JP5148499B2 - Ｖｅｇｆ受容体およびｈｇｆ受容体シグナル伝達の阻害剤 - Google Patents

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Publication number

JP5148499B2

JP5148499B2 JP2008537239A JP2008537239A JP5148499B2 JP 5148499 B2 JP5148499 B2 JP 5148499B2 JP 2008537239 A JP2008537239 A JP 2008537239A JP 2008537239 A JP2008537239 A JP 2008537239A JP 5148499 B2 JP5148499 B2 JP 5148499B2

Authority

JP

Japan

Prior art keywords

thieno

pyridin

yloxy

phenyl

imidazol

Prior art date

2005-05-20

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.)

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• 230000011664 signaling Effects 0.000 title description 32
• 239000003112 inhibitor Substances 0.000 title description 19
• 108091008603 HGF receptors Proteins 0.000 title description 17
• 108091008605 VEGF receptors Proteins 0.000 title description 15
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 title description 13
• 102000027430 HGF receptors Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 341
• 125000000217 alkyl group Chemical group 0.000 claims description 252
• 125000000623 heterocyclic group Chemical group 0.000 claims description 251
• -1 wherein T 2 are -OH Chemical group 0.000 claims description 194
• 239000000203 mixture Substances 0.000 claims description 142
• 125000003118 aryl group Chemical group 0.000 claims description 131
• 125000001072 heteroaryl group Chemical group 0.000 claims description 105
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 103
• 125000001424 substituent group Chemical group 0.000 claims description 102
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 91
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 86
• 125000005843 halogen group Chemical group 0.000 claims description 70
• 150000002367 halogens Chemical class 0.000 claims description 65
• 229910052736 halogen Inorganic materials 0.000 claims description 60
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 60
• 229920006395 saturated elastomer Polymers 0.000 claims description 58
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
• 229910052757 nitrogen Inorganic materials 0.000 claims description 52
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
• 125000004429 atom Chemical group 0.000 claims description 30
• YUZHVIIXJVNLKI-UHFFFAOYSA-N n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(N)=O YUZHVIIXJVNLKI-UHFFFAOYSA-N 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 21
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 19
• WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 18
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• GXDLBQIVQXLQCY-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1SC(C=1N(C=CN=1)C)=C2 GXDLBQIVQXLQCY-UHFFFAOYSA-N 0.000 claims description 16
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 15
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 15
• KNCCWVJEKOKTHK-UHFFFAOYSA-N n'-(2-fluorophenyl)propanediamide Chemical compound NC(=O)CC(=O)NC1=CC=CC=C1F KNCCWVJEKOKTHK-UHFFFAOYSA-N 0.000 claims description 15
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
• 150000001540 azides Chemical class 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 229940124597 therapeutic agent Drugs 0.000 claims description 11
• 125000002883 imidazolyl group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• KFKZJWJMJDRSEI-UHFFFAOYSA-N n'-[3-fluoro-4-(2-pyridin-4-ylthieno[3,2-b]pyridin-7-yl)oxyphenyl]-n-phenylpropanediamide Chemical compound C=1C=C(OC=2C=3SC(=CC=3N=CC=2)C=2C=CN=CC=2)C(F)=CC=1NC(=O)CC(=O)NC1=CC=CC=C1 KFKZJWJMJDRSEI-UHFFFAOYSA-N 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• FPLKZXIEKWJNHU-UHFFFAOYSA-N n'-(2-fluorophenyl)-n-[3-fluoro-4-[2-(1-propylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]propanediamide Chemical compound CCCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)NC=5C(=CC=CC=5)F)=CC=4)F)C=CN=C3C=2)=C1 FPLKZXIEKWJNHU-UHFFFAOYSA-N 0.000 claims description 6
• NYLRLDMHMVCHGD-UHFFFAOYSA-N n'-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-methyl-n-phenylpropanediamide Chemical compound C=1C=C(OC=2C=3SC(=CC=3N=CC=2)C=2N(C=CN=2)C)C(F)=CC=1NC(=O)C(C)C(=O)NC1=CC=CC=C1 NYLRLDMHMVCHGD-UHFFFAOYSA-N 0.000 claims description 6
• ZITWRUGKKFBWMI-UHFFFAOYSA-N n'-[3-fluoro-4-[2-[1-(2-hydroxyethyl)imidazol-4-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n-phenylpropanediamide Chemical compound OCCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)NC=5C=CC=CC=5)=CC=4)F)C=CN=C3C=2)=C1 ZITWRUGKKFBWMI-UHFFFAOYSA-N 0.000 claims description 6
• KRKOODRHCFGODQ-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-methyl-n'-phenylpropanediamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CC(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C KRKOODRHCFGODQ-UHFFFAOYSA-N 0.000 claims description 6
• QVXKBKJWHSYACD-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1h-imidazol-5-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1SC(C=1N=CNC=1)=C2 QVXKBKJWHSYACD-UHFFFAOYSA-N 0.000 claims description 6
• FUERECUWXYQOAO-UHFFFAOYSA-N n-[3-fluoro-4-[2-[1-(methoxymethyl)imidazol-4-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)NC=5C(=CC=CC=5)OC)=CC=4)F)C=CN=C3C=2)=C1 FUERECUWXYQOAO-UHFFFAOYSA-N 0.000 claims description 6
• FTQDPPZNHCWPCM-UHFFFAOYSA-N n-[3-fluoro-4-[2-[1-[2-(methylamino)ethyl]imidazol-4-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound CNCCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)NC=5C(=CC=CC=5)OC)=CC=4)F)C=CN=C3C=2)=C1 FTQDPPZNHCWPCM-UHFFFAOYSA-N 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• IGLPRAIGRXDXJI-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound CN1C=NC(C=2SC3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC(F)=CC=4)F)C=CN=C3C=2)=C1 IGLPRAIGRXDXJI-UHFFFAOYSA-N 0.000 claims description 5
• GJHSFGNZPLCXEH-UHFFFAOYSA-N 1-n'-[4-[2-(1-ethylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-1-n'-(2-methoxyphenyl)cyclopropane-1,1-dicarboxamide Chemical compound CCN1C=NC(C=2SC3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C(=CC=CC=4)OC)F)C=CN=C3C=2)=C1 GJHSFGNZPLCXEH-UHFFFAOYSA-N 0.000 claims description 5
• AOBZSQUYDRZVHW-UHFFFAOYSA-N 3-(2,3-dihydroindol-1-yl)-n-[4-[2-(1-ethylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-3-oxopropanamide Chemical compound CCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)N5C6=CC=CC=C6CC5)=CC=4)F)C=CN=C3C=2)=C1 AOBZSQUYDRZVHW-UHFFFAOYSA-N 0.000 claims description 5
• OUAZTDJDGAYBCX-UHFFFAOYSA-N N'-(1,3-thiazol-2-yl)propanediamide Chemical compound C(CC(=O)N)(=O)NC=1SC=CN=1 OUAZTDJDGAYBCX-UHFFFAOYSA-N 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• WFCIJBUVGVEVIF-UHFFFAOYSA-N n'-(4-methoxyphenyl)propanediamide Chemical compound COC1=CC=C(NC(=O)CC(N)=O)C=C1 WFCIJBUVGVEVIF-UHFFFAOYSA-N 0.000 claims description 5
• FBZAZCXRYOMJCP-UHFFFAOYSA-N n'-[2-(trifluoromethyl)phenyl]propanediamide Chemical compound NC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F FBZAZCXRYOMJCP-UHFFFAOYSA-N 0.000 claims description 5
• NNVAGNOAICOGJZ-UHFFFAOYSA-N n'-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n-phenylpropanediamide Chemical compound CN1C=CN=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=O)CC(=O)NC=4C=CC=CC=4)=CC=3)F)=C2S1 NNVAGNOAICOGJZ-UHFFFAOYSA-N 0.000 claims description 5
• RMYRXFYPDMLIOR-UHFFFAOYSA-N n'-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n-pyridin-4-ylpropanediamide Chemical compound CN1C=CN=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=O)CC(=O)NC=4C=CN=CC=4)=CC=3)F)=C2S1 RMYRXFYPDMLIOR-UHFFFAOYSA-N 0.000 claims description 5
• AQPLADVQIWUZQC-UHFFFAOYSA-N n-[3-fluoro-4-[2-(3-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1SC(C=1N(C=NC=1)C)=C2 AQPLADVQIWUZQC-UHFFFAOYSA-N 0.000 claims description 5
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• CXLIUMFPLISAHF-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-propan-2-ylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1SC(C=1N=CN(C=1)C(C)C)=C2 CXLIUMFPLISAHF-UHFFFAOYSA-N 0.000 claims description 4
• FWODWMOEVQWJKL-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-propylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound CCCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)NC=5C(=CC=CC=5)OC)=CC=4)F)C=CN=C3C=2)=C1 FWODWMOEVQWJKL-UHFFFAOYSA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
• 125000005493 quinolyl group Chemical group 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• VIGRNGONRWYGKH-UHFFFAOYSA-N N'-(2-hydroxyphenyl)propanediamide Chemical compound OC1=C(C=CC=C1)NC(CC(=O)N)=O VIGRNGONRWYGKH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• LHAAVEBXZINPLX-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-methyl-n'-phenylpropanediamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CC(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=CCN(C)CC1 LHAAVEBXZINPLX-UHFFFAOYSA-N 0.000 claims description 3
• HKFWWPIBKJQPDI-UHFFFAOYSA-N n-[3-fluoro-4-[2-(3-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-hydroxyphenyl)propanediamide Chemical compound CN1C=NC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=O)CC(=O)NC=4C(=CC=CC=4)O)=CC=3)F)=C2S1 HKFWWPIBKJQPDI-UHFFFAOYSA-N 0.000 claims description 3
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 3
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 3
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• COPBBBMOUYSXIB-UHFFFAOYSA-O CCN1C=NC([S+](C=CC2=NC=C3)C2=C3OC(C(F)=CC=C2)=C2C(C=C2)=CC=C2NC(C2(CC2)C(N)=O)=O)=C1 Chemical compound CCN1C=NC([S+](C=CC2=NC=C3)C2=C3OC(C(F)=CC=C2)=C2C(C=C2)=CC=C2NC(C2(CC2)C(N)=O)=O)=C1 COPBBBMOUYSXIB-UHFFFAOYSA-O 0.000 claims description 2
• 125000005605 benzo group Chemical group 0.000 claims description 2
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 2
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 claims description 2
• 125000005968 oxazolinyl group Chemical group 0.000 claims description 2
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 2
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• LDEGHVGGILPJGN-UHFFFAOYSA-N n'-phenylpropanediamide Chemical compound NC(=O)CC(=O)NC1=CC=CC=C1 LDEGHVGGILPJGN-UHFFFAOYSA-N 0.000 claims 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
• MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
• MCDJMWWIMJMCEG-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[2-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-n'-phenylcyclopropane-1,1-dicarboxamide Chemical compound C1N(C)CCC(C=2SC3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC=CC=4)F)C=CN=C3C=2)=C1 MCDJMWWIMJMCEG-UHFFFAOYSA-N 0.000 claims 1
• IVVJTHXSXYVDOH-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-n-phenylcyclopropane-1,1-dicarboxamide Chemical compound CN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)C5(CC5)C(=O)NC=5C=CC=CC=5)=CC=4)F)C=CN=C3C=2)=C1 IVVJTHXSXYVDOH-UHFFFAOYSA-N 0.000 claims 1
• VXDIYDMROBMDPD-UHFFFAOYSA-N 1-n'-[4-[2-[1-[2-(dimethylamino)ethyl]imidazol-4-yl]thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-1-n'-phenylcyclopropane-1,1-dicarboxamide Chemical compound CN(C)CCN1C=NC(C=2SC3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC=CC=4)F)C=CN=C3C=2)=C1 VXDIYDMROBMDPD-UHFFFAOYSA-N 0.000 claims 1
• CDNLCCFEKDHCTK-UHFFFAOYSA-N 1-n-[3-fluoro-4-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-n'-methyl-1-n'-phenylcyclopropane-1,1-dicarboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1(C(=O)NC=2C=C(F)C(OC=3C=4SC(=CC=4N=CC=3)C=3N=CN(C)C=3)=CC=2)CC1 CDNLCCFEKDHCTK-UHFFFAOYSA-N 0.000 claims 1
• MVUDDASODREVCY-UHFFFAOYSA-N 2-[4-[7-[4-[(3-anilino-3-oxopropanoyl)amino]-2-fluorophenoxy]thieno[3,2-b]pyridin-2-yl]imidazol-1-yl]acetic acid Chemical compound OC(=O)CN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(=O)NC=5C=CC=CC=5)=CC=4)F)C=CN=C3C=2)=C1 MVUDDASODREVCY-UHFFFAOYSA-N 0.000 claims 1
• VFSFCYAQBIPUSL-UHFFFAOYSA-N cyclopropylbenzene Chemical compound C1CC1C1=CC=CC=C1 VFSFCYAQBIPUSL-UHFFFAOYSA-N 0.000 claims 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
• XWVKPIIKPOYKJE-UHFFFAOYSA-N n'-(3-fluorophenyl)propanediamide Chemical compound NC(=O)CC(=O)NC1=CC=CC(F)=C1 XWVKPIIKPOYKJE-UHFFFAOYSA-N 0.000 claims 1
• ZTIZMENJNZDJFS-UHFFFAOYSA-N n'-methylpropanediamide Chemical compound CNC(=O)CC(N)=O ZTIZMENJNZDJFS-UHFFFAOYSA-N 0.000 claims 1
• MMRWFYJZBLPXLP-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-methyl-n'-phenylpropanediamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CC(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=CN(C)C=N1 MMRWFYJZBLPXLP-UHFFFAOYSA-N 0.000 claims 1
• NHFAFAPAVVCVTF-UHFFFAOYSA-N n-[3-fluoro-4-[2-(3-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-pyridin-3-ylpropanediamide Chemical compound CN1C=NC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=O)CC(=O)NC=4C=NC=CC=4)=CC=3)F)=C2S1 NHFAFAPAVVCVTF-UHFFFAOYSA-N 0.000 claims 1
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