CA2435820A1 - Phenoxy substituted benzocondensed heteroaryl derivatives as thyroid receptor ligands - Google Patents
Phenoxy substituted benzocondensed heteroaryl derivatives as thyroid receptor ligands Download PDFInfo
- Publication number
- CA2435820A1 CA2435820A1 CA002435820A CA2435820A CA2435820A1 CA 2435820 A1 CA2435820 A1 CA 2435820A1 CA 002435820 A CA002435820 A CA 002435820A CA 2435820 A CA2435820 A CA 2435820A CA 2435820 A1 CA2435820 A1 CA 2435820A1
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- Prior art keywords
- disease
- compound according
- alkyl
- acid
- disorder
- 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.)
- Abandoned
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- 125000001072 heteroaryl group Chemical group 0.000 title claims description 21
- 108090000721 thyroid hormone receptors Proteins 0.000 title abstract description 13
- 102000004217 thyroid hormone receptors Human genes 0.000 title abstract description 13
- 239000003446 ligand Substances 0.000 title abstract description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 28
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- 206010020850 Hyperthyroidism Diseases 0.000 claims abstract description 21
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- 206010003119 arrhythmia Diseases 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 208000017520 skin disease Diseases 0.000 claims description 20
- 239000005495 thyroid hormone Substances 0.000 claims description 20
- 229940036555 thyroid hormone Drugs 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
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- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims description 9
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
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- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- FXPTUUBGXUYWNY-UHFFFAOYSA-N 2-[3,5-dibromo-4-(1-methylbenzimidazol-5-yl)oxyphenyl]acetic acid Chemical compound C=1C=C2N(C)C=NC2=CC=1OC1=C(Br)C=C(CC(O)=O)C=C1Br FXPTUUBGXUYWNY-UHFFFAOYSA-N 0.000 claims description 4
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- RGNMCWJDXHARLI-UHFFFAOYSA-N 2-[3,5-dibromo-4-[(2-methyl-3h-benzimidazol-5-yl)oxy]phenyl]acetic acid Chemical compound C1=C2NC(C)=NC2=CC=C1OC1=C(Br)C=C(CC(O)=O)C=C1Br RGNMCWJDXHARLI-UHFFFAOYSA-N 0.000 claims description 3
- ZURLSWNRLDJNAH-UHFFFAOYSA-N 2-[3,5-dichloro-4-[(2-propan-2-yl-3h-benzimidazol-5-yl)oxy]phenyl]acetic acid Chemical compound C1=C2NC(C(C)C)=NC2=CC=C1OC1=C(Cl)C=C(CC(O)=O)C=C1Cl ZURLSWNRLDJNAH-UHFFFAOYSA-N 0.000 claims description 3
- GOKTWQOFFZABPC-UHFFFAOYSA-N 3-[3,5-dibromo-4-[[2-(3-methylphenyl)-1-benzofuran-5-yl]oxy]phenyl]propanoic acid Chemical compound CC1=CC=CC(C=2OC3=CC=C(OC=4C(=CC(CCC(O)=O)=CC=4Br)Br)C=C3C=2)=C1 GOKTWQOFFZABPC-UHFFFAOYSA-N 0.000 claims description 3
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- SFOATOYUCSGODX-UHFFFAOYSA-N 2-[3,5-dibromo-4-[(2-phenyl-1-benzofuran-5-yl)oxy]phenyl]acetic acid Chemical compound BrC1=CC(CC(=O)O)=CC(Br)=C1OC1=CC=C(OC(=C2)C=3C=CC=CC=3)C2=C1 SFOATOYUCSGODX-UHFFFAOYSA-N 0.000 claims description 2
- SOZCVZZTEKZSSY-UHFFFAOYSA-N 2-[4-(3h-benzimidazol-5-yloxy)-3,5-dibromophenyl]acetic acid Chemical compound BrC1=CC(CC(=O)O)=CC(Br)=C1OC1=CC=C(N=CN2)C2=C1 SOZCVZZTEKZSSY-UHFFFAOYSA-N 0.000 claims description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 7
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- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 101150058668 tra2 gene Proteins 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 108091006107 transcriptional repressors Proteins 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940035722 triiodothyronine Drugs 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- 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
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0103175.6 | 2001-02-08 | ||
| GB0103175A GB0103175D0 (en) | 2001-02-08 | 2001-02-08 | Novel compounds |
| GB0105234A GB0105234D0 (en) | 2001-03-02 | 2001-03-02 | Novel compounds |
| GB0105234.9 | 2001-03-02 | ||
| PCT/EP2002/000957 WO2002062780A2 (en) | 2001-02-08 | 2002-01-30 | Phenoxy substituted benzocondensed heteroaryl derivatives as thyroid receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2435820A1 true CA2435820A1 (en) | 2002-08-15 |
Family
ID=26245703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002435820A Abandoned CA2435820A1 (en) | 2001-02-08 | 2002-01-30 | Phenoxy substituted benzocondensed heteroaryl derivatives as thyroid receptor ligands |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7144909B2 (https=) |
| EP (1) | EP1358175A2 (https=) |
| JP (1) | JP2004531479A (https=) |
| KR (1) | KR20030072396A (https=) |
| AU (1) | AU2002237298B2 (https=) |
| CA (1) | CA2435820A1 (https=) |
| IL (1) | IL157031A0 (https=) |
| WO (1) | WO2002062780A2 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0219022D0 (en) * | 2002-08-15 | 2002-09-25 | Karobio Ab | Novel thyromimetic compounds |
| TW200504021A (en) | 2003-01-24 | 2005-02-01 | Bristol Myers Squibb Co | Substituted anilide ligands for the thyroid receptor |
| CN1882327A (zh) | 2003-11-19 | 2006-12-20 | 症变治疗公司 | 含磷的新的拟甲状腺素药 |
| WO2006128058A2 (en) | 2005-05-26 | 2006-11-30 | Metabasis Therapeutics, Inc. | Thyromimetics for the treatment of fatty liver diseases |
| US20070082907A1 (en) * | 2003-11-25 | 2007-04-12 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| RU2007111760A (ru) * | 2004-09-01 | 2008-10-10 | Трастиз Оф Бостон Юниверсити (Us) | Способ лечения гиперпролиферативного кожного нарушения |
| WO2006128056A2 (en) * | 2005-05-26 | 2006-11-30 | Metabasis Therapeutics, Inc. | Novel phosphinic acid-containing thyromimetics |
| GB0513692D0 (en) * | 2005-07-04 | 2005-08-10 | Karobio Ab | Novel pharmaceutical compositions |
| PL1919878T3 (pl) * | 2005-07-21 | 2011-03-31 | Hoffmann La Roche | Pochodne pirydazynonu jako agoniści receptora hormonu tarczycy |
| PE20070335A1 (es) | 2005-08-30 | 2007-04-21 | Novartis Ag | Benzimidazoles sustituidos y metodos para su preparacion |
| GB0608724D0 (en) * | 2006-05-03 | 2006-06-14 | Karobio Ab | Novel Pharmaceutical Compositions |
| GB0610322D0 (en) * | 2006-05-24 | 2006-07-05 | Karobio Ab | Novel pharmaceutical compositions |
| US7960567B2 (en) * | 2007-05-02 | 2011-06-14 | Amgen Inc. | Compounds and methods useful for treating asthma and allergic inflammation |
| RU2469725C2 (ru) * | 2010-07-01 | 2012-12-20 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Тверская государственная медицинская академия" Министерства здравоохранения и социального развития Российской Федерации (ГБОУ ВПО "Тверская ГМА" Минздравсоцразвития России) | Способ предоперационной подготовки больных тиреотоксикозом |
| CN102718718B (zh) * | 2012-05-31 | 2014-09-24 | 绍兴文理学院 | 一种3,5-二溴-4-（5-苯并咪唑氧基）苯乙酸的制备方法 |
| CA3044059A1 (en) | 2016-11-21 | 2018-05-24 | Viking Therapeutics, Inc. | Method of treating glycogen storage disease |
| US11707472B2 (en) | 2017-06-05 | 2023-07-25 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis |
| ES3053674T3 (en) | 2018-03-22 | 2026-01-23 | Viking Therapeutics Inc | Crystalline forms and methods of producing crystalline forms of a compound |
| WO2020117962A1 (en) | 2018-12-05 | 2020-06-11 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9226532D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| US6472387B1 (en) * | 1996-10-07 | 2002-10-29 | Eli Lilly And Company | Methods of using compounds as neuro-protective agents |
| EA001713B1 (ru) * | 1996-10-07 | 2001-08-27 | Эли Лилли Энд Компани | Соединения, полезные для использования в качестве нейрозащитных средств |
| GB9713739D0 (en) | 1997-06-27 | 1997-09-03 | Karobio Ab | Thyroid receptor ligands |
| GB9828442D0 (en) | 1998-12-24 | 1999-02-17 | Karobio Ab | Novel thyroid receptor ligands and method II |
| WO2001070687A1 (de) | 2000-03-23 | 2001-09-27 | Bayer Aktiengesellschaft | Indole zur behandlung von krankheiten die mit schilddrüsenhormonen behandeln werden können |
| WO2002051805A1 (de) | 2000-12-27 | 2002-07-04 | Bayer Aktiengesellschaft | Indol-derivate |
-
2002
- 2002-01-30 EP EP02703589A patent/EP1358175A2/en not_active Withdrawn
- 2002-01-30 IL IL15703102A patent/IL157031A0/xx unknown
- 2002-01-30 AU AU2002237298A patent/AU2002237298B2/en not_active Ceased
- 2002-01-30 CA CA002435820A patent/CA2435820A1/en not_active Abandoned
- 2002-01-30 KR KR10-2003-7010172A patent/KR20030072396A/ko not_active Withdrawn
- 2002-01-30 US US10/470,878 patent/US7144909B2/en not_active Expired - Fee Related
- 2002-01-30 JP JP2002563134A patent/JP2004531479A/ja active Pending
- 2002-01-30 WO PCT/EP2002/000957 patent/WO2002062780A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1358175A2 (en) | 2003-11-05 |
| KR20030072396A (ko) | 2003-09-13 |
| IL157031A0 (en) | 2004-02-08 |
| WO2002062780A3 (en) | 2002-09-26 |
| US20040116387A1 (en) | 2004-06-17 |
| JP2004531479A (ja) | 2004-10-14 |
| AU2002237298B2 (en) | 2006-08-03 |
| US7144909B2 (en) | 2006-12-05 |
| WO2002062780A2 (en) | 2002-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |