CA2491210A1 - Derives de thiazine et d'oxazine utilises en tant qu'inhibiteurs mmp-13 pour traiter l'arthrite - Google Patents
Derives de thiazine et d'oxazine utilises en tant qu'inhibiteurs mmp-13 pour traiter l'arthrite Download PDFInfo
- Publication number
- CA2491210A1 CA2491210A1 CA002491210A CA2491210A CA2491210A1 CA 2491210 A1 CA2491210 A1 CA 2491210A1 CA 002491210 A CA002491210 A CA 002491210A CA 2491210 A CA2491210 A CA 2491210A CA 2491210 A1 CA2491210 A1 CA 2491210A1
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- alkyl
- cndot
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- 206010003246 arthritis Diseases 0.000 title claims abstract description 9
- 239000003112 inhibitor Substances 0.000 title abstract description 12
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 title description 3
- 150000004893 oxazines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 23
- 229910052736 halogen Chemical group 0.000 claims abstract description 23
- 150000002367 halogens Chemical group 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000011159 matrix material Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 15
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 12
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
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- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 7
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- -1 hydroxy, cyano, tetrazolyl Chemical group 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 claims description 4
- 208000002780 macular degeneration Diseases 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- WVLYLQMCGHMXGZ-UHFFFAOYSA-N 6-benzylsulfonyl-1,3-benzothiazine-2,4-dione Chemical compound C=1C=C2SC(=O)NC(=O)C2=CC=1S(=O)(=O)CC1=CC=CC=C1 WVLYLQMCGHMXGZ-UHFFFAOYSA-N 0.000 claims description 2
- CRAHQTZBUAHWQO-UHFFFAOYSA-N 6-phenylsulfanyl-1,3-benzothiazine-2,4-dione Chemical compound C=1C=C2SC(=O)NC(=O)C2=CC=1SC1=CC=CC=C1 CRAHQTZBUAHWQO-UHFFFAOYSA-N 0.000 claims description 2
- 229910006124 SOCl2 Inorganic materials 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 150000003939 benzylamines Chemical class 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- VEVHNOJSQMKHGD-UHFFFAOYSA-N 4-[[2,4-dioxo-6-(3-phenylprop-1-ynyl)-1,3-benzothiazin-3-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(=O)C2=CC(C#CCC=3C=CC=CC=3)=CC=C2SC1=O VEVHNOJSQMKHGD-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
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- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2002/008062 WO2004000321A1 (fr) | 2002-06-25 | 2002-06-25 | Derives de thiazine et d'oxazine en tant qu'inhibiteurs de mmp-13 pour traiter l'arthrite |
| EPPCT/EP/02/08062 | 2002-06-25 | ||
| PCT/EP2003/006601 WO2004000322A1 (fr) | 2002-06-25 | 2003-06-24 | Derives de thiazine et d'oxazine utilises en tant qu'inhibiteurs mmp-13 pour traiter l'arthrite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2491210A1 true CA2491210A1 (fr) | 2003-12-31 |
Family
ID=29797117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002491210A Abandoned CA2491210A1 (fr) | 2002-06-25 | 2003-06-24 | Derives de thiazine et d'oxazine utilises en tant qu'inhibiteurs mmp-13 pour traiter l'arthrite |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP2005538965A (fr) |
| AU (2) | AU2002333256A1 (fr) |
| BR (1) | BR0312107A (fr) |
| CA (1) | CA2491210A1 (fr) |
| MX (1) | MXPA05000004A (fr) |
| WO (2) | WO2004000321A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8539501A1 (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Compuestos triazolo como inhibidores de mmp |
| US6962922B2 (en) | 2001-10-12 | 2005-11-08 | Warner-Lambert Company Llc | Alkynylated quinazoline compounds |
| US6894057B2 (en) | 2002-03-08 | 2005-05-17 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| AU2003249531A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Azaisoquinoline derivatives as matrix metalloproteinase inhibitors |
| EP1537098A1 (fr) | 2002-08-13 | 2005-06-08 | Warner-Lambert Company LLC | Derives monocycliques en tant qu'inhibiteurs de metalloproteinases matricielles |
| MXPA05001783A (es) | 2002-08-13 | 2005-04-25 | Warner Lambert Co | Derivados de pirimidina-2,4-diona como inhibidores de las metaloproteinasas de matriz. |
| PA8578101A1 (es) | 2002-08-13 | 2004-05-07 | Warner Lambert Co | Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz |
| AU2003250470A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Pyrimidinone fused bicyclic metalloproteinase inhibitors |
| AU2003253186A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Fused tetrahydropyridine derivatives as matrix metalloproteinase inhibitors |
| WO2004014880A1 (fr) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Derives de chromone inhibiteurs de metalloproteinase de matrice |
| WO2004014375A2 (fr) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Inhibiteurs de metalloprotease bicycliques condenses |
| CN112159347B (zh) * | 2020-10-27 | 2022-06-07 | 常州工程职业技术学院 | 吡考他胺的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6037454B2 (ja) * | 1976-12-17 | 1985-08-26 | 富士写真フイルム株式会社 | 熱現像感光材料 |
-
2002
- 2002-06-25 AU AU2002333256A patent/AU2002333256A1/en not_active Abandoned
- 2002-06-25 WO PCT/EP2002/008062 patent/WO2004000321A1/fr not_active Application Discontinuation
-
2003
- 2003-06-24 AU AU2003246574A patent/AU2003246574A1/en not_active Abandoned
- 2003-06-24 CA CA002491210A patent/CA2491210A1/fr not_active Abandoned
- 2003-06-24 BR BR0312107-0A patent/BR0312107A/pt not_active IP Right Cessation
- 2003-06-24 WO PCT/EP2003/006601 patent/WO2004000322A1/fr not_active Application Discontinuation
- 2003-06-24 MX MXPA05000004A patent/MXPA05000004A/es not_active Application Discontinuation
- 2003-06-24 JP JP2004514844A patent/JP2005538965A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR0312107A (pt) | 2005-03-29 |
| WO2004000322A1 (fr) | 2003-12-31 |
| MXPA05000004A (es) | 2005-04-08 |
| AU2002333256A1 (en) | 2004-01-06 |
| AU2003246574A1 (en) | 2004-01-06 |
| JP2005538965A (ja) | 2005-12-22 |
| WO2004000321A1 (fr) | 2003-12-31 |
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