ATE394391T1 - Indolderivate als histaminrezeptorantagonisten - Google Patents

Indolderivate als histaminrezeptorantagonisten

Info

Publication number
ATE394391T1
ATE394391T1 AT05756581T AT05756581T ATE394391T1 AT E394391 T1 ATE394391 T1 AT E394391T1 AT 05756581 T AT05756581 T AT 05756581T AT 05756581 T AT05756581 T AT 05756581T AT E394391 T1 ATE394391 T1 AT E394391T1
Authority
AT
Austria
Prior art keywords
receptor antagonists
indole derivatives
histamine receptor
histamine
indole
Prior art date
Application number
AT05756581T
Other languages
English (en)
Inventor
Mcarthur Silvia Gatti
Cornelia Hertel
Matthias Nettekoven
Susanne Raab
Olivier Roche
Rosa Rodriguez-Sarmiento
Franz Schuler
Jean-Marc Plancher
Original Assignee
Hoffmann La Roche
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Application granted granted Critical
Publication of ATE394391T1 publication Critical patent/ATE394391T1/de

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A61P25/12—Antiepileptics; Anticonvulsants for grand-mal
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • 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
    • A61P3/04—Anorexiants; Antiobesity 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
    • A61P37/08—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
    • 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
    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Immunology (AREA)
  • Addiction (AREA)
  • Psychology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
AT05756581T 2004-06-21 2005-06-13 Indolderivate als histaminrezeptorantagonisten ATE394391T1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP04102839 2004-06-21

Publications (1)

Publication Number Publication Date
ATE394391T1 true ATE394391T1 (de) 2008-05-15

Family

ID=34982342

Family Applications (1)

Application Number Title Priority Date Filing Date
AT05756581T ATE394391T1 (de) 2004-06-21 2005-06-13 Indolderivate als histaminrezeptorantagonisten

Country Status (23)

Country Link
US (1) US7361682B2 (de)
EP (1) EP1761519B1 (de)
JP (1) JP4652404B2 (de)
CN (1) CN1972926B (de)
AR (1) AR049696A1 (de)
AT (1) ATE394391T1 (de)
AU (1) AU2005254658B2 (de)
BR (1) BRPI0512335A (de)
CA (1) CA2569611C (de)
DE (1) DE602005006567D1 (de)
DK (1) DK1761519T3 (de)
ES (1) ES2306170T3 (de)
IL (1) IL179737A (de)
MX (1) MXPA06014810A (de)
MY (1) MY139941A (de)
NO (1) NO20070336L (de)
NZ (1) NZ551663A (de)
PL (1) PL1761519T3 (de)
PT (1) PT1761519E (de)
RU (1) RU2382778C2 (de)
TW (1) TW200612936A (de)
WO (1) WO2005123716A1 (de)
ZA (1) ZA200610416B (de)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2007008676A (es) * 2005-01-19 2007-07-25 Hoffmann La Roche Derivados de 5-aminoindol.
ES2359739T3 (es) 2005-11-30 2011-05-26 F. Hoffmann-La Roche Ag Derivados de indol-2-il-amida 1,5-sustituida.
CN101316835A (zh) * 2005-11-30 2008-12-03 霍夫曼-拉罗奇有限公司 5-取代的吲哚-2-甲酰胺衍生物
CN101316838B (zh) * 2005-11-30 2013-01-30 霍夫曼-拉罗奇有限公司 用作h3调节剂的1,1-二氧代-硫代吗啉基吲哚基甲酮衍生物
KR20090024115A (ko) * 2006-04-12 2009-03-06 에프. 호프만-라 로슈 아게 5-아미도-2-카복스아마이드 인돌
US7432255B2 (en) * 2006-05-16 2008-10-07 Hoffmann-La Roche Inc. 1H-indol-5-yl-piperazin-1-yl-methanone derivatives
US7514433B2 (en) * 2006-08-03 2009-04-07 Hoffmann-La Roche Inc. 1H-indole-6-yl-piperazin-1-yl-methanone derivatives
WO2008074703A1 (en) 2006-12-19 2008-06-26 F. Hoffmann-La Roche Ag Heteroaryl pyrrolidinyl and piperidinyl ketone derivatives
US8012955B2 (en) * 2006-12-28 2011-09-06 Rigel Pharmaceuticals, Inc. N-substituted-heterocycloalkyloxybenzamide compounds and methods of use
US7557108B2 (en) * 2007-02-07 2009-07-07 Hoffmann-La Roche Inc. (Indol-4-yl) or (indol-5-yl)-piperazinylmethanones
US7648979B2 (en) * 2007-02-07 2010-01-19 Hoffmann-La Roche Inc. 5-amido-(1H-indol-2-yl)-piperazin-1-yl-methanone derivatives
US7507736B2 (en) * 2007-02-07 2009-03-24 Hoffmann-La Roche Inc. Indol-2-yl-piperazin-1-yl-methanone derivatives
AU2008223142A1 (en) * 2007-03-01 2008-09-12 Janssen Pharmaceutica N.V. Indole and benzothiophene compounds as modulators of the histamine H3 receptor
BRPI0814532A2 (pt) * 2007-07-25 2015-01-27 Hoffmann La Roche Compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação dos receptores de h3, e uso desses compostos para a preparação de medicamentos.
KR20100050444A (ko) * 2007-08-31 2010-05-13 아스텔라스세이야쿠 가부시키가이샤 피페리딘 유도체
NZ585298A (en) * 2007-11-16 2012-08-31 Rigel Pharmaceuticals Inc Carboxamide, sulfonamide and amine compounds for metabolic disorders
EP2231666B1 (de) 2007-12-12 2015-07-29 Rigel Pharmaceuticals, Inc. Carbonsäureamid-, Sulfonamid- und Aminverbindungen gegen Stoffwechselerkrankungen
BRPI0911681B8 (pt) * 2008-04-23 2021-05-25 Rigel Pharmaceuticals Inc composto, composição farmacêutica, e, método para ativar a via de proteína quinase ativada por 5'-amp em uma célula in vitro
WO2009158375A1 (en) * 2008-06-25 2009-12-30 Abbott Laboratories Aza-cylic indole- 2 -carboxamides and methods of use thereof
FR2950053B1 (fr) * 2009-09-11 2014-08-01 Fournier Lab Sa Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson
HRP20161167T1 (hr) * 2012-08-23 2016-11-04 Suven Life Sciences Limited Spoj akrilamida kao ligandi histaminskog h3 receptora
EP2722329A1 (de) * 2012-10-18 2014-04-23 F. Hoffmann-La Roche AG Indolamidverbindungen als beta-Amyloid Inhbitoren
KR101551313B1 (ko) 2014-07-28 2015-09-09 충남대학교산학협력단 신규한 인덴 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물
CN106065008B (zh) * 2016-06-16 2018-06-05 黑龙江中医药大学 一种具有改善睡眠作用的吲哚-2-酰胺类化合物及其应用
AU2018221148B2 (en) 2017-02-17 2022-05-05 Trevena, Inc. 5-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same
CN110446495B (zh) 2017-02-17 2023-09-05 特维娜有限公司 含有7元氮杂杂环的δ阿片受体调节化合物及其使用和制备方法

Family Cites Families (8)

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Publication number Priority date Publication date Assignee Title
FR2705095B1 (fr) * 1993-05-12 1995-06-23 Adir Nouveaux indoles substitués, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.
DK1042287T3 (da) * 1997-12-24 2005-08-15 Aventis Pharma Gmbh Indolderivater som inhibitorer af faktor Xa
EP0978512A1 (de) * 1998-07-29 2000-02-09 Societe Civile Bioprojet Aryloxy- (oder Arylthio)alkylamine ohne Imidazolring als Histamin-H3-Antagonisten und deren therapeutische Anwendung
AU2001247906A1 (en) * 2000-03-31 2001-10-15 Ortho-Mcneil Pharmaceutical, Inc. Phenyl-substituted indoles and indazoles
HU227197B1 (en) * 2000-10-24 2010-10-28 Richter Gedeon Nyrt Nmda receptor antagonist carboxylic acid amide derivatives and pharmaceutical compositions containing them
EP1373204B1 (de) * 2001-03-09 2016-10-26 Janssen Pharmaceuticals, Inc. Heterocyclische verbindungen
US6673829B2 (en) * 2001-09-14 2004-01-06 Novo Nordisk A/S Aminoazetidine,-pyrrolidine and -piperidine derivatives
IL165863A0 (en) * 2002-06-24 2006-01-15 Schering Corp Indole derivatives useful as histamine H3 antagonists

Also Published As

Publication number Publication date
EP1761519B1 (de) 2008-05-07
MY139941A (en) 2009-11-30
IL179737A0 (en) 2007-05-15
WO2005123716A1 (en) 2005-12-29
TW200612936A (en) 2006-05-01
ES2306170T3 (es) 2008-11-01
ZA200610416B (en) 2008-09-25
DK1761519T3 (da) 2008-07-21
CA2569611A1 (en) 2005-12-29
EP1761519A1 (de) 2007-03-14
CN1972926B (zh) 2011-02-16
AR049696A1 (es) 2006-08-30
BRPI0512335A (pt) 2008-03-04
PT1761519E (pt) 2008-07-02
PL1761519T3 (pl) 2008-09-30
CN1972926A (zh) 2007-05-30
IL179737A (en) 2011-12-29
DE602005006567D1 (de) 2008-06-19
MXPA06014810A (es) 2007-02-12
NO20070336L (no) 2007-02-13
AU2005254658B2 (en) 2011-06-16
RU2007102224A (ru) 2008-07-27
JP4652404B2 (ja) 2011-03-16
RU2382778C2 (ru) 2010-02-27
US20050282864A1 (en) 2005-12-22
JP2008503511A (ja) 2008-02-07
NZ551663A (en) 2009-09-25
AU2005254658A1 (en) 2005-12-29
CA2569611C (en) 2012-12-11
US7361682B2 (en) 2008-04-22

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