JP2012532931A5 - - Google Patents
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- JP2012532931A5 JP2012532931A5 JP2012520706A JP2012520706A JP2012532931A5 JP 2012532931 A5 JP2012532931 A5 JP 2012532931A5 JP 2012520706 A JP2012520706 A JP 2012520706A JP 2012520706 A JP2012520706 A JP 2012520706A JP 2012532931 A5 JP2012532931 A5 JP 2012532931A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- triazol
- phenyl
- carboxamide
- bipyridine
- 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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- -1 pyridin-1-yl Chemical group 0.000 claims 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 125000001475 halogen functional group Chemical group 0.000 claims 30
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000001408 amides Chemical class 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 7
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 150000003857 carboxamides Chemical class 0.000 claims 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- HSSJHMGCYYTGPL-UHFFFAOYSA-N 5-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-2,4-difluorobenzamide Chemical compound FC1=CC(F)=C(C=2C=NC(=CC=2)C2CC2)C=C1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 HSSJHMGCYYTGPL-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- HFWQWJJXZZFIMY-HNNXBMFYSA-N 3-(4,5-dimethylimidazol-1-yl)-n-[6-[4-[(2s)-1,1,1-trifluoropropan-2-yl]-1,2,4-triazol-3-yl]pyridin-2-yl]benzamide Chemical compound FC(F)(F)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2C=C(C=CC=2)N2C(=C(C)N=C2)C)=N1 HFWQWJJXZZFIMY-HNNXBMFYSA-N 0.000 claims 2
- WUSUSCGYDUUQMW-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]benzamide Chemical compound C=1C=CC(N2C=C(N=C2)C2CC2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 WUSUSCGYDUUQMW-UHFFFAOYSA-N 0.000 claims 2
- PDZGDWMWTABMGZ-IBGZPJMESA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-[4-[(1s)-1-phenylethyl]-1,2,4-triazol-3-yl]pyridin-2-yl]benzamide Chemical compound C1([C@H](C)N2C(=NN=C2)C=2N=C(NC(=O)C=3C=C(C=CC=3)N3C=C(N=C3)C3CC3)C=CC=2)=CC=CC=C1 PDZGDWMWTABMGZ-IBGZPJMESA-N 0.000 claims 2
- CPRSZYIJYCFPHV-UHFFFAOYSA-N 4-(2-cyclopropylpyrimidin-5-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=NC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 CPRSZYIJYCFPHV-UHFFFAOYSA-N 0.000 claims 2
- ZGCMQKWOUIMBEP-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2C=C(N=C2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 ZGCMQKWOUIMBEP-UHFFFAOYSA-N 0.000 claims 2
- CWZONKSGCPUCFJ-AWEZNQCLSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[3-[4-[(2s)-1,1,1-trifluoropropan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=C1 CWZONKSGCPUCFJ-AWEZNQCLSA-N 0.000 claims 2
- OHYKJIGILBYHKC-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 OHYKJIGILBYHKC-UHFFFAOYSA-N 0.000 claims 2
- XDUJYPJVBLAJKJ-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 XDUJYPJVBLAJKJ-UHFFFAOYSA-N 0.000 claims 2
- UIQLWDNHZZPCHD-UHFFFAOYSA-N 4-chloro-5-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-2-fluorobenzamide Chemical compound FC1=CC(Cl)=C(C=2C=NC(=CC=2)C2CC2)C=C1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 UIQLWDNHZZPCHD-UHFFFAOYSA-N 0.000 claims 2
- PRHILGIXJLEDBO-UHFFFAOYSA-N 6-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC(C=2C=NC(=CC=2)C2CC2)=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PRHILGIXJLEDBO-UHFFFAOYSA-N 0.000 claims 2
- 229940127254 ASK1 inhibitor Drugs 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- XXOBJQOBXLLMMT-UHFFFAOYSA-N C1(CC1)N1C(=NN=C1)C1=CC=CC(=N1)N1C(C=C(C=C1)N1C=NC(=C1C)C)C Chemical compound C1(CC1)N1C(=NN=C1)C1=CC=CC(=N1)N1C(C=C(C=C1)N1C=NC(=C1C)C)C XXOBJQOBXLLMMT-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- OPARQLUIZUMIQR-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[5-methyl-4-(trifluoromethyl)-6,7-dihydro-4h-imidazo[4,5-c]pyridin-1-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1N(C)CCC2=C1N=CN2C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 OPARQLUIZUMIQR-UHFFFAOYSA-N 0.000 claims 2
- KWOXVXDOTCOBNJ-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(2,2,2-trifluoroethyl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(CC(F)(F)F)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 KWOXVXDOTCOBNJ-UHFFFAOYSA-N 0.000 claims 2
- HXMHZJPPAYHFEW-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-quinolin-3-ylbenzamide Chemical compound C=1C=CC(C=2C=C3C=CC=CC3=NC=2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 HXMHZJPPAYHFEW-UHFFFAOYSA-N 0.000 claims 2
- JDUSJBULPNMZIP-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CC=NC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 JDUSJBULPNMZIP-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 2
- UYURQXWMXAOMBK-UHFFFAOYSA-N 1-[3-[[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]carbamoyl]phenyl]-5-methylimidazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)N=CN1C1=CC=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 UYURQXWMXAOMBK-UHFFFAOYSA-N 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- PWRAOHMWIGDSPU-UHFFFAOYSA-N 2-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-4-carboxamide Chemical compound C=1C=NC(C=2C=NC(=CC=2)C2CC2)=CC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PWRAOHMWIGDSPU-UHFFFAOYSA-N 0.000 claims 1
- ANEKNGXSOTWRDL-UHFFFAOYSA-N 2-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]pyridine-4-carboxamide Chemical compound C=1C=NC(C=2C=NC(=CC=2)C2CC2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 ANEKNGXSOTWRDL-UHFFFAOYSA-N 0.000 claims 1
- ORYZBUNRYCVWJA-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-2-methylbenzamide Chemical compound CC1=C(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)C=CC=C1N(C=1)C=NC=1C1CC1 ORYZBUNRYCVWJA-UHFFFAOYSA-N 0.000 claims 1
- CLWNEOXYSGKKIM-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)C=C1N(C=1)C=NC=1C1CC1 CLWNEOXYSGKKIM-UHFFFAOYSA-N 0.000 claims 1
- QHAUPWYENQTMNO-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)C=C1N(C=1)C=NC=1C1CC1 QHAUPWYENQTMNO-UHFFFAOYSA-N 0.000 claims 1
- SVYPENLGHUOCQD-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-5-fluorobenzamide Chemical compound C=1C(F)=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=CC=1N(C=1)C=NC=1C1CC1 SVYPENLGHUOCQD-UHFFFAOYSA-N 0.000 claims 1
- ZRGFHFVCJIZWJJ-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-5-methylbenzamide Chemical compound C=1C(C)=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=CC=1N(C=1)C=NC=1C1CC1 ZRGFHFVCJIZWJJ-UHFFFAOYSA-N 0.000 claims 1
- JFRSLEBBTJAYKT-UHFFFAOYSA-N 3-(4-cyclopropylimidazol-1-yl)-n-[6-(4-propan-2-yl-1,2,4-triazol-3-yl)pyridin-2-yl]benzamide Chemical compound CC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2C=C(C=CC=2)N2C=C(N=C2)C2CC2)=N1 JFRSLEBBTJAYKT-UHFFFAOYSA-N 0.000 claims 1
- SJKYOXDWFILZJJ-UHFFFAOYSA-N 3-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]benzamide Chemical compound C=1C=CC(C=2C=NC(=CC=2)C2CC2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 SJKYOXDWFILZJJ-UHFFFAOYSA-N 0.000 claims 1
- OPVNUCOTCYNSIT-UHFFFAOYSA-N 4-(2-aminopyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound NC1=NC=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 OPVNUCOTCYNSIT-UHFFFAOYSA-N 0.000 claims 1
- WBEYBRYJAQKIBV-UHFFFAOYSA-N 4-(2-aminopyrimidin-5-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C1=NC(N)=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 WBEYBRYJAQKIBV-UHFFFAOYSA-N 0.000 claims 1
- ZLXNFEXYBUQYRS-UHFFFAOYSA-N 4-(3-aminopyrrolidin-1-yl)-n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)N2CC(N)CC2)=C1 ZLXNFEXYBUQYRS-UHFFFAOYSA-N 0.000 claims 1
- VDHWXRVYARKNEN-UHFFFAOYSA-N 4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2ON=C(N=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 VDHWXRVYARKNEN-UHFFFAOYSA-N 0.000 claims 1
- YHJZYWIEDZFZTC-UHFFFAOYSA-N 4-(3-cyclopropyl-1,2,4-triazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2N=C(N=C2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 YHJZYWIEDZFZTC-UHFFFAOYSA-N 0.000 claims 1
- ATWVMVICZNEPIS-UHFFFAOYSA-N 4-(3-methylimidazol-4-yl)-n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CN1C=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C)=C1 ATWVMVICZNEPIS-UHFFFAOYSA-N 0.000 claims 1
- COAIOYUZIYDHHI-UHFFFAOYSA-N 4-(4-chloroimidazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C1=NC(Cl)=CN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 COAIOYUZIYDHHI-UHFFFAOYSA-N 0.000 claims 1
- PVPSFOMUSUJVJD-UHFFFAOYSA-N 4-(4-cyclopropyl-2-methylimidazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CC1=NC(C2CC2)=CN1C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PVPSFOMUSUJVJD-UHFFFAOYSA-N 0.000 claims 1
- DDZYGVDJIIXACJ-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-2-methyl-1-[3-(4-pyridin-2-yl-1,2,4-triazol-3-yl)phenyl]-2H-pyridine Chemical compound C1(CC1)C=1N=CN(C=1)C1=CC(N(C=C1)C1=CC(=CC=C1)C1=NN=CN1C1=NC=CC=C1)C DDZYGVDJIIXACJ-UHFFFAOYSA-N 0.000 claims 1
- UIZCAIJJBDQQHD-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[3-(4-propan-2-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=C1 UIZCAIJJBDQQHD-UHFFFAOYSA-N 0.000 claims 1
- VJOPVYDEOJCVGW-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[3-[4-(1-phenylethyl)-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound C1=NN=C(C=2C=C(NC(=O)C=3N=CC=C(C=3)N3C=C(N=C3)C3CC3)C=CC=2)N1C(C)C1=CC=CC=C1 VJOPVYDEOJCVGW-UHFFFAOYSA-N 0.000 claims 1
- LSEDGIXFBSWZKL-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[3-[4-(cyclopropylmethyl)-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2C=C(N=C2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1CC1CC1 LSEDGIXFBSWZKL-UHFFFAOYSA-N 0.000 claims 1
- KMWDQIUOZZDYRN-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound C=1C(N2C=C(N=C2)C2CC2)=CC=NC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 KMWDQIUOZZDYRN-UHFFFAOYSA-N 0.000 claims 1
- TVDPMASDODMCGQ-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]quinoline-2-carboxamide Chemical compound C=1C(N2C=C(N=C2)C2CC2)=C2C=CC=CC2=NC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 TVDPMASDODMCGQ-UHFFFAOYSA-N 0.000 claims 1
- DLKPXPZUVSZPGK-UHFFFAOYSA-N 4-(4-cyclopropylphenyl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=CC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 DLKPXPZUVSZPGK-UHFFFAOYSA-N 0.000 claims 1
- KBRLQVBGSCHYKI-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C)=C1 KBRLQVBGSCHYKI-UHFFFAOYSA-N 0.000 claims 1
- HNYNGXKHKFGVBR-UHFFFAOYSA-N 4-(5-chloro-6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound ClC1=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=CN=C1C1CC1 HNYNGXKHKFGVBR-UHFFFAOYSA-N 0.000 claims 1
- XMIDMDWLWJGOJO-UHFFFAOYSA-N 4-(5-chloro-6-ethylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C1=C(Cl)C(CC)=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 XMIDMDWLWJGOJO-UHFFFAOYSA-N 0.000 claims 1
- PPJNKMGNBFLTBW-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound ClC1=CN=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 PPJNKMGNBFLTBW-UHFFFAOYSA-N 0.000 claims 1
- MPPHLNGBNOKFMV-UHFFFAOYSA-N 4-(5-cyanopyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=C(C=NC=2)C#N)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 MPPHLNGBNOKFMV-UHFFFAOYSA-N 0.000 claims 1
- NGSRPODQIQEEMR-UHFFFAOYSA-N 4-(5-cyclopropyl-1,2,4-triazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2C(=NC=N2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 NGSRPODQIQEEMR-UHFFFAOYSA-N 0.000 claims 1
- CZIUEMXDLQZYGK-UHFFFAOYSA-N 4-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2SC(=NN=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 CZIUEMXDLQZYGK-UHFFFAOYSA-N 0.000 claims 1
- RLGFHCROFVRTAF-UHFFFAOYSA-N 4-(5-cyclopropylpyrazin-2-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2N=CC(=NC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 RLGFHCROFVRTAF-UHFFFAOYSA-N 0.000 claims 1
- HZRLUTSOXHJXOK-UHFFFAOYSA-N 4-(5-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=C(C=NC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 HZRLUTSOXHJXOK-UHFFFAOYSA-N 0.000 claims 1
- IFASTQOSKKEWDD-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound COC1=CN=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C)=C1 IFASTQOSKKEWDD-UHFFFAOYSA-N 0.000 claims 1
- QXPYZSBTIUATJG-UHFFFAOYSA-N 4-(6-aminopyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C1=NC(N)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 QXPYZSBTIUATJG-UHFFFAOYSA-N 0.000 claims 1
- BDFOJJBACAFICD-UHFFFAOYSA-N 4-(6-cyclobutyloxypyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(OC3CCC3)=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 BDFOJJBACAFICD-UHFFFAOYSA-N 0.000 claims 1
- FDGVSBVOFQXYQJ-UHFFFAOYSA-N 4-(6-cyclobutylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CCC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 FDGVSBVOFQXYQJ-UHFFFAOYSA-N 0.000 claims 1
- JDCRZLPHKMOKSG-UHFFFAOYSA-N 4-(6-cyclopentylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CCCC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 JDCRZLPHKMOKSG-UHFFFAOYSA-N 0.000 claims 1
- IDDSYESOBQTNGY-UHFFFAOYSA-N 4-(6-cyclopropyl-5-fluoropyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound FC1=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=CN=C1C1CC1 IDDSYESOBQTNGY-UHFFFAOYSA-N 0.000 claims 1
- KDAQKBWZTUGFQY-UHFFFAOYSA-N 4-(6-cyclopropyloxypyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(OC3CC3)=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 KDAQKBWZTUGFQY-UHFFFAOYSA-N 0.000 claims 1
- HEQPLJOZGXWHRJ-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[2-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-4-yl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=NC=1C1=NN=CN1C1CC1 HEQPLJOZGXWHRJ-UHFFFAOYSA-N 0.000 claims 1
- JCGCGDWQFBXIFS-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)-2-fluorophenyl]pyridine-2-carboxamide Chemical compound C1=CC=C(C=2N(C=NN=2)C2CC2)C(F)=C1NC(=O)C(N=CC=1)=CC=1C(C=N1)=CC=C1C1CC1 JCGCGDWQFBXIFS-UHFFFAOYSA-N 0.000 claims 1
- ZWUQCUNTWFRCNU-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)-4-fluorophenyl]pyridine-2-carboxamide Chemical compound C1=C(C=2N(C=NN=2)C2CC2)C(F)=CC=C1NC(=O)C(N=CC=1)=CC=1C(C=N1)=CC=C1C1CC1 ZWUQCUNTWFRCNU-UHFFFAOYSA-N 0.000 claims 1
- OSWJOKQOVKCHDS-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)-5-fluorophenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2N(C=NN=2)C2CC2)=CC(F)=CC=1NC(=O)C(N=CC=1)=CC=1C(C=N1)=CC=C1C1CC1 OSWJOKQOVKCHDS-UHFFFAOYSA-N 0.000 claims 1
- HQMYIKNYYOEUJH-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-5-methylpyridine-2-carboxamide Chemical compound CC1=CN=C(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)C=C1C(C=N1)=CC=C1C1CC1 HQMYIKNYYOEUJH-UHFFFAOYSA-N 0.000 claims 1
- PZAFLBLEILTJLN-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-6-methylpyridine-2-carboxamide Chemical compound N=1C(C)=CC(C=2C=NC(=CC=2)C2CC2)=CC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PZAFLBLEILTJLN-UHFFFAOYSA-N 0.000 claims 1
- XQPSTZRYCDCPTJ-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-pentan-3-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CCC(CC)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 XQPSTZRYCDCPTJ-UHFFFAOYSA-N 0.000 claims 1
- PQMGWGOFVWECKF-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-phenyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1=CC=CC=C1 PQMGWGOFVWECKF-UHFFFAOYSA-N 0.000 claims 1
- VDXZIYAQWPGUPS-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-propan-2-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 VDXZIYAQWPGUPS-UHFFFAOYSA-N 0.000 claims 1
- INTURJDUCNJHIF-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-pyridin-2-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1=CC=CC=N1 INTURJDUCNJHIF-UHFFFAOYSA-N 0.000 claims 1
- LCKILEVPLUIPKT-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-pyridin-3-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1=CC=CN=C1 LCKILEVPLUIPKT-UHFFFAOYSA-N 0.000 claims 1
- UPJTWKYDWVAZPN-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-pyridin-4-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1=CC=NC=C1 UPJTWKYDWVAZPN-UHFFFAOYSA-N 0.000 claims 1
- PTGTWYUFALWBHL-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-pyrimidin-5-yl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1=CN=CN=C1 PTGTWYUFALWBHL-UHFFFAOYSA-N 0.000 claims 1
- GORYCFWKSUNYCW-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-(1-pyridin-3-yloxypropan-2-yl)-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound C1=NN=C(C=2C=C(NC(=O)C=3N=CC=C(C=3)C=3C=NC(=CC=3)C3CC3)C=CC=2)N1C(C)COC1=CC=CN=C1 GORYCFWKSUNYCW-UHFFFAOYSA-N 0.000 claims 1
- NZVFKCPECCNKPL-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-(2-phenylcyclopropyl)-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1C1=CC=CC=C1 NZVFKCPECCNKPL-UHFFFAOYSA-N 0.000 claims 1
- WHDVUGOEWSJVPZ-HSZRJFAPSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-[(2r)-1-(2,6-dimethylphenoxy)propan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound C([C@@H](C)N1C(=NN=C1)C=1C=C(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)C=CC=1)OC1=C(C)C=CC=C1C WHDVUGOEWSJVPZ-HSZRJFAPSA-N 0.000 claims 1
- VWUVSQBHGIBXRT-HNNXBMFYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-[(2s)-1,1,1-trifluoropropan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 VWUVSQBHGIBXRT-HNNXBMFYSA-N 0.000 claims 1
- VRBJAMNRLJKDBF-KRWDZBQOSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-[(2s)-1-methoxypropan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound COC[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 VRBJAMNRLJKDBF-KRWDZBQOSA-N 0.000 claims 1
- TYFCBULBGOMMNM-SFHVURJKSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-[(2s)-3,3-dimethylbutan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound CC(C)(C)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 TYFCBULBGOMMNM-SFHVURJKSA-N 0.000 claims 1
- FXNORAMBZTUWTL-SFHVURJKSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-[(2s)-3-methylbutan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound CC(C)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 FXNORAMBZTUWTL-SFHVURJKSA-N 0.000 claims 1
- MFEGGOYIQWZCMZ-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-[4-[1-(2,2,2-trifluoroethoxy)propan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)COCC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 MFEGGOYIQWZCMZ-UHFFFAOYSA-N 0.000 claims 1
- HXYAABYWDBLUKS-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-5-methylpyridine-2-carboxamide Chemical compound CC1=CN=C(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)C=C1C(C=N1)=CC=C1C1CC1 HXYAABYWDBLUKS-UHFFFAOYSA-N 0.000 claims 1
- DEOJOKGSDYNDJQ-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-7,8-dimethylquinoline-2-carboxamide Chemical compound N=1C2=C(C)C(C)=CC=C2C(C=2C=NC(=CC=2)C2CC2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 DEOJOKGSDYNDJQ-UHFFFAOYSA-N 0.000 claims 1
- WEQUSOAFGUTBRD-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]quinoline-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=C2C=CC=CC2=NC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 WEQUSOAFGUTBRD-UHFFFAOYSA-N 0.000 claims 1
- IGQVVOYLYKCVIZ-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-(4-propan-2-yl-1,2,4-triazol-3-yl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound CC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=N1 IGQVVOYLYKCVIZ-UHFFFAOYSA-N 0.000 claims 1
- JFLVKJCZAVMEAA-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-[4-(1-pyrrolidin-1-ylpropan-2-yl)-1,2,4-triazol-3-yl]pyridin-2-yl]pyridine-2-carboxamide Chemical compound C1=NN=C(C=2N=C(NC(=O)C=3N=CC=C(C=3)C=3C=NC(=CC=3)C3CC3)C=CC=2)N1C(C)CN1CCCC1 JFLVKJCZAVMEAA-UHFFFAOYSA-N 0.000 claims 1
- MXYHSDMJCZGCDL-AAFJCEBUSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-[4-[(2r)-3-hydroxybutan-2-yl]-1,2,4-triazol-3-yl]pyridin-2-yl]pyridine-2-carboxamide Chemical compound CC(O)[C@@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=N1 MXYHSDMJCZGCDL-AAFJCEBUSA-N 0.000 claims 1
- MXYHSDMJCZGCDL-JKSUJKDBSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-[4-[(2s,3r)-3-hydroxybutan-2-yl]-1,2,4-triazol-3-yl]pyridin-2-yl]pyridine-2-carboxamide Chemical compound C[C@@H](O)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=N1 MXYHSDMJCZGCDL-JKSUJKDBSA-N 0.000 claims 1
- MXYHSDMJCZGCDL-HOTGVXAUSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[6-[4-[(2s,3s)-3-hydroxybutan-2-yl]-1,2,4-triazol-3-yl]pyridin-2-yl]pyridine-2-carboxamide Chemical compound C[C@H](O)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=N1 MXYHSDMJCZGCDL-HOTGVXAUSA-N 0.000 claims 1
- HTLNKQRNTPZZPF-UHFFFAOYSA-N 4-(6-tert-butylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C1=NC(C(C)(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 HTLNKQRNTPZZPF-UHFFFAOYSA-N 0.000 claims 1
- RHTBEYULLGYGIC-UHFFFAOYSA-N 4-(benzimidazol-1-yl)-n-[3-(3-cyclopropylimidazol-4-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2C3=CC=CC=C3N=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=CN=CN1C1CC1 RHTBEYULLGYGIC-UHFFFAOYSA-N 0.000 claims 1
- QYNIPIQABZPLGE-UHFFFAOYSA-N 4-(benzimidazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2C3=CC=CC=C3N=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 QYNIPIQABZPLGE-UHFFFAOYSA-N 0.000 claims 1
- HYJLJPAFUKVVIP-UHFFFAOYSA-N 4-(benzotriazol-1-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(N2C3=CC=CC=C3N=N2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 HYJLJPAFUKVVIP-UHFFFAOYSA-N 0.000 claims 1
- YMVHVUXATZHVLX-UHFFFAOYSA-N 4-[4-(cyclopropylsulfamoyl)phenyl]-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=CC(=CC=2)S(=O)(=O)NC2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 YMVHVUXATZHVLX-UHFFFAOYSA-N 0.000 claims 1
- PZHAJKQCOKCKIS-UHFFFAOYSA-N 4-[6-(cyclopropylamino)pyridin-3-yl]-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(NC3CC3)=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PZHAJKQCOKCKIS-UHFFFAOYSA-N 0.000 claims 1
- JYWXDSFQZPJKKN-UHFFFAOYSA-N 4-[6-(cyclopropylmethyl)pyridin-3-yl]-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(CC3CC3)=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 JYWXDSFQZPJKKN-UHFFFAOYSA-N 0.000 claims 1
- FTZBXWOSEDDENS-UHFFFAOYSA-N 4-imidazo[1,2-a]pyridin-3-yl-n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2)=C1 FTZBXWOSEDDENS-UHFFFAOYSA-N 0.000 claims 1
- DPIAFQOMVXIMSB-UHFFFAOYSA-N 4-pyridin-3-yl-n-[3-[4-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 DPIAFQOMVXIMSB-UHFFFAOYSA-N 0.000 claims 1
- LMBGTCSOQZKXEM-AWEZNQCLSA-N 4-pyridin-3-yl-n-[3-[4-[(2s)-1,1,1-trifluoropropan-2-yl]-1,2,4-triazol-3-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 LMBGTCSOQZKXEM-AWEZNQCLSA-N 0.000 claims 1
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- ZZGMGULKPVQEMW-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-propan-2-ylsulfonylphenyl)pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 ZZGMGULKPVQEMW-UHFFFAOYSA-N 0.000 claims 1
- PQLJPIXGFQFBLQ-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-sulfamoylphenyl)pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 PQLJPIXGFQFBLQ-UHFFFAOYSA-N 0.000 claims 1
- MOEIRIXQBVJSDL-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)pyridine-2-carboxamide Chemical compound C=1C(C=2C=C3CNCCC3=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 MOEIRIXQBVJSDL-UHFFFAOYSA-N 0.000 claims 1
- MGNBENZAYRLHPD-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(5,6-diethylpyridin-3-yl)pyridine-2-carboxamide Chemical compound N1=C(CC)C(CC)=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 MGNBENZAYRLHPD-UHFFFAOYSA-N 0.000 claims 1
- FPHNFBWCCUYIGD-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(5-ethylpyridin-3-yl)pyridine-2-carboxamide Chemical compound CCC1=CN=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 FPHNFBWCCUYIGD-UHFFFAOYSA-N 0.000 claims 1
- APNDFXWFNYAUPK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(5-fluoropyridin-3-yl)pyridine-2-carboxamide Chemical compound FC1=CN=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 APNDFXWFNYAUPK-UHFFFAOYSA-N 0.000 claims 1
- RKWNPZYNQWHMNW-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(5-methoxypyridin-3-yl)pyridine-2-carboxamide Chemical compound COC1=CN=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 RKWNPZYNQWHMNW-UHFFFAOYSA-N 0.000 claims 1
- SDDOJDLRNYWTLO-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-ethyl-5-fluoropyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=C(F)C(CC)=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 SDDOJDLRNYWTLO-UHFFFAOYSA-N 0.000 claims 1
- JVULQTVUMUMRAP-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-fluoro-5-methylpyridin-3-yl)pyridine-2-carboxamide Chemical compound N1=C(F)C(C)=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 JVULQTVUMUMRAP-UHFFFAOYSA-N 0.000 claims 1
- VEIPVPSITFJJBD-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-fluoropyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(F)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 VEIPVPSITFJJBD-UHFFFAOYSA-N 0.000 claims 1
- OCWFSCGCBTYILD-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-methoxypyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 OCWFSCGCBTYILD-UHFFFAOYSA-N 0.000 claims 1
- YGHFHYNCRXPLDS-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-methoxyquinolin-3-yl)pyridine-2-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2N=CC=1C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 YGHFHYNCRXPLDS-UHFFFAOYSA-N 0.000 claims 1
- BTZVLKJJVVPPJV-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-methylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 BTZVLKJJVVPPJV-UHFFFAOYSA-N 0.000 claims 1
- ULAMEPHYFLWXOF-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-methylsulfanylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(SC)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 ULAMEPHYFLWXOF-UHFFFAOYSA-N 0.000 claims 1
- LOXGOQPJODPIND-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-oxo-1h-pyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(O)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 LOXGOQPJODPIND-UHFFFAOYSA-N 0.000 claims 1
- ROXITARWDFOLPR-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-propan-2-yloxypyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(OC(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 ROXITARWDFOLPR-UHFFFAOYSA-N 0.000 claims 1
- KKPWBZLVANVAJH-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-propan-2-ylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(C(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 KKPWBZLVANVAJH-UHFFFAOYSA-N 0.000 claims 1
- QDYWHKKQBLXWBA-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-propylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(CCC)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 QDYWHKKQBLXWBA-UHFFFAOYSA-N 0.000 claims 1
- PTMFZWYUDDQMDS-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-pyrrolidin-1-ylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)N2CCCC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PTMFZWYUDDQMDS-UHFFFAOYSA-N 0.000 claims 1
- FMODEHMEPLTKHQ-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[1-(2,2,2-trifluoroethyl)pyrrolo[3,2-b]pyridin-6-yl]pyridine-2-carboxamide Chemical compound C1=C2N(CC(F)(F)F)C=CC2=NC=C1C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 FMODEHMEPLTKHQ-UHFFFAOYSA-N 0.000 claims 1
- IMIYTEJJZKVFNR-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(2,2,2-trifluoro-1-hydroxyethyl)imidazol-1-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(O)C(F)(F)F)=CN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 IMIYTEJJZKVFNR-UHFFFAOYSA-N 0.000 claims 1
- MLENIDSWDIOPDU-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(2-oxoimidazolidin-1-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=CC(=CC=2)N2C(NCC2)=O)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 MLENIDSWDIOPDU-UHFFFAOYSA-N 0.000 claims 1
- MCFXHZHKKLHALL-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(propan-2-ylsulfamoyl)phenyl]pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)NC(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 MCFXHZHKKLHALL-UHFFFAOYSA-N 0.000 claims 1
- MKBOTAVPIZHXSY-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(trifluoromethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridin-1-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1NCCC2=C1N=CN2C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 MKBOTAVPIZHXSY-UHFFFAOYSA-N 0.000 claims 1
- IQCMDAGESBTEGG-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(trifluoromethyl)imidazol-1-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(F)(F)F)=CN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 IQCMDAGESBTEGG-UHFFFAOYSA-N 0.000 claims 1
- PDPRUTBJSBYJMK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[5-(trifluoromethyl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1=CN=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 PDPRUTBJSBYJMK-UHFFFAOYSA-N 0.000 claims 1
- PKKTWVWHPTYOAW-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(1-methyl-2-oxopyrrolidin-3-yl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound O=C1N(C)CCC1C1=CC=C(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)C=N1 PKKTWVWHPTYOAW-UHFFFAOYSA-N 0.000 claims 1
- CDSVDQUEAQEVNU-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(OCC(F)(F)F)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 CDSVDQUEAQEVNU-UHFFFAOYSA-N 0.000 claims 1
- WLBOLZRNHWXDAF-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(2,2,2-trifluoroethyl)-7,8-dihydro-5h-1,6-naphthyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=C2CN(CC(F)(F)F)CCC2=NC=C1C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 WLBOLZRNHWXDAF-UHFFFAOYSA-N 0.000 claims 1
- HHYPKBOJJRBKOA-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(2,2-dimethylpropyl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(CC(C)(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 HHYPKBOJJRBKOA-UHFFFAOYSA-N 0.000 claims 1
- DVJLXJHDFJUWIS-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(2-methoxyethylamino)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(NCCOC)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 DVJLXJHDFJUWIS-UHFFFAOYSA-N 0.000 claims 1
- QJBICXBKPIAIDN-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(2-methylpropylsulfanyl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(SCC(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 QJBICXBKPIAIDN-UHFFFAOYSA-N 0.000 claims 1
- KQWPJCHHUHXQIW-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(dimethylamino)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 KQWPJCHHUHXQIW-UHFFFAOYSA-N 0.000 claims 1
- WIJIZIFAAWYWSS-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(ethylamino)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(NCC)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 WIJIZIFAAWYWSS-UHFFFAOYSA-N 0.000 claims 1
- CCAJGWCPXSPDAF-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[6-(trifluoromethyl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 CCAJGWCPXSPDAF-UHFFFAOYSA-N 0.000 claims 1
- PSIMXSRMFLQFGJ-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-furo[3,2-b]pyridin-6-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=C3OC=CC3=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 PSIMXSRMFLQFGJ-UHFFFAOYSA-N 0.000 claims 1
- GQHFMRSHSWGKLA-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-imidazo[1,2-a]pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2N3C=CC=CC3=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 GQHFMRSHSWGKLA-UHFFFAOYSA-N 0.000 claims 1
- WFGZWQJMZCICOK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-imidazo[4,5-b]pyridin-1-ylpyridine-2-carboxamide Chemical compound C=1C(N2C3=CC=CN=C3N=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 WFGZWQJMZCICOK-UHFFFAOYSA-N 0.000 claims 1
- BSAGZPRHCTWICK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-imidazo[4,5-b]pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(N2C3=NC=CC=C3N=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 BSAGZPRHCTWICK-UHFFFAOYSA-N 0.000 claims 1
- AWTXUPWCHCJCQT-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-imidazo[4,5-c]pyridin-1-ylpyridine-2-carboxamide Chemical compound C=1C(N2C3=CC=NC=C3N=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 AWTXUPWCHCJCQT-UHFFFAOYSA-N 0.000 claims 1
- SSBHVJGIWMTWBB-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-imidazol-1-ylpyridine-2-carboxamide Chemical compound C=1C(N2C=NC=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 SSBHVJGIWMTWBB-UHFFFAOYSA-N 0.000 claims 1
- CLPUKMIIBZWEIT-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-isoquinolin-4-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C3=CC=CC=C3C=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 CLPUKMIIBZWEIT-UHFFFAOYSA-N 0.000 claims 1
- FDENWWSRCRMZTK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-phenylpyridine-2-carboxamide Chemical compound C=1C(C=2C=CC=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 FDENWWSRCRMZTK-UHFFFAOYSA-N 0.000 claims 1
- QSLDECRRWPIQFB-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-pyrazin-2-ylpyridine-2-carboxamide Chemical compound C=1C(C=2N=CC=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 QSLDECRRWPIQFB-UHFFFAOYSA-N 0.000 claims 1
- WZOKIKOXWFAJPO-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-pyridin-3-yl-6-(trifluoromethyl)pyridine-2-carboxamide Chemical compound N=1C(C(F)(F)F)=CC(C=2C=NC=CC=2)=CC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 WZOKIKOXWFAJPO-UHFFFAOYSA-N 0.000 claims 1
- SZZKJPNBENKCOL-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 SZZKJPNBENKCOL-UHFFFAOYSA-N 0.000 claims 1
- CEUXPAJIHAMDHP-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-pyridin-3-ylquinoline-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=C2C=CC=CC2=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 CEUXPAJIHAMDHP-UHFFFAOYSA-N 0.000 claims 1
- DCOLXDBAPJCAFC-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-quinolin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=C3C=CC=CC3=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 DCOLXDBAPJCAFC-UHFFFAOYSA-N 0.000 claims 1
- WYJWCEANLTYWTF-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-2-phenylpyridine-4-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 WYJWCEANLTYWTF-UHFFFAOYSA-N 0.000 claims 1
- WOMAYAFDTFYGQZ-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-4-(3-oxopiperazin-1-yl)pyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)N2CC(=O)NCC2)=C1 WOMAYAFDTFYGQZ-UHFFFAOYSA-N 0.000 claims 1
- PKYSWTANUVYWLS-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-4-morpholin-4-ylpyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)N2CCOCC2)=C1 PKYSWTANUVYWLS-UHFFFAOYSA-N 0.000 claims 1
- PFSJJBKGIXSPHS-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-4-phenylpyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=CC=CC=2)=C1 PFSJJBKGIXSPHS-UHFFFAOYSA-N 0.000 claims 1
- JYQLUKILLCAADR-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 JYQLUKILLCAADR-UHFFFAOYSA-N 0.000 claims 1
- IAFYRYKGLRMXEU-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-5-phenylpyridine-3-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2C=C(C=NC=2)C=2C=CC=CC=2)=C1 IAFYRYKGLRMXEU-UHFFFAOYSA-N 0.000 claims 1
- ZSROJHFZIVYSMI-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-5-pyridin-3-ylpyridine-3-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2C=C(C=NC=2)C=2C=NC=CC=2)=C1 ZSROJHFZIVYSMI-UHFFFAOYSA-N 0.000 claims 1
- MKJSHVZGTNLRAM-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-6-phenylpyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=C(C=CC=2)C=2C=CC=CC=2)=C1 MKJSHVZGTNLRAM-UHFFFAOYSA-N 0.000 claims 1
- XZHNORWGXWLOLL-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-6-pyridin-3-ylpyridine-2-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=C(C=CC=2)C=2C=NC=CC=2)=C1 XZHNORWGXWLOLL-UHFFFAOYSA-N 0.000 claims 1
- YOZDNZWJLCHYAF-UHFFFAOYSA-N n-[3-(4-propan-2-yl-1,2,4-triazol-3-yl)phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound CC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 YOZDNZWJLCHYAF-UHFFFAOYSA-N 0.000 claims 1
- ZWGFJPOMULUDJA-UHFFFAOYSA-N n-[3-[4-(2-acetamidoethyl)-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound CC(=O)NCCN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 ZWGFJPOMULUDJA-UHFFFAOYSA-N 0.000 claims 1
- QJDGQFRJJWEABP-UHFFFAOYSA-N n-[3-[4-(3-amino-3-oxopropyl)-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound NC(=O)CCN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 QJDGQFRJJWEABP-UHFFFAOYSA-N 0.000 claims 1
- MMLSXESZMOJTSL-UHFFFAOYSA-N n-[3-[4-(cyclopropylmethyl)-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1CC1CC1 MMLSXESZMOJTSL-UHFFFAOYSA-N 0.000 claims 1
- CJMHCJTZSYOBPU-UHFFFAOYSA-N n-[3-[4-(oxan-4-yl)-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CCOCC1 CJMHCJTZSYOBPU-UHFFFAOYSA-N 0.000 claims 1
- CSCUXDGJDWIJCL-UHFFFAOYSA-N n-[3-[4-[(1-hydroxycyclopropyl)methyl]-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C1=NN=C(C=2C=C(NC(=O)C=3N=CC=C(C=3)C=3C=NC=CC=3)C=CC=2)N1CC1(O)CC1 CSCUXDGJDWIJCL-UHFFFAOYSA-N 0.000 claims 1
- BVOBNMVXPBIOMV-KRWDZBQOSA-N n-[3-[4-[(1s)-1-cyclopropylethyl]-1,2,4-triazol-3-yl]phenyl]-4-(6-cyclopropylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C1([C@H](C)N2C(=NN=C2)C=2C=C(NC(=O)C=3N=CC=C(C=3)C=3C=NC(=CC=3)C3CC3)C=CC=2)CC1 BVOBNMVXPBIOMV-KRWDZBQOSA-N 0.000 claims 1
- QSBUJZCNLVMSKA-OAHLLOKOSA-N n-[3-[4-[(2r)-1-hydroxypropan-2-yl]-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound OC[C@@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 QSBUJZCNLVMSKA-OAHLLOKOSA-N 0.000 claims 1
- LBFWQZDYRKJISZ-OAHLLOKOSA-N n-[3-[4-[(2r)-2-hydroxypropyl]-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C[C@@H](O)CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 LBFWQZDYRKJISZ-OAHLLOKOSA-N 0.000 claims 1
- QSBUJZCNLVMSKA-HNNXBMFYSA-N n-[3-[4-[(2s)-1-hydroxypropan-2-yl]-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound OC[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 QSBUJZCNLVMSKA-HNNXBMFYSA-N 0.000 claims 1
- LBFWQZDYRKJISZ-HNNXBMFYSA-N n-[3-[4-[(2s)-2-hydroxypropyl]-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C[C@H](O)CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC=CC=2)=C1 LBFWQZDYRKJISZ-HNNXBMFYSA-N 0.000 claims 1
- ZYYCJXOQDWDLGN-KRWDZBQOSA-N n-[3-[4-[(2s)-butan-2-yl]-1,2,4-triazol-3-yl]phenyl]-4-(6-cyclopropylpyridin-3-yl)pyridine-2-carboxamide Chemical compound CC[C@H](C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 ZYYCJXOQDWDLGN-KRWDZBQOSA-N 0.000 claims 1
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- FCPPUDFGPFUSRX-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-(4,5,6,7-tetrahydrobenzimidazol-1-yl)benzamide Chemical compound C=1C=CC(N2C=3CCCCC=3N=C2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 FCPPUDFGPFUSRX-UHFFFAOYSA-N 0.000 claims 1
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- PHLIEZXYUULPHF-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-(3-hydroxypiperidin-1-yl)pyridine-2-carboxamide Chemical compound C1C(O)CCCN1C1=CC=NC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 PHLIEZXYUULPHF-UHFFFAOYSA-N 0.000 claims 1
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- KJARSCYCCLZWRM-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-(4-ethyl-3-oxopiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1C(=O)N(CC)CCN1C1=CC=NC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 KJARSCYCCLZWRM-UHFFFAOYSA-N 0.000 claims 1
- VQPJSWDNPZOEKX-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-(4-methylimidazol-1-yl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CN1C1=CC=NC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 VQPJSWDNPZOEKX-UHFFFAOYSA-N 0.000 claims 1
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- HLVLRZLEIYSGOP-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-4-[4-(trifluoromethyl)imidazol-1-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(F)(F)F)=CN1C1=CC=NC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 HLVLRZLEIYSGOP-UHFFFAOYSA-N 0.000 claims 1
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- 2010-07-12 EP EP15151030.2A patent/EP2933252B1/en active Active
- 2010-07-12 PL PL17208659T patent/PL3363797T3/pl unknown
- 2010-07-12 KR KR1020187018679A patent/KR20180077338A/ko not_active Ceased
- 2010-07-12 HU HUE15151030A patent/HUE038529T2/hu unknown
- 2010-07-12 MX MX2012000708A patent/MX2012000708A/es active IP Right Grant
- 2010-07-12 NZ NZ597533A patent/NZ597533A/en unknown
- 2010-07-12 SI SI201030851T patent/SI2454250T1/sl unknown
- 2010-07-12 EP EP10733116.7A patent/EP2454250B1/en active Active
- 2010-07-12 PT PT151510302T patent/PT2933252T/pt unknown
- 2010-07-12 PL PL15151030T patent/PL2933252T3/pl unknown
- 2010-07-13 UY UY0001032786A patent/UY32786A/es not_active Application Discontinuation
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2012
- 2012-09-13 US US13/615,259 patent/US8552196B2/en not_active Ceased
- 2012-09-14 US US13/618,841 patent/US8598360B2/en active Active
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2013
- 2013-07-02 US US13/934,020 patent/US9067933B2/en active Active
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2015
- 2015-03-03 JP JP2015040924A patent/JP2015098500A/ja not_active Withdrawn
- 2015-04-13 SM SM201500090T patent/SMT201500090B/xx unknown
- 2015-05-19 US US14/716,526 patent/US9586932B2/en active Active
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2017
- 2017-01-19 JP JP2017007269A patent/JP2017071647A/ja not_active Withdrawn
- 2017-01-23 US US15/413,101 patent/US20170196844A1/en not_active Abandoned
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2018
- 2018-03-07 CY CY20181100283T patent/CY1119889T1/el unknown
- 2018-03-09 HR HRP20180413TT patent/HRP20180413T1/hr unknown
- 2018-08-01 JP JP2018144888A patent/JP2018184464A/ja active Pending
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2019
- 2019-08-01 US US16/529,631 patent/USRE48711E1/en active Active
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