JP2010513444A5 - - Google Patents
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- Publication number
- JP2010513444A5 JP2010513444A5 JP2009542220A JP2009542220A JP2010513444A5 JP 2010513444 A5 JP2010513444 A5 JP 2010513444A5 JP 2009542220 A JP2009542220 A JP 2009542220A JP 2009542220 A JP2009542220 A JP 2009542220A JP 2010513444 A5 JP2010513444 A5 JP 2010513444A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- ethyl
- alkyl
- dimethoxyphenyl
- alkoxy
- 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.)
- Granted
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- 229910052736 halogen Inorganic materials 0.000 claims 109
- 150000002367 halogens Chemical class 0.000 claims 109
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 107
- 125000001424 substituent group Chemical group 0.000 claims 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 71
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 70
- 229910052739 hydrogen Inorganic materials 0.000 claims 62
- 239000001257 hydrogen Substances 0.000 claims 62
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 55
- -1 cyano, hydroxyl Chemical group 0.000 claims 55
- 150000002431 hydrogen Chemical class 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 47
- 229910052757 nitrogen Inorganic materials 0.000 claims 39
- 125000000623 heterocyclic group Chemical group 0.000 claims 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- 125000003282 alkyl amino group Chemical group 0.000 claims 25
- 125000004414 alkyl thio group Chemical group 0.000 claims 25
- 125000004429 atom Chemical group 0.000 claims 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 18
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000003373 pyrazinyl group Chemical group 0.000 claims 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 11
- 125000001544 thienyl group Chemical group 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 9
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- PFZTXTPVKAGHPW-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(3,4-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CC(C)N(C)CC3)C=2)=C1 PFZTXTPVKAGHPW-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 2
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 2
- BYNNMWGWFIGTIC-LLVKDONJSA-N (2r)-3-naphthalen-1-yloxypropane-1,2-diol Chemical compound C1=CC=C2C(OC[C@H](O)CO)=CC=CC2=C1 BYNNMWGWFIGTIC-LLVKDONJSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 1
- LZZYDLADMOQZTD-UHFFFAOYSA-N 2-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC4CCCCN4CC3)=C2)=C1 LZZYDLADMOQZTD-UHFFFAOYSA-N 0.000 claims 1
- SAXDDBYCUJXAIQ-UHFFFAOYSA-N 2-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 SAXDDBYCUJXAIQ-UHFFFAOYSA-N 0.000 claims 1
- IDPLQWNTAFBGOW-UHFFFAOYSA-N 2-(4-cyclopropylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CCN(CC3)C3CC3)=C2)=C1 IDPLQWNTAFBGOW-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- NHSNMCZCQCZMKT-UHFFFAOYSA-N 4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4NCCCC4C3)=C2)=C1 NHSNMCZCQCZMKT-UHFFFAOYSA-N 0.000 claims 1
- XUNYGASTGARZMD-UHFFFAOYSA-N 4-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4CCCCN4CC3)=C2)=C1 XUNYGASTGARZMD-UHFFFAOYSA-N 0.000 claims 1
- PLAXUYJGONDQAU-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCNCCC3)=C2)=C1 PLAXUYJGONDQAU-UHFFFAOYSA-N 0.000 claims 1
- VQZLJZIEDTZTQJ-UHFFFAOYSA-N 4-(1-cyclopropylpiperidin-4-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C3CCN(CC3)C3CC3)=C2)=C1 VQZLJZIEDTZTQJ-UHFFFAOYSA-N 0.000 claims 1
- NPPNBNZVHZLBMR-UHFFFAOYSA-N 4-(2-aminopropyl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CC(C)N)=CC=3)C=2)=C1 NPPNBNZVHZLBMR-UHFFFAOYSA-N 0.000 claims 1
- AJRZAIWDKUDXTA-UHFFFAOYSA-N 4-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4CCCN4CC3)=C2)=C1 AJRZAIWDKUDXTA-UHFFFAOYSA-N 0.000 claims 1
- FILOJIFKRJXQCS-UHFFFAOYSA-N 4-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4CCCN4CC3)=C2)=C1 FILOJIFKRJXQCS-UHFFFAOYSA-N 0.000 claims 1
- CKNIRFFXNOGDAM-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C(C)=O)C=2)=C1 CKNIRFFXNOGDAM-UHFFFAOYSA-N 0.000 claims 1
- CPYWICDXAPUQNJ-UHFFFAOYSA-N 4-(4-cyclobutylpiperazin-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CCC3)=C2)=C1 CPYWICDXAPUQNJ-UHFFFAOYSA-N 0.000 claims 1
- LHCIFVUABPXLJF-UHFFFAOYSA-N 4-(4-cyclobutylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CCC3)C=2)=C1 LHCIFVUABPXLJF-UHFFFAOYSA-N 0.000 claims 1
- REPFWMXEYOBBGF-UHFFFAOYSA-N 4-(4-cyclopropyl-1,4-diazepan-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CCC3)C3CC3)=C2)=C1 REPFWMXEYOBBGF-UHFFFAOYSA-N 0.000 claims 1
- FICSDJQCXTVTCL-UHFFFAOYSA-N 4-(4-cyclopropylpiperazin-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CC3)=C2)=C1 FICSDJQCXTVTCL-UHFFFAOYSA-N 0.000 claims 1
- AAKMLYNRXVOJET-UHFFFAOYSA-N 4-(4-cyclopropylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CC3)C=2)=C1 AAKMLYNRXVOJET-UHFFFAOYSA-N 0.000 claims 1
- GPJKIUMNZAQZFH-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=CC=CC=3)C=2)C=C1 GPJKIUMNZAQZFH-UHFFFAOYSA-N 0.000 claims 1
- KNJZJTPWIMKMLS-UHFFFAOYSA-N 4-cyano-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C#N)=C2)=C1 KNJZJTPWIMKMLS-UHFFFAOYSA-N 0.000 claims 1
- RSLUCSKUCDYSQI-UHFFFAOYSA-N 4-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzene-1,4-dicarboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C(N)=O)=C2)=C1 RSLUCSKUCDYSQI-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- DTNXPDAEHCDVIB-UHFFFAOYSA-N 5-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCCN4CC3)=C2)=C1 DTNXPDAEHCDVIB-UHFFFAOYSA-N 0.000 claims 1
- WHUJVYOGWOQXJA-UHFFFAOYSA-N 5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 WHUJVYOGWOQXJA-UHFFFAOYSA-N 0.000 claims 1
- AABBJGRKPVKZBZ-UHFFFAOYSA-N 5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 AABBJGRKPVKZBZ-UHFFFAOYSA-N 0.000 claims 1
- CEIPMDRYPQMWNG-UHFFFAOYSA-N 5-[3-(diethylamino)pyrrolidin-1-yl]-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound C1C(N(CC)CC)CCN1C1=CN=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 CEIPMDRYPQMWNG-UHFFFAOYSA-N 0.000 claims 1
- HRCNSDLFNYOODP-UHFFFAOYSA-N 5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(=CC=3)C(O)=O)=C2)=C1 HRCNSDLFNYOODP-UHFFFAOYSA-N 0.000 claims 1
- DOVOTUJDSHELKJ-UHFFFAOYSA-N 6-chloro-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(Cl)=CC=3)=C2)=C1 DOVOTUJDSHELKJ-UHFFFAOYSA-N 0.000 claims 1
- VRQMAABPASPXMW-HDICACEKSA-N AZD4547 Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3C[C@@H](C)N[C@@H](C)C3)C=2)=C1 VRQMAABPASPXMW-HDICACEKSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 108091008794 FGF receptors Proteins 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- LBDQPXFVZSAJPM-UHFFFAOYSA-N ethyl 5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 LBDQPXFVZSAJPM-UHFFFAOYSA-N 0.000 claims 1
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- NJMBQRNWBHNVOZ-UHFFFAOYSA-N methyl 5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 NJMBQRNWBHNVOZ-UHFFFAOYSA-N 0.000 claims 1
- YUVSEEWMRSXTRL-UHFFFAOYSA-N methyl 6-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 YUVSEEWMRSXTRL-UHFFFAOYSA-N 0.000 claims 1
- KABBUICSDDSZHY-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(COC=2NN=C(NC(=O)C=3C=NC(=NC=3)N3CCN(C)CC3)C=2)=C1 KABBUICSDDSZHY-UHFFFAOYSA-N 0.000 claims 1
- BXUCLDIBYXBAKH-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-3-piperazin-1-ylbenzamide Chemical compound COC1=CC(OC)=CC(COC=2NN=C(NC(=O)C=3C=C(C=CC=3)N3CCNCC3)C=2)=C1 BXUCLDIBYXBAKH-UHFFFAOYSA-N 0.000 claims 1
- APPRGXHIUOWFLJ-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(1-methylpiperidin-4-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)C3CCN(C)CC3)=C2)=C1 APPRGXHIUOWFLJ-UHFFFAOYSA-N 0.000 claims 1
- KZTLOKUXUKISRM-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(3,3-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC(C)(C)NCC3)=C2)=C1 KZTLOKUXUKISRM-UHFFFAOYSA-N 0.000 claims 1
- DFDRSTKZIRHZJZ-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(3,4-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC(C)N(C)CC3)=C2)=C1 DFDRSTKZIRHZJZ-UHFFFAOYSA-N 0.000 claims 1
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- IHTGUNPCPCXBLL-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(3,4-dimethylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3CC(C)N(C)CC3)=C2)=C1 IHTGUNPCPCXBLL-UHFFFAOYSA-N 0.000 claims 1
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- PQOAVCZIWSDZRF-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(4-methylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3CCN(C)CC3)=C2)=C1 PQOAVCZIWSDZRF-UHFFFAOYSA-N 0.000 claims 1
- BZYIETPSKLUOBV-IYBDPMFKSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3C[C@@H](C)N(C)[C@@H](C)C3)=C2)=C1 BZYIETPSKLUOBV-IYBDPMFKSA-N 0.000 claims 1
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- FVNRGESZWOWIOE-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(3,4-dimethylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC(C)N(C)CC3)=C2)=C1 FVNRGESZWOWIOE-UHFFFAOYSA-N 0.000 claims 1
- CZXNOIODNKWIMD-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(4-ethyl-1,4-diazepan-1-yl)pyrimidine-5-carboxamide Chemical compound C1CN(CC)CCCN1C1=NC=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 CZXNOIODNKWIMD-UHFFFAOYSA-N 0.000 claims 1
- FAHBNVACFBFOJF-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(4-ethyl-3-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound C1C(C)N(CC)CCN1C1=NC=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 FAHBNVACFBFOJF-UHFFFAOYSA-N 0.000 claims 1
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- MJXRPIUNMFYPIO-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC(=O)N(C)CC3)=C2)=C1 MJXRPIUNMFYPIO-UHFFFAOYSA-N 0.000 claims 1
- SBOMLRJHYLXHOT-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CCN(C)CC3)=C2)=C1 SBOMLRJHYLXHOT-UHFFFAOYSA-N 0.000 claims 1
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- VHIJSBLWIJRAQN-CALCHBBNSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3C[C@@H](C)N(C)[C@@H](C)C3)=C2)=C1 VHIJSBLWIJRAQN-CALCHBBNSA-N 0.000 claims 1
- NSMXFXVYCUXPCS-JOCHJYFZSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-[(3s)-3-propan-2-ylpiperazin-1-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3C[C@@H](NCC3)C(C)C)=C2)=C1 NSMXFXVYCUXPCS-JOCHJYFZSA-N 0.000 claims 1
- NBGAVLHIQQGGBW-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-[3-(methoxymethyl)piperazin-1-yl]pyrimidine-5-carboxamide Chemical compound C1CNC(COC)CN1C1=NC=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 NBGAVLHIQQGGBW-UHFFFAOYSA-N 0.000 claims 1
- RZDKJOIXLSDHEY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-methoxybenzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C(=CC=CC=3)OC)C=2)=C1 RZDKJOIXLSDHEY-UHFFFAOYSA-N 0.000 claims 1
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- BVJBIYYANCOBPH-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(1-ethylpiperidin-4-yl)benzamide Chemical compound C1CN(CC)CCC1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=C1 BVJBIYYANCOBPH-UHFFFAOYSA-N 0.000 claims 1
- QEAUOXZTRVBQEI-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(1-methylpiperidin-4-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)C3CCN(C)CC3)C=2)=C1 QEAUOXZTRVBQEI-UHFFFAOYSA-N 0.000 claims 1
- KJHGWDAUJWJTCZ-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(1-prop-2-enylpiperidin-4-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C3CCN(CC=C)CC3)=C2)=C1 KJHGWDAUJWJTCZ-UHFFFAOYSA-N 0.000 claims 1
- LJZRBNAGMCJTIR-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(1-prop-2-ynylpiperidin-4-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C3CCN(CC#C)CC3)=C2)=C1 LJZRBNAGMCJTIR-UHFFFAOYSA-N 0.000 claims 1
- DCXJUCGEYZYQKT-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(2-ethoxyethoxy)benzamide Chemical compound C1=CC(OCCOCC)=CC=C1C(=O)NC1=NNC(CCC=2C=C(OC)C=C(OC)C=2)=C1 DCXJUCGEYZYQKT-UHFFFAOYSA-N 0.000 claims 1
- DPYYBBUVHIZEPV-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(2-hydroxyethoxy)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(OCCO)=CC=3)C=2)=C1 DPYYBBUVHIZEPV-UHFFFAOYSA-N 0.000 claims 1
- OLOIRPDQVXBXAY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(2-morpholin-4-ylethyl)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CCN4CCOCC4)=CC=3)C=2)=C1 OLOIRPDQVXBXAY-UHFFFAOYSA-N 0.000 claims 1
- OFPZHPFNAAUZHU-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(3,3-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC(C)(C)NCC3)=C2)=C1 OFPZHPFNAAUZHU-UHFFFAOYSA-N 0.000 claims 1
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- VRQMAABPASPXMW-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC(C)NC(C)C3)=C2)=C1 VRQMAABPASPXMW-UHFFFAOYSA-N 0.000 claims 1
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- UJJSGJULFHMHMJ-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-ethylpiperazin-1-yl)benzamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=C1 UJJSGJULFHMHMJ-UHFFFAOYSA-N 0.000 claims 1
- WTLALQRLHBXTHM-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-methyl-1,4-diazepan-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CCC3)=C2)=C1 WTLALQRLHBXTHM-UHFFFAOYSA-N 0.000 claims 1
- KTFGJFQSPXGZHE-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazine-1-carbonyl)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)C(=O)N3CCN(C)CC3)C=2)=C1 KTFGJFQSPXGZHE-UHFFFAOYSA-N 0.000 claims 1
- WVIFYEUDNSJDCL-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-prop-2-enyl-1,4-diazepan-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CC=C)CCC3)=C2)=C1 WVIFYEUDNSJDCL-UHFFFAOYSA-N 0.000 claims 1
- KJPXHCOJCLZPHO-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-propan-2-yl-1,4-diazepan-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CCC3)C(C)C)=C2)=C1 KJPXHCOJCLZPHO-UHFFFAOYSA-N 0.000 claims 1
- OLTKVTPQMIIGOU-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-propan-2-ylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C(C)C)C=2)=C1 OLTKVTPQMIIGOU-UHFFFAOYSA-N 0.000 claims 1
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- BPELTTMGJQPXIY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[(3-fluoropiperidin-1-yl)methyl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CN4CC(F)CCC4)=CC=3)C=2)=C1 BPELTTMGJQPXIY-UHFFFAOYSA-N 0.000 claims 1
- WCSHYWQDZXNEEQ-KDURUIRLSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[(3s,5r)-3,4,5-trimethylpiperazin-1-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3C[C@@H](C)N(C)[C@@H](C)C3)=C2)=C1 WCSHYWQDZXNEEQ-KDURUIRLSA-N 0.000 claims 1
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- SRVZIPFKDSFEGJ-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[(dimethylamino)methyl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CN(C)C)=CC=3)C=2)=C1 SRVZIPFKDSFEGJ-UHFFFAOYSA-N 0.000 claims 1
- UTGYYSGHKXUZKG-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[1-(2-methoxyethyl)piperidin-4-yl]benzamide Chemical compound C1CN(CCOC)CCC1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=C1 UTGYYSGHKXUZKG-UHFFFAOYSA-N 0.000 claims 1
- CCFZQBPNVWLORY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[4-(1-hydroxypropan-2-yl)piperazin-1-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C(C)CO)=C2)=C1 CCFZQBPNVWLORY-UHFFFAOYSA-N 0.000 claims 1
- MJPBGKOMAIKXKT-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[4-(2-hydroxyethyl)piperazin-1-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CCO)CC3)C=2)=C1 MJPBGKOMAIKXKT-UHFFFAOYSA-N 0.000 claims 1
- YRUSWYQIJJOVDF-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[[methyl(oxolan-2-ylmethyl)amino]methyl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CN(C)CC4OCCC4)=CC=3)C=2)=C1 YRUSWYQIJJOVDF-UHFFFAOYSA-N 0.000 claims 1
- UWEOHTNKAYJXLK-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-fluorobenzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(F)=CC=3)=C2)=C1 UWEOHTNKAYJXLK-UHFFFAOYSA-N 0.000 claims 1
- XCNZLIDTXJNYHX-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-iodobenzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(I)=CC=3)=C2)=C1 XCNZLIDTXJNYHX-UHFFFAOYSA-N 0.000 claims 1
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- LENFIJCVVDHYLK-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-piperazin-1-ylbenzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCNCC3)C=2)=C1 LENFIJCVVDHYLK-UHFFFAOYSA-N 0.000 claims 1
- QFFQLQYWNFGCKQ-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(3,3-dimethylpiperazin-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC(C)(C)NCC3)=C2)=C1 QFFQLQYWNFGCKQ-UHFFFAOYSA-N 0.000 claims 1
- JFUSILMVWGCWLX-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(3,4-dimethylpiperazin-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC(C)N(C)CC3)=C2)=C1 JFUSILMVWGCWLX-UHFFFAOYSA-N 0.000 claims 1
- ZNGRBVZIZAFWNU-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(4-ethyl-1,4-diazepan-1-yl)pyrazine-2-carboxamide Chemical compound C1CN(CC)CCCN1C1=CN=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 ZNGRBVZIZAFWNU-UHFFFAOYSA-N 0.000 claims 1
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| BRPI0815591B8 (pt) | 2007-08-22 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, e, uso de um composto. |
| GB0720038D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New compounds |
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