NZ534238A - Compounds that inhibit factor Xa activity - Google Patents
Compounds that inhibit factor Xa activityInfo
- Publication number
- NZ534238A NZ534238A NZ534238A NZ53423803A NZ534238A NZ 534238 A NZ534238 A NZ 534238A NZ 534238 A NZ534238 A NZ 534238A NZ 53423803 A NZ53423803 A NZ 53423803A NZ 534238 A NZ534238 A NZ 534238A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- formula
- phenyl
- compounds
- heteroaryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 77
- 108010074860 Factor Xa Proteins 0.000 title claims abstract description 15
- 230000000694 effects Effects 0.000 title claims description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 19
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000009424 thromboembolic effect Effects 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000003147 glycosyl group Chemical group 0.000 claims description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 239000008118 PEG 6000 Substances 0.000 claims 1
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 claims 1
- 230000003024 amidolytic effect Effects 0.000 claims 1
- 230000006957 competitive inhibition Effects 0.000 claims 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- 230000005284 excitation Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 1
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- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000001425 electrospray ionisation time-of-flight mass spectrometry Methods 0.000 description 63
- -1 heteroaralkyl radical Chemical class 0.000 description 54
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- 150000003254 radicals Chemical class 0.000 description 9
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- 239000004480 active ingredient Substances 0.000 description 6
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- 238000005345 coagulation Methods 0.000 description 6
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- 102000009123 Fibrin Human genes 0.000 description 4
- 108010073385 Fibrin Proteins 0.000 description 4
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
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- 150000001299 aldehydes Chemical class 0.000 description 4
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- FLCJAEREAWXGKS-UHFFFAOYSA-N 2-(5-carbamimidoyl-2-hydroxyanilino)-N-(4-morpholin-4-ylphenyl)-2-[2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetamide Chemical compound NC(=N)C1=CC=C(O)C(NC(C(=O)NC=2C=CC(=CC=2)N2CCOCC2)C=2C(=CC=CC=2)OC2C(C(O)C(O)C(CO)O2)O)=C1 FLCJAEREAWXGKS-UHFFFAOYSA-N 0.000 description 2
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- 108010014173 Factor X Proteins 0.000 description 2
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- QOJGJRLIMDOLGY-UHFFFAOYSA-N 2-(3-carbamimidoylanilino)-n-(2-methoxy-5-phenylphenyl)-2-[2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetamide Chemical compound COC1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)C(C=1C(=CC=CC=1)OC1C(C(O)C(O)C(CO)O1)O)NC1=CC=CC(C(N)=N)=C1 QOJGJRLIMDOLGY-UHFFFAOYSA-N 0.000 description 1
- WZZUQFJIUKMERK-UHFFFAOYSA-N 2-(3-carbamimidoylanilino)-n-(3,3-dimethylbutan-2-yl)-2-[2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetamide Chemical compound C=1C=CC=C(OC2C(C(O)C(O)C(CO)O2)O)C=1C(C(=O)NC(C)C(C)(C)C)NC1=CC=CC(C(N)=N)=C1 WZZUQFJIUKMERK-UHFFFAOYSA-N 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- 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
- A61P35/00—Antineoplastic 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Genetics & Genomics (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10204072A DE10204072A1 (de) | 2002-01-31 | 2002-01-31 | Neue Verbindungen, die Faktor Xa-Aktivität inhibieren |
| DE10300049A DE10300049A1 (de) | 2003-01-03 | 2003-01-03 | Neue Verbindungen, die Faktor VIIa inhibieren |
| PCT/EP2003/001011 WO2003064440A1 (de) | 2002-01-31 | 2003-01-31 | Verbindungen, die faktor xa-aktivät inhibieren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ534238A true NZ534238A (en) | 2006-09-29 |
Family
ID=27664555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ534238A NZ534238A (en) | 2002-01-31 | 2003-01-31 | Compounds that inhibit factor Xa activity |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20050049283A1 (enExample) |
| EP (1) | EP1470143B1 (enExample) |
| JP (1) | JP2005525325A (enExample) |
| KR (1) | KR20040096541A (enExample) |
| CN (1) | CN1322001C (enExample) |
| AT (1) | ATE377017T1 (enExample) |
| BR (1) | BR0307266A (enExample) |
| CA (1) | CA2473169A1 (enExample) |
| DE (1) | DE50308492D1 (enExample) |
| MX (1) | MXPA04007461A (enExample) |
| NZ (1) | NZ534238A (enExample) |
| PL (1) | PL369772A1 (enExample) |
| WO (1) | WO2003064440A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2283833A3 (en) * | 2004-02-25 | 2013-07-10 | La Jolla Pharmaceutical Co. | Amines and amides for the treatment of diseases |
| CN101341129B (zh) * | 2005-12-14 | 2011-12-14 | 布里斯托尔-迈尔斯斯奎布公司 | 作为因子xia抑制剂的芳基丙酰胺，芳基丙烯酰胺，芳基丙炔酰胺，或芳基甲基脲类似物 |
| AR058379A1 (es) * | 2005-12-14 | 2008-01-30 | Bristol Myers Squibb Co | Derivados de arilpropionamida arilacrilamida arilpropinamida o arilmetilurea como inhibidores del factor xia. proceso de obtencion y composiciones farmaceuticas. |
| WO2017156071A1 (en) | 2016-03-09 | 2017-09-14 | Blade Therapeutics, Inc. | Cyclic keto-amide compounds as calpain modulators and methods of production and use thereof |
| AU2017292646A1 (en) | 2016-07-05 | 2019-02-07 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| WO2018064119A1 (en) | 2016-09-28 | 2018-04-05 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2614893B1 (fr) * | 1987-05-04 | 1989-12-22 | Fournier Innovation Synergie | Nouveaux b-d-phenyl-thioxylosides, leur procede de preparation et leur application en therapeutique |
| EP0560568A3 (en) * | 1992-03-13 | 1994-06-29 | Takeda Chemical Industries Ltd | Hydroquinone derivatives and intermediates for production thereof |
| SI0921116T1 (en) * | 1997-12-04 | 2003-10-31 | F. Hoffmann - La Roche Ag | N-(4-carbamimido-phenyl)-glycine amide derivatives |
| KR20010082515A (ko) * | 1998-02-17 | 2001-08-30 | 우에노 도시오 | 아미디노 유도체 및 그 유도체를 유효 성분으로서함유하는 약제 |
| SK286755B6 (sk) * | 1998-06-17 | 2009-05-07 | Universiteit Leiden | Antitrombotické zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie |
| DE10041402A1 (de) * | 2000-08-23 | 2002-03-14 | Morphochem Ag | Neue Verbindungen, die Faktor Xa-Aktivität inhibieren |
| EP1336605B1 (en) * | 2000-11-22 | 2006-04-12 | Astellas Pharma Inc. | Substituted phenol derivatives or salts thereof as inhibitors of coagulation factor x |
-
2003
- 2003-01-31 NZ NZ534238A patent/NZ534238A/en unknown
- 2003-01-31 EP EP03734605A patent/EP1470143B1/de not_active Expired - Lifetime
- 2003-01-31 AT AT03734605T patent/ATE377017T1/de not_active IP Right Cessation
- 2003-01-31 JP JP2003564060A patent/JP2005525325A/ja active Pending
- 2003-01-31 WO PCT/EP2003/001011 patent/WO2003064440A1/de not_active Ceased
- 2003-01-31 DE DE50308492T patent/DE50308492D1/de not_active Expired - Fee Related
- 2003-01-31 CN CNB038031558A patent/CN1322001C/zh not_active Expired - Fee Related
- 2003-01-31 BR BR0307266-5A patent/BR0307266A/pt not_active IP Right Cessation
- 2003-01-31 CA CA002473169A patent/CA2473169A1/en not_active Abandoned
- 2003-01-31 PL PL03369772A patent/PL369772A1/xx not_active Application Discontinuation
- 2003-01-31 US US10/501,932 patent/US20050049283A1/en not_active Abandoned
- 2003-01-31 KR KR10-2004-7011732A patent/KR20040096541A/ko not_active Withdrawn
- 2003-01-31 MX MXPA04007461A patent/MXPA04007461A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| PL369772A1 (en) | 2005-05-02 |
| WO2003064440A1 (de) | 2003-08-07 |
| KR20040096541A (ko) | 2004-11-16 |
| US20050049283A1 (en) | 2005-03-03 |
| EP1470143A1 (de) | 2004-10-27 |
| MXPA04007461A (es) | 2005-07-13 |
| CA2473169A1 (en) | 2003-08-07 |
| ATE377017T1 (de) | 2007-11-15 |
| BR0307266A (pt) | 2004-12-07 |
| EP1470143B1 (de) | 2007-10-31 |
| DE50308492D1 (de) | 2007-12-13 |
| CN1625559A (zh) | 2005-06-08 |
| CN1322001C (zh) | 2007-06-20 |
| JP2005525325A (ja) | 2005-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |