EA039808B1 - Аминотриазолопиридины в качестве ингибиторов киназ - Google Patents

Info

Publication number

EA039808B1

EA039808B1 EA201991915A EA201991915A EA039808B1 EA 039808 B1 EA039808 B1 EA 039808B1 EA 201991915 A EA201991915 A EA 201991915A EA 201991915 A EA201991915 A EA 201991915A EA 039808 B1 EA039808 B1 EA 039808B1

Authority

EA

Eurasian Patent Office

Prior art keywords

triazolo

amino

pyridin

methyl

carboxamide

Prior art date

2017-02-13

Links

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• Global Dossier
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• 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 3
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 149
• 150000003839 salts Chemical class 0.000 claims abstract description 54
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 213
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 157
• -1 C 1-4 deuteroalkoxy Chemical group 0.000 claims description 155
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 137
• 239000011570 nicotinamide Substances 0.000 claims description 100
• 235000005152 nicotinamide Nutrition 0.000 claims description 99
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• 238000000034 method Methods 0.000 claims description 45
• 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims description 41
• 102100022501 Receptor-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 229960003966 nicotinamide Drugs 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 230000000694 effects Effects 0.000 claims description 16
• 125000006712 (C1-C4) deuteroalkyl group Chemical group 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000005345 deuteroalkyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 8
• GOIWNSRZUNIIRY-UHFFFAOYSA-N 6-Methylnicotinamide Chemical compound CCC1=NC=CC=C1C(N)=O GOIWNSRZUNIIRY-UHFFFAOYSA-N 0.000 claims description 8
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 8
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 8
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
• 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 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• 206010019280 Heart failures Diseases 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• YNJXVWIPWJKJJD-UHFFFAOYSA-N 2-methoxypyridine-3-carboxamide Chemical compound COC1=NC=CC=C1C(N)=O YNJXVWIPWJKJJD-UHFFFAOYSA-N 0.000 claims description 2
• JRYYVMDEUJQWRO-UHFFFAOYSA-N 2-methylnicotinamide Chemical compound CC1=NC=CC=C1C(N)=O JRYYVMDEUJQWRO-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• VNCRYKVYTCTHHQ-KBMKNGFXSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[dideuterio-[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-methoxypyridine-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)=N1 VNCRYKVYTCTHHQ-KBMKNGFXSA-N 0.000 claims description 2
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• DHAUBWZUAWPASK-KRWDZBQOSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-[(3S)-3-[(3-fluorophenyl)methyl]piperidin-1-yl]methanone Chemical compound FC=1C=C(C=CC=1)C[C@H]1CN(CCC1)C(=O)C=1C=C(C=NC=1OC)C1=CC=2N(C=C1)N=C(N=2)N DHAUBWZUAWPASK-KRWDZBQOSA-N 0.000 claims description 2
• LGCUXQDAKZJMMD-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-[3-[(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]methanone Chemical compound COC1=NC=C(C=C1C(=O)N1CCCC(C1)C(O)C1=CC=C(F)C=C1)C1=CC2=NC(N)=NN2C=C1 LGCUXQDAKZJMMD-UHFFFAOYSA-N 0.000 claims description 2
• GTKKODLPPDMVNT-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-[3-[(4-methoxyphenyl)methyl]piperidin-1-yl]methanone Chemical compound COC1=C(C=C(C=N1)C1=CC=2N(C=C1)N=C(N=2)N)C(=O)N1CC(CCC1)CC1=CC=C(C=C1)OC GTKKODLPPDMVNT-UHFFFAOYSA-N 0.000 claims description 2
• BAQFNAPWECEQAP-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridin-3-yl]-[3-[(4-methylphenyl)methyl]piperidin-1-yl]methanone Chemical compound CC1=CC=C(CC(CCC2)CN2C(C(C=C(C=N2)C3=CC4=NC(N)=NN4C=C3)=C2OC)=O)C=C1 BAQFNAPWECEQAP-UHFFFAOYSA-N 0.000 claims description 2
• VUYVTBJRPXRFNB-UHFFFAOYSA-N [5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methylpyridin-3-yl]-[3-[(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]methanone Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)N2CC(CCC2)C(O)C2=CC=C(C=C2)F)=N1 VUYVTBJRPXRFNB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
• 150000003857 carboxamides Chemical class 0.000 claims description 2
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 2
• JIHUNHANXLPSIB-UHFFFAOYSA-N tert-butyl N-[3-[[5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxypyridine-3-carbonyl]amino]cyclohexyl]carbamate Chemical compound NC1=NN2C(C=C(C=C2)C=2C=NC(=C(C(=O)NC3CC(CCC3)NC(OC(C)(C)C)=O)C=2)OC)=N1 JIHUNHANXLPSIB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 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
• MPQHBWNDIOJYNP-UHFFFAOYSA-N 2,6-dimethylpyridine-3-carboxamide Chemical compound CC1=CC=C(C(N)=O)C(C)=N1 MPQHBWNDIOJYNP-UHFFFAOYSA-N 0.000 claims 1
• YNJXVWIPWJKJJD-FIBGUPNXSA-N 2-(trideuteriomethoxy)pyridine-3-carboxamide Chemical compound [2H]C([2H])([2H])OC1=NC=CC=C1C(N)=O YNJXVWIPWJKJJD-FIBGUPNXSA-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
• 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
• 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
• 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
• UJLPXCXPCXTYPU-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methoxy-N-[(2-phenylphenyl)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)C2=CC=CC=C2)=N1 UJLPXCXPCXTYPU-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
• PKEVLPKBYXRYQJ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-methyl-N-[[2-(3-methylcyclopentyl)oxyphenyl]methyl]pyridine-3-carboxamide Chemical compound NC1=NN2C(C=C(C=C2)C=2C=C(C(=NC=2)C)C(=O)NCC2=C(C=CC=C2)OC2CC(CC2)C)=N1 PKEVLPKBYXRYQJ-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
• 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
• RDCAEKQSSBDOKV-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-(cyclopentylmethoxy)-4,6-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=C(C=C2F)F)OCC2CCCC2)=N1 RDCAEKQSSBDOKV-UHFFFAOYSA-N 0.000 claims 1
• VNCRYKVYTCTHHQ-UHFFFAOYSA-N 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-[[2-fluoro-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)F)=N1 VNCRYKVYTCTHHQ-UHFFFAOYSA-N 0.000 claims 1
• UFXWMRWKXHASGJ-UHFFFAOYSA-N COC(C(C(N)=O)=C1)=NC=C1C1=CC2=NC(N)=NN2C=C1 Chemical compound COC(C(C(N)=O)=C1)=NC=C1C1=CC2=NC(N)=NN2C=C1 UFXWMRWKXHASGJ-UHFFFAOYSA-N 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 552
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 243
• 239000012071 phase Substances 0.000 description 186
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