OA13113A - Pyrimidin-4-One Derivatives and their use as P38 Kinase Modulators. - Google Patents
Pyrimidin-4-One Derivatives and their use as P38 Kinase Modulators. Download PDFInfo
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- OA13113A OA13113A OA1200500271A OA1200500271A OA13113A OA 13113 A OA13113 A OA 13113A OA 1200500271 A OA1200500271 A OA 1200500271A OA 1200500271 A OA1200500271 A OA 1200500271A OA 13113 A OA13113 A OA 13113A
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- OA
- OAPI
- Prior art keywords
- alkyl
- alkoxy
- independently
- halogen
- nr6r7
- Prior art date
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- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title description 70
- 108091000080 Phosphotransferase Proteins 0.000 title description 5
- 102000020233 phosphotransferase Human genes 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 243
- 125000000217 alkyl group Chemical group 0.000 claims description 1662
- 125000003545 alkoxy group Chemical group 0.000 claims description 484
- 229910052736 halogen Inorganic materials 0.000 claims description 460
- 150000002367 halogens Chemical class 0.000 claims description 460
- -1 -OSO2-aryl Chemical group 0.000 claims description 286
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 270
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 246
- 125000002252 acyl group Chemical group 0.000 claims description 192
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 192
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 163
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 149
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 129
- 125000001188 haloalkyl group Chemical group 0.000 claims description 116
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 113
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 101
- 125000004193 piperazinyl group Chemical group 0.000 claims description 97
- 125000004076 pyridyl group Chemical group 0.000 claims description 92
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 82
- 229910052757 nitrogen Inorganic materials 0.000 claims description 81
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 79
- 125000002757 morpholinyl group Chemical group 0.000 claims description 79
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 77
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 71
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 125000003386 piperidinyl group Chemical group 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 61
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 61
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 59
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 59
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 46
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 44
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 43
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 42
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 42
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 41
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 36
- 125000001041 indolyl group Chemical group 0.000 claims description 36
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 28
- 125000001544 thienyl group Chemical group 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 23
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 21
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 19
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 14
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 14
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
- 125000005495 pyridazyl group Chemical group 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 10
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 9
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 24
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 abstract description 17
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 abstract description 17
- 102100040247 Tumor necrosis factor Human genes 0.000 abstract description 15
- 201000010099 disease Diseases 0.000 abstract description 15
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 description 309
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
- 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 description 26
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 20
- 125000001246 bromo group Chemical group Br* 0.000 description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 10
- 125000002071 phenylalkoxy group Chemical group 0.000 description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 9
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 9
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
- 206010003246 arthritis Diseases 0.000 description 8
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- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 7
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- 125000003884 phenylalkyl group Chemical group 0.000 description 7
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- YRUBIFAMCRFPPC-UHFFFAOYSA-N 2-chloro-7-fluoro-1h-quinazolin-4-one Chemical compound N1C(Cl)=NC(=O)C=2C1=CC(F)=CC=2 YRUBIFAMCRFPPC-UHFFFAOYSA-N 0.000 description 5
- QWIDYOLZFAQBOB-UHFFFAOYSA-N 2-methyl-1h-pyrimidin-6-one Chemical compound CC1=NC=CC(=O)N1 QWIDYOLZFAQBOB-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
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- 230000001404 mediated effect Effects 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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- HECLZDGCCLYIEG-UHFFFAOYSA-N 5-[[5-bromo-4-[(2,4-difluorophenyl)methoxy]-2-methyl-6-oxopyrimidin-1-yl]methyl]-n,n-dimethylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)C)=CN=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)N=C1C HECLZDGCCLYIEG-UHFFFAOYSA-N 0.000 description 3
- RZMBDBOGTBGQGJ-UHFFFAOYSA-N 5-bromo-3-[(3-fluorophenyl)methyl]-6-[[2-(hydroxymethyl)phenyl]methoxy]pyrimidin-4-one Chemical compound OCC1=CC=CC=C1COC1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=N1 RZMBDBOGTBGQGJ-UHFFFAOYSA-N 0.000 description 3
- QXEWZAJIYUUXAD-UHFFFAOYSA-N 5-bromo-6-[(4-fluorophenyl)methoxy]-3-[(3-fluorophenyl)methyl]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=N1 QXEWZAJIYUUXAD-UHFFFAOYSA-N 0.000 description 3
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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Classifications
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EP (1) | EP1753731A2 (pt) |
JP (1) | JP3981398B1 (pt) |
KR (1) | KR100776120B1 (pt) |
CN (1) | CN1968937A (pt) |
AP (1) | AP2005003403A0 (pt) |
AU (1) | AU2004226165C1 (pt) |
BR (1) | BRPI0408990A (pt) |
CA (1) | CA2521081C (pt) |
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UA (1) | UA81658C2 (pt) |
WO (1) | WO2004087677A2 (pt) |
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BRPI0517555A (pt) * | 2004-10-13 | 2008-10-14 | Upjohn Co | n-alquilpirimidinonas substituìdas |
US8324230B2 (en) * | 2004-10-13 | 2012-12-04 | Pfizer Inc. | Crystalline forms of 3-[5-chloro-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-Yl]-N-(2-hydroxyethyl)-4-methylbenzamide |
WO2007081901A2 (en) * | 2006-01-05 | 2007-07-19 | The Scripps Research Institute | Pyrimidinone derivatives as protein kinase inhibitors |
CA2640665A1 (en) * | 2006-02-10 | 2007-08-16 | Pfizer Products Inc. | Pyridinone pyrazole urea and pyrimidinone pyrazole urea derivatives |
US7588924B2 (en) | 2006-03-07 | 2009-09-15 | Procter & Gamble Company | Crystal of hypoxia inducible factor 1 alpha prolyl hydroxylase |
HUE041300T2 (hu) | 2006-06-26 | 2019-05-28 | Akebia Therapeutics Inc | Prolilhidroxiláz inhibitorok és alkalmazási eljárások |
AU2007287601B2 (en) | 2006-08-25 | 2012-12-20 | Boehringer Ingelheim International Gmbh | New pyridone derivatives with MCH antagonistic activity and medicaments comprising these compounds |
TW200831485A (en) | 2006-12-11 | 2008-08-01 | Boehringer Ingelheim Int | New pyridazine derivatives with MCH antagonistic activity and medicaments comprising these compounds |
TW200845994A (en) * | 2007-01-12 | 2008-12-01 | Smithkline Beecham Corp | N-substituted glycine derivatives: prolyl hydroxylase inhibitors |
WO2008153942A1 (en) * | 2007-06-06 | 2008-12-18 | Xcovery, Inc. | Kinase inhibitor compounds |
WO2010138585A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Sharp & Dohme Corp. | Pyrimidinones as pde10 inhibitors |
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KR20220161390A (ko) | 2020-03-27 | 2022-12-06 | 어클라리스 쎄라퓨틱스, 인코포레이티드 | 면역 병태의 치료를 위한 mk2 경로 억제제의 경구 조성물 |
CN112209886A (zh) * | 2020-11-09 | 2021-01-12 | 沈阳药科大学 | 2-(3-氰基-4-烷氧基)苯基嘧啶衍生物及其制备方法和用途 |
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TW202317544A (zh) | 2021-07-09 | 2023-05-01 | 美商辛瑟拉股份有限公司 | 吡啶酮mk2抑制劑及其用途 |
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JPS61205261A (ja) * | 1985-03-08 | 1986-09-11 | Sagami Chem Res Center | 6―置換―5―フルオロウラシル誘導体 |
WO1995011235A1 (en) * | 1993-10-20 | 1995-04-27 | The Upjohn Company | Pyrimidinones as antiarthritic and anti-inflammatories |
JP2002514196A (ja) * | 1996-12-05 | 2002-05-14 | アムジエン・インコーポレーテツド | 置換ピリミジノンおよびピリドン化合物ならびに使用方法 |
EP1086085A1 (en) * | 1998-06-12 | 2001-03-28 | Vertex Pharmaceuticals Incorporated | INHIBITORS OF p38 |
AU2247701A (en) * | 1999-10-21 | 2001-04-30 | Merck & Co., Inc. | Gram-positive selective antibacterial compounds, compositions containing such compounds and methods of treatment |
WO2004014868A2 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Pyrimidine-2,4-dione derivatives as matrix metalloproteinase inhibitors |
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2004
- 2004-03-24 US US10/808,146 patent/US7183287B2/en not_active Expired - Fee Related
- 2004-03-29 AU AU2004226165A patent/AU2004226165C1/en not_active Ceased
- 2004-03-29 AP AP2005003403A patent/AP2005003403A0/xx unknown
- 2004-03-29 NZ NZ542139A patent/NZ542139A/en unknown
- 2004-03-29 CN CNA2004800156300A patent/CN1968937A/zh active Pending
- 2004-03-29 CA CA2521081A patent/CA2521081C/en not_active Expired - Fee Related
- 2004-03-29 KR KR1020057018627A patent/KR100776120B1/ko not_active IP Right Cessation
- 2004-03-29 BR BRPI0408990-1A patent/BRPI0408990A/pt not_active IP Right Cessation
- 2004-03-29 EA EA200501332A patent/EA009743B1/ru unknown
- 2004-03-29 JP JP2006506466A patent/JP3981398B1/ja not_active Expired - Fee Related
- 2004-03-29 MX MXPA05010621A patent/MXPA05010621A/es active IP Right Grant
- 2004-03-29 EP EP04724083A patent/EP1753731A2/en not_active Withdrawn
- 2004-03-29 GE GEAP20049005A patent/GEP20074255B/en unknown
- 2004-03-29 WO PCT/IB2004/001121 patent/WO2004087677A2/en active Application Filing
- 2004-03-29 UA UAA200508500A patent/UA81658C2/ru unknown
- 2004-03-29 RS YUP-2005/0732A patent/RS20050732A/sr unknown
- 2004-03-29 OA OA1200500271A patent/OA13113A/en unknown
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2005
- 2005-08-29 IS IS8006A patent/IS8006A/is unknown
- 2005-08-31 ZA ZA200506976A patent/ZA200506976B/en unknown
- 2005-09-27 CR CR8007A patent/CR8007A/es not_active Application Discontinuation
- 2005-10-03 MA MA28531A patent/MA27754A1/fr unknown
- 2005-10-03 EC EC2005006072A patent/ECSP056072A/es unknown
- 2005-10-03 TN TNP2005000250A patent/TNSN05250A1/fr unknown
- 2005-11-01 NO NO20055092A patent/NO20055092L/no not_active Application Discontinuation
Also Published As
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US20040242608A1 (en) | 2004-12-02 |
AP2005003403A0 (en) | 2005-12-31 |
AU2004226165A1 (en) | 2004-10-14 |
EA200501332A1 (ru) | 2006-06-30 |
ECSP056072A (es) | 2006-03-01 |
US7183287B2 (en) | 2007-02-27 |
CN1968937A (zh) | 2007-05-23 |
NZ542139A (en) | 2008-11-28 |
ZA200506976B (en) | 2006-10-25 |
JP3981398B1 (ja) | 2007-09-26 |
AU2004226165A2 (en) | 2004-10-14 |
MA27754A1 (fr) | 2006-02-01 |
CA2521081C (en) | 2010-09-07 |
AU2004226165C1 (en) | 2008-07-03 |
AU2004226165B2 (en) | 2007-11-08 |
WO2004087677A2 (en) | 2004-10-14 |
CA2521081A1 (en) | 2004-10-14 |
IS8006A (is) | 2005-08-29 |
MXPA05010621A (es) | 2005-11-23 |
EP1753731A2 (en) | 2007-02-21 |
JP2007528353A (ja) | 2007-10-11 |
TNSN05250A1 (fr) | 2007-07-10 |
KR20060006906A (ko) | 2006-01-20 |
EA009743B1 (ru) | 2008-04-28 |
CR8007A (es) | 2006-02-13 |
RS20050732A (en) | 2007-08-03 |
KR100776120B1 (ko) | 2007-11-16 |
NO20055092L (no) | 2005-11-01 |
BRPI0408990A (pt) | 2006-04-04 |
UA81658C2 (en) | 2008-01-25 |
WO2004087677A3 (en) | 2004-12-16 |
GEP20074255B (en) | 2007-12-10 |
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