JP2009504804A5 - - Google Patents
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- JP2009504804A5 JP2009504804A5 JP2008537239A JP2008537239A JP2009504804A5 JP 2009504804 A5 JP2009504804 A5 JP 2009504804A5 JP 2008537239 A JP2008537239 A JP 2008537239A JP 2008537239 A JP2008537239 A JP 2008537239A JP 2009504804 A5 JP2009504804 A5 JP 2009504804A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- phenyl
- thieno
- pyridin
- 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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- 125000000623 heterocyclic group Chemical group 0.000 claims description 290
- 125000000217 alkyl group Chemical group 0.000 claims description 227
- -1 cyano, nitro, tetrazolyl Chemical group 0.000 claims description 213
- 125000003118 aryl group Chemical group 0.000 claims description 169
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 160
- 125000001072 heteroaryl group Chemical group 0.000 claims description 126
- 125000001424 substituent group Chemical group 0.000 claims description 115
- 125000005843 halogen group Chemical group 0.000 claims description 109
- 229910052736 halogen Inorganic materials 0.000 claims description 90
- 150000002367 halogens Chemical class 0.000 claims description 90
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 86
- 125000003545 alkoxy group Chemical group 0.000 claims description 80
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 78
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 49
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 43
- 125000004429 atom Chemical group 0.000 claims description 42
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 229920006395 saturated elastomer Polymers 0.000 claims description 39
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 28
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 27
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- YUZHVIIXJVNLKI-UHFFFAOYSA-N n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(N)=O YUZHVIIXJVNLKI-UHFFFAOYSA-N 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 20
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 230000011664 signaling Effects 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 16
- 125000006413 ring segment Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 102000005962 receptors Human genes 0.000 claims description 14
- 108020003175 receptors Proteins 0.000 claims description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000001540 azides Chemical class 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 9
- GIOZVUBIPCPOAS-UHFFFAOYSA-N 1-azido-3-(diaminomethylidene)-2-(diaminomethylideneamino)-1-methylguanidine Chemical compound N(C(=N)N)NC(N(N=[N+]=[N-])C)=NC(N)=N GIOZVUBIPCPOAS-UHFFFAOYSA-N 0.000 claims description 8
- 108091008603 HGF receptors Proteins 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 108091008605 VEGF receptors Proteins 0.000 claims description 8
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 8
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 6
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 125000004069 aziridinyl group Chemical group 0.000 claims description 4
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 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 3
- 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 3
- ULOZSCMRMJIUOM-UHFFFAOYSA-N n-[4-[2-(1-ethylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-2-oxo-1-phenylpyrrolidine-3-carboxamide Chemical compound CCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)C5C(N(CC5)C=5C=CC=CC=5)=O)=CC=4)F)C=CN=C3C=2)=C1 ULOZSCMRMJIUOM-UHFFFAOYSA-N 0.000 claims description 3
- ULFUOACTDDTWGR-UHFFFAOYSA-N N-(4-fluorophenyl)sulfanylacetamide Chemical compound C(C)(=O)NSC1=CC=C(C=C1)F ULFUOACTDDTWGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl 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 15
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims 11
- KNCCWVJEKOKTHK-UHFFFAOYSA-N n'-(2-fluorophenyl)propanediamide Chemical compound NC(=O)CC(=O)NC1=CC=CC=C1F KNCCWVJEKOKTHK-UHFFFAOYSA-N 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 102000027430 HGF receptors Human genes 0.000 claims 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 238000000338 in vitro Methods 0.000 claims 4
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims 3
- 150000001721 carbon Chemical class 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 230000001413 cellular effect Effects 0.000 claims 2
- 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 2
- BGHOGQNFMBHPKJ-UHFFFAOYSA-N n-[4-[2-(1-ethylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-3-(2-fluorophenyl)-2-oxoimidazolidine-1-carboxamide Chemical compound CCN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)N5C(N(CC5)C=5C(=CC=CC=5)F)=O)=CC=4)F)C=CN=C3C=2)=C1 BGHOGQNFMBHPKJ-UHFFFAOYSA-N 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- UDBMSQJXDRHQKR-UHFFFAOYSA-N 1-N'-[3-fluoro-4-[methyl(thieno[3,2-b]pyridin-7-yl)amino]phenyl]-1-N'-phenylcyclopropane-1,1-dicarboxamide Chemical compound CN(c1ccc(cc1F)N(C(=O)C1(CC1)C(N)=O)c1ccccc1)c1ccnc2ccsc12 UDBMSQJXDRHQKR-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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 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
- FWPGZFBNQBRYJP-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]amino]phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound CN1C=NC(C=2SC3=C(NC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC(F)=CC=4)F)C=CN=C3C=2)=C1 FWPGZFBNQBRYJP-UHFFFAOYSA-N 0.000 claims 1
- ILOBUFKVNRILLR-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]amino]phenyl]-1-n'-phenylcyclopropane-1,1-dicarboxamide Chemical compound CN1C=NC(C=2SC3=C(NC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC=CC=4)F)C=CN=C3C=2)=C1 ILOBUFKVNRILLR-UHFFFAOYSA-N 0.000 claims 1
- VUGIEPDDOZOEHY-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[methyl-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]amino]phenyl]-1-n'-phenylcyclopropane-1,1-dicarboxamide Chemical compound C=1C=NC=2C=C(C=3N=CN(C)C=3)SC=2C=1N(C)C(C(=C1)F)=CC=C1N(C=1C=CC=CC=1)C(=O)C1(C(N)=O)CC1 VUGIEPDDOZOEHY-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- QZYVPGZQJAOSPR-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzoxazin-4-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=C6OCC5)=CC=4)F)C=CN=C3C=2)=C1 QZYVPGZQJAOSPR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PVZJXHRZGMDPPA-UHFFFAOYSA-N 3-(2-fluorophenyl)-n-[3-fluoro-4-[2-[1-(3-pyrrolidin-1-ylpropyl)imidazol-4-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxoimidazolidine-1-carboxamide Chemical compound C=1C=C(OC=2C=3SC(=CC=3N=CC=2)C=2N=CN(CCCN3CCCC3)C=2)C(F)=CC=1NC(=O)N(C1=O)CCN1C1=CC=CC=C1F PVZJXHRZGMDPPA-UHFFFAOYSA-N 0.000 claims 1
- GRKVEPSQIQTNLR-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[3-fluoro-4-[2-[1-(3-pyrrolidin-1-ylpropyl)imidazol-4-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxoimidazolidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)N(C(=O)NC=2C=C(F)C(OC=3C=4SC(=CC=4N=CC=3)C=3N=CN(CCCN4CCCC4)C=3)=CC=2)CC1 GRKVEPSQIQTNLR-UHFFFAOYSA-N 0.000 claims 1
- OMVHEGLHTFATRT-UHFFFAOYSA-N 3-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyanilino]-3-oxopropanoic acid Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C=1N(C=CN=1)C)NC(CC(=O)O)=O OMVHEGLHTFATRT-UHFFFAOYSA-N 0.000 claims 1
- UXBXTSWBNHTFRX-UHFFFAOYSA-N 3-anilino-4,4,4-trifluoro-n-[3-fluoro-4-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]butanamide Chemical compound CN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)CC(NC=5C=CC=CC=5)C(F)(F)F)=CC=4)F)C=CN=C3C=2)=C1 UXBXTSWBNHTFRX-UHFFFAOYSA-N 0.000 claims 1
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- 2006-05-19 WO PCT/IB2006/004306 patent/WO2008041053A2/en not_active Ceased
- 2006-05-19 CN CN2006800266085A patent/CN101796055B/zh active Active
- 2006-05-19 US US11/438,133 patent/US8093264B2/en active Active
- 2006-05-19 JP JP2008537239A patent/JP5148499B2/ja active Active
- 2006-05-19 BR BRPI0610322A patent/BRPI0610322B8/pt active IP Right Grant
- 2006-05-19 AU AU2006343808A patent/AU2006343808B2/en active Active
- 2006-05-19 KR KR1020077029798A patent/KR101378716B1/ko active Active
- 2006-05-19 CA CA2611370A patent/CA2611370C/en active Active
- 2006-05-19 MX MX2007014616A patent/MX2007014616A/es active IP Right Grant
- 2006-05-19 EP EP06851548.5A patent/EP1957498B1/en active Active
- 2006-05-19 ES ES06851548.5T patent/ES2623221T3/es active Active
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2007
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2011
- 2011-12-08 US US13/314,362 patent/US8329726B2/en active Active
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