MXPA02012595A - Tienopirrolidinonas. - Google Patents
Tienopirrolidinonas.Info
- Publication number
- MXPA02012595A MXPA02012595A MXPA02012595A MXPA02012595A MXPA02012595A MX PA02012595 A MXPA02012595 A MX PA02012595A MX PA02012595 A MXPA02012595 A MX PA02012595A MX PA02012595 A MXPA02012595 A MX PA02012595A MX PA02012595 A MXPA02012595 A MX PA02012595A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- lower alkyl
- thieno
- pyrrol
- dihydro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 11
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
- 201000011529 cardiovascular cancer Diseases 0.000 claims abstract description 10
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 4
- 230000001413 cellular effect Effects 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- -1 nitro, hydroxy Chemical group 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 125000003107 substituted aryl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- BQMPGKPTOHKYHS-UHFFFAOYSA-N 1h-pyrrole-2-carbonitrile Chemical compound N#CC1=CC=CN1 BQMPGKPTOHKYHS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
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- 150000002431 hydrogen Chemical group 0.000 claims 4
- 102000003390 tumor necrosis factor Human genes 0.000 claims 2
- YMOYTSSMKXZCFR-VURMDHGXSA-N (4z)-4-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-6h-thieno[2,3-b]pyrrol-5-one Chemical group C1=CNC(\C=C/2C=3C=CSC=3NC\2=O)=C1OC YMOYTSSMKXZCFR-VURMDHGXSA-N 0.000 claims 1
- CSYFNTWWAJGUAC-WTKPLQERSA-N (4z)-4-[(5-methyl-1h-pyrazol-4-yl)methylidene]-6h-thieno[2,3-b]pyrrol-5-one Chemical compound CC1=NNC=C1\C=C/1C(C=CS2)=C2NC\1=O CSYFNTWWAJGUAC-WTKPLQERSA-N 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- SXVURCAXJDJGSG-UHFFFAOYSA-N 4,6-dihydrothieno[2,3-b]pyrrol-5-one Chemical class C1=CSC2=C1CC(=O)N2 SXVURCAXJDJGSG-UHFFFAOYSA-N 0.000 abstract description 5
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- 239000000243 solution Substances 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 239000000203 mixture Substances 0.000 description 33
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- 238000006243 chemical reaction Methods 0.000 description 27
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
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- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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- 235000019341 magnesium sulphate Nutrition 0.000 description 17
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- 238000001914 filtration Methods 0.000 description 12
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- 239000007858 starting material Substances 0.000 description 10
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- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000004017 serum-free culture medium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZGNSDJLWXXTCT-CLFYSBASSA-N tert-butyl (4z)-4-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-5-oxo-6h-thieno[2,3-b]pyrrole-2-carboxylate Chemical compound C1=CNC(\C=C/2C=3C=C(SC=3NC\2=O)C(=O)OC(C)(C)C)=C1OC VZGNSDJLWXXTCT-CLFYSBASSA-N 0.000 description 1
- UEFKYPIKRCFJGA-YFHOEESVSA-N tert-butyl (4z)-5-oxo-4-(1h-pyrrol-2-ylmethylidene)-6h-thieno[2,3-b]pyrrole-2-carboxylate Chemical compound O=C1NC=2SC(C(=O)OC(C)(C)C)=CC=2\C1=C\C1=CC=CN1 UEFKYPIKRCFJGA-YFHOEESVSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0016454.1A GB0016454D0 (en) | 2000-07-04 | 2000-07-04 | Thienopyrrolidinones |
| PCT/EP2001/007423 WO2002002567A1 (en) | 2000-07-04 | 2001-06-28 | Thienopyrrolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02012595A true MXPA02012595A (es) | 2003-04-10 |
Family
ID=9895032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02012595A MXPA02012595A (es) | 2000-07-04 | 2001-06-28 | Tienopirrolidinonas. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6528653B2 (enExample) |
| EP (1) | EP1301517B1 (enExample) |
| JP (1) | JP3878128B2 (enExample) |
| KR (1) | KR100519831B1 (enExample) |
| CN (1) | CN1186346C (enExample) |
| AR (1) | AR030241A1 (enExample) |
| AT (1) | ATE284887T1 (enExample) |
| AU (2) | AU2001287568B2 (enExample) |
| BR (1) | BR0112147A (enExample) |
| CA (1) | CA2414705A1 (enExample) |
| DE (1) | DE60107852T2 (enExample) |
| ES (1) | ES2233677T3 (enExample) |
| GB (1) | GB0016454D0 (enExample) |
| MX (1) | MXPA02012595A (enExample) |
| PT (1) | PT1301517E (enExample) |
| WO (1) | WO2002002567A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004035507A (ja) * | 2002-07-05 | 2004-02-05 | Nippon Soda Co Ltd | ピロール誘導体及びその製造方法 |
| WO2005012311A1 (en) * | 2003-07-31 | 2005-02-10 | Wyeth | N-sulfonylheterocyclopyrrolylalkylamine compounds as 5-hydroxytryptamine-6 ligands |
| CN1939922B (zh) * | 2005-09-27 | 2010-10-13 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的5H-噻吩[3，4-c]吡咯-4，6-二酮衍生物 |
| US20070185929A1 (en) * | 2006-02-01 | 2007-08-09 | Sap Portals Isreal Ltd. | Method and apparatus for processing monitoring |
| TWI873092B (zh) | 2018-04-06 | 2025-02-21 | 美商百歐克斯製藥公司 | 取代的苯并呋喃、苯并吡咯、苯并噻吩及結構相關的補體抑制劑 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4797413A (en) | 1986-05-14 | 1989-01-10 | Merck & Co., Inc. | Thieno thiopyran sulfonamide derivatives, pharmaceutical compositions and use |
| US4863092A (en) | 1988-09-01 | 1989-09-05 | Robertshaw Controls Company | Apparatus for making a diaphragm assembly and method of making the apparatus |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| GB9610964D0 (en) | 1996-05-24 | 1996-07-31 | Pharmacia & Upjohn Spa | Substituted tetralylmethylen-oxindole analogues as tyrosine kinase inhibitors |
| EP0929520B1 (en) | 1996-08-23 | 2005-11-02 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| AU7622698A (en) | 1996-12-05 | 1998-06-29 | Sugen, Inc. | Use of indolinone compounds as modulators of protein kinases |
| CA2289102A1 (en) | 1997-05-07 | 1998-11-12 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
| GB9716557D0 (en) | 1997-08-06 | 1997-10-08 | Glaxo Group Ltd | Benzylidene-1,3-dihydro-indol-2-one derivatives having anti-cancer activity |
| GB9718913D0 (en) | 1997-09-05 | 1997-11-12 | Glaxo Group Ltd | Substituted oxindole derivatives |
| FR2770215B1 (fr) | 1997-10-28 | 2000-01-14 | Pf Medicament | Derives d'aminomethyl-benzo[a]quinolizidine, leur preparation et leur application en therapeutique pour les maladies neurodegeneratives |
| US6153634A (en) | 1998-12-17 | 2000-11-28 | Hoffmann-La Roche Inc. | 4,5-azolo-oxindoles |
| ES2301255T3 (es) | 1998-12-17 | 2008-06-16 | F. Hoffmann-La Roche Ag | 4,5-pirazinaxindoles como inhibidores de proteinoquinasas. |
-
2000
- 2000-07-04 GB GBGB0016454.1A patent/GB0016454D0/en not_active Ceased
-
2001
- 2001-06-26 US US09/891,588 patent/US6528653B2/en not_active Expired - Fee Related
- 2001-06-28 AT AT01967106T patent/ATE284887T1/de not_active IP Right Cessation
- 2001-06-28 KR KR10-2003-7000084A patent/KR100519831B1/ko not_active Expired - Fee Related
- 2001-06-28 ES ES01967106T patent/ES2233677T3/es not_active Expired - Lifetime
- 2001-06-28 EP EP01967106A patent/EP1301517B1/en not_active Expired - Lifetime
- 2001-06-28 DE DE60107852T patent/DE60107852T2/de not_active Expired - Fee Related
- 2001-06-28 JP JP2002507819A patent/JP3878128B2/ja not_active Expired - Fee Related
- 2001-06-28 WO PCT/EP2001/007423 patent/WO2002002567A1/en not_active Ceased
- 2001-06-28 AU AU2001287568A patent/AU2001287568B2/en not_active Ceased
- 2001-06-28 MX MXPA02012595A patent/MXPA02012595A/es active IP Right Grant
- 2001-06-28 PT PT01967106T patent/PT1301517E/pt unknown
- 2001-06-28 AU AU8756801A patent/AU8756801A/xx active Pending
- 2001-06-28 CA CA002414705A patent/CA2414705A1/en not_active Abandoned
- 2001-06-28 BR BR0112147-2A patent/BR0112147A/pt not_active IP Right Cessation
- 2001-06-28 CN CNB01812349XA patent/CN1186346C/zh not_active Expired - Fee Related
- 2001-07-03 AR ARP010103167A patent/AR030241A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1440412A (zh) | 2003-09-03 |
| US6528653B2 (en) | 2003-03-04 |
| DE60107852T2 (de) | 2005-12-08 |
| EP1301517B1 (en) | 2004-12-15 |
| ES2233677T3 (es) | 2005-06-16 |
| ATE284887T1 (de) | 2005-01-15 |
| CA2414705A1 (en) | 2002-01-10 |
| BR0112147A (pt) | 2003-07-01 |
| GB0016454D0 (en) | 2000-08-23 |
| WO2002002567A1 (en) | 2002-01-10 |
| JP3878128B2 (ja) | 2007-02-07 |
| EP1301517A1 (en) | 2003-04-16 |
| AU8756801A (en) | 2002-01-14 |
| JP2004502694A (ja) | 2004-01-29 |
| CN1186346C (zh) | 2005-01-26 |
| US20020028841A1 (en) | 2002-03-07 |
| KR100519831B1 (ko) | 2005-10-06 |
| KR20030013522A (ko) | 2003-02-14 |
| AU2001287568B2 (en) | 2007-01-11 |
| DE60107852D1 (en) | 2005-01-20 |
| AR030241A1 (es) | 2003-08-13 |
| PT1301517E (pt) | 2005-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |