JPWO2021202874A5 - - Google Patents
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- JPWO2021202874A5 JPWO2021202874A5 JP2022560236A JP2022560236A JPWO2021202874A5 JP WO2021202874 A5 JPWO2021202874 A5 JP WO2021202874A5 JP 2022560236 A JP2022560236 A JP 2022560236A JP 2022560236 A JP2022560236 A JP 2022560236A JP WO2021202874 A5 JPWO2021202874 A5 JP WO2021202874A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridin
- oxy
- dichlorophenyl
- piperidin
- 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.)
- Pending
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 43
- 239000008194 pharmaceutical composition Substances 0.000 claims 26
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 241000711573 Coronaviridae Species 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 241000700605 Viruses Species 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- -1 (1-((2-(3,5-dichlorophenyl)-6-((2-(piperazin-1-yl)pyrimidin-5-yl)oxy)pyridin-4-yl)methyl)piperidin-4-yl)methyl Chemical group 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 241000004176 Alphacoronavirus Species 0.000 claims 2
- 241000008904 Betacoronavirus Species 0.000 claims 2
- 241001678559 COVID-19 virus Species 0.000 claims 2
- 229940122055 Serine protease inhibitor Drugs 0.000 claims 2
- 101710102218 Serine protease inhibitor Proteins 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 2
- WQAWEUZTDVWTDB-UHFFFAOYSA-N dimethyl(oxo)phosphanium Chemical compound C[P+](C)=O WQAWEUZTDVWTDB-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- YEHDDQDXQLZCPX-UHFFFAOYSA-N methyl N-[3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoyl]carbamate Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)NC(OC)=O YEHDDQDXQLZCPX-UHFFFAOYSA-N 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 239000008177 pharmaceutical agent Substances 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 239000003001 serine protease inhibitor Substances 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- DZPXARBHSNBMCW-HXUWFJFHSA-N (2R)-3-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)C[C@H](C(=O)O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C DZPXARBHSNBMCW-HXUWFJFHSA-N 0.000 claims 1
- DZPXARBHSNBMCW-FQEVSTJZSA-N (2S)-3-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)C[C@@H](C(=O)O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C DZPXARBHSNBMCW-FQEVSTJZSA-N 0.000 claims 1
- AFVOZNISEYCWRY-UHFFFAOYSA-N 1-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-3-methylsulfonylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)NC(=O)NS(=O)(=O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C AFVOZNISEYCWRY-UHFFFAOYSA-N 0.000 claims 1
- NKKNUMPNQBYZRN-UHFFFAOYSA-N 1-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]oxycyclopropane-1-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)OC1(CC1)C(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C NKKNUMPNQBYZRN-UHFFFAOYSA-N 0.000 claims 1
- XWUNSCLZJGAQAA-UHFFFAOYSA-N 1-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]propan-2-ol Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C)O)OC=1C=NC(=NC=1)N1CCN(CC1)C XWUNSCLZJGAQAA-UHFFFAOYSA-N 0.000 claims 1
- OQHOMPBZZAFXAU-UHFFFAOYSA-N 1-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]propan-2-one Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C)=O)OC=1C=NC(=NC=1)N1CCN(CC1)C OQHOMPBZZAFXAU-UHFFFAOYSA-N 0.000 claims 1
- SOMRWFBPSUFXCP-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]-N-methylmethanamine Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CNC)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)C SOMRWFBPSUFXCP-UHFFFAOYSA-N 0.000 claims 1
- VDDJCWROUASGBF-UHFFFAOYSA-N 1-[2-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]ethyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC1(CC1)C(=O)O VDDJCWROUASGBF-UHFFFAOYSA-N 0.000 claims 1
- WXAWSOSENJECMG-UHFFFAOYSA-N 1-[5-[6-(3-chloro-5-methylphenyl)-4-(methylaminomethyl)pyridin-2-yl]oxypyridin-2-yl]piperidin-4-amine Chemical compound ClC=1C=C(C=C(C=1)C)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCC(CC1)N)CNC WXAWSOSENJECMG-UHFFFAOYSA-N 0.000 claims 1
- TWHWNKJMOUMLGU-UHFFFAOYSA-N 1-[7-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]-2-hydroxyethanone Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC2(CN(C2)C(CO)=O)CC1)OC=1C=NC(=NC=1)N1CCN(CC1)C TWHWNKJMOUMLGU-UHFFFAOYSA-N 0.000 claims 1
- WDAYBDXLXUXMOV-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCNCC1 WDAYBDXLXUXMOV-UHFFFAOYSA-N 0.000 claims 1
- DLIIAMDDSBJZQZ-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]-4-hydroxypiperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)(O)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCNCC1 DLIIAMDDSBJZQZ-UHFFFAOYSA-N 0.000 claims 1
- ZFNIEZAQMUDSTP-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylsulfonylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NS(=O)(=O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C ZFNIEZAQMUDSTP-UHFFFAOYSA-N 0.000 claims 1
- KPMPEWPLXPVVIN-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)C KPMPEWPLXPVVIN-UHFFFAOYSA-N 0.000 claims 1
- USJUUVXZEGTZAO-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2-hydroxyethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCO USJUUVXZEGTZAO-UHFFFAOYSA-N 0.000 claims 1
- JTZDFWQPNAEAQN-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2-methoxyethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCOC JTZDFWQPNAEAQN-UHFFFAOYSA-N 0.000 claims 1
- KPLFJQSZBMMFHZ-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-hydroxybutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)O KPLFJQSZBMMFHZ-UHFFFAOYSA-N 0.000 claims 1
- FBNHKNOITKSSBL-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-hydroxypropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCCO FBNHKNOITKSSBL-UHFFFAOYSA-N 0.000 claims 1
- FGXGXGLCKDQRHK-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfinylbutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)S(=O)C FGXGXGLCKDQRHK-UHFFFAOYSA-N 0.000 claims 1
- FLPKMKVZJGIDSI-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylbutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)S(=O)(=O)C FLPKMKVZJGIDSI-UHFFFAOYSA-N 0.000 claims 1
- UVONHVPZRCLRAM-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)C UVONHVPZRCLRAM-UHFFFAOYSA-N 0.000 claims 1
- SASYMGHFTFWCKQ-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-sulfamoylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)N)CN1CCC(CC1)CNC(=O)NC SASYMGHFTFWCKQ-UHFFFAOYSA-N 0.000 claims 1
- GXICYQKEICYJGT-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(4-hydroxybutan-2-yl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)CCO GXICYQKEICYJGT-UHFFFAOYSA-N 0.000 claims 1
- GOTXSDCHVRMSBJ-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(4-methylsulfonylbutan-2-yl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)CCS(=O)(=O)C GOTXSDCHVRMSBJ-UHFFFAOYSA-N 0.000 claims 1
- KZWOIEIPARUHSL-OAQYLSRUSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)C[C@@H](C)O KZWOIEIPARUHSL-OAQYLSRUSA-N 0.000 claims 1
- KCAMKOIMXKKORN-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)C KCAMKOIMXKKORN-UHFFFAOYSA-N 0.000 claims 1
- WKELXCFDAVLUNR-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(2-hydroxyethyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)CCO WKELXCFDAVLUNR-UHFFFAOYSA-N 0.000 claims 1
- OMXZTUYZKCNSKJ-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)CCOC OMXZTUYZKCNSKJ-UHFFFAOYSA-N 0.000 claims 1
- KNUJQCPMMDZZAA-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(2-methylsulfonylethyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)CCS(=O)(=O)C KNUJQCPMMDZZAA-UHFFFAOYSA-N 0.000 claims 1
- ROYVPUGPANDVKE-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylbutyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)CCC(C)S(=O)(=O)C ROYVPUGPANDVKE-UHFFFAOYSA-N 0.000 claims 1
- ABKPIKBYUFOGCN-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(=O)(=O)C ABKPIKBYUFOGCN-UHFFFAOYSA-N 0.000 claims 1
- XZQBCZDSCSLWOQ-UHFFFAOYSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-sulfamoylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)N)CN1CCC(CC1)CNC(=O)NC XZQBCZDSCSLWOQ-UHFFFAOYSA-N 0.000 claims 1
- XAISUIZQUBKJBH-JOCHJYFZSA-N 1-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=CC=1)N1CCN(CC1)C[C@@H](C)O XAISUIZQUBKJBH-JOCHJYFZSA-N 0.000 claims 1
- UJUFOLDAPKPKMH-UHFFFAOYSA-N 1-[[1-[[2-(3-chloro-5-fluorophenyl)-6-[2-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)F)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)C UJUFOLDAPKPKMH-UHFFFAOYSA-N 0.000 claims 1
- XQAOLROUGWUCCN-UHFFFAOYSA-N 1-[[1-[[2-(3-chloro-5-fluorophenyl)-6-[2-[4-(4-methylsulfonylbutan-2-yl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]-3-methylurea Chemical compound ClC=1C=C(C=C(C=1)F)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(=O)NC)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)CCS(=O)(=O)C XQAOLROUGWUCCN-UHFFFAOYSA-N 0.000 claims 1
- MJGDEMMDRQQTFT-DEOSSOPVSA-N 2-[(7S)-4-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]-1,4-oxazepan-7-yl]ethanol Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCO[C@@H](CC1)CCO)OC=1C=NC(=NC=1)N1CCN(CC1)C MJGDEMMDRQQTFT-DEOSSOPVSA-N 0.000 claims 1
- NUOYGSNJOPJRFU-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]acetamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)N)OC=1C=NC(=NC=1)N1CCNCC1 NUOYGSNJOPJRFU-UHFFFAOYSA-N 0.000 claims 1
- RCXRKDSECTVFOM-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCNCC1 RCXRKDSECTVFOM-UHFFFAOYSA-N 0.000 claims 1
- ALYLHJNDRVMZAO-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]oxyacetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)OCC(=O)O)OC=1C=NC(=NC=1)N1CCNCC1 ALYLHJNDRVMZAO-UHFFFAOYSA-N 0.000 claims 1
- ROZNNAUNLQUDRA-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]-N,N-dimethylethanamine oxide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC[N+](C)(C)[O-])OC=1C=NC(=CC=1)N1CCNCC1 ROZNNAUNLQUDRA-UHFFFAOYSA-N 0.000 claims 1
- SDEJHJKGDDPMAW-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCNCC1 SDEJHJKGDDPMAW-UHFFFAOYSA-N 0.000 claims 1
- ZNCSXEDOPKOGCK-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]ethanesulfonic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCS(=O)(=O)O)OC=1C=NC(=CC=1)N1CCNCC1 ZNCSXEDOPKOGCK-UHFFFAOYSA-N 0.000 claims 1
- FADDYAKDLGQPHK-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CC2CN(CC2C1)C FADDYAKDLGQPHK-UHFFFAOYSA-N 0.000 claims 1
- SJUQEDZVANTTMO-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(3,3-dimethylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CC(NCC1)(C)C SJUQEDZVANTTMO-UHFFFAOYSA-N 0.000 claims 1
- QHUIXLHLPZLIMK-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-ethyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CCC1)CC QHUIXLHLPZLIMK-UHFFFAOYSA-N 0.000 claims 1
- JZNGNDDVXZOGOX-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-ethylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CC JZNGNDDVXZOGOX-UHFFFAOYSA-N 0.000 claims 1
- RHMYVCZSMOIFAS-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CCC1)C RHMYVCZSMOIFAS-UHFFFAOYSA-N 0.000 claims 1
- YCWULLBAWJMDTL-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]oxyacetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)OCC(=O)O)OC=1C=NC(=NC=1)N1CCN(CCC1)C YCWULLBAWJMDTL-UHFFFAOYSA-N 0.000 claims 1
- QRPCIPJAEVDQQP-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)N)OC=1C=NC(=NC=1)N1CCN(CC1)C QRPCIPJAEVDQQP-UHFFFAOYSA-N 0.000 claims 1
- AZEJIKZNBHEXCM-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C AZEJIKZNBHEXCM-UHFFFAOYSA-N 0.000 claims 1
- BAPINCRGBBFJDB-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]ethanesulfonamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCS(=O)(=O)N)OC=1C=NC(=NC=1)N1CCN(CC1)C BAPINCRGBBFJDB-UHFFFAOYSA-N 0.000 claims 1
- FYLPKMOYILCRDF-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]ethanol Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCO)OC=1C=NC(=NC=1)N1CCN(CC1)C FYLPKMOYILCRDF-UHFFFAOYSA-N 0.000 claims 1
- KGJOHKYXCLOVID-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]ethylboronic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCB(O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C KGJOHKYXCLOVID-UHFFFAOYSA-N 0.000 claims 1
- WCHGPESKTRKZOY-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]oxy-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)OC(C(=O)O)(C)C)OC=1C=NC(=NC=1)N1CCN(CC1)C WCHGPESKTRKZOY-UHFFFAOYSA-N 0.000 claims 1
- IZKMXUBRKPZLTL-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]oxyacetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)OCC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C IZKMXUBRKPZLTL-UHFFFAOYSA-N 0.000 claims 1
- NPVPASPENGAFSC-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]pyrrolidin-3-yl]oxyacetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CC(CC1)OCC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C NPVPASPENGAFSC-UHFFFAOYSA-N 0.000 claims 1
- CKAAPGPMWZFCOW-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-propan-2-ylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)C CKAAPGPMWZFCOW-UHFFFAOYSA-N 0.000 claims 1
- AHNYKNJXYRHFTJ-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-fluoro-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCNCC(C1)F AHNYKNJXYRHFTJ-UHFFFAOYSA-N 0.000 claims 1
- NCSPMNRHMIVKBF-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-fluoro-4-methyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC(C1)F)C NCSPMNRHMIVKBF-UHFFFAOYSA-N 0.000 claims 1
- JCYVGILALJXHJG-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-hydroxy-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCNCC(C1)O JCYVGILALJXHJG-UHFFFAOYSA-N 0.000 claims 1
- BLBHGPCWQIYXOF-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-hydroxy-4,6-dimethyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC(C1)(C)O)C BLBHGPCWQIYXOF-UHFFFAOYSA-N 0.000 claims 1
- NGKDDRVRCYHOEH-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-hydroxy-4-methyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC(C1)O)C NGKDDRVRCYHOEH-UHFFFAOYSA-N 0.000 claims 1
- CTFGGUUIKCFANT-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-methoxy-4-methyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC(C1)OC)C CTFGGUUIKCFANT-UHFFFAOYSA-N 0.000 claims 1
- JTKHTEMATCXRRP-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(6-methyl-3,6-diazabicyclo[3.1.1]heptan-3-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CC2N(C(C1)C2)C JTKHTEMATCXRRP-UHFFFAOYSA-N 0.000 claims 1
- OSAJLDHWUIDPHY-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CC2CCC(C1)N2C OSAJLDHWUIDPHY-UHFFFAOYSA-N 0.000 claims 1
- BYBWOHAVQQRHIH-DQEYMECFSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[(1S,4S)-5-ethyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1[C@@H]2CN([C@H](C1)C2)CC BYBWOHAVQQRHIH-DQEYMECFSA-N 0.000 claims 1
- NENSRYYLZNRUSQ-ZEQRLZLVSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1[C@@H]2CN([C@H](C1)C2)C NENSRYYLZNRUSQ-ZEQRLZLVSA-N 0.000 claims 1
- LYDQKYGPLCCBIN-SFHVURJKSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[(3S)-3-methylpiperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1C[C@@H](NCC1)C LYDQKYGPLCCBIN-SFHVURJKSA-N 0.000 claims 1
- ZMLSGPFKTLQRBT-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[3-(methylamino)pyrrolidin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CC(CC1)NC ZMLSGPFKTLQRBT-UHFFFAOYSA-N 0.000 claims 1
- KMZRPZHTZYJNCM-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(1,3-dihydroxypropan-2-yl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C(CO)CO KMZRPZHTZYJNCM-UHFFFAOYSA-N 0.000 claims 1
- QVMPXIXVHHAEGH-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(1-hydroxypropan-2-yl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C(CO)C QVMPXIXVHHAEGH-UHFFFAOYSA-N 0.000 claims 1
- AYLXYASCQWNACW-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CC(CO)O AYLXYASCQWNACW-UHFFFAOYSA-N 0.000 claims 1
- RVQJNKOIZKJNGH-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2-fluoroethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCF RVQJNKOIZKJNGH-UHFFFAOYSA-N 0.000 claims 1
- XZKGLRKBFXECOM-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2-hydroxyethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCO XZKGLRKBFXECOM-UHFFFAOYSA-N 0.000 claims 1
- WZXUTZNFFFBBEK-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2-methoxyethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCOC WZXUTZNFFFBBEK-UHFFFAOYSA-N 0.000 claims 1
- MFYJWGWIBQDEHK-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2H-triazol-4-ylmethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound N1N=NC=C1CN1CCN(CC1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl MFYJWGWIBQDEHK-UHFFFAOYSA-N 0.000 claims 1
- LCRJZDOELKQBHQ-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-hydroxy-2,2-dimethylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CC(CO)(C)C LCRJZDOELKQBHQ-UHFFFAOYSA-N 0.000 claims 1
- YLJJABGXZWXZOR-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-hydroxy-3-methylbutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)(C)O YLJJABGXZWXZOR-UHFFFAOYSA-N 0.000 claims 1
- OETPDWYLICVMMI-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-hydroxybutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)O OETPDWYLICVMMI-UHFFFAOYSA-N 0.000 claims 1
- BRRZTSFCKGPYTG-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-hydroxycyclobutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C1CC(C1)O BRRZTSFCKGPYTG-UHFFFAOYSA-N 0.000 claims 1
- PYXXTSDGIBYDFY-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfinylbutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)S(=O)C PYXXTSDGIBYDFY-UHFFFAOYSA-N 0.000 claims 1
- IJYMLGZIEOKWBI-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylbutyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C)S(=O)(=O)C IJYMLGZIEOKWBI-UHFFFAOYSA-N 0.000 claims 1
- SNPSOUBNBXTISO-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)C SNPSOUBNBXTISO-UHFFFAOYSA-N 0.000 claims 1
- DMZBFQQCFPWAPD-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-sulfamoylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(N)(=O)=O DMZBFQQCFPWAPD-UHFFFAOYSA-N 0.000 claims 1
- VEPVVRISRPIOHE-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(4-hydroxybutan-2-yl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)CCO VEPVVRISRPIOHE-UHFFFAOYSA-N 0.000 claims 1
- BMMWWERINDBDLN-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(dimethylamino)piperidin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCC(CC1)N(C)C BMMWWERINDBDLN-UHFFFAOYSA-N 0.000 claims 1
- MSPWBBKJKNRIQD-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[(1-hydroxycyclopropyl)methyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CC1(CC1)O MSPWBBKJKNRIQD-UHFFFAOYSA-N 0.000 claims 1
- BUVTTYFXRWVEJU-HXUWFJFHSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C[C@@H](C)O BUVTTYFXRWVEJU-HXUWFJFHSA-N 0.000 claims 1
- HHEWUAIKSZWNGP-HXUWFJFHSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]oxyacetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)OCC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C[C@@H](C)O HHEWUAIKSZWNGP-HXUWFJFHSA-N 0.000 claims 1
- SPMMCBXXGGNOQR-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[2-(1-hydroxycyclopropyl)ethyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCC1(CC1)O SPMMCBXXGGNOQR-UHFFFAOYSA-N 0.000 claims 1
- QXEDGKCVXMPAJI-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[2-(methylcarbamoyloxy)ethyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCOC(NC)=O QXEDGKCVXMPAJI-UHFFFAOYSA-N 0.000 claims 1
- IVHYHWFSBVJZCQ-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[4-(dimethylamino)butan-2-yl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)CCN(C)C IVHYHWFSBVJZCQ-UHFFFAOYSA-N 0.000 claims 1
- PDBGKKMNOGDHQG-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[4-(methylamino)butan-2-yl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C(C)CCNC PDBGKKMNOGDHQG-UHFFFAOYSA-N 0.000 claims 1
- FVNYZWBRFJBAIU-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[2-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C(=NC(=CC=1)N1CCN(CC1)C)C FVNYZWBRFJBAIU-UHFFFAOYSA-N 0.000 claims 1
- HNGLYJIAKWIQQA-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[4-methyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C(=NC(=NC=1)N1CCN(CC1)C)C HNGLYJIAKWIQQA-UHFFFAOYSA-N 0.000 claims 1
- RCOZJDHVNBQPAH-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[5-fluoro-6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=C(C=1)F)N1CCN(CC1)C RCOZJDHVNBQPAH-UHFFFAOYSA-N 0.000 claims 1
- XSYRJHRGZVWTDL-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-(4-methyl-1,4-diazepan-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CCC1)C XSYRJHRGZVWTDL-UHFFFAOYSA-N 0.000 claims 1
- AWMJWDCCUXONEH-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)C AWMJWDCCUXONEH-UHFFFAOYSA-N 0.000 claims 1
- NUTYHECMBAOZIB-DQEYMECFSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1[C@@H]2CN([C@H](C1)C2)C NUTYHECMBAOZIB-DQEYMECFSA-N 0.000 claims 1
- PXHSRGZVZWWOSI-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(2-hydroxyethyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)CCO PXHSRGZVZWWOSI-UHFFFAOYSA-N 0.000 claims 1
- CZTOGJLVLISLTA-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)CCOC CZTOGJLVLISLTA-UHFFFAOYSA-N 0.000 claims 1
- VGBJOWWKCHRYDK-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-N-ethylacetamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)NCC)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(=O)(=O)C VGBJOWWKCHRYDK-UHFFFAOYSA-N 0.000 claims 1
- DLANLBKDYFQYEC-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)N)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(=O)(=O)C DLANLBKDYFQYEC-UHFFFAOYSA-N 0.000 claims 1
- DHKNGKGYCUONKT-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(=O)(=O)C DHKNGKGYCUONKT-UHFFFAOYSA-N 0.000 claims 1
- YQZXMUCZGZCQQB-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-sulfamoylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(N)(=O)=O YQZXMUCZGZCQQB-UHFFFAOYSA-N 0.000 claims 1
- OTCLOANOPONIOE-OAQYLSRUSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)C[C@@H](C)O OTCLOANOPONIOE-OAQYLSRUSA-N 0.000 claims 1
- KOUVZSVAYWEVGP-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-propan-2-ylamino]pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)N(C=1C=NC(=NC=1)N1CCN(CC1)C)C(C)C KOUVZSVAYWEVGP-UHFFFAOYSA-N 0.000 claims 1
- HXLIPKCQIMNKQD-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino]pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)NC=1C=NC(=NC=1)N1CCN(CC1)C HXLIPKCQIMNKQD-UHFFFAOYSA-N 0.000 claims 1
- MEXGBWBRSSAHCM-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[ethyl-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino]pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)N(C=1C=NC(=NC=1)N1CCN(CC1)C)CC MEXGBWBRSSAHCM-UHFFFAOYSA-N 0.000 claims 1
- IOJDGVMUMJJVRT-UHFFFAOYSA-N 2-[1-[[2-(3,5-dichlorophenyl)-6-[methyl-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino]pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)N(C=1C=NC(=NC=1)N1CCN(CC1)C)C IOJDGVMUMJJVRT-UHFFFAOYSA-N 0.000 claims 1
- OTDGDFRWRZRFGC-UHFFFAOYSA-N 2-[1-[[2-(3-chloro-5-fluorophenyl)-6-[2-(4-methyl-1,4-diazepan-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)F)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CCC1)C OTDGDFRWRZRFGC-UHFFFAOYSA-N 0.000 claims 1
- PMWGLSGYZGTXKW-UHFFFAOYSA-N 2-[1-[[2-[2-(1,4-diazabicyclo[3.2.1]octan-4-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound N12CCN(C(CC1)C2)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl PMWGLSGYZGTXKW-UHFFFAOYSA-N 0.000 claims 1
- NJCICWFDIHZRTG-UHFFFAOYSA-N 2-[1-[[2-[2-(1,4-diazepan-1-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound N1(CCNCCC1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl NJCICWFDIHZRTG-UHFFFAOYSA-N 0.000 claims 1
- OWXJTTCCGNEYPG-UHFFFAOYSA-N 2-[1-[[2-[2-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)OC=1C=NC(=NC=1)N1CC2CNCC2C1 OWXJTTCCGNEYPG-UHFFFAOYSA-N 0.000 claims 1
- FNYXWJCLQVJDDY-UHFFFAOYSA-N 2-[1-[[2-[2-(3,6-diazabicyclo[3.1.1]heptan-3-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound C12CN(CC(N1)C2)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl FNYXWJCLQVJDDY-UHFFFAOYSA-N 0.000 claims 1
- DBDSKIYILUCOAH-UHFFFAOYSA-N 2-[1-[[2-[2-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)-3-fluoropyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound C12CN(CC(CC1)N2)C1=NC=C(C=N1)OC1=NC(=CC(=C1F)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl DBDSKIYILUCOAH-UHFFFAOYSA-N 0.000 claims 1
- ZMTFZELEZNPAST-UHFFFAOYSA-N 2-[1-[[2-[2-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound C12CN(CC(CC1)N2)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl ZMTFZELEZNPAST-UHFFFAOYSA-N 0.000 claims 1
- LZUMWNRBZQQEOM-UHFFFAOYSA-N 2-[1-[[2-[2-(4,7-diazaspiro[2.5]octan-7-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC11NCCN(C1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl LZUMWNRBZQQEOM-UHFFFAOYSA-N 0.000 claims 1
- JQOLXWIADFCQHK-UHFFFAOYSA-N 2-[1-[[2-[2-(4-aminopiperidin-1-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound NC1CCN(CC1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl JQOLXWIADFCQHK-UHFFFAOYSA-N 0.000 claims 1
- HFBZNXHRBLBXGE-UHFFFAOYSA-N 2-[1-[[2-[2-(4-cyclopropylpiperazin-1-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound C1(CC1)N1CCN(CC1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl HFBZNXHRBLBXGE-UHFFFAOYSA-N 0.000 claims 1
- QPAOXJWKOIWCDO-UHFFFAOYSA-N 2-[1-[[2-[2-[4-amino-4-(2-hydroxyethyl)piperidin-1-yl]pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound NC1(CCN(CC1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl)CCO QPAOXJWKOIWCDO-UHFFFAOYSA-N 0.000 claims 1
- ORLQRZQCDFPHTG-UHFFFAOYSA-N 2-[1-[[2-[2-[4-amino-4-(hydroxymethyl)piperidin-1-yl]pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound NC1(CCN(CC1)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl)CO ORLQRZQCDFPHTG-UHFFFAOYSA-N 0.000 claims 1
- MIIPWEPBHOOZOT-UHFFFAOYSA-N 2-[1-[[2-[6-(1,4-diazepan-1-yl)pyridin-3-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound N1(CCNCCC1)C1=CC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CC(=O)O)C1=CC(=CC(=C1)Cl)Cl MIIPWEPBHOOZOT-UHFFFAOYSA-N 0.000 claims 1
- SWDIGXKGTIKYKO-ZEQRLZLVSA-N 2-[1-[[2-[6-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-3-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound [C@@H]12N(C[C@@H](NC1)C2)C2=CC=C(C=N2)OC2=NC(=CC(=C2)CN2CCC(CC2)CC(=O)O)C2=CC(=CC(=C2)Cl)Cl SWDIGXKGTIKYKO-ZEQRLZLVSA-N 0.000 claims 1
- RMSSDEZLJBZPAT-UHFFFAOYSA-N 2-[1-[[6-(3,5-dichlorophenyl)-3-fluoro-2-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=C(C(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)C)F)CN1CCC(CC1)CC(=O)O RMSSDEZLJBZPAT-UHFFFAOYSA-N 0.000 claims 1
- QMSJTWDTLACGJG-UHFFFAOYSA-N 2-[1-[[6-(3,5-dichlorophenyl)-3-fluoro-2-[2-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=C(C(=N1)OC=1C=NC(=NC=1)N1CC2CCC(C1)N2C)F)CN1CCC(CC1)CC(=O)O QMSJTWDTLACGJG-UHFFFAOYSA-N 0.000 claims 1
- MAAQFHPMDQYLSZ-UHFFFAOYSA-N 2-[1-[[6-(3,5-dichlorophenyl)-3-fluoro-2-[2-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=C(C(=N1)OC=1C(=NC(=CC=1)N1CCN(CC1)C)C)F)CN1CCC(CC1)CC(=O)O MAAQFHPMDQYLSZ-UHFFFAOYSA-N 0.000 claims 1
- WDKJKCSRACACCB-UHFFFAOYSA-N 2-[1-[[6-(3,5-dichlorophenyl)-3-fluoro-2-[4-methyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=C(C(=N1)OC=1C(=NC(=NC=1)N1CCN(CC1)C)C)F)CN1CCC(CC1)CC(=O)O WDKJKCSRACACCB-UHFFFAOYSA-N 0.000 claims 1
- UUZZKGHOAMZHJI-UHFFFAOYSA-N 2-[1-[[6-(3,5-dichlorophenyl)-3-fluoro-2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=C(C(=N1)OC=1C=NC(=CC=1)N1CCN(CC1)C)F)CN1CCC(CC1)CC(=O)O UUZZKGHOAMZHJI-UHFFFAOYSA-N 0.000 claims 1
- YRPKDMKWHSUYKS-UHFFFAOYSA-N 2-[1-[[6-(3,5-dichlorophenyl)-3-methyl-2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=C(C(=N1)OC=1C=NC(=CC=1)N1CCN(CC1)C)C)CN1CCC(CC1)CC(=O)O YRPKDMKWHSUYKS-UHFFFAOYSA-N 0.000 claims 1
- KJSBUZCREZKGJL-UHFFFAOYSA-N 2-[2-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CC2C(C1)CC(C2)CC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C KJSBUZCREZKGJL-UHFFFAOYSA-N 0.000 claims 1
- WGRNTRPTSUMYAD-UHFFFAOYSA-N 2-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]acetic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CC(=O)O WGRNTRPTSUMYAD-UHFFFAOYSA-N 0.000 claims 1
- GBLKCQPGPROIOJ-UHFFFAOYSA-N 2-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]ethanesulfonic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCS(=O)(=O)O GBLKCQPGPROIOJ-UHFFFAOYSA-N 0.000 claims 1
- NNBOEOHJHJRLDP-UHFFFAOYSA-N 2-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]ethyl carbamate Chemical compound C(N)(OCCN1CCN(CC1)C1=NC=C(C=C1)OC1=NC(=CC(=C1)CN1CCC(CC1)CNC(C)=O)C1=CC(=CC(=C1)Cl)Cl)=O NNBOEOHJHJRLDP-UHFFFAOYSA-N 0.000 claims 1
- VEBQXOBSVMVIKY-UHFFFAOYSA-N 2-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]ethylphosphonic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCP(O)(O)=O VEBQXOBSVMVIKY-UHFFFAOYSA-N 0.000 claims 1
- QZSRTHDKVBOSRL-UHFFFAOYSA-N 2-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]ethylboronic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCB(O)O QZSRTHDKVBOSRL-UHFFFAOYSA-N 0.000 claims 1
- HRYHXFHXZVJLJK-UHFFFAOYSA-N 2-[4-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]piperazin-1-yl]-N-methylacetamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCN(CC1)CC(=O)NC)OC=1C=NC(=CC=1)N1CCNCC1 HRYHXFHXZVJLJK-UHFFFAOYSA-N 0.000 claims 1
- UNIDEGTZLGHJTK-UHFFFAOYSA-N 2-[[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]methyl]butanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CC(C(=O)O)CC UNIDEGTZLGHJTK-UHFFFAOYSA-N 0.000 claims 1
- WGBUVBWWWKVESR-ISILISOKSA-N 3-[(1S,5R)-3-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1C[C@H]2CC[C@@H](C1)N2CCC(=O)O WGBUVBWWWKVESR-ISILISOKSA-N 0.000 claims 1
- ISUBQZLSVNOIDI-QFIPXVFZSA-N 3-[(2S)-4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1C[C@@H](N(CC1)CCC(=O)O)C ISUBQZLSVNOIDI-QFIPXVFZSA-N 0.000 claims 1
- KPYRQEHFHYFONR-NRFANRHFSA-N 3-[(2S)-4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methoxycarbonylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1C[C@@H](N(CC1)CCC(=O)O)C)CN1CCC(CC1)CNC(=O)OC KPYRQEHFHYFONR-NRFANRHFSA-N 0.000 claims 1
- YSIBHUAVANCUQW-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C(=O)O)C)OC=1C=NC(=NC=1)N1CCNCC1 YSIBHUAVANCUQW-UHFFFAOYSA-N 0.000 claims 1
- NFEXBHGYAKOEIC-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCC(=O)O)OC=1C=NC(=CC=1)N1CCNCC1 NFEXBHGYAKOEIC-UHFFFAOYSA-N 0.000 claims 1
- NDHVYFLDZGNGOP-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]azetidin-3-yl]butanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CC(C1)C(CC(=O)O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C NDHVYFLDZGNGOP-UHFFFAOYSA-N 0.000 claims 1
- AILLYPQKEJKKQU-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-2-hydroxypropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C(=O)O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C AILLYPQKEJKKQU-UHFFFAOYSA-N 0.000 claims 1
- DZPXARBHSNBMCW-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C(=O)O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C DZPXARBHSNBMCW-UHFFFAOYSA-N 0.000 claims 1
- FTJAICRAXZPDTP-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)C FTJAICRAXZPDTP-UHFFFAOYSA-N 0.000 claims 1
- ZQIHXQLCIRSQKL-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCC(=O)O)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)C ZQIHXQLCIRSQKL-UHFFFAOYSA-N 0.000 claims 1
- SMGBCEXNTVJFOQ-FOIFJWKZSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C(=O)O)C)OC=1C=NC(=NC=1)N1CCN(CC1)C[C@@H](C)O SMGBCEXNTVJFOQ-FOIFJWKZSA-N 0.000 claims 1
- GUWZQPRSWCZCLV-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CC(C(=O)O)C)OC=1C=NC(=CC=1)N1CCN(CC1)C GUWZQPRSWCZCLV-UHFFFAOYSA-N 0.000 claims 1
- WIWOEJXBVFWBJO-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(2-hydroxyethyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)CCO WIWOEJXBVFWBJO-UHFFFAOYSA-N 0.000 claims 1
- GWKPDJYVHOUQAY-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CCC(=O)O)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(=O)(=O)C GWKPDJYVHOUQAY-UHFFFAOYSA-N 0.000 claims 1
- FZABWKUTLZYFGR-UHFFFAOYSA-N 3-[3-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CC2CCC(C1)N2CCC(=O)O FZABWKUTLZYFGR-UHFFFAOYSA-N 0.000 claims 1
- OCCYVWVAGIUREZ-UHFFFAOYSA-N 3-[3-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methoxycarbonylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CC2CCC(C1)N2CCC(=O)O)CN1CCC(CC1)CNC(=O)OC OCCYVWVAGIUREZ-UHFFFAOYSA-N 0.000 claims 1
- HAFOUJCBWUBLTN-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(2-amino-2-oxoethyl)piperazin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound NC(CN1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)=O HAFOUJCBWUBLTN-UHFFFAOYSA-N 0.000 claims 1
- PPZLCSSCMFXLEO-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(2-carbamoyloxyethyl)piperazin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=O)OCCN1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O PPZLCSSCMFXLEO-UHFFFAOYSA-N 0.000 claims 1
- WYTHEEPLFPJTGI-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(2-carbamoyloxyethyl)piperazin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=O)OCCN1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O WYTHEEPLFPJTGI-UHFFFAOYSA-N 0.000 claims 1
- IGISMSHVUOFFFA-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(3-amino-3-oxopropyl)piperazin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound NC(CCN1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)=O IGISMSHVUOFFFA-UHFFFAOYSA-N 0.000 claims 1
- GCSCMNUYGUOWFY-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxy-3-fluoropyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=C(C(=NC=1)N1CCN(CC1)CCC(=O)O)F GCSCMNUYGUOWFY-UHFFFAOYSA-N 0.000 claims 1
- SQNPBLTTXRJFDR-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]-1,4-diazepan-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CCC1)CCC(=O)O SQNPBLTTXRJFDR-UHFFFAOYSA-N 0.000 claims 1
- BXJGZCOEQLYXOK-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]-2,2-dimethylpiperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CC(N(CC1)CCC(=O)O)(C)C BXJGZCOEQLYXOK-UHFFFAOYSA-N 0.000 claims 1
- MYIOGWRORXATBZ-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]-2,2-dimethylpropanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CC(C(=O)O)(C)C MYIOGWRORXATBZ-UHFFFAOYSA-N 0.000 claims 1
- PGUCQMJFBJMXGX-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]butanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)C(CC(=O)O)C PGUCQMJFBJMXGX-UHFFFAOYSA-N 0.000 claims 1
- SRIFUIFCXHGOKD-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanamide Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)N SRIFUIFCXHGOKD-UHFFFAOYSA-N 0.000 claims 1
- YLKNCNAEPRSZSL-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O YLKNCNAEPRSZSL-UHFFFAOYSA-N 0.000 claims 1
- NLQBEDHVGYRHAZ-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]-2-hydroxypropanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CC(C(=O)O)O NLQBEDHVGYRHAZ-UHFFFAOYSA-N 0.000 claims 1
- ATBAQBLKRFTELF-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]-2-methylpropanamide Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CC(C(=O)N)C ATBAQBLKRFTELF-UHFFFAOYSA-N 0.000 claims 1
- FJBKTIFXTBIKFY-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]-2-methylpropanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CC(C(=O)O)C FJBKTIFXTBIKFY-UHFFFAOYSA-N 0.000 claims 1
- VYYLLVDEHPHISD-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]-N-methylpropanamide Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)NC VYYLLVDEHPHISD-UHFFFAOYSA-N 0.000 claims 1
- NFIQXXQFBPAEGV-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]butanamide Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)C(CC(=O)N)C NFIQXXQFBPAEGV-UHFFFAOYSA-N 0.000 claims 1
- XBTFDELNNXKOQL-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]butanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)C(CC(=O)O)C XBTFDELNNXKOQL-UHFFFAOYSA-N 0.000 claims 1
- OJEZMYXSGCZVCU-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]cyclobutane-1-carboxylic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)C1CC(C1)C(=O)O OJEZMYXSGCZVCU-UHFFFAOYSA-N 0.000 claims 1
- MAQHVCWTNAAYMI-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanamide Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)N MAQHVCWTNAAYMI-UHFFFAOYSA-N 0.000 claims 1
- DIZGFRSKRZZKAK-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O DIZGFRSKRZZKAK-UHFFFAOYSA-N 0.000 claims 1
- UZCPNKCNMLNQDF-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3-bromo-5-fluorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)F)Br)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O UZCPNKCNMLNQDF-UHFFFAOYSA-N 0.000 claims 1
- XQMDUMCMPTYZPZ-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3-chloro-4,5-difluorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanamide Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=C(C(=C1)F)F)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)N XQMDUMCMPTYZPZ-UHFFFAOYSA-N 0.000 claims 1
- GTVPXSCDPKRMDA-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3-chloro-5-fluorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)F)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O GTVPXSCDPKRMDA-UHFFFAOYSA-N 0.000 claims 1
- NQDSJNTVTYBYGV-UHFFFAOYSA-N 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-[3-chloro-5-(difluoromethyl)phenyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)C(F)F)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O NQDSJNTVTYBYGV-UHFFFAOYSA-N 0.000 claims 1
- BGXBDFVQPYZDLY-UHFFFAOYSA-N 3-[4-[5-[4-[[4-[(cyclopropanecarbonylamino)methyl]piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C1(CC1)C(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O BGXBDFVQPYZDLY-UHFFFAOYSA-N 0.000 claims 1
- YWVCLWUEOMASGI-UHFFFAOYSA-N 3-[4-[5-[4-[[4-[(cyclopropanecarbonylamino)methyl]piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C1(CC1)C(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O YWVCLWUEOMASGI-UHFFFAOYSA-N 0.000 claims 1
- SOUOUKOCSPXAGN-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-(methylaminomethyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CNC SOUOUKOCSPXAGN-UHFFFAOYSA-N 0.000 claims 1
- ISLDIHMIPGDOMM-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(2-methylsulfonylethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CCS(=O)(=O)C ISLDIHMIPGDOMM-UHFFFAOYSA-N 0.000 claims 1
- ZPFLLYVHVNYWKO-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(2-sulfamoylethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CCS(N)(=O)=O ZPFLLYVHVNYWKO-UHFFFAOYSA-N 0.000 claims 1
- CUZGBMRVPFIDGG-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(dimethylphosphorylmethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CP(=O)(C)C CUZGBMRVPFIDGG-UHFFFAOYSA-N 0.000 claims 1
- BAIUJVZGILSXTP-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(methanesulfonamidomethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CNS(=O)(=O)C BAIUJVZGILSXTP-UHFFFAOYSA-N 0.000 claims 1
- SYVGOKUTDSGVOF-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(methylcarbamoyloxymethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)COC(NC)=O SYVGOKUTDSGVOF-UHFFFAOYSA-N 0.000 claims 1
- QPHCUAVSHDYATD-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(methylcarbamoyloxymethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]cyclobutane-1-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)C1CC(C1)C(=O)O)CN1CCC(CC1)COC(NC)=O QPHCUAVSHDYATD-UHFFFAOYSA-N 0.000 claims 1
- MKKBPROGCXUAMN-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(methylcarbamoyloxymethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)COC(NC)=O MKKBPROGCXUAMN-UHFFFAOYSA-N 0.000 claims 1
- MACKPBPMUDSERF-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(methylsulfonylmethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CS(=O)(=O)C MACKPBPMUDSERF-UHFFFAOYSA-N 0.000 claims 1
- IZVBHOGCZSHVDH-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-(sulfamoylmethyl)piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CS(N)(=O)=O IZVBHOGCZSHVDH-UHFFFAOYSA-N 0.000 claims 1
- UZSRCCAUCAXPSD-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(ethoxycarbonylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CNC(=O)OCC UZSRCCAUCAXPSD-UHFFFAOYSA-N 0.000 claims 1
- NKTCQGNRVMEMDD-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methoxycarbonylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CNC(=O)OC NKTCQGNRVMEMDD-UHFFFAOYSA-N 0.000 claims 1
- DQVSCMUKWLHSNX-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxy-3-fluoropyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=C(C(=NC=1)N1CCN(CC1)CCC(=O)O)F)CN1CCC(CC1)CNC(=O)NC DQVSCMUKWLHSNX-UHFFFAOYSA-N 0.000 claims 1
- XHGOUJUCYUYWRN-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CNC(=O)NC XHGOUJUCYUYWRN-UHFFFAOYSA-N 0.000 claims 1
- CYOIADMGZQAPHK-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]-2-methylpropanamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CC(C(=O)N)C)CN1CCC(CC1)CNC(=O)NC CYOIADMGZQAPHK-UHFFFAOYSA-N 0.000 claims 1
- WPYCEJOOFZXOJZ-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]cyclobutane-1-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)C1CC(C1)C(=O)O)CN1CCC(CC1)CNC(=O)NC WPYCEJOOFZXOJZ-UHFFFAOYSA-N 0.000 claims 1
- YDYSAQMBJICACE-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)N)CN1CCC(CC1)CNC(=O)NC YDYSAQMBJICACE-UHFFFAOYSA-N 0.000 claims 1
- AMIIINFQRNFYAA-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CNC(=O)NC AMIIINFQRNFYAA-UHFFFAOYSA-N 0.000 claims 1
- VCNPPXARUSGRDF-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-[2-(ethylamino)-2-oxoethyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)CC(=O)NCC VCNPPXARUSGRDF-UHFFFAOYSA-N 0.000 claims 1
- ISOYIASXTSAFHJ-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-fluoro-4-[(methoxycarbonylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)O)CN1CCC(CC1)(CNC(=O)OC)F ISOYIASXTSAFHJ-UHFFFAOYSA-N 0.000 claims 1
- LBXBFSZAOFNKOG-UHFFFAOYSA-N 3-[4-[5-[6-(3,5-dichlorophenyl)-4-[[4-hydroxy-4-[(methylcarbamoylamino)methyl]piperidin-1-yl]methyl]pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanamide Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=CC(=CC(=N1)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)N)CN1CCC(CC1)(CNC(=O)NC)O LBXBFSZAOFNKOG-UHFFFAOYSA-N 0.000 claims 1
- GYOSYUQTOXVNCP-UHFFFAOYSA-N 4-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)-3-fluoropyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]-2-methylbutanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=C(C(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(C(=O)O)C)F GYOSYUQTOXVNCP-UHFFFAOYSA-N 0.000 claims 1
- BVVOGLXAECFGHV-UHFFFAOYSA-N 4-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]-2-ethylbutanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(C(=O)O)CC BVVOGLXAECFGHV-UHFFFAOYSA-N 0.000 claims 1
- CSSLXMCVNNKBHV-UHFFFAOYSA-N 4-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]-2-methylbutanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(C(=O)O)C CSSLXMCVNNKBHV-UHFFFAOYSA-N 0.000 claims 1
- JIULTJUKZWNUQG-UHFFFAOYSA-N 4-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]butanoic acid Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCCC(=O)O JIULTJUKZWNUQG-UHFFFAOYSA-N 0.000 claims 1
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- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- XASIMHXSUQUHLV-UHFFFAOYSA-N camostat Chemical group C1=CC(CC(=O)OCC(=O)N(C)C)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 XASIMHXSUQUHLV-UHFFFAOYSA-N 0.000 claims 1
- 229960000772 camostat Drugs 0.000 claims 1
- PIHPSKJRLDSJPX-UHFFFAOYSA-N ethyl n-carbamoylcarbamate Chemical compound CCOC(=O)NC(N)=O PIHPSKJRLDSJPX-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000035800 maturation Effects 0.000 claims 1
- ZEMFZMXOSDVLJF-UHFFFAOYSA-N methyl 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoate Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)OC ZEMFZMXOSDVLJF-UHFFFAOYSA-N 0.000 claims 1
- KFTQAHLVLBNYQW-UHFFFAOYSA-N methyl 3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyrimidin-2-yl]piperazin-1-yl]propanoate Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=NC(=NC=1)N1CCN(CC1)CCC(=O)OC KFTQAHLVLBNYQW-UHFFFAOYSA-N 0.000 claims 1
- LCYYGKQJAFAREH-UHFFFAOYSA-N methyl N-[3-[4-[5-[4-[[4-(acetamidomethyl)piperidin-1-yl]methyl]-6-(3,5-dichlorophenyl)pyridin-2-yl]oxypyridin-2-yl]piperazin-1-yl]propanoyl]carbamate Chemical compound C(C)(=O)NCC1CCN(CC1)CC1=CC(=NC(=C1)C1=CC(=CC(=C1)Cl)Cl)OC=1C=CC(=NC=1)N1CCN(CC1)CCC(=O)NC(OC)=O LCYYGKQJAFAREH-UHFFFAOYSA-N 0.000 claims 1
- QNDUHJPDVXSFJI-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=NC=1)N1CCNCC1 QNDUHJPDVXSFJI-UHFFFAOYSA-N 0.000 claims 1
- OMHJCKLDTXYQGJ-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]-4-hydroxypiperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)(O)CNC(OC)=O)OC=1C=NC(=CC=1)N1CCNCC1 OMHJCKLDTXYQGJ-UHFFFAOYSA-N 0.000 claims 1
- IPHVEJLPTDGKLQ-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-(6-piperazin-1-ylpyridin-3-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=CC=1)N1CCNCC1 IPHVEJLPTDGKLQ-UHFFFAOYSA-N 0.000 claims 1
- MCTNDUNMSMVTAF-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=NC=1)N1CCN(CC1)C MCTNDUNMSMVTAF-UHFFFAOYSA-N 0.000 claims 1
- CSSSNJFUGKHZRX-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(2-hydroxyethyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=NC=1)N1CCN(CC1)CCO CSSSNJFUGKHZRX-UHFFFAOYSA-N 0.000 claims 1
- PNICXPHIMYQUQE-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=NC=1)N1CCN(CC1)CCCS(=O)(=O)C PNICXPHIMYQUQE-UHFFFAOYSA-N 0.000 claims 1
- PZJGFTBFNVJVGC-OAQYLSRUSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-[2-[4-[(2R)-2-hydroxypropyl]piperazin-1-yl]pyrimidin-5-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=NC=1)N1CCN(CC1)C[C@@H](C)O PZJGFTBFNVJVGC-OAQYLSRUSA-N 0.000 claims 1
- STMJMWVJSYGCHO-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=CC=1)N1CCN(CC1)C STMJMWVJSYGCHO-UHFFFAOYSA-N 0.000 claims 1
- AXWBZUYAVMNCGI-UHFFFAOYSA-N methyl N-[[1-[[2-(3,5-dichlorophenyl)-6-[6-[4-(3-methylsulfonylpropyl)piperazin-1-yl]pyridin-3-yl]oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)Cl)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=CC=1)N1CCN(CC1)CCCS(=O)(=O)C AXWBZUYAVMNCGI-UHFFFAOYSA-N 0.000 claims 1
- TUNBKYBPBGMALQ-UHFFFAOYSA-N methyl N-[[1-[[2-(3-chloro-5-fluorophenyl)-6-(2-piperazin-1-ylpyrimidin-5-yl)oxypyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound ClC=1C=C(C=C(C=1)F)C1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)OC=1C=NC(=NC=1)N1CCNCC1 TUNBKYBPBGMALQ-UHFFFAOYSA-N 0.000 claims 1
- XYIVZVWUVKAPNH-UHFFFAOYSA-N methyl N-[[1-[[2-[2-(1,4-diazabicyclo[3.2.1]octan-4-yl)pyrimidin-5-yl]oxy-6-(3,5-dichlorophenyl)pyridin-4-yl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound N12CCN(C(CC1)C2)C1=NC=C(C=N1)OC1=NC(=CC(=C1)CN1CCC(CC1)CNC(OC)=O)C1=CC(=CC(=C1)Cl)Cl XYIVZVWUVKAPNH-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
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PCT/US2021/025382 WO2021202874A1 (en) | 2020-04-02 | 2021-04-01 | Furin inhibitors for treating coronavirus infections |
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US (1) | US20230149401A1 (he) |
EP (1) | EP4125897A1 (he) |
JP (1) | JP2023521032A (he) |
KR (1) | KR20220167296A (he) |
CN (1) | CN115666567A (he) |
AU (1) | AU2021249149A1 (he) |
CA (1) | CA3173921A1 (he) |
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CN112384509B (zh) * | 2018-05-11 | 2024-04-30 | 葛兰素史密斯克莱知识产权发展有限公司 | 弗林蛋白酶抑制剂 |
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