CA2465247C - Benzimidazoles et analogues et leur utilisation comme inhibiteurs de proteines kinases - Google Patents
Benzimidazoles et analogues et leur utilisation comme inhibiteurs de proteines kinases Download PDFInfo
- Publication number
- CA2465247C CA2465247C CA2465247A CA2465247A CA2465247C CA 2465247 C CA2465247 C CA 2465247C CA 2465247 A CA2465247 A CA 2465247A CA 2465247 A CA2465247 A CA 2465247A CA 2465247 C CA2465247 C CA 2465247C
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- CA
- Canada
- Prior art keywords
- benzoimidazol
- pyrazol
- carboxylic acid
- dimethyl
- amide
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title claims description 19
- 102000001253 Protein Kinase Human genes 0.000 title description 14
- 108060006633 protein kinase Proteins 0.000 title description 14
- 150000001556 benzimidazoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 537
- 229940002612 prodrug Drugs 0.000 claims abstract description 103
- 239000000651 prodrug Substances 0.000 claims abstract description 103
- 150000003839 salts Chemical class 0.000 claims abstract description 97
- 239000012453 solvate Substances 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 20
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- -1 cyclic amine Chemical class 0.000 claims description 294
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 198
- 125000000217 alkyl group Chemical group 0.000 claims description 181
- 150000003254 radicals Chemical class 0.000 claims description 128
- 125000003118 aryl group Chemical group 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 114
- 239000001257 hydrogen Substances 0.000 claims description 113
- 229910052757 nitrogen Inorganic materials 0.000 claims description 101
- 150000001204 N-oxides Chemical class 0.000 claims description 99
- 125000001072 heteroaryl group Chemical group 0.000 claims description 94
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 91
- 239000002253 acid Substances 0.000 claims description 85
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 83
- 125000005843 halogen group Chemical group 0.000 claims description 75
- 125000006519 CCH3 Chemical group 0.000 claims description 73
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 49
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 49
- AMOPFYWXZYVTHJ-UHFFFAOYSA-N 2-(1H-indazol-3-yl)-3H-benzimidazole-5-carboxylic acid Chemical compound C1=CC=C2C(C=3NC4=CC=C(C=C4N=3)C(=O)O)=NNC2=C1 AMOPFYWXZYVTHJ-UHFFFAOYSA-N 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000006414 CCl Chemical group ClC* 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
- 125000006416 CBr Chemical group BrC* 0.000 claims description 34
- 150000001408 amides Chemical class 0.000 claims description 34
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 34
- 239000011707 mineral Substances 0.000 claims description 34
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 30
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
- 206010028980 Neoplasm Diseases 0.000 claims description 29
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- 125000006415 CF Chemical group FC* 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical group 0.000 claims description 25
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 23
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 19
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
- 150000007524 organic acids Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000007522 mineralic acids Chemical class 0.000 claims description 17
- TUMYIMPCCZYJBR-UHFFFAOYSA-N 5-(5,6-dimethyl-1H-benzimidazol-2-yl)-N-propan-2-yl-1H-pyrazole-4-carboxamide Chemical compound CC(C)NC(=O)C1=CNN=C1C1=NC2=CC(C)=C(C)C=C2N1 TUMYIMPCCZYJBR-UHFFFAOYSA-N 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000004442 acylamino group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- ZJWSUBBYGLYXJW-UHFFFAOYSA-N 2-(1H-indazol-3-yl)-N-propan-2-yl-3H-benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(C=3NC4=CC=C(C=C4N=3)C(=O)NC(C)C)=NNC2=C1 ZJWSUBBYGLYXJW-UHFFFAOYSA-N 0.000 claims description 12
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 12
- BDHQHIDGWYHKRI-UHFFFAOYSA-N N-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1NC(=O)N1CCCCC1 BDHQHIDGWYHKRI-UHFFFAOYSA-N 0.000 claims description 12
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 12
- 206010040047 Sepsis Diseases 0.000 claims description 12
- 206010040070 Septic Shock Diseases 0.000 claims description 12
- 206010003246 arthritis Diseases 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 12
- 230000006870 function Effects 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- VLGWDXACUDRERL-UHFFFAOYSA-N 2-(1H-indazol-3-yl)-N-methyl-3H-benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(C=3NC4=CC=C(C=C4N=3)C(=O)NC)=NNC2=C1 VLGWDXACUDRERL-UHFFFAOYSA-N 0.000 claims description 11
- HIINOAIHCLLWSU-UHFFFAOYSA-N 5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-amine Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1N HIINOAIHCLLWSU-UHFFFAOYSA-N 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 11
- HBJQMWYZPPEODA-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]urea Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1NC(=O)NCC1CC1 HBJQMWYZPPEODA-UHFFFAOYSA-N 0.000 claims description 10
- LUPAWELXHKXOKC-UHFFFAOYSA-N 1-tert-butyl-3-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]urea Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1NC(=O)NC(C)(C)C LUPAWELXHKXOKC-UHFFFAOYSA-N 0.000 claims description 10
- QCMGTTCZMJLKGF-UHFFFAOYSA-N 3-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(C)=C(C)C=C2N1 QCMGTTCZMJLKGF-UHFFFAOYSA-N 0.000 claims description 10
- FYGVGYRSIRCCSW-UHFFFAOYSA-N 5-(5,6-dimethyl-1H-benzimidazol-2-yl)-N-(2-methylpropyl)-1H-pyrazole-4-carboxamide Chemical compound CC(C)CNC(=O)C1=CNN=C1C1=NC2=CC(C)=C(C)C=C2N1 FYGVGYRSIRCCSW-UHFFFAOYSA-N 0.000 claims description 10
- QHMISEVHTRPSBS-UHFFFAOYSA-N 5-(5,6-dimethyl-1H-benzimidazol-2-yl)-N-(oxan-4-yl)-1H-pyrazole-4-carboxamide Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1C(=O)NC1CCOCC1 QHMISEVHTRPSBS-UHFFFAOYSA-N 0.000 claims description 10
- 101001050476 Homo sapiens Tyrosine-protein kinase ITK/TSK Proteins 0.000 claims description 10
- CADXAOGQUUFNSV-UHFFFAOYSA-N N-[5-(3,5,6,7-tetrahydrocyclopenta[f]benzimidazol-2-yl)-1H-pyrazol-4-yl]cyclopropanecarboxamide Chemical compound C=1NN=C(C=2NC3=CC=4CCCC=4C=C3N=2)C=1NC(=O)C1CC1 CADXAOGQUUFNSV-UHFFFAOYSA-N 0.000 claims description 10
- DCNULZAURHKTQZ-UHFFFAOYSA-N N-[5-(5-ethyl-6-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound N1C=2C=C(C)C(CC)=CC=2N=C1C1=NNC=C1NC(=O)N1CCCCC1 DCNULZAURHKTQZ-UHFFFAOYSA-N 0.000 claims description 10
- UMTCMYQTQNLQQD-UHFFFAOYSA-N N-[5-(5-fluoro-6-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound N=1C=2C=C(F)C(C)=CC=2NC=1C1=NNC=C1NC(=O)N1CCCCC1 UMTCMYQTQNLQQD-UHFFFAOYSA-N 0.000 claims description 10
- GIKAUWKPIVJVMD-UHFFFAOYSA-N N-[5-(6-methoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound N=1C2=CC(OC)=CC=C2NC=1C1=NNC=C1NC(=O)N1CCCCC1 GIKAUWKPIVJVMD-UHFFFAOYSA-N 0.000 claims description 10
- BHSKNPIBWMRTJO-UHFFFAOYSA-N N-[5-[6-(difluoromethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound N=1C2=CC(OC(F)F)=CC=C2NC=1C1=NNC=C1NC(=O)N1CCCCC1 BHSKNPIBWMRTJO-UHFFFAOYSA-N 0.000 claims description 10
- 102100023345 Tyrosine-protein kinase ITK/TSK Human genes 0.000 claims description 10
- 230000001668 ameliorated effect Effects 0.000 claims description 10
- 230000033115 angiogenesis Effects 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 10
- 229940126601 medicinal product Drugs 0.000 claims description 10
- UYUKDGXSGBSMAQ-UHFFFAOYSA-N 1,1-dimethyl-3-[5-(1,5,6,7-tetrahydro-s-indacen-2-yl)-1h-pyrazol-4-yl]urea Chemical compound CN(C)C(=O)NC1=CNN=C1C(CC1=C2)=CC1=CC1=C2CCC1 UYUKDGXSGBSMAQ-UHFFFAOYSA-N 0.000 claims description 9
- KRVZUBAZHMSAAJ-UHFFFAOYSA-N 1-cyclopropyl-3-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]urea Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1NC(=O)NC1CC1 KRVZUBAZHMSAAJ-UHFFFAOYSA-N 0.000 claims description 9
- ZEAWEWOVZAWJHI-UHFFFAOYSA-N 1-cyclopropyl-3-[5-(5-ethyl-6-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]urea Chemical compound N1C=2C=C(C)C(CC)=CC=2N=C1C1=NNC=C1NC(=O)NC1CC1 ZEAWEWOVZAWJHI-UHFFFAOYSA-N 0.000 claims description 9
- RXOZHGAHKKRFRF-UHFFFAOYSA-N 2-(1H-indazol-3-yl)-N-phenyl-3H-benzimidazole-5-carboxamide Chemical compound C=1C=C2NC(C=3C4=CC=CC=C4NN=3)=NC2=CC=1C(=O)NC1=CC=CC=C1 RXOZHGAHKKRFRF-UHFFFAOYSA-N 0.000 claims description 9
- YKSOVXFYHNDXGI-UHFFFAOYSA-N 3-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CNN=C1C1=NC2=CC(C)=C(C)C=C2N1 YKSOVXFYHNDXGI-UHFFFAOYSA-N 0.000 claims description 9
- XVPBQHKGZGFXNV-UHFFFAOYSA-N 3-[5-[6-(difluoromethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(OC(F)F)=CC=C2N1 XVPBQHKGZGFXNV-UHFFFAOYSA-N 0.000 claims description 9
- PIQGQTLRAVEOAX-UHFFFAOYSA-N 5-(5-methoxy-6-methyl-1H-benzimidazol-2-yl)-N-propan-2-yl-1H-pyrazole-4-carboxamide Chemical compound N1C=2C=C(C)C(OC)=CC=2N=C1C1=NNC=C1C(=O)NC(C)C PIQGQTLRAVEOAX-UHFFFAOYSA-N 0.000 claims description 9
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- JEIARJZYPBXYDA-UHFFFAOYSA-N N-cyclopropyl-5-(3,5,6,7-tetrahydrocyclopenta[f]benzimidazol-2-yl)-1H-pyrazole-4-carboxamide Chemical compound C=1NN=C(C=2NC3=CC=4CCCC=4C=C3N=2)C=1C(=O)NC1CC1 JEIARJZYPBXYDA-UHFFFAOYSA-N 0.000 claims description 9
- WXOXDSOEEYDPKW-UHFFFAOYSA-N N-ethyl-2-(1H-indazol-3-yl)-3H-benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(C=3NC4=CC=C(C=C4N=3)C(=O)NCC)=NNC2=C1 WXOXDSOEEYDPKW-UHFFFAOYSA-N 0.000 claims description 9
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 125000001475 halogen functional group Chemical group 0.000 claims description 9
- LBTKRCNOZTXVHD-UHFFFAOYSA-N methyl 2-(1H-indazol-3-yl)-3H-benzimidazole-5-carboxylate Chemical compound C1=CC=C2C(C=3NC4=CC=C(C=C4N=3)C(=O)OC)=NNC2=C1 LBTKRCNOZTXVHD-UHFFFAOYSA-N 0.000 claims description 9
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- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- WLAMNBDJUVNPJU-BYPYZUCNSA-N (S)-2-methylbutyric acid Chemical compound CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 claims description 8
- RGPAZRQVZSELHY-UHFFFAOYSA-N 1-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NC1=CNN=C1C1=NC2=CC(C)=C(C)C=C2N1 RGPAZRQVZSELHY-UHFFFAOYSA-N 0.000 claims description 8
- XMAMBHAPBFNGJB-UHFFFAOYSA-N 1-[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-3-phenylurea Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NNC=C1NC(=O)NC1=CC=CC=C1 XMAMBHAPBFNGJB-UHFFFAOYSA-N 0.000 claims description 8
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- KCPLPTVRRQMNFZ-UHFFFAOYSA-N 1-[5-(5-fluoro-6-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-3-methylurea Chemical compound CNC(=O)NC1=CNN=C1C1=NC2=CC(F)=C(C)C=C2N1 KCPLPTVRRQMNFZ-UHFFFAOYSA-N 0.000 claims description 8
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- NFSHSHTXBHQFCV-UHFFFAOYSA-N 4-methyl-N-[5-(3,5,6,7-tetrahydrocyclopenta[f]benzimidazol-2-yl)-1H-pyrazol-4-yl]piperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CNN=C1C(NC1=C2)=NC1=CC1=C2CCC1 NFSHSHTXBHQFCV-UHFFFAOYSA-N 0.000 claims description 8
- BTEJQCHINNWUPE-UHFFFAOYSA-N 5-(5,6-dimethyl-1H-benzimidazol-2-yl)-N-(2-methoxyethyl)-1H-pyrazole-4-carboxamide Chemical compound COCCNC(=O)C1=CNN=C1C1=NC2=CC(C)=C(C)C=C2N1 BTEJQCHINNWUPE-UHFFFAOYSA-N 0.000 claims description 8
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- NUKRSHCGWAXYQS-UHFFFAOYSA-N 5-(6-ethyl-5-methoxy-1H-benzimidazol-2-yl)-N-propan-2-yl-1H-pyrazole-4-carboxamide Chemical compound N=1C=2C=C(OC)C(CC)=CC=2NC=1C1=NNC=C1C(=O)NC(C)C NUKRSHCGWAXYQS-UHFFFAOYSA-N 0.000 claims description 8
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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Abstract
L'invention concerne des composés physiologiquement actifs représentés par la formule générale (Ix), des compositions qui renferment ces composés, leurs promédicaments, des sels ou solvates de ces composés acceptables sur le plan pharmaceutique et leurs promédicaments, ainsi que de nouveaux médicaments entrant dans le champ d'application de la formule (Ix) et des procédés pour leur préparation. Ces composés et compositions possèdent des propriétés pharmaceutiques intéressantes, notamment la capacité d'inhiber les kinases.
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0113868A FR2831537B1 (fr) | 2001-10-26 | 2001-10-26 | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation |
| FR01/13868 | 2001-10-26 | ||
| GB0206895A GB0206895D0 (en) | 2002-03-22 | 2002-03-22 | Chemical compounds |
| GB0206895.5 | 2002-03-22 | ||
| GB0206893A GB0206893D0 (en) | 2002-03-22 | 2002-03-22 | Chemical compounds |
| GB0206893.0 | 2002-03-22 | ||
| US39506002P | 2002-07-11 | 2002-07-11 | |
| US39515102P | 2002-07-11 | 2002-07-11 | |
| US60/395,151 | 2002-07-11 | ||
| US60/395,060 | 2002-07-11 | ||
| PCT/GB2002/004763 WO2003035065A1 (fr) | 2001-10-26 | 2002-10-24 | Benzimidazoles et analogues et leur utilisation comme inhibiteurs de proteines kinases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2465247A1 CA2465247A1 (fr) | 2003-05-01 |
| CA2465247C true CA2465247C (fr) | 2010-05-18 |
Family
ID=27515325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2465247A Expired - Fee Related CA2465247C (fr) | 2001-10-26 | 2002-10-24 | Benzimidazoles et analogues et leur utilisation comme inhibiteurs de proteines kinases |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1441725A1 (fr) |
| JP (1) | JP5039268B2 (fr) |
| AU (1) | AU2002334217B2 (fr) |
| BR (1) | BR0213562A (fr) |
| CA (1) | CA2465247C (fr) |
| IL (1) | IL161576A0 (fr) |
| MX (1) | MXPA04003954A (fr) |
| UY (1) | UY27516A1 (fr) |
| WO (1) | WO2003035065A1 (fr) |
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| DE2130029A1 (de) * | 1971-06-18 | 1972-12-21 | Bayer Ag | Verfahren zur Herstellung von 2-[Pyrazolyl-(1)]-benzimidazolen |
| DE2130030A1 (de) * | 1971-06-18 | 1972-12-21 | Bayer Ag | Fungizide und bakterizide Mittel |
| BE793501A (fr) * | 1971-12-31 | 1973-06-29 | Ciba Geigy | Composes heterocycliques et produits phytopharmaceutiques qui en contiennent |
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| US6136831A (en) * | 1997-04-11 | 2000-10-24 | Grelan Pharmaceutical Co., Ltd. | Pyrazole derivatives and COX inhibitors containing them |
| PL206826B1 (pl) * | 1999-06-23 | 2010-09-30 | Sanofi Aventis Deutschland | Podstawione benzimidazole |
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| YU54202A (sh) * | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| US7064215B2 (en) * | 2001-07-03 | 2006-06-20 | Chiron Corporation | Indazole benzimidazole compounds |
-
2002
- 2002-10-24 CA CA2465247A patent/CA2465247C/fr not_active Expired - Fee Related
- 2002-10-24 MX MXPA04003954A patent/MXPA04003954A/es active IP Right Grant
- 2002-10-24 JP JP2003537632A patent/JP5039268B2/ja not_active Expired - Fee Related
- 2002-10-24 WO PCT/GB2002/004763 patent/WO2003035065A1/fr not_active Ceased
- 2002-10-24 BR BR0213562-0A patent/BR0213562A/pt not_active Application Discontinuation
- 2002-10-24 EP EP02801954A patent/EP1441725A1/fr not_active Withdrawn
- 2002-10-24 IL IL16157602A patent/IL161576A0/xx unknown
- 2002-10-24 AU AU2002334217A patent/AU2002334217B2/en not_active Ceased
- 2002-10-25 UY UY27516A patent/UY27516A1/es unknown
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| Publication number | Publication date |
|---|---|
| WO2003035065A1 (fr) | 2003-05-01 |
| JP2005509633A (ja) | 2005-04-14 |
| JP5039268B2 (ja) | 2012-10-03 |
| UY27516A1 (es) | 2003-04-30 |
| IL161576A0 (en) | 2004-09-27 |
| CA2465247A1 (fr) | 2003-05-01 |
| EP1441725A1 (fr) | 2004-08-04 |
| MXPA04003954A (es) | 2004-11-29 |
| BR0213562A (pt) | 2004-08-31 |
| AU2002334217B2 (en) | 2008-07-03 |
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