JP2002536359A - インドール誘導体およびｍｃｐ−１拮抗物質としての該化合物の使用 - Google Patents
インドール誘導体およびｍｃｐ−１拮抗物質としての該化合物の使用Info
- Publication number
- JP2002536359A JP2002536359A JP2000597267A JP2000597267A JP2002536359A JP 2002536359 A JP2002536359 A JP 2002536359A JP 2000597267 A JP2000597267 A JP 2000597267A JP 2000597267 A JP2000597267 A JP 2000597267A JP 2002536359 A JP2002536359 A JP 2002536359A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- ethyl
- chlorophenyl
- chloro
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 150000002475 indoles Chemical class 0.000 title description 2
- 229940123313 MCP-1 antagonist Drugs 0.000 title 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- -1 carboxy, tetrazolyl Chemical group 0.000 claims abstract description 94
- 102100021943 C-C motif chemokine 2 Human genes 0.000 claims abstract description 32
- 101710155857 C-C motif chemokine 2 Proteins 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 22
- 239000000651 prodrug Substances 0.000 claims abstract description 22
- 229940002612 prodrug Drugs 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 6
- 102100032367 C-C motif chemokine 5 Human genes 0.000 claims abstract description 5
- 108010055166 Chemokine CCL5 Proteins 0.000 claims abstract description 5
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 210000001744 T-lymphocyte Anatomy 0.000 claims abstract description 4
- 230000004913 activation Effects 0.000 claims abstract description 3
- 230000033228 biological regulation Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 57
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- 239000000047 product Substances 0.000 description 31
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
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- 239000004480 active ingredient Substances 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000012981 Hank's balanced salt solution Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- 238000002360 preparation method Methods 0.000 description 8
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- 239000007858 starting material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 102000004497 CCR2 Receptors Human genes 0.000 description 6
- 108010017312 CCR2 Receptors Proteins 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002975 chemoattractant Substances 0.000 description 6
- 230000035605 chemotaxis Effects 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- KQQVKJLQXPXHNT-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-5-hydroxy-3-methoxyindole-2-carboxylate Chemical compound CCOC(=O)C1=C(OC)C2=CC(O)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 KQQVKJLQXPXHNT-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 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 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
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- QHPPUHQLQLSMHC-UHFFFAOYSA-N 1h-indol-5-yl acetate Chemical compound CC(=O)OC1=CC=C2NC=CC2=C1 QHPPUHQLQLSMHC-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| GBGB9902461.4A GB9902461D0 (en) | 1999-02-05 | 1999-02-05 | Chemical compounds |
| GB9902461.4 | 1999-02-05 | ||
| PCT/GB2000/000265 WO2000046196A1 (en) | 1999-02-05 | 2000-01-31 | Indole derivatives and their use as mcp-1 antagonists |
Publications (2)
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| JP2002536359A true JP2002536359A (ja) | 2002-10-29 |
| JP2002536359A5 JP2002536359A5 (enExample) | 2007-04-19 |
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| JP2000597267A Pending JP2002536359A (ja) | 1999-02-05 | 2000-01-31 | インドール誘導体およびｍｃｐ−１拮抗物質としての該化合物の使用 |
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| AT (1) | ATE280757T1 (enExample) |
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| DE (1) | DE60015296T2 (enExample) |
| EE (1) | EE200100403A (enExample) |
| GB (1) | GB9902461D0 (enExample) |
| HU (1) | HUP0105079A3 (enExample) |
| ID (1) | ID30401A (enExample) |
| IL (1) | IL144611A0 (enExample) |
| IS (1) | IS5980A (enExample) |
| MY (1) | MY133209A (enExample) |
| NO (1) | NO20013809L (enExample) |
| NZ (1) | NZ512680A (enExample) |
| PL (1) | PL350184A1 (enExample) |
| RU (1) | RU2235090C2 (enExample) |
| SK (1) | SK11152001A3 (enExample) |
| TR (1) | TR200102233T2 (enExample) |
| WO (1) | WO2000046196A1 (enExample) |
| ZA (1) | ZA200105311B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007100066A1 (ja) * | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | １７βＨＳＤｔｙｐｅ５阻害剤 |
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| GB9716657D0 (en) | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9902461D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB0000625D0 (en) * | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
| GB0000626D0 (en) * | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
| CN1505613A (zh) | 2000-10-10 | 2004-06-16 | ʷ��˿�������ȳ�ķ����˾ | 取代的吲哚、含这类吲哚的药物组合物及它们作为PPAR-γ结合剂的用途 |
| AU2002241724A1 (en) | 2000-12-20 | 2002-07-01 | Bristol-Myers Squibb Company | Diamines as modulators of chemokine receptor activity |
| WO2002060859A2 (en) | 2000-12-20 | 2002-08-08 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7842693B2 (en) | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
| KR101255356B1 (ko) | 2002-06-12 | 2013-04-17 | 케모센트릭스, 인크. | 염증 및 면역 질병의 치료를 위한 ｃｃｒ１ 길항물질로서사용하기 위한 1-아릴-4-치환된 피페라진 유도체 |
| US7589199B2 (en) | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
| TW200508224A (en) | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
| JP4736043B2 (ja) | 2003-03-14 | 2011-07-27 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| WO2004092169A1 (ja) | 2003-04-18 | 2004-10-28 | Ono Pharmaceutical Co., Ltd. | スピロピペリジン化合物およびその医薬用途 |
| US7291615B2 (en) | 2003-05-01 | 2007-11-06 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7230133B2 (en) | 2003-05-01 | 2007-06-12 | Bristol-Myers Squibb Company | Malonamides and malonamide derivatives as modulators of chemokine receptor activity |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| US7479496B2 (en) | 2004-02-19 | 2009-01-20 | Bristol-Myers Squibb Company | Substituted spiro azabicyclics as modulators of chemokine receptor activity |
| US7230022B2 (en) | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| US7288563B2 (en) | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7381738B2 (en) | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7435831B2 (en) | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| US7435830B2 (en) | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| US8481035B2 (en) | 2004-04-27 | 2013-07-09 | Northwestern University | Methods for treating chronic pelvic pain syndrome with antibodies that binds MCP-1 or MIP-1A |
| EP1802331A2 (en) * | 2004-09-08 | 2007-07-04 | Boys Town National Research Hospital | Treatment of glomerular basement membrane disease involving matrix metalloproteinase-12 |
| AU2005283326B2 (en) | 2004-09-13 | 2011-07-21 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
| JPWO2006129679A1 (ja) | 2005-05-31 | 2009-01-08 | 小野薬品工業株式会社 | スピロピペリジン化合物およびその医薬用途 |
| FR2890071B1 (fr) | 2005-08-30 | 2007-11-09 | Fournier Sa Sa Lab | Nouveaux composes de l'indole |
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| ES2407115T3 (es) | 2005-11-18 | 2013-06-11 | Ono Pharmaceutical Co., Ltd. | Compuesto que contiene un grupo básico y uso del mismo |
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| WO2007100066A1 (ja) * | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | １７βＨＳＤｔｙｐｅ５阻害剤 |
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Also Published As
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| NZ512680A (en) | 2003-11-28 |
| TR200102233T2 (tr) | 2001-12-21 |
| NO20013809D0 (no) | 2001-08-03 |
| HUP0105079A2 (hu) | 2002-04-29 |
| AR022461A1 (es) | 2002-09-04 |
| CN1339025A (zh) | 2002-03-06 |
| MY133209A (en) | 2007-10-31 |
| DE60015296T2 (de) | 2006-02-02 |
| IL144611A0 (en) | 2002-05-23 |
| US6737435B1 (en) | 2004-05-18 |
| WO2000046196A1 (en) | 2000-08-10 |
| RU2235090C2 (ru) | 2004-08-27 |
| EP1150952B1 (en) | 2004-10-27 |
| GB9902461D0 (en) | 1999-03-24 |
| DE60015296D1 (de) | 2004-12-02 |
| CA2356898A1 (en) | 2000-08-10 |
| SK11152001A3 (sk) | 2001-12-03 |
| PL350184A1 (en) | 2002-11-18 |
| HUP0105079A3 (en) | 2002-11-28 |
| AU2121300A (en) | 2000-08-25 |
| AU770856B2 (en) | 2004-03-04 |
| CZ20012807A3 (cs) | 2001-10-17 |
| EP1150952A1 (en) | 2001-11-07 |
| RU2001124567A (ru) | 2004-01-10 |
| BR0007984A (pt) | 2001-11-06 |
| ZA200105311B (en) | 2002-09-27 |
| ATE280757T1 (de) | 2004-11-15 |
| NO20013809L (no) | 2001-10-02 |
| IS5980A (is) | 2001-06-26 |
| EE200100403A (et) | 2002-10-15 |
| KR20010094755A (ko) | 2001-11-01 |
| ID30401A (id) | 2001-11-29 |
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