ZA200502750B - (1H-Benzoimidazol-2-UL)-(Piperazinyl)-Methanone derivatives and realted compounds as histamine H4-receptor antagonists for the treatment of inflammatory and allergic disorders - Google Patents
(1H-Benzoimidazol-2-UL)-(Piperazinyl)-Methanone derivatives and realted compounds as histamine H4-receptor antagonists for the treatment of inflammatory and allergic disorders Download PDFInfo
- Publication number
- ZA200502750B ZA200502750B ZA200502750A ZA200502750A ZA200502750B ZA 200502750 B ZA200502750 B ZA 200502750B ZA 200502750 A ZA200502750 A ZA 200502750A ZA 200502750 A ZA200502750 A ZA 200502750A ZA 200502750 B ZA200502750 B ZA 200502750B
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- South Africa
- Prior art keywords
- methyl
- piperazin
- methanone
- benzoimidazol
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 96
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 22
- 238000011282 treatment Methods 0.000 title claims description 18
- 208000010668 atopic eczema Diseases 0.000 title claims description 5
- 230000000172 allergic effect Effects 0.000 title claims description 4
- 230000002757 inflammatory effect Effects 0.000 title description 2
- 229940119240 Histamine H4 receptor antagonist Drugs 0.000 title 1
- 239000003396 histamine H4 receptor antagonist Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims description 58
- -1 hydroxy, amino Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 15
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 13
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- KCVXUVKSHFDJIV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC=CC=C2N1 KCVXUVKSHFDJIV-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- JQTLCZZJXYVAEB-UHFFFAOYSA-N (4-methyl-1h-benzimidazol-2-yl)-(3-methylpiperazin-1-yl)methanone Chemical compound C1CNC(C)CN1C(=O)C1=NC2=C(C)C=CC=C2N1 JQTLCZZJXYVAEB-UHFFFAOYSA-N 0.000 claims description 4
- RURXHJWOGXWBLU-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(C(F)(F)F)=CC=C2N1 RURXHJWOGXWBLU-UHFFFAOYSA-N 0.000 claims description 4
- MOIWSUQWIOVGRH-UHFFFAOYSA-N (6-chloro-1H-benzimidazol-2-yl)-(4-methyl-1-piperazinyl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(Cl)=CC=C2N1 MOIWSUQWIOVGRH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- OYCPMRKNILHXGZ-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-(4-methyl-1h-benzimidazol-2-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC2=C(C)C=CC=C2N1 OYCPMRKNILHXGZ-UHFFFAOYSA-N 0.000 claims description 3
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- KQCYNSQKCRQOBH-UHFFFAOYSA-N (5,6-difluoro-1h-benzimidazol-2-yl)-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC2=CC(F)=C(F)C=C2N1 KQCYNSQKCRQOBH-UHFFFAOYSA-N 0.000 claims description 3
- ZKHRNNFTOCMWPM-UHFFFAOYSA-N (5,6-difluoro-1h-benzimidazol-2-yl)-(4-methyl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C)CCCN1C(=O)C1=NC2=CC(F)=C(F)C=C2N1 ZKHRNNFTOCMWPM-UHFFFAOYSA-N 0.000 claims description 3
- SNVJVMUSOXLYCD-UHFFFAOYSA-N (5-chloro-6-fluoro-1h-benzimidazol-2-yl)-(4-methyl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C)CCCN1C(=O)C1=NC2=CC(F)=C(Cl)C=C2N1 SNVJVMUSOXLYCD-UHFFFAOYSA-N 0.000 claims description 3
- KGPQRUZBGJGBKX-UHFFFAOYSA-N (5-chloro-6-fluoro-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(F)=C(Cl)C=C2N1 KGPQRUZBGJGBKX-UHFFFAOYSA-N 0.000 claims description 3
- YYCGKGXDBYVUEH-UHFFFAOYSA-N (5-chloro-6-methyl-1h-benzimidazol-2-yl)-piperazin-1-ylmethanone Chemical compound N=1C=2C=C(Cl)C(C)=CC=2NC=1C(=O)N1CCNCC1 YYCGKGXDBYVUEH-UHFFFAOYSA-N 0.000 claims description 3
- INSXYBBGCMREFN-UHFFFAOYSA-N (6-chloro-1h-benzimidazol-2-yl)-piperazin-1-ylmethanone Chemical compound N=1C2=CC(Cl)=CC=C2NC=1C(=O)N1CCNCC1 INSXYBBGCMREFN-UHFFFAOYSA-N 0.000 claims description 3
- ADOGRQLMMRRBHN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-(3-methylpiperazin-1-yl)methanone Chemical compound C1CNC(C)CN1C(=O)C1=NC2=CC=CC=C2N1 ADOGRQLMMRRBHN-UHFFFAOYSA-N 0.000 claims description 3
- NXBBUCGRKYLQFY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC2=CC=CC=C2N1 NXBBUCGRKYLQFY-UHFFFAOYSA-N 0.000 claims description 3
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- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
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- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- QBROMMVCQKIILN-UHFFFAOYSA-N piperazin-1-yl-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]methanone Chemical compound N=1C2=CC(C(F)(F)F)=CC=C2NC=1C(=O)N1CCNCC1 QBROMMVCQKIILN-UHFFFAOYSA-N 0.000 claims description 3
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- KVHNNAFIEYQJFP-UHFFFAOYSA-N (4-amino-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(N)C=CC=C2N1 KVHNNAFIEYQJFP-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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| US40856902P | 2002-09-06 | 2002-09-06 |
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| US (1) | US7504426B2 (de) |
| EP (1) | EP1545532A2 (de) |
| JP (1) | JP2006500390A (de) |
| KR (1) | KR20050033662A (de) |
| CN (1) | CN1694704A (de) |
| AR (1) | AR041170A1 (de) |
| AU (1) | AU2003265886A1 (de) |
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| IS (1) | IS7716A (de) |
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| JP2006510590A (ja) * | 2002-09-06 | 2006-03-30 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | アレルギー及び喘息の処置のためのヒスタミンｈ４受容体モジュレーターの使用 |
| EP1479676A1 (de) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Benzimidazolderivate als Faktor Xa-Inhibitoren |
| US7741341B2 (en) | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| EP1685406A4 (de) * | 2003-09-26 | 2008-11-12 | Janssen Pharmaceutica Nv | Analyse von durch histamin-4-rezeptor vermittelten effekten in vollblut |
| JP2008513463A (ja) | 2004-09-15 | 2008-05-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | チアゾロピリジンキナーゼ阻害剤 |
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| US7507737B2 (en) | 2006-03-31 | 2009-03-24 | Janssen Pharmaceutica, N.V. | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine H4receptor |
| EP2010172B1 (de) * | 2006-04-07 | 2012-08-29 | Janssen Pharmaceutica N.V. | Indole und benzoimidazole als modulatoren des histamin-h4-rezeptors |
| WO2007120690A2 (en) * | 2006-04-10 | 2007-10-25 | Janssen Pharmaceutica N.V. | Combination histamine h1r and h4r antagonist therapy for treating pruritus |
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| EP2201982A1 (de) | 2008-12-24 | 2010-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Histamin-H4-Rezeptorantagonisten zur Behandlung von Vestibularisstörungen |
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| CN102512421B (zh) * | 2011-10-28 | 2013-11-06 | 中国科学院广州生物医药与健康研究院 | 哌嗪酰胺类化合物在制药中的应用 |
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| SG11201507117XA (en) | 2013-03-06 | 2015-10-29 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine modulators of the histamine h4 receptor |
| WO2014165128A2 (en) | 2013-03-12 | 2014-10-09 | Novira Therapeutics, Inc. | Hepatitis b antiviral agents |
| ES2640063T3 (es) | 2013-04-03 | 2017-10-31 | Janssen Sciences Ireland Uc | Derivados de n-fenil-carboxamida y su uso como medicamentos para el tratamiento de la hepatitis B |
| JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| JP6348978B2 (ja) | 2013-07-25 | 2018-06-27 | ヤンセン・サイエンシズ・アイルランド・ユーシー | グリオキサミド置換ピロールアミド誘導体およびｂ型肝炎を処置するための医薬品としてのその使用 |
| ES2655518T3 (es) | 2013-10-23 | 2018-02-20 | Janssen Sciences Ireland Uc | Derivados de carboxamida y su uso como medicamentos para el tratamiento de la hepatitis B |
| US9181288B2 (en) | 2014-01-16 | 2015-11-10 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| KR20160128305A (ko) | 2014-02-05 | 2016-11-07 | 노비라 테라퓨틱스, 인코포레이티드 | Hbv 감염의 치료를 위한 병용 요법 |
| CN110483484A (zh) | 2014-02-06 | 2019-11-22 | 爱尔兰詹森科学公司 | 氨磺酰基吡咯酰胺衍生物及其作为药物用于治疗乙型肝炎的用途 |
| EP3110799A4 (de) * | 2014-02-27 | 2017-10-11 | Epirus Biopharmaceuticals, Inc. | Heterocyclische inhibitoren des natriumkanals |
| US9400280B2 (en) | 2014-03-27 | 2016-07-26 | Novira Therapeutics, Inc. | Piperidine derivatives and methods of treating hepatitis B infections |
| US9884831B2 (en) | 2015-03-19 | 2018-02-06 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis B infections |
| US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| EP3356328A1 (de) | 2015-09-29 | 2018-08-08 | Novira Therapeutics, Inc. | Kristalline formen eines hepatitis-b-viruzids |
| KR20180129943A (ko) | 2016-04-15 | 2018-12-05 | 노비라 테라퓨틱스, 인코포레이티드 | 캡시드 조립 억제제를 포함하는 배합물 및 방법 |
| CA3090125A1 (en) | 2018-03-14 | 2019-09-19 | Janssen Sciences Ireland Unlimited Company | Capsid assembly modulator dosing regimen |
| CN113454077A (zh) | 2019-02-22 | 2021-09-28 | 爱尔兰詹森科学公司 | 用于治疗hbv感染或hbv诱发的疾病的酰胺衍生物 |
| BR112021021454A2 (pt) | 2019-05-06 | 2021-12-21 | Janssen Sciences Ireland Unlimited Co | Derivados de amida úteis no tratamento da infecção por hbv ou doenças induzidas por hbv |
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| ATE277037T1 (de) | 1996-07-09 | 2004-10-15 | Nikem Research Srl | Indolderivate zur behandlung von osteoporose |
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| WO1999058120A1 (en) | 1998-05-08 | 1999-11-18 | Rolf Berge | USE OF NON-β-OXIDIZABLE FATTY ACID ANALOGUES FOR TREATMENT OF SYNDROME-X CONDITIONS |
| EP0978512A1 (de) | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Aryloxy- (oder Arylthio)alkylamine ohne Imidazolring als Histamin-H3-Antagonisten und deren therapeutische Anwendung |
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2003
- 2003-09-04 US US10/655,381 patent/US7504426B2/en active Active
- 2003-09-04 PL PL377087A patent/PL377087A1/pl not_active Application Discontinuation
- 2003-09-04 AU AU2003265886A patent/AU2003265886A1/en not_active Abandoned
- 2003-09-04 KR KR1020057003818A patent/KR20050033662A/ko not_active Application Discontinuation
- 2003-09-04 CN CNA038249693A patent/CN1694704A/zh active Pending
- 2003-09-04 WO PCT/US2003/027461 patent/WO2004022060A2/en active Application Filing
- 2003-09-04 MX MXPA05002575A patent/MXPA05002575A/es unknown
- 2003-09-04 RU RU2005106274/04A patent/RU2005106274A/ru not_active Application Discontinuation
- 2003-09-04 CA CA002497827A patent/CA2497827A1/en not_active Abandoned
- 2003-09-04 BR BR0314059-8A patent/BR0314059A/pt not_active IP Right Cessation
- 2003-09-04 RS YUP-2005/0201A patent/RS20050201A/sr unknown
- 2003-09-04 EP EP03794573A patent/EP1545532A2/de not_active Withdrawn
- 2003-09-04 UA UAA200503209A patent/UA79309C2/uk unknown
- 2003-09-04 JP JP2004534443A patent/JP2006500390A/ja not_active Withdrawn
- 2003-09-04 NZ NZ538401A patent/NZ538401A/en unknown
- 2003-09-05 AR ARP030103235A patent/AR041170A1/es not_active Application Discontinuation
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2005
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- 2005-03-04 EC EC2005005647A patent/ECSP055647A/es unknown
- 2005-04-05 ZA ZA200502750A patent/ZA200502750B/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| UA79309C2 (en) | 2007-06-11 |
| AR041170A1 (es) | 2005-05-04 |
| MXPA05002575A (es) | 2005-09-08 |
| RS20050201A (en) | 2007-06-04 |
| WO2004022060A2 (en) | 2004-03-18 |
| CN1694704A (zh) | 2005-11-09 |
| US20040058934A1 (en) | 2004-03-25 |
| WO2004022060A8 (en) | 2004-06-03 |
| KR20050033662A (ko) | 2005-04-12 |
| RU2005106274A (ru) | 2005-11-10 |
| US7504426B2 (en) | 2009-03-17 |
| CA2497827A1 (en) | 2004-03-18 |
| ECSP055647A (es) | 2005-05-30 |
| IS7716A (is) | 2005-02-24 |
| NO20051694L (no) | 2005-04-05 |
| BR0314059A (pt) | 2005-07-05 |
| NZ538401A (en) | 2008-03-28 |
| AU2003265886A1 (en) | 2004-03-29 |
| JP2006500390A (ja) | 2006-01-05 |
| WO2004022060A3 (en) | 2004-07-08 |
| PL377087A1 (pl) | 2006-01-23 |
| EP1545532A2 (de) | 2005-06-29 |
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