SI2933252T1 - Kinase inhibitors as apoptotic signal regulators - Google Patents
Kinase inhibitors as apoptotic signal regulators Download PDFInfo
- Publication number
- SI2933252T1 SI2933252T1 SI201031622T SI201031622T SI2933252T1 SI 2933252 T1 SI2933252 T1 SI 2933252T1 SI 201031622 T SI201031622 T SI 201031622T SI 201031622 T SI201031622 T SI 201031622T SI 2933252 T1 SI2933252 T1 SI 2933252T1
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- SI
- Slovenia
- Prior art keywords
- cyclopropyl
- triazol
- phenyl
- carboxamide
- bipyridine
- Prior art date
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- 230000006907 apoptotic process Effects 0.000 title abstract 2
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- -1 oxa Chemical group 0.000 claims 79
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 239000003814 drug Substances 0.000 claims 15
- 229940124597 therapeutic agent Drugs 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 239000003242 anti bacterial agent Substances 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 208000030159 metabolic disease Diseases 0.000 claims 3
- 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
- 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 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 229940005513 antidepressants Drugs 0.000 claims 2
- 239000002220 antihypertensive agent Substances 0.000 claims 2
- 229940030600 antihypertensive agent Drugs 0.000 claims 2
- 239000003524 antilipemic agent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims 1
- 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
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 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
- 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 1
- VOTLSCJEAIOEMI-UHFFFAOYSA-N 3-(4-cyclopropyl-1,2,4-triazol-3-yl)aniline Chemical compound NC1=CC=CC(C=2N(C=NN=2)C2CC2)=C1 VOTLSCJEAIOEMI-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
- 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 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
- VXKNIUIYRGFKTJ-UHFFFAOYSA-N 3-(4-cyclopropyltriazol-1-yl)-n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]benzamide Chemical compound C=1C=CC(N2N=NC(=C2)C2CC2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 VXKNIUIYRGFKTJ-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
- 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 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
- 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
- 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 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
- 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
- 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
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- 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
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- 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
- 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
- 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
- DXTDBGZVYUUAGG-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-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(C=1)=CC=CC=1C1=NN=CN1C1CC1 DXTDBGZVYUUAGG-UHFFFAOYSA-N 0.000 claims 1
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- SOSKKYYLWDMZID-UHFFFAOYSA-N n-[3-(3-cyclopropylimidazol-4-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=CN=CN1C1CC1 SOSKKYYLWDMZID-UHFFFAOYSA-N 0.000 claims 1
- HKBWYBCOWCJXNN-UHFFFAOYSA-N n-[3-(3-cyclopropylimidazol-4-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=CN=CN1C1CC1 HKBWYBCOWCJXNN-UHFFFAOYSA-N 0.000 claims 1
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- ZYYCJXOQDWDLGN-UHFFFAOYSA-N n-[3-(4-butan-2-yl-1,2,4-triazol-3-yl)phenyl]-4-(6-cyclopropylpyridin-3-yl)pyridine-2-carboxamide Chemical compound CCC(C)N1C=NN=C1C1=CC=CC(NC(=O)C=2N=CC=C(C=2)C=2C=NC(=CC=2)C2CC2)=C1 ZYYCJXOQDWDLGN-UHFFFAOYSA-N 0.000 claims 1
- AOSNBVFWJSGSEZ-UHFFFAOYSA-N n-[3-(4-cyclobutyl-1,2,4-triazol-3-yl)phenyl]-4-(6-cyclopropylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CCC1 AOSNBVFWJSGSEZ-UHFFFAOYSA-N 0.000 claims 1
- XXESGZXHEMVWTN-UHFFFAOYSA-N n-[3-(4-cyclobutyl-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=CN1C1CCC1 XXESGZXHEMVWTN-UHFFFAOYSA-N 0.000 claims 1
- UZIRCFXJGVIITM-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)-2-fluorophenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C1=CC=C(C=2N(C=NN=2)C2CC2)C(F)=C1NC(=O)C(N=CC=1)=CC=1C1=CC=CN=C1 UZIRCFXJGVIITM-UHFFFAOYSA-N 0.000 claims 1
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- ZTXCAYUULVSBRA-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)-5-fluorophenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2N(C=NN=2)C2CC2)=CC(F)=CC=1NC(=O)C(N=CC=1)=CC=1C1=CC=CN=C1 ZTXCAYUULVSBRA-UHFFFAOYSA-N 0.000 claims 1
- KTYYSBXAPOFXOE-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(1,2,4-triazol-1-yl)pyridine-2-carboxamide Chemical compound C=1C(N2N=CN=C2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 KTYYSBXAPOFXOE-UHFFFAOYSA-N 0.000 claims 1
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- UDFRABUCTSRYSZ-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(1-propan-2-ylpyrrolo[3,2-b]pyridin-6-yl)pyridine-2-carboxamide Chemical compound C1=C2N(C(C)C)C=CC2=NC=C1C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 UDFRABUCTSRYSZ-UHFFFAOYSA-N 0.000 claims 1
- JPMSYGDPZSKASB-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyridine-2-carboxamide Chemical compound C=1C(C=2C=C3C=CNC3=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 JPMSYGDPZSKASB-UHFFFAOYSA-N 0.000 claims 1
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- ZLQWOOSBLKFTJK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(2,3-dimethylimidazol-4-yl)pyridine-2-carboxamide Chemical compound CN1C(C)=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 ZLQWOOSBLKFTJK-UHFFFAOYSA-N 0.000 claims 1
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- OYJLIFQRHBFKCI-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(2-methoxypyridin-3-yl)pyridine-2-carboxamide Chemical compound COC1=NC=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 OYJLIFQRHBFKCI-UHFFFAOYSA-N 0.000 claims 1
- NVEXBDJERAOQLO-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(2-methoxypyrimidin-5-yl)pyridine-2-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 NVEXBDJERAOQLO-UHFFFAOYSA-N 0.000 claims 1
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- XKEAFANWKQKVSQ-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(3-methylimidazol-4-yl)pyridine-2-carboxamide Chemical compound CN1C=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 XKEAFANWKQKVSQ-UHFFFAOYSA-N 0.000 claims 1
- NADWNJBMCHMGNU-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(3-methylsulfonylphenyl)pyridine-2-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=C(N=CC=2)C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 NADWNJBMCHMGNU-UHFFFAOYSA-N 0.000 claims 1
- MXTLRGXDTZELPI-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4,5-dimethylimidazol-1-yl)pyridine-2-carboxamide Chemical compound CC1=C(C)N=CN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 MXTLRGXDTZELPI-UHFFFAOYSA-N 0.000 claims 1
- QBFIQWYNEBNHJP-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-ethyl-3-oxopiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1C(=O)N(CC)CCN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 QBFIQWYNEBNHJP-UHFFFAOYSA-N 0.000 claims 1
- YYJOZAHLGAHACX-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-methylimidazol-1-yl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 YYJOZAHLGAHACX-UHFFFAOYSA-N 0.000 claims 1
- SJPPAAGARFZWNS-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-methylpyridin-3-yl)pyridine-2-carboxamide Chemical compound CC1=CC=NC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 SJPPAAGARFZWNS-UHFFFAOYSA-N 0.000 claims 1
- YBXKCRBRCJYTKT-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-methylsulfonylphenyl)pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 YBXKCRBRCJYTKT-UHFFFAOYSA-N 0.000 claims 1
- BZBRGMWUSRCAFW-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-methylsulfonylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 BZBRGMWUSRCAFW-UHFFFAOYSA-N 0.000 claims 1
- YDDYRHXYGUNVIH-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(4-phenylimidazol-1-yl)pyridine-2-carboxamide Chemical compound C=1C(N2C=C(N=C2)C=2C=CC=CC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 YDDYRHXYGUNVIH-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- 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
- 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
- IKZZRZXSTVSMGK-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-(6-methyl-7,8-dihydro-5h-1,6-naphthyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=C2CN(C)CCC2=NC=C1C(C=1)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 IKZZRZXSTVSMGK-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
- 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
- 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
- CGFCTORCZQUIRW-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(1,1,2,2,2-pentafluoroethyl)imidazol-1-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(F)(F)C(F)(F)F)=CN1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 CGFCTORCZQUIRW-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
- WINSJHXUMGUFNC-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-[4-(methylsulfamoyl)phenyl]pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=NC(C(=O)NC=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 WINSJHXUMGUFNC-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
- 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
- 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 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
- 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 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
- GXYQTJPYHJWXBU-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-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=2C=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 GXYQTJPYHJWXBU-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
- LXVWJNKBAUBAPV-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-imidazo[2,1-b][1,3,4]thiadiazol-5-ylpyridine-2-carboxamide Chemical compound C=1C(C=2N3N=CSC3=NC=2)=CC=NC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 LXVWJNKBAUBAPV-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
- 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
- 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
- UWSIKOMZQIASHE-UHFFFAOYSA-N n-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-4-quinolin-3-yl-6-(trifluoromethyl)pyridine-2-carboxamide Chemical compound N=1C(C(F)(F)F)=CC(C=2C=C3C=CC=CC3=NC=2)=CC=1C(=O)NC(C=1)=CC=CC=1C1=NN=CN1C1CC1 UWSIKOMZQIASHE-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
- SRXPGSUMSMKMPL-UHFFFAOYSA-N n-[3-(4-methyl-1,2,4-triazol-3-yl)phenyl]-2-oxo-4-phenyl-1h-pyrimidine-6-carboxamide Chemical compound CN1C=NN=C1C1=CC=CC(NC(=O)C=2N=C(O)N=C(C=2)C=2C=CC=CC=2)=C1 SRXPGSUMSMKMPL-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
- 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
- DLNQWRWREPCCDJ-BTYIYWSLSA-N n-[3-[4-[(1s,2s)-2-methylcyclopropyl]-1,2,4-triazol-3-yl]phenyl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C[C@H]1C[C@@H]1N1C(C=2C=C(NC(=O)C=3N=CC=C(C=3)C=3C=NC=CC=3)C=CC=2)=NN=C1 DLNQWRWREPCCDJ-BTYIYWSLSA-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
- JOAGLBRFMWKWAY-UHFFFAOYSA-N n-[6-(3-cyclopropylimidazol-4-yl)pyridin-2-yl]-4-(6-cyclopropylpyridin-3-yl)pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(N=1)=CC=CC=1C1=CN=CN1C1CC1 JOAGLBRFMWKWAY-UHFFFAOYSA-N 0.000 claims 1
- BZSPITOKXNYMIL-UHFFFAOYSA-N n-[6-(3-cyclopropylimidazol-4-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=NC=2)C2CC2)=C1 BZSPITOKXNYMIL-UHFFFAOYSA-N 0.000 claims 1
- QSBJEMJHIREIDF-UHFFFAOYSA-N n-[6-(3-cyclopropylimidazol-4-yl)pyridin-2-yl]-4-quinolin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=C3C=CC=CC3=NC=2)=CC=NC=1C(=O)NC(N=1)=CC=CC=1C1=CN=CN1C1CC1 QSBJEMJHIREIDF-UHFFFAOYSA-N 0.000 claims 1
- LTLQDJLAQRIRKR-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-(1,5-naphthyridin-3-yl)benzamide Chemical compound C=1C=CC(C=2C=C3N=CC=CC3=NC=2)=CC=1C(=O)NC(N=1)=CC=CC=1C1=NN=CN1C1CC1 LTLQDJLAQRIRKR-UHFFFAOYSA-N 0.000 claims 1
- 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
- CUPFKQJBPJLHMP-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-(4,5-dimethylimidazol-1-yl)benzamide Chemical compound CC1=C(C)N=CN1C1=CC=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 CUPFKQJBPJLHMP-UHFFFAOYSA-N 0.000 claims 1
- MMQIDSMZFJLWGS-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-(4-propan-2-ylimidazol-1-yl)benzamide Chemical compound C1=NC(C(C)C)=CN1C1=CC=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 MMQIDSMZFJLWGS-UHFFFAOYSA-N 0.000 claims 1
- HHNJQIRNAMVSNX-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-[4-(2,2,2-trifluoro-1-hydroxyethyl)imidazol-1-yl]benzamide Chemical compound C1=NC(C(O)C(F)(F)F)=CN1C1=CC=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 HHNJQIRNAMVSNX-UHFFFAOYSA-N 0.000 claims 1
- AIYXIYDKEYUQDS-UHFFFAOYSA-N n-[6-(4-cyclopropyl-1,2,4-triazol-3-yl)pyridin-2-yl]-3-[4-(2,2,2-trifluoro-1-methoxyethyl)imidazol-1-yl]benzamide Chemical compound C1=NC(C(OC)C(F)(F)F)=CN1C1=CC=CC(C(=O)NC=2N=C(C=CC=2)C=2N(C=NN=2)C2CC2)=C1 AIYXIYDKEYUQDS-UHFFFAOYSA-N 0.000 claims 1
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- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims 1
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- 101001018196 Homo sapiens Mitogen-activated protein kinase kinase kinase 5 Proteins 0.000 abstract 2
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Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Applications Claiming Priority (4)
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| US22507909P | 2009-07-13 | 2009-07-13 | |
| US22507609P | 2009-07-13 | 2009-07-13 | |
| US28926309P | 2009-12-22 | 2009-12-22 | |
| EP15151030.2A EP2933252B1 (en) | 2009-07-13 | 2010-07-12 | Apoptosis signal-regulating kinase inhibitors |
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| SI2933252T1 true SI2933252T1 (en) | 2018-02-28 |
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| SI201031622T SI2933252T1 (en) | 2009-07-13 | 2010-07-12 | Kinase inhibitors as apoptotic signal regulators |
| SI201032055T SI3363797T1 (sl) | 2009-07-13 | 2010-07-12 | Peroralna farmacevtska oblika zaviralcev kinaze, ki uravnava signal apoptoze |
| SI201030851T SI2454250T1 (sl) | 2009-07-13 | 2010-07-12 | Apoptozni signalni regulacijski kinazni inhibitorji |
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