related
- 2006-06-19 EP EP06785079A patent/EP1893246A4/fr not_active Withdrawn
-
2007
- 2007-12-11 NO NO20076349A patent/NO20076349L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2376282C2 (ru) | 2009-12-20 |
| EP1893246A2 (fr) | 2008-03-05 |
| RU2008100844A (ru) | 2009-07-27 |
| CA2612187C (fr) | 2013-05-07 |
| CA2612187A1 (fr) | 2007-01-04 |
| WO2007001958A3 (fr) | 2007-05-31 |
| JP2008546783A (ja) | 2008-12-25 |
| WO2007001958A2 (fr) | 2007-01-04 |
| US20060292073A1 (en) | 2006-12-28 |
| EP1893246A4 (fr) | 2009-05-06 |
| AU2006262425B2 (en) | 2011-12-08 |
| AU2006262425A1 (en) | 2007-01-04 |
| JP5349960B2 (ja) | 2013-11-20 |
| AU2006262425C1 (en) | 2012-06-21 |
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