ES2259419T3 - Imidazo(1,2-a)piridinas. - Google Patents
Imidazo(1,2-a)piridinas.Info
- Publication number
- ES2259419T3 ES2259419T3 ES03766355T ES03766355T ES2259419T3 ES 2259419 T3 ES2259419 T3 ES 2259419T3 ES 03766355 T ES03766355 T ES 03766355T ES 03766355 T ES03766355 T ES 03766355T ES 2259419 T3 ES2259419 T3 ES 2259419T3
- Authority
- ES
- Spain
- Prior art keywords
- pyridin
- alkyl
- methyl
- mmol
- hydrogen
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 125000005843 halogen group Chemical group 0.000 claims abstract description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 239000000460 chlorine Substances 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- -1 -CF 3 Chemical group 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- NPPIXSXSFGFFON-UHFFFAOYSA-N 3-[2-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-4-yl]-2-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=C1 NPPIXSXSFGFFON-UHFFFAOYSA-N 0.000 claims description 11
- CQTUYMRZAZVKDQ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-[2-(4-methylsulfonylphenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 CQTUYMRZAZVKDQ-UHFFFAOYSA-N 0.000 claims description 10
- XGGCDVFQPLAMKA-UHFFFAOYSA-N 7-methyl-2-(6-methylpyridin-2-yl)-3-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound N1=C2C=C(C)C=CN2C(C=2C=C(N=CC=2)C=2C=CC(OCCN3CCCC3)=CC=2)=C1C1=CC=CC(C)=N1 XGGCDVFQPLAMKA-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 208000017169 kidney disease Diseases 0.000 claims description 10
- CCGRXCIJCYWWOY-UHFFFAOYSA-N 4-[4-[4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=C1 CCGRXCIJCYWWOY-UHFFFAOYSA-N 0.000 claims description 9
- NQQMVZUQPDMLHG-UHFFFAOYSA-N 4-[[4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenyl]methyl]morpholine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(CN3CCOCC3)=CC=2)=N1 NQQMVZUQPDMLHG-UHFFFAOYSA-N 0.000 claims description 9
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- YSMRWZHDCKWGEE-UHFFFAOYSA-N [4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(=CC=2)C(=O)N2CCOCC2)=N1 YSMRWZHDCKWGEE-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
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- SFHCTSWZYNNONF-UHFFFAOYSA-N 2-pyridin-2-yl-3-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C=1C=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=CC=1OCCN1CCCC1 SFHCTSWZYNNONF-UHFFFAOYSA-N 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
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- 230000005855 radiation Effects 0.000 description 1
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- 230000008929 regeneration Effects 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/08—Vasodilators for multiple indications
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- A—HUMAN NECESSITIES
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Surgery (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0217783 | 2002-07-31 | ||
| GBGB0217783.0A GB0217783D0 (en) | 2002-07-31 | 2002-07-31 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2259419T3 true ES2259419T3 (es) | 2006-10-01 |
Family
ID=9941484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03766355T Expired - Lifetime ES2259419T3 (es) | 2002-07-31 | 2003-07-29 | Imidazo(1,2-a)piridinas. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20050234029A1 (enExample) |
| EP (1) | EP1543003B1 (enExample) |
| JP (1) | JP2005537291A (enExample) |
| AR (1) | AR040724A1 (enExample) |
| AT (1) | ATE326467T1 (enExample) |
| AU (1) | AU2003255323A1 (enExample) |
| DE (1) | DE60305332T2 (enExample) |
| ES (1) | ES2259419T3 (enExample) |
| GB (1) | GB0217783D0 (enExample) |
| TW (1) | TW200413366A (enExample) |
| WO (1) | WO2004013138A2 (enExample) |
Families Citing this family (21)
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| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| EP1539748A1 (en) * | 2002-07-31 | 2005-06-15 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
| UA80296C2 (en) * | 2002-09-06 | 2007-09-10 | Biogen Inc | Imidazolopyridines and methods of making and using the same |
| PA8595001A1 (es) * | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| MX2007011453A (es) | 2005-04-22 | 2008-02-12 | Alantos Pharmaceuticals Holding Inc | Inhibidores de la dipeptidil peptidasa-iv. |
| EP1928237A4 (en) * | 2005-09-02 | 2011-03-09 | Abbott Lab | NEW HETEROCYCLES BASED ON IMIDAZO |
| CN101611007A (zh) | 2006-12-20 | 2009-12-23 | 先灵公司 | 新颖的jnk抑制剂 |
| CA2672960A1 (en) * | 2006-12-20 | 2008-07-10 | Schering Corporation | Novel jnk inhibitors |
| EA201000615A1 (ru) | 2007-10-17 | 2010-12-30 | Новартис Аг | Производные имидазо[1,2-а]пиридина, применимые в качестве ингибиторов апк (активиноподобной киназы) |
| WO2009086123A1 (en) * | 2007-12-21 | 2009-07-09 | Wyeth | Imidazo [1,2-a] pyridine compounds |
| EP2307402B1 (en) * | 2008-04-29 | 2012-11-07 | Novartis AG | Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors |
| PH12012500778A1 (en) | 2009-10-30 | 2012-11-26 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| WO2011074658A1 (ja) | 2009-12-18 | 2011-06-23 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| WO2011146287A1 (en) | 2010-05-20 | 2011-11-24 | Takeda Pharmaceutical Company Limited | Pyrazolo[4,3-b]pyridine-7-amine inhibitors of alk5 |
| US20120309796A1 (en) | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| JP6115962B2 (ja) | 2011-06-27 | 2017-04-19 | ヤンセン ファーマシューティカ エヌ．ベー． | １−アリール−４−メチル−［１，２，４］トリアゾロ［４，３−ａ］キノキサリン誘導体 |
| WO2014001314A1 (en) | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| AU2013289284B2 (en) | 2012-07-09 | 2017-03-30 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| CN108341769A (zh) * | 2018-05-13 | 2018-07-31 | 浙江凯普化工有限公司 | 多取代的6-氟皮考啉酸的制备方法 |
| CN115975224B (zh) * | 2023-03-16 | 2023-08-08 | 四川大学 | 一种pH/ROS双响应的组织粘附载药水凝胶及其制备方法和应用 |
Family Cites Families (7)
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|---|---|---|---|---|
| JPH11302177A (ja) * | 1998-04-27 | 1999-11-02 | Otsuka Pharmaceut Factory Inc | 腎炎治療剤 |
| GB0007405D0 (en) * | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| GB0027987D0 (en) * | 2000-11-16 | 2001-01-03 | Smithkline Beecham Plc | Compounds |
| EP1349851A4 (en) * | 2000-11-16 | 2004-09-08 | Smithkline Beecham Corp | COMPOUNDS |
| GB0100762D0 (en) * | 2001-01-11 | 2001-02-21 | Smithkline Beecham Plc | Novel use |
| EP1539748A1 (en) * | 2002-07-31 | 2005-06-15 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
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2002
- 2002-07-31 GB GBGB0217783.0A patent/GB0217783D0/en not_active Ceased
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2003
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- 2003-07-29 ES ES03766355T patent/ES2259419T3/es not_active Expired - Lifetime
- 2003-07-29 AU AU2003255323A patent/AU2003255323A1/en not_active Abandoned
- 2003-07-29 AT AT03766355T patent/ATE326467T1/de not_active IP Right Cessation
- 2003-07-29 EP EP03766355A patent/EP1543003B1/en not_active Expired - Lifetime
- 2003-07-29 TW TW092120589A patent/TW200413366A/zh unknown
- 2003-07-29 AR AR20030102720A patent/AR040724A1/es not_active Application Discontinuation
- 2003-07-29 US US10/522,967 patent/US20050234029A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
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| AU2003255323A1 (en) | 2004-02-23 |
| AU2003255323A8 (en) | 2004-02-23 |
| GB0217783D0 (en) | 2002-09-11 |
| AR040724A1 (es) | 2005-04-20 |
| TW200413366A (en) | 2004-08-01 |
| EP1543003B1 (en) | 2006-05-17 |
| DE60305332D1 (de) | 2006-06-22 |
| WO2004013138A3 (en) | 2004-03-25 |
| US20050234029A1 (en) | 2005-10-20 |
| DE60305332T2 (de) | 2007-04-19 |
| JP2005537291A (ja) | 2005-12-08 |
| EP1543003A2 (en) | 2005-06-22 |
| ATE326467T1 (de) | 2006-06-15 |
| WO2004013138A2 (en) | 2004-02-12 |
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