DE60322680D1 - Opioid-rezeptor-aktive 4-(3-hydroxyphenyl) oder 4-(3-alkoxyphenyl)-1,2,4-triazol-verbindungen - Google Patents

Opioid-rezeptor-aktive 4-(3-hydroxyphenyl) oder 4-(3-alkoxyphenyl)-1,2,4-triazol-verbindungen

Info

Publication number
DE60322680D1
DE60322680D1 DE60322680T DE60322680T DE60322680D1 DE 60322680 D1 DE60322680 D1 DE 60322680D1 DE 60322680 T DE60322680 T DE 60322680T DE 60322680 T DE60322680 T DE 60322680T DE 60322680 D1 DE60322680 D1 DE 60322680D1
Authority
DE
Germany
Prior art keywords
formula
compounds
alkoxyphenyl
hydroxyphenyl
opioid receptor
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
DE60322680T
Other languages
German (de)
English (en)
Inventor
William J Welsh
Seong-Jae Yu
Anil Nair
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Missouri Columbia
University of Missouri St Louis
Original Assignee
University of Missouri Columbia
University of Missouri St Louis
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 University of Missouri Columbia, University of Missouri St Louis filed Critical University of Missouri Columbia
Application granted granted Critical
Publication of DE60322680D1 publication Critical patent/DE60322680D1/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P11/02—Nasal agents, e.g. decongestants
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • A61P17/04—Antipruritics
    • 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
    • A61P19/00—Drugs for skeletal disorders
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • 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
    • A61P25/18—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
    • A61P25/22—Anxiolytics
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • 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
    • 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • 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
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Epidemiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Ophthalmology & Optometry (AREA)
  • Urology & Nephrology (AREA)
  • Reproductive Health (AREA)
  • Child & Adolescent Psychology (AREA)
  • Vascular Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
DE60322680T 2002-02-07 2003-02-07 Opioid-rezeptor-aktive 4-(3-hydroxyphenyl) oder 4-(3-alkoxyphenyl)-1,2,4-triazol-verbindungen Expired - Fee Related DE60322680D1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35499002P 2002-02-07 2002-02-07
PCT/US2003/003746 WO2003066050A1 (en) 2002-02-07 2003-02-07 Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds

Publications (1)

Publication Number Publication Date
DE60322680D1 true DE60322680D1 (de) 2008-09-18

Family

ID=27734448

Family Applications (1)

Application Number Title Priority Date Filing Date
DE60322680T Expired - Fee Related DE60322680D1 (de) 2002-02-07 2003-02-07 Opioid-rezeptor-aktive 4-(3-hydroxyphenyl) oder 4-(3-alkoxyphenyl)-1,2,4-triazol-verbindungen

Country Status (10)

Country Link
US (3) US7045520B2 (enExample)
EP (1) EP1485088B1 (enExample)
JP (1) JP2005521676A (enExample)
AT (1) ATE403426T1 (enExample)
AU (1) AU2003210916B9 (enExample)
CA (1) CA2475767A1 (enExample)
DE (1) DE60322680D1 (enExample)
ES (1) ES2311711T3 (enExample)
MX (1) MXPA04007719A (enExample)
WO (1) WO2003066050A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2475767A1 (en) * 2002-02-07 2003-08-14 The Curators Of The University Of Missouri Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds
KR20140006070A (ko) 2004-11-18 2014-01-15 신타 파마슈티칼스 코프. Ｈｓｐ90 활성을 조절하는 트리아졸 화합물
WO2006124687A1 (en) * 2005-05-12 2006-11-23 University Of Medicine And Dentistry Of New Jersey Opioid receptor subtype-selective agents
WO2008064310A2 (en) * 2006-11-22 2008-05-29 University Of Medicine And Dentistry Of New Jersey Mixed opioid receptor active compounds
WO2011069951A1 (en) 2009-12-11 2011-06-16 Glaxo Group Limited Imidazolidinedione derivatives
KR101862375B1 (ko) 2010-12-06 2018-05-29 오티포니 세라피틱스 리미티드 Kv3 억제제로서 유용한 하이단토인 유도체
EP3502236B1 (en) 2011-02-18 2023-08-23 The Scripps Research Institute Directed differentiation of oligodendrocyte precursor cells to a myelinating cell fate
US9193704B2 (en) 2011-06-07 2015-11-24 Autifony Therapeutics Limited Hydantoin derivatives as KV3 inhibitors
WO2013040321A1 (en) 2011-09-15 2013-03-21 University Of Kansas Kappa opioid receptor effectors and uses thereof
EP2613277A1 (en) * 2012-01-06 2013-07-10 MathPharm GmbH Method and system for indentifying compounds that bind and preferably activate a target opioid receptor in a pH-dependent manner
EP2822931B1 (en) 2012-03-09 2017-05-03 Inception 2, Inc. Triazolone compounds and uses thereof
BR112014028991A2 (pt) 2012-05-22 2017-06-27 Autifony Therapeutics Ltd triazóis como inibidores de kv3
BR112014028718A2 (pt) 2012-05-22 2017-06-27 Autifony Therapeutics Ltd derivados de hidantoína como inibidores de kv3
JP6404230B2 (ja) 2012-12-20 2018-10-10 インセプション ２、 インコーポレイテッド トリアゾロン化合物およびその使用
PT2953942T (pt) 2013-02-06 2018-01-17 Bayer Cropscience Ag Derivados de pirazol substituídos com halogéneo como agentes pesticidas
CA2921420A1 (en) 2013-09-06 2015-03-12 Inception 2, Inc. Triazolone compounds and uses thereof
BR112016017527B1 (pt) 2014-01-03 2021-01-05 Bayer Animal Health Gmbh compostos, usos de compostos, composições farmacêuticas, processo para produzir composições e método não terapêutico para controlar pragas
WO2016142394A1 (de) 2015-03-10 2016-09-15 Bayer Animal Health Gmbh Pyrazolyl-derivate als schädlingsbekämpfungsmittel
EP3344997B1 (en) * 2015-08-31 2020-11-18 Regents of the University of Minnesota Opioid receptor modulators and use thereof
CN111574368B (zh) * 2020-05-15 2023-03-28 西安瑞联新材料股份有限公司 一种5-叔丁基-2-羟基苯甲酸甲酯的合成方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2269938A2 (en) 1974-05-08 1975-12-05 Delalande Sa 5-Hydroxymethyl-3,4-diphenyl-1,2,4-triazoles - with anticholinergic, bronchodilator, antidepressant, analgesic, vasodilator activity, etc.
FR2488891A1 (fr) * 1980-08-22 1982-02-26 Roussel Uclaf Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament
US4481360A (en) * 1983-08-26 1984-11-06 The Upjohn Company 4H-1,2,4-Triazol-3-yl compounds
US5108486A (en) * 1990-02-09 1992-04-28 Kanagawa Chemical Laboratory, Ltd. Herbicidal substituted-phenyl-1,2,4-triazol-5(1H)-thiones and -ones
US5310724A (en) * 1990-02-09 1994-05-10 Fmc Corporation Herbicidal substituted phenyl-1,2,4-triazol-5(1H)-thiones
AU9297798A (en) 1997-09-16 1999-04-05 G.D. Searle & Co. Substituted 1,2,4-triazoles useful for inhibiting cholesteryl ester transfer protein activity
JP2000063363A (ja) 1998-08-12 2000-02-29 Yamanouchi Pharmaceut Co Ltd 新規なトリアゾール誘導体
HN1999000149A (es) * 1998-09-09 2000-01-12 Pfizer Prod Inc Derivados de 4,4-biarilpiperidina
CA2475767A1 (en) * 2002-02-07 2003-08-14 The Curators Of The University Of Missouri Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds

Also Published As

Publication number Publication date
US20080070964A1 (en) 2008-03-20
AU2003210916A1 (en) 2003-09-02
EP1485088B1 (en) 2008-08-06
AU2003210916B2 (en) 2008-10-23
US7045520B2 (en) 2006-05-16
CA2475767A1 (en) 2003-08-14
ATE403426T1 (de) 2008-08-15
AU2003210916B9 (en) 2008-12-18
WO2003066050A1 (en) 2003-08-14
US7776898B2 (en) 2010-08-17
US20030225072A1 (en) 2003-12-04
MXPA04007719A (es) 2005-09-08
US7294720B2 (en) 2007-11-13
US20060128776A1 (en) 2006-06-15
JP2005521676A (ja) 2005-07-21
ES2311711T3 (es) 2009-02-16
EP1485088A1 (en) 2004-12-15

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