ES2902676T3 - Aminotriazolopiridinas como inhibidores de cinasa - Google Patents
Aminotriazolopiridinas como inhibidores de cinasa Download PDFInfo
- Publication number
- ES2902676T3 ES2902676T3 ES18707498T ES18707498T ES2902676T3 ES 2902676 T3 ES2902676 T3 ES 2902676T3 ES 18707498 T ES18707498 T ES 18707498T ES 18707498 T ES18707498 T ES 18707498T ES 2902676 T3 ES2902676 T3 ES 2902676T3
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- ES
- Spain
- Prior art keywords
- pyridin
- amino
- triazolo
- methyl
- carboxamide
- 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.)
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- 229940043355 kinase inhibitor Drugs 0.000 title description 5
- KGUHUVQIJHGHLX-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyridin-5-amine Chemical class NC1=CC=C2NN=NC2=N1 KGUHUVQIJHGHLX-UHFFFAOYSA-N 0.000 title description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 161
- 150000003839 salts Chemical class 0.000 claims abstract description 94
- -1 C1-4 deuteroalkoxy Chemical group 0.000 claims abstract description 88
- 125000003118 aryl group Chemical group 0.000 claims abstract description 60
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 44
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000006712 (C1-C4) deuteroalkyl group Chemical group 0.000 claims abstract description 28
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
- 125000005345 deuteroalkyl group Chemical group 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims abstract description 20
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 17
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims abstract description 4
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 125
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 100
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 238000000034 method Methods 0.000 claims description 84
- 235000005152 nicotinamide Nutrition 0.000 claims description 57
- 239000011570 nicotinamide Substances 0.000 claims description 57
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- 229960003966 nicotinamide Drugs 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 201000010099 disease Diseases 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 8
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 8
- 208000011231 Crohn disease Diseases 0.000 claims description 7
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- KDRRVHXTWYLSJY-UHFFFAOYSA-N 1-[1-[5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridine-3-carbonyl]piperidin-3-yl]-2-phenylethanone Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)N3CC(CCC3)C(CC3=CC=CC=C3)=O)C=2)OC)=N1 KDRRVHXTWYLSJY-UHFFFAOYSA-N 0.000 claims 1
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
- GPSHMKMHKNPMML-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-5-methoxy-N-(3-phenylbutyl)pyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCCC(C)C3=CC=CC=C3)C(=CN=2)OC)=N1 GPSHMKMHKNPMML-UHFFFAOYSA-N 0.000 claims 1
- JALSUPXWAGDVIK-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-5-methyl-N-(3-phenylbutyl)pyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCCC(C)C3=CC=CC=C3)C(=CN=2)C)=N1 JALSUPXWAGDVIK-UHFFFAOYSA-N 0.000 claims 1
- ZZVMOYDGLSUIMW-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-5-methyl-N-(3-phenylbutyl)pyrimidine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=NC=C(C(=N2)C(=O)NCCC(C)C2=CC=CC=C2)C)=N1 ZZVMOYDGLSUIMW-UHFFFAOYSA-N 0.000 claims 1
- CBIXMYAHBFPRGV-LLVKDONJSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-5-methoxypyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)N[C@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C(=CN=2)OC)=N1 CBIXMYAHBFPRGV-LLVKDONJSA-N 0.000 claims 1
- RWGMAGRPZMHQDV-GFCCVEGCSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-5-methylpyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)N[C@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C(=CN=2)C)=N1 RWGMAGRPZMHQDV-GFCCVEGCSA-N 0.000 claims 1
- GBAHCMOUBLEPDQ-LJQANCHMSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-methylpyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCC[C@@H](O)C3=CC=C(C=C3)Cl)C(=CN=2)C)=N1 GBAHCMOUBLEPDQ-LJQANCHMSA-N 0.000 claims 1
- GBAHCMOUBLEPDQ-IBGZPJMESA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-methylpyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCC[C@H](O)C3=CC=C(C=C3)Cl)C(=CN=2)C)=N1 GBAHCMOUBLEPDQ-IBGZPJMESA-N 0.000 claims 1
- HUTOHVKGVJIGNL-INIZCTEOSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-methylpyrimidine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=NC=C(C(=N2)C(=O)NCC[C@H](O)C2=CC=C(C=C2)Cl)C)=N1 HUTOHVKGVJIGNL-INIZCTEOSA-N 0.000 claims 1
- SDCJPHMZQOCHHI-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-5-methoxypyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCC3=C(C=CC(=C3)OC(F)(F)F)F)C(=CN=2)OC)=N1 SDCJPHMZQOCHHI-UHFFFAOYSA-N 0.000 claims 1
- QDWNKRBJJSVFES-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-5-methylpyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCC3=C(C=CC(=C3)OC(F)(F)F)F)C(=CN=2)C)=N1 QDWNKRBJJSVFES-UHFFFAOYSA-N 0.000 claims 1
- LUEGAYLEPPSDQR-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-5-methoxypyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCC3=C(C=CC(=C3)C(F)(F)F)F)C(=CN=2)OC)=N1 LUEGAYLEPPSDQR-UHFFFAOYSA-N 0.000 claims 1
- SLCGMQMDSBTLSL-UHFFFAOYSA-N 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-5-methylpyridine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=O)NCC3=C(C=CC(=C3)C(F)(F)F)F)C(=CN=2)C)=N1 SLCGMQMDSBTLSL-UHFFFAOYSA-N 0.000 claims 1
- GAWNOZOKPKBYKC-UHFFFAOYSA-N 2-methoxy-6-methylpyridine-3-carboxamide Chemical compound COC1=NC(C)=CC=C1C(N)=O GAWNOZOKPKBYKC-UHFFFAOYSA-N 0.000 claims 1
- SVDCHHNZOLWYTR-UHFFFAOYSA-N 4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-5-methyl-N-(3-phenylbutyl)pyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC(=NC=C2C)C(=O)NCCC(C)C2=CC=CC=C2)=N1 SVDCHHNZOLWYTR-UHFFFAOYSA-N 0.000 claims 1
- FPRQKSVYSQTMGN-UHFFFAOYSA-N 4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-5-methylpyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC(=NC=C2C)C(=O)NCC2=C(C=CC(=C2)OC(F)(F)F)F)=N1 FPRQKSVYSQTMGN-UHFFFAOYSA-N 0.000 claims 1
- BOUFASNPDHJSDN-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2,6-dimethyl-N-(3-phenylbutyl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCCC(C)C2=CC=CC=C2)=N1 BOUFASNPDHJSDN-UHFFFAOYSA-N 0.000 claims 1
- WUVJWYBGSLPNPL-IBIJPGRPSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2,6-dimethyl-N-[(1R)-2,2,2-trideuterio-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)N[C@H](C([2H])([2H])[2H])C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)C)C)=N1 WUVJWYBGSLPNPL-IBIJPGRPSA-N 0.000 claims 1
- YPBKZXKVISABDP-IBIJPGRPSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2,6-dimethyl-N-[(1R)-2,2,2-trideuterio-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)N[C@H](C([2H])([2H])[2H])C3=C(C=CC(=C3)C(F)(F)F)F)C=2)C)C)=N1 YPBKZXKVISABDP-IBIJPGRPSA-N 0.000 claims 1
- ZGYSGPOBNBSPTI-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2,6-dimethyl-N-[2-[3-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCCC2=CC(=CC=C2)OC(F)(F)F)=N1 ZGYSGPOBNBSPTI-UHFFFAOYSA-N 0.000 claims 1
- XQQRMANNNYYHHU-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2,6-dimethyl-N-[[3-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=CC(=CC=C2)OC(F)(F)F)=N1 XQQRMANNNYYHHU-UHFFFAOYSA-N 0.000 claims 1
- AOIVHTCEBQXLGQ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-chloro-N-(3-phenylbutyl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)Cl)C(=O)NCCC(C)C2=CC=CC=C2)=N1 AOIVHTCEBQXLGQ-UHFFFAOYSA-N 0.000 claims 1
- NZZOLYDWFWOAHC-LLVKDONJSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-chloro-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)N[C@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)Cl)C)=N1 NZZOLYDWFWOAHC-LLVKDONJSA-N 0.000 claims 1
- HJWSTRACTDJYRW-SNVBAGLBSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-chloro-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)N[C@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)Cl)=N1 HJWSTRACTDJYRW-SNVBAGLBSA-N 0.000 claims 1
- AIXMVEAMLLPCFC-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-chloro-N-[(3,5-difluoro-2-propan-2-yloxyphenyl)methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)Cl)C(=O)NCC2=C(C(=CC(=C2)F)F)OC(C)C)=N1 AIXMVEAMLLPCFC-UHFFFAOYSA-N 0.000 claims 1
- UGVQCRNLNPAJKA-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-chloro-N-[[2-(oxolan-3-yloxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)Cl)C(=O)NCC2=C(C=CC=C2)OC2COCC2)=N1 UGVQCRNLNPAJKA-UHFFFAOYSA-N 0.000 claims 1
- DZQAENMBSUPHOD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-chloro-N-[[3-(cyclopropylmethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)Cl)C(=O)NCC2=CC(=CC=C2)OCC2CC2)=N1 DZQAENMBSUPHOD-UHFFFAOYSA-N 0.000 claims 1
- GPSQSOOVKARKBJ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-ethoxy-N-(3-phenylbutyl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OCC)C(=O)NCCC(C)C2=CC=CC=C2)=N1 GPSQSOOVKARKBJ-UHFFFAOYSA-N 0.000 claims 1
- MASJAKGKXKQCRF-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-ethoxy-N-[(2-phenoxyphenyl)methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OCC)C(=O)NCC2=C(C=CC=C2)OC2=CC=CC=C2)=N1 MASJAKGKXKQCRF-UHFFFAOYSA-N 0.000 claims 1
- DZHDUUGWAVBVTM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-ethoxy-N-[[1-(2-fluorophenyl)cyclopropyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OCC)C(=O)NCC2(CC2)C2=C(C=CC=C2)F)=N1 DZHDUUGWAVBVTM-UHFFFAOYSA-N 0.000 claims 1
- OYEUVJIQKVNPNZ-GFCCVEGCSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-ethyl-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)N[C@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)CC)=N1 OYEUVJIQKVNPNZ-GFCCVEGCSA-N 0.000 claims 1
- OYEUVJIQKVNPNZ-LBPRGKRZSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-ethyl-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)N[C@@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)CC)=N1 OYEUVJIQKVNPNZ-LBPRGKRZSA-N 0.000 claims 1
- YSVNZRINTUXEJF-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-ethyl-N-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC(=C3)C(F)(F)F)F)C=2)CC)=N1 YSVNZRINTUXEJF-UHFFFAOYSA-N 0.000 claims 1
- CRFNFWMRLOPZNF-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-(3-phenylbutyl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCCC(C)C2=CC=CC=C2)=N1 CRFNFWMRLOPZNF-UHFFFAOYSA-N 0.000 claims 1
- WGHFNAVRGMDLLN-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[(2-propan-2-yloxyphenyl)methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2)OC(C)C)=N1 WGHFNAVRGMDLLN-UHFFFAOYSA-N 0.000 claims 1
- GBHQMOHQCDIASD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[2-[2-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCCC2=C(C=CC=C2)OC(F)(F)F)=N1 GBHQMOHQCDIASD-UHFFFAOYSA-N 0.000 claims 1
- YKIWFRYGOAMINY-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[2-[3-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCCC2=CC(=CC=C2)OC(F)(F)F)=N1 YKIWFRYGOAMINY-UHFFFAOYSA-N 0.000 claims 1
- GSLJTKCAGWGTEM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[2-(2,2,2-trifluoroethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C=CC=C3)OCC(F)(F)F)C=2)OC)C)=N1 GSLJTKCAGWGTEM-UHFFFAOYSA-N 0.000 claims 1
- XGENMMUBUBNADK-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[2-(2-methylpropoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C=CC=C3)OCC(C)C)C=2)OC)C)=N1 XGENMMUBUBNADK-UHFFFAOYSA-N 0.000 claims 1
- DSZDTUDZQQAPFA-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[2-(oxan-4-yloxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2)OC2CCOCC2)=N1 DSZDTUDZQQAPFA-UHFFFAOYSA-N 0.000 claims 1
- KWPMLWJXQZQWLT-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[2-(propan-2-yloxymethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C=CC=C3)COC(C)C)C=2)OC)C)=N1 KWPMLWJXQZQWLT-UHFFFAOYSA-N 0.000 claims 1
- CFXNEFZIKBEOHJ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[2-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2)OC(F)(F)F)=N1 CFXNEFZIKBEOHJ-UHFFFAOYSA-N 0.000 claims 1
- UMVMLSIMAQAHJZ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[3-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=CC(=CC=C2)OC(F)(F)F)=N1 UMVMLSIMAQAHJZ-UHFFFAOYSA-N 0.000 claims 1
- BCSUWMMZXBVJDA-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-6-methyl-N-[[3-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=CC(=CC=C2)C(F)(F)F)=N1 BCSUWMMZXBVJDA-UHFFFAOYSA-N 0.000 claims 1
- UDQMKNPRLPYGSM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-(2-methyl-3-phenylpropyl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC(CC2=CC=CC=C2)C)=N1 UDQMKNPRLPYGSM-UHFFFAOYSA-N 0.000 claims 1
- UKEFSDVYSWIQKE-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-(3-phenylpropyl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCCCC2=CC=CC=C2)=N1 UKEFSDVYSWIQKE-UHFFFAOYSA-N 0.000 claims 1
- UELLPYQSIHWAFA-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-(4-phenylbutan-2-yl)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NC(C)CCC2=CC=CC=C2)=N1 UELLPYQSIHWAFA-UHFFFAOYSA-N 0.000 claims 1
- VNIVMDMSMAMBGR-LBBMYNEISA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[(1R)-2,2,2-trideuterio-1-[3-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)N[C@H](C([2H])([2H])[2H])C3=CC(=CC=C3)OC(F)(F)F)C=2)OC)=N1 VNIVMDMSMAMBGR-LBBMYNEISA-N 0.000 claims 1
- BRWACOUEISVFHX-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[(2-methoxyphenyl)methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)OC)=N1 BRWACOUEISVFHX-UHFFFAOYSA-N 0.000 claims 1
- CWABMHRFNQZDMV-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[(2-phenoxyphenyl)methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)OC2=CC=CC=C2)=N1 CWABMHRFNQZDMV-UHFFFAOYSA-N 0.000 claims 1
- PRWKDRLURTXQPH-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[(5-phenyl-1H-pyrazol-4-yl)methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC=2C(=NNC=2)C2=CC=CC=C2)=N1 PRWKDRLURTXQPH-UHFFFAOYSA-N 0.000 claims 1
- HDROYTKKHDNYRL-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[[2-(2,2,2-trifluoroethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)OCC(F)(F)F)C=2)OC)=N1 HDROYTKKHDNYRL-UHFFFAOYSA-N 0.000 claims 1
- RNCVIFFJQDTVDR-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[[2-(2-methylpropoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)OCC(C)C)C=2)OC)=N1 RNCVIFFJQDTVDR-UHFFFAOYSA-N 0.000 claims 1
- FUNZBKPNPDUDOE-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[[2-(oxan-4-yloxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)OC2CCOCC2)=N1 FUNZBKPNPDUDOE-UHFFFAOYSA-N 0.000 claims 1
- FQHRDRXWGYQBSQ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[[2-(propan-2-yloxymethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)COC(C)C)C=2)OC)=N1 FQHRDRXWGYQBSQ-UHFFFAOYSA-N 0.000 claims 1
- WWJSVBRRRYMJAL-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[[2-(pyrrolidine-1-carbonyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)C(=O)N3CCCC3)C=2)OC)=N1 WWJSVBRRRYMJAL-UHFFFAOYSA-N 0.000 claims 1
- KYDZMIHICCXBSC-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[[3-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=CC(=CC=C2)C(F)(F)F)=N1 KYDZMIHICCXBSC-UHFFFAOYSA-N 0.000 claims 1
- IRYRKPQXFMEUNY-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-methyl-N-[[3-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)N(CC2=CC(=CC=C2)OC(F)(F)F)C)=N1 IRYRKPQXFMEUNY-UHFFFAOYSA-N 0.000 claims 1
- YHPYSANTMYSECD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methyl-N-[[2-(2,2,2-trifluoroethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)OCC(F)(F)F)C=2)C)=N1 YHPYSANTMYSECD-UHFFFAOYSA-N 0.000 claims 1
- NNEXOBFADGAKPG-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methyl-N-[[2-(2-methylpropoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)OCC(C)C)C=2)C)=N1 NNEXOBFADGAKPG-UHFFFAOYSA-N 0.000 claims 1
- PWTFSZYOSLVDPE-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methyl-N-[[3-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC2=CC(=CC=C2)OC(F)(F)F)=N1 PWTFSZYOSLVDPE-UHFFFAOYSA-N 0.000 claims 1
- LICWGWARGCTPGJ-LLVKDONJSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-[(1R)-1-[2-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC=C(C(=O)N[C@H](C)C3=C(C=CC=C3)OC(F)(F)F)C=2)Cl)=N1 LICWGWARGCTPGJ-LLVKDONJSA-N 0.000 claims 1
- LIOILPGZIMYGLX-JTQLQIEISA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC=C(C(=O)N[C@@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)Cl)=N1 LIOILPGZIMYGLX-JTQLQIEISA-N 0.000 claims 1
- CPQOSZDGUORUCT-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-[[2-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC=C(C(=O)NCC3=C(C=CC=C3)OC(F)(F)F)C=2)Cl)=N1 CPQOSZDGUORUCT-UHFFFAOYSA-N 0.000 claims 1
- GGYZVSPZUYFWRU-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C=CC(=CC2=N1)C1=C(Cl)N=CC(=C1)C(=O)NCC1=C(F)C=CC(OC(F)(F)F)=C1 GGYZVSPZUYFWRU-UHFFFAOYSA-N 0.000 claims 1
- VRJZHHDZPRVFEU-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC=C(C(=O)NCC3=C(C=CC(=C3)C(F)(F)F)F)C=2)Cl)=N1 VRJZHHDZPRVFEU-UHFFFAOYSA-N 0.000 claims 1
- NEUKEZRLRZDTQS-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-[[5-fluoro-2-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC=C(C(=O)NCC3=C(C=CC(=C3)F)OC(F)(F)F)C=2)Cl)=N1 NEUKEZRLRZDTQS-UHFFFAOYSA-N 0.000 claims 1
- TUBWGZNHDMHXKR-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(1-benzylimidazol-4-yl)-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NC=3N=CN(C=3)CC3=CC=CC=C3)C=2)C)=N1 TUBWGZNHDMHXKR-UHFFFAOYSA-N 0.000 claims 1
- CLHUFYYMHMQKCJ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(2-hydroxy-3-phenoxypropyl)-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC(COC2=CC=CC=C2)O)=N1 CLHUFYYMHMQKCJ-UHFFFAOYSA-N 0.000 claims 1
- LAJIJRWZDWSILF-CYBMUJFWSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methoxy-N,6-dimethylpyridine-3-carboxamide Chemical compound COC1=NC(C)=C(C=C1C(=O)N(C)[C@H](C)C1=C(F)C=CC(OC(F)(F)F)=C1)C1=CC2=NC(N)=NN2C=C1 LAJIJRWZDWSILF-CYBMUJFWSA-N 0.000 claims 1
- JMPWCWLRGLADRZ-CYBMUJFWSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-N,2-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)N(C)[C@H](C)C3=C(C=CC(=C3)OC(F)(F)F)F)C=2)C)=N1 JMPWCWLRGLADRZ-CYBMUJFWSA-N 0.000 claims 1
- QNCSNFUAEIVMCT-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-cyclopentyloxy-5-fluorophenyl)methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC(=C2)F)OC2CCCC2)=N1 QNCSNFUAEIVMCT-UHFFFAOYSA-N 0.000 claims 1
- HTGWORFQVPYZIY-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-cyclopentyloxy-6-fluorophenyl)methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2F)OC2CCCC2)=N1 HTGWORFQVPYZIY-UHFFFAOYSA-N 0.000 claims 1
- IUKPZJNHRWOFCP-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-cyclopentyloxyphenyl)methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)OC2CCCC2)=N1 IUKPZJNHRWOFCP-UHFFFAOYSA-N 0.000 claims 1
- CSVGEFGRBXNRCD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-cyclopentyloxyphenyl)methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC2=C(C=CC=C2)OC2CCCC2)=N1 CSVGEFGRBXNRCD-UHFFFAOYSA-N 0.000 claims 1
- ZSBXMMULSJNJMM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-cyclopentyloxypyridin-3-yl)methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC=2C(=NC=CC=2)OC2CCCC2)=N1 ZSBXMMULSJNJMM-UHFFFAOYSA-N 0.000 claims 1
- XHUIMAYBTGSKEC-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-cyclopropyloxy-3,5-difluorophenyl)methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC3)C=2)OC)=N1 XHUIMAYBTGSKEC-UHFFFAOYSA-N 0.000 claims 1
- DTOJTZUPWPUAPH-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-ethoxyphenyl)methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)OCC)=N1 DTOJTZUPWPUAPH-UHFFFAOYSA-N 0.000 claims 1
- JEMONVMZAYQPMP-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-ethylphenyl)methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)CC)=N1 JEMONVMZAYQPMP-UHFFFAOYSA-N 0.000 claims 1
- IXAPPSSPMNQUCY-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(2-fluoro-5-methoxyphenyl)methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C=CC(=C3)OC)F)C=2)OC)C)=N1 IXAPPSSPMNQUCY-UHFFFAOYSA-N 0.000 claims 1
- JGKVEIHLYOIAKC-HXUWFJFHSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC[C@@H](O)C2=CC=C(C=C2)Cl)=N1 JGKVEIHLYOIAKC-HXUWFJFHSA-N 0.000 claims 1
- AAUXZIKATMUCTI-LJQANCHMSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-2-ethoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OCC)C(=O)NCC[C@@H](O)C2=CC=C(C=C2)Cl)=N1 AAUXZIKATMUCTI-LJQANCHMSA-N 0.000 claims 1
- JGKVEIHLYOIAKC-FQEVSTJZSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC[C@H](O)C2=CC=C(C=C2)Cl)=N1 JGKVEIHLYOIAKC-FQEVSTJZSA-N 0.000 claims 1
- FUARSVCNRXAGKF-IBGZPJMESA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC[C@H](O)C2=CC=C(C=C2)Cl)=N1 FUARSVCNRXAGKF-IBGZPJMESA-N 0.000 claims 1
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- DVBXOBNOQIIWQT-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[3-(4-fluorophenyl)-2-hydroxy-2-methylpropyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC(CC3=CC=C(C=C3)F)(C)O)C=2)C)=N1 DVBXOBNOQIIWQT-UHFFFAOYSA-N 0.000 claims 1
- ISBUGGSQKVFFDC-SJLPKXTDSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[(1S,2S)-2-(4-fluorophenyl)cyclopropyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NC[C@@H]2[C@H](C2)C2=CC=C(C=C2)F)=N1 ISBUGGSQKVFFDC-SJLPKXTDSA-N 0.000 claims 1
- QUNXJDWPMCFVHP-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(1-cyclopentylethoxy)phenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)OC(C)C2CCCC2)=N1 QUNXJDWPMCFVHP-UHFFFAOYSA-N 0.000 claims 1
- QVPRQHOAVOQMAY-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(2,6-dimethyloxan-4-yl)oxy-3,5-difluorophenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OC(C3)C)C)C=2)C)C)=N1 QVPRQHOAVOQMAY-UHFFFAOYSA-N 0.000 claims 1
- AWSFLDLZYSACLD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(2,6-dimethyloxan-4-yl)oxy-3,5-difluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OC(C3)C)C)C=2)OC)C)=N1 AWSFLDLZYSACLD-UHFFFAOYSA-N 0.000 claims 1
- KHKZXMRSAFSWGL-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(2,6-dimethyloxan-4-yl)oxy-3,5-difluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OC(C3)C)C)C=2)OC)=N1 KHKZXMRSAFSWGL-UHFFFAOYSA-N 0.000 claims 1
- HIXGYVFKZXFEJL-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(2,6-dimethyloxan-4-yl)oxy-3,5-difluorophenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OC(C3)C)C)C=2)C)=N1 HIXGYVFKZXFEJL-UHFFFAOYSA-N 0.000 claims 1
- APEWMUSCVSJKKM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(3,3-difluoropyrrolidine-1-carbonyl)-3-fluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC=C3)F)C(=O)N3CC(CC3)(F)F)C=2)OC)C)=N1 APEWMUSCVSJKKM-UHFFFAOYSA-N 0.000 claims 1
- HIAUNIJEHOSAIR-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(3,3-difluoropyrrolidine-1-carbonyl)-3-fluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC=C3)F)C(=O)N3CC(CC3)(F)F)C=2)OC)=N1 HIAUNIJEHOSAIR-UHFFFAOYSA-N 0.000 claims 1
- RHKHCNGGBBHTRP-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(3,3-difluoropyrrolidine-1-carbonyl)-5-fluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C=CC(=C3)F)C(=O)N3CC(CC3)(F)F)C=2)OC)C)=N1 RHKHCNGGBBHTRP-UHFFFAOYSA-N 0.000 claims 1
- XURHWFDGDCWPHE-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(3,3-difluoropyrrolidine-1-carbonyl)-5-fluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound COC1=NC=C(C=C1C(=O)NCC1=C(C=CC(F)=C1)C(=O)N1CCC(F)(F)C1)C1=CC2=NC(N)=NN2C=C1 XURHWFDGDCWPHE-UHFFFAOYSA-N 0.000 claims 1
- RPUBZSHCEVWKDP-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(3,3-difluoropyrrolidine-1-carbonyl)phenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C=CC=C3)C(=O)N3CC(CC3)(F)F)C=2)OC)=N1 RPUBZSHCEVWKDP-UHFFFAOYSA-N 0.000 claims 1
- CGCORBOXVUSONI-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclobutylmethoxy)-6-fluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2F)OCC2CCC2)=N1 CGCORBOXVUSONI-UHFFFAOYSA-N 0.000 claims 1
- OCVMVNIUTJHXPJ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclobutylmethoxy)-6-fluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2F)OCC2CCC2)=N1 OCVMVNIUTJHXPJ-UHFFFAOYSA-N 0.000 claims 1
- TWRHRAIZBUWCEZ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclobutylmethoxy)pyridin-3-yl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC=2C(=NC=CC=2)OCC2CCC2)=N1 TWRHRAIZBUWCEZ-UHFFFAOYSA-N 0.000 claims 1
- GRQVHYNEOVZYOZ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclobutylmethoxy)pyridin-3-yl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC=2C(=NC=CC=2)OCC2CCC2)=N1 GRQVHYNEOVZYOZ-UHFFFAOYSA-N 0.000 claims 1
- XDKFWVYKZUPQFM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclobutylmethoxy)pyridin-3-yl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC=2C(=NC=CC=2)OCC2CCC2)=N1 XDKFWVYKZUPQFM-UHFFFAOYSA-N 0.000 claims 1
- LMYRYXIJHKNHKB-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclobutylmethoxy)pyridin-3-yl]methyl]-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C=NC=2C)C(=O)NCC=2C(=NC=CC=2)OCC2CCC2)=N1 LMYRYXIJHKNHKB-UHFFFAOYSA-N 0.000 claims 1
- FBDVLDAHMWHMAO-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-3,5-difluorophenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=C(C(=CC(=C2)F)F)OCC2CCCC2)=N1 FBDVLDAHMWHMAO-UHFFFAOYSA-N 0.000 claims 1
- OHVDCKUMMUPYIE-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-3,5-difluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C(=CC(=C2)F)F)OCC2CCCC2)=N1 OHVDCKUMMUPYIE-UHFFFAOYSA-N 0.000 claims 1
- CBITUJNEDATPAH-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-3,5-difluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C(=CC(=C2)F)F)OCC2CCCC2)=N1 CBITUJNEDATPAH-UHFFFAOYSA-N 0.000 claims 1
- NGTNNVLKBPFCKN-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-4,6-difluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=C(C=C2F)F)OCC2CCCC2)=N1 NGTNNVLKBPFCKN-UHFFFAOYSA-N 0.000 claims 1
- RUETYUMINIEOPR-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-4-fluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=C(C=C2)F)OCC2CCCC2)=N1 RUETYUMINIEOPR-UHFFFAOYSA-N 0.000 claims 1
- ZDMHOXACTPMSCL-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-5-fluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC(=C2)F)OCC2CCCC2)=N1 ZDMHOXACTPMSCL-UHFFFAOYSA-N 0.000 claims 1
- GXBFNRUYAFGWMA-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-6-fluorophenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=C(C=CC=C2F)OCC2CCCC2)=N1 GXBFNRUYAFGWMA-UHFFFAOYSA-N 0.000 claims 1
- VIEMBQKRFCMBQX-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)phenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2)OCC2CCCC2)=N1 VIEMBQKRFCMBQX-UHFFFAOYSA-N 0.000 claims 1
- NEPCGTOOWNBYFX-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)phenyl]methyl]-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C=NC=2C)C(=O)NCC2=C(C=CC=C2)OCC2CCCC2)=N1 NEPCGTOOWNBYFX-UHFFFAOYSA-N 0.000 claims 1
- ONUNGHZYWZJJAS-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)pyridin-3-yl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC=2C(=NC=CC=2)OCC2CCCC2)=N1 ONUNGHZYWZJJAS-UHFFFAOYSA-N 0.000 claims 1
- PORZBVNZFYOHJT-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)pyridin-3-yl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC=2C(=NC=CC=2)OCC2CCCC2)=N1 PORZBVNZFYOHJT-UHFFFAOYSA-N 0.000 claims 1
- GAURRJFMLZVXNT-WORMITQPSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)-3,5-difluorophenyl]-deuteriomethyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NC([2H])C2=C(C(=CC(=C2)F)F)OCC2CC2)=N1 GAURRJFMLZVXNT-WORMITQPSA-N 0.000 claims 1
- XQRWNHMCBPFFFD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=C(C(=CC(=C2)F)F)OCC2CC2)=N1 XQRWNHMCBPFFFD-UHFFFAOYSA-N 0.000 claims 1
- WWEODBXGLDIPCB-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C(=CC(=C2)F)F)OCC2CC2)=N1 WWEODBXGLDIPCB-UHFFFAOYSA-N 0.000 claims 1
- ZIVJKRFMWGVMTR-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl]-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C=NC=2C)C(=O)NCC2=C(C(=CC(=C2)F)F)OCC2CC2)=N1 ZIVJKRFMWGVMTR-UHFFFAOYSA-N 0.000 claims 1
- FFWVYOPRGXVDBQ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)-6-fluorophenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2F)OCC2CC2)=N1 FFWVYOPRGXVDBQ-UHFFFAOYSA-N 0.000 claims 1
- AEVHAEYUQRPBLV-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)-6-fluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2F)OCC2CC2)=N1 AEVHAEYUQRPBLV-UHFFFAOYSA-N 0.000 claims 1
- HANRYQQBYHIBEY-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)phenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=C(C=CC=C2)OCC2CC2)=N1 HANRYQQBYHIBEY-UHFFFAOYSA-N 0.000 claims 1
- CGDLAECEGSRRRC-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopropylmethoxy)phenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC=C2)OCC2CC2)=N1 CGDLAECEGSRRRC-UHFFFAOYSA-N 0.000 claims 1
- NYAPDFZLBSHDTC-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-[2-(hydroxymethyl)phenyl]sulfanylphenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC=C2)SC2=C(C=CC=C2)CO)=N1 NYAPDFZLBSHDTC-UHFFFAOYSA-N 0.000 claims 1
- XQRWNHMCBPFFFD-XUWBISKJSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-[cyclopropyl(dideuterio)methoxy]-3,5-difluorophenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC([2H])([2H])C3CC3)C=2)C)C)=N1 XQRWNHMCBPFFFD-XUWBISKJSA-N 0.000 claims 1
- OIJNDMDILVSJJL-VTNORMIGSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-[cyclopropyl(dideuterio)methoxy]-3,5-difluorophenyl]methyl]-6-methyl-2-(trideuteriomethoxy)pyridine-3-carboxamide Chemical compound [2H]C([2H])([2H])Oc1nc(C)c(cc1C(=O)NCc1cc(F)cc(F)c1OC([2H])([2H])C1CC1)-c1ccn2nc(N)nc2c1 OIJNDMDILVSJJL-VTNORMIGSA-N 0.000 claims 1
- SOPAERBFNJVLTK-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=C(C=CC(=C2)C(F)(F)F)Cl)=N1 SOPAERBFNJVLTK-UHFFFAOYSA-N 0.000 claims 1
- AHHQOQSADBNMAZ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC2=C(C=CC(=C2)C(F)(F)F)Cl)=N1 AHHQOQSADBNMAZ-UHFFFAOYSA-N 0.000 claims 1
- UPWPGDIMVGXUSC-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=C(C=CC(=C2)OC(F)(F)F)F)=N1 UPWPGDIMVGXUSC-UHFFFAOYSA-N 0.000 claims 1
- LNIJDPPSFWHQCM-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC(=C2)OC(F)(F)F)F)=N1 LNIJDPPSFWHQCM-UHFFFAOYSA-N 0.000 claims 1
- XCYLBCUYTNJHRZ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC2=C(C=CC(=C2)OC(F)(F)F)F)=N1 XCYLBCUYTNJHRZ-UHFFFAOYSA-N 0.000 claims 1
- UANKDRSWTOLJDI-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=C(C=CC(=C2)C(F)(F)F)F)=N1 UANKDRSWTOLJDI-UHFFFAOYSA-N 0.000 claims 1
- VFBRSOPRSZKVJI-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=C(C=CC(=C2)C(F)(F)F)F)=N1 VFBRSOPRSZKVJI-UHFFFAOYSA-N 0.000 claims 1
- YTLSDLUDKQHQCO-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(2-methyloxan-4-yl)oxyphenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OCC3)C)C=2)C)C)=N1 YTLSDLUDKQHQCO-UHFFFAOYSA-N 0.000 claims 1
- FJOODPAYANULCW-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(2-methyloxan-4-yl)oxyphenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OCC3)C)C=2)OC)C)=N1 FJOODPAYANULCW-UHFFFAOYSA-N 0.000 claims 1
- HNBWTTLAWUXGCK-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(2-methyloxan-4-yl)oxyphenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OCC3)C)C=2)OC)=N1 HNBWTTLAWUXGCK-UHFFFAOYSA-N 0.000 claims 1
- ZRHHKYVITMMFLF-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(2-methyloxan-4-yl)oxyphenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3CC(OCC3)C)C=2)C)=N1 ZRHHKYVITMMFLF-UHFFFAOYSA-N 0.000 claims 1
- QPAJNXKHYNBAJT-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(2-methylpropoxy)phenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound O(C)C1=NC=C(C2=CC3=NC(N)=NN3C=C2)C=C1C(=O)NCC1=CC(=CC(=C1OCC(C)C)F)F QPAJNXKHYNBAJT-UHFFFAOYSA-N 0.000 claims 1
- BALHVCBJIJZNCA-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(2-methylpropoxy)phenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OCC(C)C)C=2)C)=N1 BALHVCBJIJZNCA-UHFFFAOYSA-N 0.000 claims 1
- QSGWWQWMDFNJBF-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(oxetan-3-yloxy)phenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3COC3)C=2)OC)=N1 QSGWWQWMDFNJBF-UHFFFAOYSA-N 0.000 claims 1
- ANNOCDZKGCASAX-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-(oxolan-3-yloxy)phenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)OC3COCC3)C=2)C)=N1 ANNOCDZKGCASAX-UHFFFAOYSA-N 0.000 claims 1
- HCDPCXRQIWINJG-GOSISDBHSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-[(3R)-1-methylpyrrolidin-3-yl]oxyphenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)O[C@H]3CN(CC3)C)C=2)OC)C)=N1 HCDPCXRQIWINJG-GOSISDBHSA-N 0.000 claims 1
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- LLCAFFLVACGLJE-QGZVFWFLSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-[(3R)-oxolan-3-yl]oxyphenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)O[C@H]3COCC3)C=2)OC)=N1 LLCAFFLVACGLJE-QGZVFWFLSA-N 0.000 claims 1
- ZUJIOUSECXNDRI-SFHVURJKSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-[(3S)-oxolan-3-yl]oxyphenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)O[C@@H]3COCC3)C=2)C)C)=N1 ZUJIOUSECXNDRI-SFHVURJKSA-N 0.000 claims 1
- XQMTYQGAYKMCNK-KRWDZBQOSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-[(3S)-oxolan-3-yl]oxyphenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)O[C@@H]3COCC3)C=2)OC)C)=N1 XQMTYQGAYKMCNK-KRWDZBQOSA-N 0.000 claims 1
- LLCAFFLVACGLJE-KRWDZBQOSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3,5-difluoro-2-[(3S)-oxolan-3-yl]oxyphenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC(=C3)F)F)O[C@@H]3COCC3)C=2)OC)=N1 LLCAFFLVACGLJE-KRWDZBQOSA-N 0.000 claims 1
- RZFLCELXPRBDLB-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3-(cyclobutylmethoxy)pyridin-2-yl]methyl]-2-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC2=NC=CC=C2OCC2CCC2)=N1 RZFLCELXPRBDLB-UHFFFAOYSA-N 0.000 claims 1
- UJDQMHMNKJMMGX-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3-(cyclopentylmethoxy)pyridin-2-yl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NCC2=NC=CC=C2OCC2CCCC2)=N1 UJDQMHMNKJMMGX-UHFFFAOYSA-N 0.000 claims 1
- PKHYOAJFTYCSSU-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3-(cyclopentylmethoxy)pyridin-2-yl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=NC=CC=C2OCC2CCCC2)=N1 PKHYOAJFTYCSSU-UHFFFAOYSA-N 0.000 claims 1
- NBVLPDWQIQGWLO-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3-(cyclopropylmethoxy)pyridin-2-yl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)NCC2=NC=CC=C2OCC2CC2)=N1 NBVLPDWQIQGWLO-UHFFFAOYSA-N 0.000 claims 1
- GUGBFQIDARZOTN-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3-(difluoromethoxy)phenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)OC)C(=O)NCC2=CC(=CC=C2)OC(F)F)=N1 GUGBFQIDARZOTN-UHFFFAOYSA-N 0.000 claims 1
- WJAUEAVOFICJPQ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[3-fluoro-2-(pyrrolidin-1-ylmethyl)phenyl]methyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound COC1=NC(C)=C(C=C1C(=O)NCC1=C(CN2CCCC2)C(F)=CC=C1)C1=CC2=NC(N)=NN2C=C1 WJAUEAVOFICJPQ-UHFFFAOYSA-N 0.000 claims 1
- UOMROTZCBHNSGQ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C(=NC(=C(C(=O)NCC3=C(C=CC(=C3)OCC3CC3)F)C=2)C)C)=N1 UOMROTZCBHNSGQ-UHFFFAOYSA-N 0.000 claims 1
- XKHFTNUAIIODCD-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[5-fluoro-2-(1-methylpyrazol-3-yl)phenyl]methyl]-2-methylpyridine-3-carboxamide Chemical compound CN1C=CC(=N1)C1=C(CNC(=O)C2=CC(=CN=C2C)C2=CC3=NC(N)=NN3C=C2)C=C(F)C=C1 XKHFTNUAIIODCD-UHFFFAOYSA-N 0.000 claims 1
- KRLUKYSNQUNABP-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[6-(cyclopropylmethoxy)-2,3-difluorophenyl]methyl]-2-methoxypyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NCC3=C(C(=CC=C3OCC3CC3)F)F)C=2)OC)=N1 KRLUKYSNQUNABP-UHFFFAOYSA-N 0.000 claims 1
- UPWPGDIMVGXUSC-MMIHMFRQSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[deuterio-[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-2,6-dimethylpyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2C)C)C(=O)NC([2H])C2=C(C=CC(=C2)OC(F)(F)F)F)=N1 UPWPGDIMVGXUSC-MMIHMFRQSA-N 0.000 claims 1
- VNCRYKVYTCTHHQ-NJFDCKJNSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[dideuterio-[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-(trideuteriomethoxy)pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NC([2H])([2H])C3=C(C=CC(=C3)C(F)(F)F)F)C=2)OC([2H])([2H])[2H])=N1 VNCRYKVYTCTHHQ-NJFDCKJNSA-N 0.000 claims 1
- YWHLQRBHQNPUNT-UHFFFAOYSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-methoxy-N-(3-phenylbutyl)pyrazine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CN=C(C(=N2)C(=O)NCCC(C)C2=CC=CC=C2)OC)=N1 YWHLQRBHQNPUNT-UHFFFAOYSA-N 0.000 claims 1
- IDGPQAAVVVRENK-UHFFFAOYSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-methoxy-N-(3-phenylbutyl)pyridazine-4-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC(=C(N=N2)OC)C(=O)NCCC(C)C2=CC=CC=C2)=N1 IDGPQAAVVVRENK-UHFFFAOYSA-N 0.000 claims 1
- VBEVQWLFSITJHZ-WQRHAFOGSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-methoxy-N-[(1R)-2,2,2-trideuterio-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyrazine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CN=C(C(=N2)C(=O)N[C@H](C([2H])([2H])[2H])C2=C(C=CC(=C2)OC(F)(F)F)F)OC)=N1 VBEVQWLFSITJHZ-WQRHAFOGSA-N 0.000 claims 1
- HFIYDMRBOZOWEA-UHFFFAOYSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-methyl-N-(3-phenylbutyl)pyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC=C(C(=N2)C(=O)NCCC(C)C2=CC=CC=C2)C)=N1 HFIYDMRBOZOWEA-UHFFFAOYSA-N 0.000 claims 1
- LYIBAQNEVDDFDX-LLVKDONJSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-3-methoxypyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC=C(C(=N2)C(=O)N[C@H](C)C2=C(C=CC(=C2)OC(F)(F)F)F)OC)=N1 LYIBAQNEVDDFDX-LLVKDONJSA-N 0.000 claims 1
- IEOPIHKULRKCDE-GOSISDBHSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-methylpyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC=C(C(=N2)C(=O)NCC[C@@H](O)C2=CC=C(C=C2)Cl)C)=N1 IEOPIHKULRKCDE-GOSISDBHSA-N 0.000 claims 1
- IEOPIHKULRKCDE-SFHVURJKSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-methylpyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC=C(C(=N2)C(=O)NCC[C@H](O)C2=CC=C(C=C2)Cl)C)=N1 IEOPIHKULRKCDE-SFHVURJKSA-N 0.000 claims 1
- FNZUUHXSNSWPRB-UHFFFAOYSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-3-methoxypyrazine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CN=C(C(=N2)C(=O)NCC2=C(C=CC(=C2)OC(F)(F)F)F)OC)=N1 FNZUUHXSNSWPRB-UHFFFAOYSA-N 0.000 claims 1
- CJFQDUXFGQSNKL-UHFFFAOYSA-N 6-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]-3-methylpyridine-2-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C2=CC=C(C(=N2)C(=O)NCC2=C(C=CC(=C2)OC(F)(F)F)F)C)=N1 CJFQDUXFGQSNKL-UHFFFAOYSA-N 0.000 claims 1
- OPCUBLPGWGVKNN-HPABDLATSA-N N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methyl-5-[2-(trideuteriomethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)[C@@H](C)NC(C1=C(N=CC(=C1)C1=CC=2N(C=C1)N=C(N=2)NC([2H])([2H])[2H])C)=O OPCUBLPGWGVKNN-HPABDLATSA-N 0.000 claims 1
- UJMLSENILXLUBC-UHFFFAOYSA-N N-[5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methylpyridin-3-yl]-1-benzylpyrazole-4-carboxamide Chemical compound CC1=NC=C(C=C1NC(=O)C1=CN(CC2=CC=CC=C2)N=C1)C1=CC2=NC(N)=NN2C=C1 UJMLSENILXLUBC-UHFFFAOYSA-N 0.000 claims 1
- MGHWNSZORDQLMI-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-(2-benzylmorpholin-4-yl)methanone Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)N2CC(OCC2)CC2=CC=CC=C2)=N1 MGHWNSZORDQLMI-UHFFFAOYSA-N 0.000 claims 1
- FLOACSJHDBYARJ-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-(2-phenylmorpholin-4-yl)methanone Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)N2CC(OCC2)C2=CC=CC=C2)=N1 FLOACSJHDBYARJ-UHFFFAOYSA-N 0.000 claims 1
- FQBNQXUXGRFRMK-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-(3-phenylsulfanylpiperidin-1-yl)methanone Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)OC)C(=O)N2CC(CCC2)SC2=CC=CC=C2)=N1 FQBNQXUXGRFRMK-UHFFFAOYSA-N 0.000 claims 1
- ATLYVSRDLCQYKJ-QGZVFWFLSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-[(3R)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methanone Chemical compound FC1=CC=C(C=C1)C[C@@H]1CN(CCC1)C(=O)C=1C=C(C=NC=1OC)C1=CC=2N(C=C1)N=C(N=2)N ATLYVSRDLCQYKJ-QGZVFWFLSA-N 0.000 claims 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- 230000014616 translation Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- FTNWXGFYRHWUKG-UHFFFAOYSA-N triflupromazine hydrochloride Chemical compound [H+].[Cl-].C1=C(C(F)(F)F)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 FTNWXGFYRHWUKG-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229960003824 ustekinumab Drugs 0.000 description 1
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- 229960004914 vedolizumab Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762458144P | 2017-02-13 | 2017-02-13 | |
| PCT/US2018/017755 WO2018148626A1 (en) | 2017-02-13 | 2018-02-12 | Aminotriazolopyridines as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2902676T3 true ES2902676T3 (es) | 2022-03-29 |
Family
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Family Applications (1)
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| ES18707498T Active ES2902676T3 (es) | 2017-02-13 | 2018-02-12 | Aminotriazolopiridinas como inhibidores de cinasa |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US10913738B2 (enExample) |
| EP (1) | EP3580220B1 (enExample) |
| JP (1) | JP7097373B2 (enExample) |
| KR (1) | KR102549952B1 (enExample) |
| CN (1) | CN110520423B (enExample) |
| AU (1) | AU2018217488B2 (enExample) |
| BR (1) | BR112019016635A2 (enExample) |
| CA (1) | CA3053484A1 (enExample) |
| CY (1) | CY1124978T1 (enExample) |
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| EA (1) | EA039808B1 (enExample) |
| ES (1) | ES2902676T3 (enExample) |
| HR (1) | HRP20212000T1 (enExample) |
| HU (1) | HUE057801T2 (enExample) |
| IL (1) | IL268614B (enExample) |
| LT (1) | LT3580220T (enExample) |
| MA (1) | MA47460A (enExample) |
| MX (1) | MX378515B (enExample) |
| PL (1) | PL3580220T3 (enExample) |
| PT (1) | PT3580220T (enExample) |
| RS (1) | RS62801B1 (enExample) |
| SG (1) | SG11201907335UA (enExample) |
| SI (1) | SI3580220T1 (enExample) |
| SM (1) | SMT202200001T1 (enExample) |
| WO (1) | WO2018148626A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| MA47460A (fr) * | 2017-02-13 | 2019-12-18 | Bristol Myers Squibb Co | Aminotriazolopyridines utilisées en tant qu'inhibiteurs de kinase |
| LT3704118T (lt) * | 2017-10-30 | 2022-02-25 | Bristol-Myers Squibb Company | Aminoimidazopiridazinai, kaip kinazės inhibitoriai |
| MX2020007531A (es) | 2018-01-26 | 2020-09-09 | Bristol Myers Squibb Co | Aminopirrolotriazinas como inhibidores de cinasa. |
| AU2019302534B2 (en) * | 2018-07-09 | 2024-10-03 | Lieber Institute, Inc. | Pyridazine compounds for inhibiting NaV1.8 |
| JP2021530478A (ja) | 2018-07-09 | 2021-11-11 | リーバー インスティチュート インコーポレイテッドLieber Institute, Inc. | ＮａＶ１．８を阻害するためのピリジンカルボキシアミド化合物 |
| US12084426B2 (en) | 2018-09-13 | 2024-09-10 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| EA202190718A1 (ru) | 2018-09-13 | 2021-07-01 | Бристол-Маерс Сквибб Компани | Индазолкарбоксамиды в качестве ингибиторов киназ |
| KR102769633B1 (ko) * | 2019-01-25 | 2025-02-19 | 베이징 사이텍-엠큐 파마슈티컬즈 리미티드 | 아실아미노 가교된 헤테로사이클릭 화합물, 및 이의 조성물 및 응용 |
| JP7323637B2 (ja) * | 2019-03-22 | 2023-08-08 | ▲勁▼方医▲薬▼科技（上海）有限公司 | 置換複素環式アミド化合物、その調製方法、及びその医薬的使用 |
| WO2021067654A1 (en) | 2019-10-03 | 2021-04-08 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| BR112022016124A2 (pt) * | 2020-02-13 | 2022-10-25 | Genfleet Therapeutics Shanghai Inc | Composto de di-hidronaftiridinona, e método de preparação para este e uso médico deste |
| CN114230565B (zh) * | 2020-09-09 | 2023-10-27 | 成都奥睿药业有限公司 | 5-取代吲哚3-酰胺衍生物及其制备方法和用途 |
| CN114262322A (zh) * | 2020-09-16 | 2022-04-01 | 中国科学院上海有机化学研究所 | 一类细胞程序性坏死抑制剂及其制备方法和用途 |
| AR123793A1 (es) | 2020-10-19 | 2023-01-11 | Bristol Myers Squibb Co | Compuestos de triazolopiridinilo como inhibidores de quinasas |
| TWI824626B (zh) * | 2021-08-02 | 2023-12-01 | 大陸商勁方醫藥科技(上海)有限公司 | Ripk1抑制劑的晶型及其酸式鹽和其酸式鹽的晶型 |
| AU2022328136A1 (en) | 2021-08-10 | 2023-11-30 | Abbvie Inc. | Nicotinamide ripk1 inhibitors |
| WO2023174374A1 (zh) | 2022-03-16 | 2023-09-21 | 江苏恒瑞医药股份有限公司 | 稠杂环类化合物、其制备方法及其在医药上的应用 |
| CN116574053A (zh) * | 2022-06-21 | 2023-08-11 | 中国药科大学 | Ripk1激酶靶点抑制剂及其医药用途 |
| AR131541A1 (es) | 2023-01-07 | 2025-04-09 | Syngenta Crop Protection Ag | Compuestos de carboxamida novedosos |
| TW202521107A (zh) * | 2023-09-27 | 2025-06-01 | 美商必治妥美雅史谷比公司 | 作為激酶抑制劑之三唑并吡啶化合物 |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| WO2025149637A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| WO2025149629A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
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| MXPA06014637A (es) | 2004-06-25 | 2007-02-12 | Amgen Inc | Triazoles e indazoles condensados utiles en el tratamiento de enfermedades mediadas por citocinas y otras enfermedades. |
| EP2001480A4 (en) * | 2006-03-31 | 2011-06-15 | Abbott Lab | Indazole CONNECTIONS |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| EA201000797A1 (ru) | 2007-11-27 | 2011-02-28 | Целльзом Лимитид | Аминотриазолы в качестве ингибиторов pi3k |
| WO2010007100A1 (en) * | 2008-07-15 | 2010-01-21 | Cellzome Ltd | 7-substituted amino triazoles as pi3k inhibitors |
| WO2010057877A1 (en) | 2008-11-18 | 2010-05-27 | Cellzome Limited | 7-pyridinyl- or phenyl- substituted triazolo [1, 5 -a] pyridines as pi3k inhibitors |
| CA2750517A1 (en) | 2009-02-04 | 2010-08-12 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2897949B1 (en) | 2012-09-18 | 2018-01-10 | Bristol-Myers Squibb Company | Iap antagonists |
| CN105246891A (zh) | 2013-06-10 | 2016-01-13 | 拜耳制药股份公司 | 用于治疗癌症的新化合物 |
| EP3182974A1 (en) * | 2014-08-21 | 2017-06-28 | GlaxoSmithKline Intellectual Property Development Limited | Heterocyclic amides as rip1 kinase inhibitors as medicaments |
| BR112018008765B1 (pt) * | 2015-11-05 | 2022-05-24 | Sumitomo Chemical Company, Limited | Composto heterocíclico condensado, composição e método para o controle de um artrópode nocivo |
| WO2018017435A1 (en) | 2016-07-22 | 2018-01-25 | Accro Bioscience Inc. | Heteroaryl compounds as inhibitors of necrosis, composition and application thereof |
| JP7190906B2 (ja) | 2017-01-24 | 2022-12-16 | 住友化学株式会社 | 縮合複素環化合物及びそれを含有する組成物 |
| MA47460A (fr) * | 2017-02-13 | 2019-12-18 | Bristol Myers Squibb Co | Aminotriazolopyridines utilisées en tant qu'inhibiteurs de kinase |
| LT3704118T (lt) | 2017-10-30 | 2022-02-25 | Bristol-Myers Squibb Company | Aminoimidazopiridazinai, kaip kinazės inhibitoriai |
| MX2020007531A (es) | 2018-01-26 | 2020-09-09 | Bristol Myers Squibb Co | Aminopirrolotriazinas como inhibidores de cinasa. |
| AR123793A1 (es) * | 2020-10-19 | 2023-01-11 | Bristol Myers Squibb Co | Compuestos de triazolopiridinilo como inhibidores de quinasas |
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2018
- 2018-02-12 MA MA047460A patent/MA47460A/fr unknown
- 2018-02-12 PL PL18707498T patent/PL3580220T3/pl unknown
- 2018-02-12 LT LTEPPCT/US2018/017755T patent/LT3580220T/lt unknown
- 2018-02-12 DK DK18707498.4T patent/DK3580220T3/da active
- 2018-02-12 PT PT187074984T patent/PT3580220T/pt unknown
- 2018-02-12 BR BR112019016635A patent/BR112019016635A2/pt not_active Application Discontinuation
- 2018-02-12 CA CA3053484A patent/CA3053484A1/en active Pending
- 2018-02-12 SG SG11201907335UA patent/SG11201907335UA/en unknown
- 2018-02-12 JP JP2019543377A patent/JP7097373B2/ja active Active
- 2018-02-12 ES ES18707498T patent/ES2902676T3/es active Active
- 2018-02-12 SI SI201830511T patent/SI3580220T1/sl unknown
- 2018-02-12 HU HUE18707498A patent/HUE057801T2/hu unknown
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- 2018-02-12 SM SM20220001T patent/SMT202200001T1/it unknown
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- 2018-02-12 CN CN201880024064.1A patent/CN110520423B/zh active Active
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- 2018-02-12 AU AU2018217488A patent/AU2018217488B2/en not_active Ceased
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- 2018-02-12 HR HRP20212000TT patent/HRP20212000T1/hr unknown
- 2018-02-12 EA EA201991915A patent/EA039808B1/ru unknown
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2019
- 2019-08-09 IL IL268614A patent/IL268614B/en unknown
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2020
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2022
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2024
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