WO2009022721A1 - ３環系アミド化合物 - Google Patents

３環系アミド化合物 Download PDF

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Publication number
WO2009022721A1
WO2009022721A1 PCT/JP2008/064576 JP2008064576W WO2009022721A1 WO 2009022721 A1 WO2009022721 A1 WO 2009022721A1 JP 2008064576 W JP2008064576 W JP 2008064576W WO 2009022721 A1 WO2009022721 A1 WO 2009022721A1
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hydrogen atom
alkyl group
amide compound
group
tricyclic amide
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PCT/JP2008/064576
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English (en)
French (fr)
Inventor
Yohei Amano
Masayuki Noguchi
Koichi Shudo
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Research Foundation Itsuu Laboratory
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Publication date
Application filed by Research Foundation Itsuu Laboratory filed Critical Research Foundation Itsuu Laboratory
Priority to AU2008287818A priority Critical patent/AU2008287818A1/en
Priority to CA2695977A priority patent/CA2695977A1/en
Priority to NZ583876A priority patent/NZ583876A/en
Priority to EA201070273A priority patent/EA201070273A1/ru
Priority to US12/673,207 priority patent/US8232300B2/en
Priority to CN200880111357A priority patent/CN101855199A/zh
Priority to EP08792457.7A priority patent/EP2189443B1/en
Priority to JP2009528146A priority patent/JP5399248B2/ja
Publication of WO2009022721A1 publication Critical patent/WO2009022721A1/ja

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    • 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
    • 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
    • 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
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid
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    • C07C2603/00—Systems containing at least three condensed rings
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/28—Phenalenes; Hydrogenated phenalenes
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/34—Benzoheptalenes; Hydrogenated benzoheptalenes

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  • Chemical & Material Sciences (AREA)
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Abstract

　レチノイド作用を有し、医薬の有効成分として有用な一般式(I)： 〔R1は水素原子又はC1-6アルキル基を示し、A及びBは-(CH2)2-、-(CH2)3-、又は-(CH2)4-を示し、Xは-N(R2)-CO-（R2は水素原子又はC1-6アルキル基を示す）、-CO-N(R3)-（R3は水素原子又はC1-6アルキル基を示す）、-C(R4)=C(R5)-（R4及びR5は水素原子又はC1-6アルキル基を示す）、又は-N(R6)-SO2-（R6は水素原子又はC1-6アルキル基を示す）を示し、Arはアリールジイル基又はヘテロアリールジイル基を示す〕で表される化合物。
PCT/JP2008/064576 2007-08-15 2008-08-14 ３環系アミド化合物 WO2009022721A1 (ja)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AU2008287818A AU2008287818A1 (en) 2007-08-15 2008-08-14 Tricyclic amide compound
CA2695977A CA2695977A1 (en) 2007-08-15 2008-08-14 Tricyclic amide compound
NZ583876A NZ583876A (en) 2007-08-15 2008-08-14 Tricyclic amide compound
EA201070273A EA201070273A1 (ru) 2007-08-15 2008-08-14 Трициклическое амидное соединение
US12/673,207 US8232300B2 (en) 2007-08-15 2008-08-14 Tricyclic amide compound
CN200880111357A CN101855199A (zh) 2007-08-15 2008-08-14 三环类酰胺化合物
EP08792457.7A EP2189443B1 (en) 2007-08-15 2008-08-14 Tricyclic amide compound
JP2009528146A JP5399248B2 (ja) 2007-08-15 2008-08-14 ３環系アミド化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007211650 2007-08-15
JP2007-211650 2007-08-15

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WO2009022721A1 true WO2009022721A1 (ja) 2009-02-19

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PCT/JP2008/064576 WO2009022721A1 (ja) 2007-08-15 2008-08-14 ３環系アミド化合物

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US (1) US8232300B2 (ja)
EP (1) EP2189443B1 (ja)
JP (1) JP5399248B2 (ja)
CN (1) CN101855199A (ja)
AU (1) AU2008287818A1 (ja)
CA (1) CA2695977A1 (ja)
EA (1) EA201070273A1 (ja)
NZ (1) NZ583876A (ja)
TW (1) TW200920351A (ja)
WO (1) WO2009022721A1 (ja)

Families Citing this family (2)

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Publication number Priority date Publication date Assignee Title
WO2013041621A1 (de) 2011-09-20 2013-03-28 Basf Se Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung
CN107304172B (zh) * 2016-04-20 2020-04-03 沈阳药科大学 八氢蒽类化合物及其制备方法和用途

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0344348A (ja) * 1989-06-30 1991-02-26 Firmenich Sa 新規芳香族化合物、その製法、該化合物を含有する賦香組成物または香料添加製品、ならびに芳香特性を改良、強調または変更する方法および該化合物の中間体

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6176440A (ja) 1984-09-19 1986-04-18 Koichi Shiyudo 安息香酸誘導体
JPS6122047A (ja) 1984-07-07 1986-01-30 Koichi Shiyudo 安息香酸誘導体
US5185318A (en) 1989-06-30 1993-02-09 Firmenich S.A. Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients
US5442124A (en) 1989-06-30 1995-08-15 Firmenich Sa Process for the preparation of novel aromatic compounds
US5420145A (en) * 1993-03-22 1995-05-30 Koichi Shudo Carboxylic acid derivative
US5977125A (en) * 1994-10-31 1999-11-02 Eisai Co., Ltd. Mono-or polyenic carboxylic acid derivatives
JP3964478B2 (ja) 1995-06-30 2007-08-22 エーザイ・アール・アンド・ディー・マネジメント株式会社 ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬
JP3044348B1 (ja) 1998-12-28 2000-05-22 株式会社大阪冷研 プリフォ―ム口首部の内径規制用コア

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0344348A (ja) * 1989-06-30 1991-02-26 Firmenich Sa 新規芳香族化合物、その製法、該化合物を含有する賦香組成物または香料添加製品、ならびに芳香特性を改良、強調または変更する方法および該化合物の中間体

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DAVIDSON J.P. ET AL.: "First Enantiospecific Total Synthesis of the Antitubercular Marine Natural Product Pseudopteroxazole. Revision of Assigned Stereochemistry", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 44, 2003, pages 13486 - 13489, XP008131575 *
EKLUND L. ET AL.: "Synthetic studies towards pseudopterosin A", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, no. 4, 1996, pages 303 - 305, XP008131576 *
PIERS E. ET AL.: "Synthesis of functionalized hexahydro-, octahydro-, and decarhydro-1H-phenalenes via Diels-Alder reactions of 1-methylene-4a-methoxycarbonyl1-1,2,3,4,4a,5,6,7-octahydronap thalene and related dienes", CANADIAN JOURNAL OF CHEMISTRY, vol. 71, no. 9, 1993, pages 1463 - 1483, XP008131573 *

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CA2695977A1 (en) 2009-02-19
JP5399248B2 (ja) 2014-01-29
US8232300B2 (en) 2012-07-31
TW200920351A (en) 2009-05-16
JPWO2009022721A1 (ja) 2010-11-18
EA201070273A1 (ru) 2010-10-29
CN101855199A (zh) 2010-10-06
EP2189443A1 (en) 2010-05-26
EP2189443A4 (en) 2010-08-04
EP2189443B1 (en) 2013-10-23
NZ583876A (en) 2011-11-25
AU2008287818A1 (en) 2009-02-19
US20110213157A1 (en) 2011-09-01

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