EA035739B1 - Конденсированные бициклические гетероарильные производные с активностью ингибиторов пролилгидроксилазы - Google Patents

Info

Publication number

EA035739B1

EA035739B1 EA201792057A EA201792057A EA035739B1 EA 035739 B1 EA035739 B1 EA 035739B1 EA 201792057 A EA201792057 A EA 201792057A EA 201792057 A EA201792057 A EA 201792057A EA 035739 B1 EA035739 B1 EA 035739B1

Authority

EA

Eurasian Patent Office

Prior art keywords

triazolo

pyridin

benzonitrile

pyridine

cyano

Prior art date

2015-03-18

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• 102000004079 Prolyl Hydroxylases Human genes 0.000 title claims description 7
• 108010043005 Prolyl Hydroxylases Proteins 0.000 title claims description 7
• 230000000694 effects Effects 0.000 title description 7
• 239000003112 inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 184
• 238000000034 method Methods 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 239000003814 drug Substances 0.000 claims abstract description 11
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 353
• -1 NR9R 10 Chemical group 0.000 claims description 243
• 125000001424 substituent group Chemical group 0.000 claims description 113
• 125000000623 heterocyclic group Chemical group 0.000 claims description 82
• 229910052757 nitrogen Inorganic materials 0.000 claims description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 78
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 56
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• 150000002367 halogens Chemical class 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 50
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 34
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 125000004043 oxo group Chemical group O=* 0.000 claims description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
• GWXSXJAQYVBOTK-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-fluorobenzonitrile Chemical compound NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N GWXSXJAQYVBOTK-UHFFFAOYSA-N 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000001153 fluoro group Chemical group F* 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 28
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
• 239000001301 oxygen Chemical group 0.000 claims description 26
• 150000002431 hydrogen Chemical class 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 239000000460 chlorine Substances 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 21
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• 229910052801 chlorine Inorganic materials 0.000 claims description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 239000011737 fluorine Chemical group 0.000 claims description 11
• 125000003566 oxetanyl group Chemical group 0.000 claims description 11
• 125000005475 oxolanyl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• HNUCQKUWOZDYFO-UHFFFAOYSA-N 4-(7-benzylsulfanyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(SCC2=CC=CC=C2)=CC2=NC=NN12 HNUCQKUWOZDYFO-UHFFFAOYSA-N 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 206010019280 Heart failures Diseases 0.000 claims description 9
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
• 208000010125 myocardial infarction Diseases 0.000 claims description 9
• 229910052717 sulfur Chemical group 0.000 claims description 9
• OGXGCIBHOYGYDL-UHFFFAOYSA-N 2-fluoro-4-(6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=C(F)C=CC2=NC=NN12)C#N OGXGCIBHOYGYDL-UHFFFAOYSA-N 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
• BPNLOIPAXMBVJV-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-[2-(dimethylamino)ethyl]-[1,2,4]triazolo[1,5-a]pyridine-7-sulfonamide Chemical compound CN(C)CCNS(=O)(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N BPNLOIPAXMBVJV-UHFFFAOYSA-N 0.000 claims description 7
• 206010007556 Cardiac failure acute Diseases 0.000 claims description 7
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 239000011593 sulfur Chemical group 0.000 claims description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• ZKHPNASIRYLBNH-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound NC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N ZKHPNASIRYLBNH-UHFFFAOYSA-N 0.000 claims description 6
• 208000009304 Acute Kidney Injury Diseases 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
• FBDODZQVKOVCDF-UHFFFAOYSA-N OC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N Chemical compound OC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N FBDODZQVKOVCDF-UHFFFAOYSA-N 0.000 claims description 6
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 6
• 208000033626 Renal failure acute Diseases 0.000 claims description 6
• 201000011040 acute kidney failure Diseases 0.000 claims description 6
• 208000012998 acute renal failure Diseases 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 208000020832 chronic kidney disease Diseases 0.000 claims description 6
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• XSJCELJOUMSZNZ-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-fluoro-3-methylbenzonitrile hydrochloride Chemical compound Cl.Cc1c(F)c(ccc1-c1cc(N)cc2ncnn12)C#N XSJCELJOUMSZNZ-UHFFFAOYSA-N 0.000 claims description 5
• DAEJAOGCSBFGTO-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-methylbenzonitrile Chemical compound NC1=CC=2N(C(=C1)C1=C(C=C(C#N)C=C1)C)N=CN=2 DAEJAOGCSBFGTO-UHFFFAOYSA-N 0.000 claims description 5
• NULNJTASVWHGGJ-UHFFFAOYSA-N 4-(7-piperazin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(=CC2=NC=NN12)N1CCNCC1 NULNJTASVWHGGJ-UHFFFAOYSA-N 0.000 claims description 5
• ZZNRUONACXNPDC-UHFFFAOYSA-N 4-[7-(hydroxymethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound OCC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N ZZNRUONACXNPDC-UHFFFAOYSA-N 0.000 claims description 5
• IPSCFFIGHRZVOS-UHFFFAOYSA-N 5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound NC(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N IPSCFFIGHRZVOS-UHFFFAOYSA-N 0.000 claims description 5
• JAXSSSXHKOWZPV-UHFFFAOYSA-N 5-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-6-methylpyridine-2-carbonitrile Chemical compound CC1=C(C=CC(=N1)C#N)C1=CC(N)=CC2=NC=NN12 JAXSSSXHKOWZPV-UHFFFAOYSA-N 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• XOVKTGISWRVRDQ-UHFFFAOYSA-N N-[[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]methyl]acetamide Chemical compound CC(=O)NCC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N XOVKTGISWRVRDQ-UHFFFAOYSA-N 0.000 claims description 5
• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• BHBTZAUVKXSOJJ-UHFFFAOYSA-N 1-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3-phenylurea Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)NC2=CC=CC=C2)=CC2=NC=NN12)C#N BHBTZAUVKXSOJJ-UHFFFAOYSA-N 0.000 claims description 4
• WWTWZEXZURTRAX-UHFFFAOYSA-N 2,6-difluoro-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=CC(=CC(F)=C1C#N)C1=CC=CC2=NC=NN12 WWTWZEXZURTRAX-UHFFFAOYSA-N 0.000 claims description 4
• SANJZTJYISVNMU-UHFFFAOYSA-N 2-(azetidin-1-yl)-N-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound N1(CCC1)CC(=O)NC1=CC=2N(C(=C1)C1=CC=C(C=C1)C#N)N=CN=2 SANJZTJYISVNMU-UHFFFAOYSA-N 0.000 claims description 4
• DYYNCYBQURWPHG-UHFFFAOYSA-N 2-fluoro-3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=C(C=CC(C#N)=C1F)C1=CC=CC2=NC=NN12 DYYNCYBQURWPHG-UHFFFAOYSA-N 0.000 claims description 4
• CUZZZFBECBOGRY-UHFFFAOYSA-N 2-fluoro-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=CC=CC2=NC=NN12)C#N CUZZZFBECBOGRY-UHFFFAOYSA-N 0.000 claims description 4
• UCFYQUDHDDRQFP-UHFFFAOYSA-N 2-fluoro-4-([1,2,4]triazolo[1,5-c]pyrimidin-5-yl)benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=NC=CC2=NC=NN12)C#N UCFYQUDHDDRQFP-UHFFFAOYSA-N 0.000 claims description 4
• YFUPQNBWHXCVAW-UHFFFAOYSA-N 3,5-difluoro-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC=1C=C(C#N)C=C(C=1C1=CC=CC=2N1N=CN=2)F YFUPQNBWHXCVAW-UHFFFAOYSA-N 0.000 claims description 4
• JCKPMHQVYXQULF-UHFFFAOYSA-N 3-fluoro-4-(6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=C(C=CC(=C1)C#N)C1=C(F)C=CC2=NC=NN12 JCKPMHQVYXQULF-UHFFFAOYSA-N 0.000 claims description 4
• URBXKEHMAICHMQ-UHFFFAOYSA-N 3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=C(C=CC(=C1)C#N)C1=CC=CC2=NC=NN12 URBXKEHMAICHMQ-UHFFFAOYSA-N 0.000 claims description 4
• UFFIQCONOMTRNB-UHFFFAOYSA-N 4-(6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-methylbenzonitrile Chemical compound CC1=C(C=CC(=C1)C#N)C1=C(F)C=CC2=NC=NN12 UFFIQCONOMTRNB-UHFFFAOYSA-N 0.000 claims description 4
• KJJREHAQJJBUEW-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-fluoro-5-methylbenzonitrile Chemical compound NC1=CC=2N(C(=C1)C1=CC(=C(C#N)C=C1C)F)N=CN=2 KJJREHAQJJBUEW-UHFFFAOYSA-N 0.000 claims description 4
• VNYPOTBWRCUJAW-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-fluorobenzonitrile Chemical compound NC1=CC=2N(C(=C1)C1=C(C=C(C#N)C=C1)F)N=CN=2 VNYPOTBWRCUJAW-UHFFFAOYSA-N 0.000 claims description 4
• SCANPRRUXSCKFM-UHFFFAOYSA-N 4-(7-chloro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2,3-difluorobenzonitrile Chemical compound FC1=C(C=CC(=C1F)C1=CC(Cl)=CC2=NC=NN12)C#N SCANPRRUXSCKFM-UHFFFAOYSA-N 0.000 claims description 4
• GMMZUSBSRMJYMT-UHFFFAOYSA-N 4-(7-chloro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC(C#N)=C(F)C=C1C1=CC(Cl)=CC2=NC=NN12 GMMZUSBSRMJYMT-UHFFFAOYSA-N 0.000 claims description 4
• USVLWCODEVAHRR-UHFFFAOYSA-N 4-(7-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(=CC2=NC=NN12)C1CC1 USVLWCODEVAHRR-UHFFFAOYSA-N 0.000 claims description 4
• HAYKWHIVYOQGOH-UHFFFAOYSA-N 4-[7-(cyclopropylmethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(NCC2CC2)=CC2=NC=NN12 HAYKWHIVYOQGOH-UHFFFAOYSA-N 0.000 claims description 4
• NGYRNGMPXPBBFT-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-(2-methoxyethyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound COCCNC(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N NGYRNGMPXPBBFT-UHFFFAOYSA-N 0.000 claims description 4
• GRZVEPGDKJIDAY-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=CC3=NC=NN3C(=C2)C2=CC=C(C=C2)C#N)=C1 GRZVEPGDKJIDAY-UHFFFAOYSA-N 0.000 claims description 4
• PNZVJNFRTDGQNR-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-(cyclopropylmethyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)C1=CC(=CC=2N1N=CN=2)C(=O)NCC1CC1 PNZVJNFRTDGQNR-UHFFFAOYSA-N 0.000 claims description 4
• GQZLLNMBCOFNNK-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-(oxetan-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound O=C(NC1COC1)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N GQZLLNMBCOFNNK-UHFFFAOYSA-N 0.000 claims description 4
• BOFLQVCHXQZMPZ-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-[2-(3-methoxyphenyl)ethyl]-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound COC1=CC=CC(CCNC(=O)C2=CC3=NC=NN3C(=C2)C2=CC=C(C=C2)C#N)=C1 BOFLQVCHXQZMPZ-UHFFFAOYSA-N 0.000 claims description 4
• QHASUZQZHCPRHM-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-[2-(4-methylpiperazin-1-yl)ethyl]-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound CN1CCN(CCNC(=O)C2=CC3=NC=NN3C(=C2)C2=CC=C(C=C2)C#N)CC1 QHASUZQZHCPRHM-UHFFFAOYSA-N 0.000 claims description 4
• XEHZSSQNQZTTAC-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-propan-2-yl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound CC(C)NC(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N XEHZSSQNQZTTAC-UHFFFAOYSA-N 0.000 claims description 4
• SZXOXIUXMHQIGQ-UHFFFAOYSA-N 5-(4-ethynylphenyl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(#C)C1=CC=C(C=C1)C1=CC=CC=2N1N=CN=2 SZXOXIUXMHQIGQ-UHFFFAOYSA-N 0.000 claims description 4
• DTZRLWJTMXBNFI-UHFFFAOYSA-N N-[[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]methyl]cyclopropanecarboxamide Chemical compound O=C(NCC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N)C1CC1 DTZRLWJTMXBNFI-UHFFFAOYSA-N 0.000 claims description 4
• GNOYFDYKXJPUML-UHFFFAOYSA-N OC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N Chemical compound OC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N GNOYFDYKXJPUML-UHFFFAOYSA-N 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• PBWWNLBOKZZRNH-UHFFFAOYSA-N methyl 5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate Chemical compound COC(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N PBWWNLBOKZZRNH-UHFFFAOYSA-N 0.000 claims description 4
• OUUKGGARMJMPSU-INIZCTEOSA-N (2S)-N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]oxolane-2-carboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)[C@@H]2CCCO2)=CC2=NC=NN12)C#N OUUKGGARMJMPSU-INIZCTEOSA-N 0.000 claims description 3
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
• LVBPHSQMFKIYMO-UHFFFAOYSA-N 1-([1,2,4]triazolo[1,5-a]pyridin-5-yl)piperidine-4-carbonitrile Chemical compound N=1C=NN2C=1C=CC=C2N1CCC(CC1)C#N LVBPHSQMFKIYMO-UHFFFAOYSA-N 0.000 claims description 3
• PAQNXWWTZCDJGC-UHFFFAOYSA-N 2,3-difluoro-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=C(C=CC(=C1F)C1=CC=CC2=NC=NN12)C#N PAQNXWWTZCDJGC-UHFFFAOYSA-N 0.000 claims description 3
• MHHKFALIEJDOHF-UHFFFAOYSA-N 2-chloro-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound ClC1=C(C=CC(=C1)C1=CC=CC2=NC=NN12)C#N MHHKFALIEJDOHF-UHFFFAOYSA-N 0.000 claims description 3
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• JLBXPVLATDUNKH-UHFFFAOYSA-N N-[5-(4-cyano-2-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound CC(=O)NC1=CC2=NC=NN2C(=C1)C1=C(F)C=C(C=C1)C#N JLBXPVLATDUNKH-UHFFFAOYSA-N 0.000 claims description 3
• GXMMIFQMKFWLCL-UHFFFAOYSA-N N-[5-(4-cyano-2-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanecarboxamide Chemical compound FC1=C(C=CC(=C1)C#N)C1=CC(NC(=O)C2CC2)=CC2=NC=NN12 GXMMIFQMKFWLCL-UHFFFAOYSA-N 0.000 claims description 3
• FMODJHVQEMMQRV-UHFFFAOYSA-N N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-hydroxy-2-methylpropanamide Chemical compound CC1=C(C=CC(=C1)C#N)C1=CC(NC(=O)C(C)(C)O)=CC2=NC=NN12 FMODJHVQEMMQRV-UHFFFAOYSA-N 0.000 claims description 3
• JDQJVFORFISJLJ-UHFFFAOYSA-N N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3,3,3-trifluoropropanamide Chemical compound CC1=C(C=CC(=C1)C#N)C1=CC(NC(=O)CC(F)(F)F)=CC2=NC=NN12 JDQJVFORFISJLJ-UHFFFAOYSA-N 0.000 claims description 3
• KSFLSVYCJRTRHZ-UHFFFAOYSA-N N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanecarboxamide Chemical compound C(#N)C1=CC(=C(C=C1)C1=CC(=CC=2N1N=CN=2)NC(=O)C1CC1)C KSFLSVYCJRTRHZ-UHFFFAOYSA-N 0.000 claims description 3
• MDNAODMPSFGANZ-UHFFFAOYSA-N N-[5-(4-cyano-3-fluoro-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound CC(=O)NC1=CC2=NC=NN2C(=C1)C1=C(C)C(F)=C(C=C1)C#N MDNAODMPSFGANZ-UHFFFAOYSA-N 0.000 claims description 3
• WIOXTBUBGWILPP-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2,2-difluorocyclopropane-1-carboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2CC2(F)F)=CC2=NC=NN12)C#N WIOXTBUBGWILPP-UHFFFAOYSA-N 0.000 claims description 3
• PCJZGCNAUIEGIR-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-(dimethylamino)acetamide Chemical compound C(#N)C1=C(C=C(C=C1)C1=CC(=CC=2N1N=CN=2)NC(CN(C)C)=O)F PCJZGCNAUIEGIR-UHFFFAOYSA-N 0.000 claims description 3
• AGMBCMBVTBGQHK-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-(oxan-4-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)CC2CCOCC2)=CC2=NC=NN12)C#N AGMBCMBVTBGQHK-UHFFFAOYSA-N 0.000 claims description 3
• OFQIHMZPWBHZJH-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-(oxetan-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)CC2COC2)=CC2=NC=NN12)C#N OFQIHMZPWBHZJH-UHFFFAOYSA-N 0.000 claims description 3
• KIGRYOILNDDRNN-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-methoxy-2-methylpropanamide Chemical compound COC(C)(C)C(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N KIGRYOILNDDRNN-UHFFFAOYSA-N 0.000 claims description 3
• OHOWYXITQIKSMS-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N OHOWYXITQIKSMS-UHFFFAOYSA-N 0.000 claims description 3
• VVARASXIQIPEOX-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-methylcyclopropane-1-carboxamide Chemical compound CC1CC1C(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N VVARASXIQIPEOX-UHFFFAOYSA-N 0.000 claims description 3
• GXHZGUGQNLOZMX-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-piperidin-1-ylacetamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)CN2CCCCC2)=CC2=NC=NN12)C#N GXHZGUGQNLOZMX-UHFFFAOYSA-N 0.000 claims description 3
• DTMNYSLOZMVPTA-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3,3,3-trifluoropropanamide Chemical compound C(#N)C1=C(C=C(C=C1)C1=CC(=CC=2N1N=CN=2)NC(CC(F)(F)F)=O)F DTMNYSLOZMVPTA-UHFFFAOYSA-N 0.000 claims description 3
• RBCCWUJRBHHFSC-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3-fluorocyclobutane-1-carboxamide Chemical compound FC1CC(C1)C(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N RBCCWUJRBHHFSC-UHFFFAOYSA-N 0.000 claims description 3
• FSIXIAPEJFNDOD-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3-methyloxetane-3-carboxamide Chemical compound CC1(COC1)C(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N FSIXIAPEJFNDOD-UHFFFAOYSA-N 0.000 claims description 3
• VZGYESHGCNJQID-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-4-methyloxane-4-carboxamide Chemical compound CC1(CCOCC1)C(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N VZGYESHGCNJQID-UHFFFAOYSA-N 0.000 claims description 3
• KNWCVKCQYXQFAS-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclobutanecarboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2CCC2)=CC2=NC=NN12)C#N KNWCVKCQYXQFAS-UHFFFAOYSA-N 0.000 claims description 3
• KIDNTTIYEICQIJ-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanecarboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2CC2)=CC2=NC=NN12)C#N KIDNTTIYEICQIJ-UHFFFAOYSA-N 0.000 claims description 3
• QVQTXFSQVFHTHR-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]formamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC=O)=CC2=NC=NN12)C#N QVQTXFSQVFHTHR-UHFFFAOYSA-N 0.000 claims description 3
• PNFRXPLISINJNC-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]oxetane-3-carboxamide Chemical compound O1CC(C1)C(=O)NC1=CC=2N(C(=C1)C1=CC(=C(C=C1)C#N)F)N=CN=2 PNFRXPLISINJNC-UHFFFAOYSA-N 0.000 claims description 3
• HKQJTNMAMVRCEK-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]oxolane-3-carboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2CCOC2)=CC2=NC=NN12)C#N HKQJTNMAMVRCEK-UHFFFAOYSA-N 0.000 claims description 3
• JRHAOBSKRZJMBX-UHFFFAOYSA-N N-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-phenylacetamide Chemical compound O=C(CC1=CC=CC=C1)NC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N JRHAOBSKRZJMBX-UHFFFAOYSA-N 0.000 claims description 3
• PTTWJWRRPHSFRN-UHFFFAOYSA-N N-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound CC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N PTTWJWRRPHSFRN-UHFFFAOYSA-N 0.000 claims description 3
• OXBZAXBNVZSIFP-UHFFFAOYSA-N N-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]benzamide Chemical compound O=C(NC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N)C1=CC=CC=C1 OXBZAXBNVZSIFP-UHFFFAOYSA-N 0.000 claims description 3
• SMWXNMVLXVAZKH-UHFFFAOYSA-N N-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanecarboxamide Chemical compound O=C(NC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N)C1CC1 SMWXNMVLXVAZKH-UHFFFAOYSA-N 0.000 claims description 3
• KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
• OUUKGGARMJMPSU-MRXNPFEDSA-N (2R)-N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]oxolane-2-carboxamide Chemical compound O1[C@H](CCC1)C(=O)NC1=CC=2N(C(=C1)C1=CC(=C(C=C1)C#N)F)N=CN=2 OUUKGGARMJMPSU-MRXNPFEDSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• KPLCYCWZNQGMKF-UHFFFAOYSA-N 2-fluoro-4-[7-(2-oxopyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=CC(=CC2=NC=NN12)N1CCCC1=O)C#N KPLCYCWZNQGMKF-UHFFFAOYSA-N 0.000 claims description 2
• HTNBFLTXQKEDBA-UHFFFAOYSA-N 2-fluoro-4-[7-(oxolan-2-ylmethoxy)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=CC(OCC2CCCO2)=CC2=NC=NN12)C#N HTNBFLTXQKEDBA-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• CPQYTURIYBICGL-UHFFFAOYSA-N 3-methyl-4-[7-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound CC1=C(C=CC(=C1)C#N)C1=CC(=CC2=NC=NN12)N1CC2(COC2)C1 CPQYTURIYBICGL-UHFFFAOYSA-N 0.000 claims description 2
• BXRZVLHTIWMPBC-UHFFFAOYSA-N 4-(6-methyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=C(N2N=CN=C2C=C1)C1=CC=C(C=C1)C#N BXRZVLHTIWMPBC-UHFFFAOYSA-N 0.000 claims description 2
• RVSQXEPIPJUJSE-UHFFFAOYSA-N 4-[7-(2,2-difluoroethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC(CNC1=CC=2N(C(=C1)C1=CC=C(C#N)C=C1)N=CN=2)F RVSQXEPIPJUJSE-UHFFFAOYSA-N 0.000 claims description 2
• OVJABDQLRNCOTE-UHFFFAOYSA-N 4-[7-(2,3-dihydroxypropylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-3-methylbenzonitrile Chemical compound OC(CNC1=CC=2N(C(=C1)C1=C(C=C(C#N)C=C1)C)N=CN=2)CO OVJABDQLRNCOTE-UHFFFAOYSA-N 0.000 claims description 2
• AIEXTHXNUBVWKC-UHFFFAOYSA-N 4-[7-(pyrrolidine-1-carbonyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound O=C(N1CCCC1)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N AIEXTHXNUBVWKC-UHFFFAOYSA-N 0.000 claims description 2
• QWPUYQJBBNNHQJ-UHFFFAOYSA-N 4-[7-[(2-hydroxy-2-methylpropyl)amino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound CC(C)(O)CNC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N QWPUYQJBBNNHQJ-UHFFFAOYSA-N 0.000 claims description 2
• DUKBFVQAMAGALG-UHFFFAOYSA-N 4-[7-[(3-fluorophenyl)methylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC=1C=C(C=CC=1)CNC1=CC=2N(C(=C1)C1=CC=C(C#N)C=C1)N=CN=2 DUKBFVQAMAGALG-UHFFFAOYSA-N 0.000 claims description 2
• DDBNRFRBPGDKLB-UHFFFAOYSA-N 4-[7-[(4-fluorophenyl)methylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=CC=C(C=C1)CNC1=CC=2N(C(=C1)C1=CC=C(C#N)C=C1)N=CN=2 DDBNRFRBPGDKLB-UHFFFAOYSA-N 0.000 claims description 2
• PWQKUIKFWFPZEP-UHFFFAOYSA-N 5-(7-chloro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-6-methylpyridine-2-carbonitrile Chemical compound CC1=C(C=CC(=N1)C#N)C1=CC(Cl)=CC2=NC=NN12 PWQKUIKFWFPZEP-UHFFFAOYSA-N 0.000 claims description 2
• KFOGCVZDTSAKDZ-UHFFFAOYSA-N 6-([1,2,4]triazolo[1,5-a]pyridin-5-yl)pyridine-3-carbonitrile Chemical compound N=1C=NN2C=1C=CC=C2C1=CC=C(C=N1)C#N KFOGCVZDTSAKDZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
• PHSYGPOCIUXUSY-UHFFFAOYSA-N N-[5-(2-chloro-4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound CC(=O)NC1=CC2=NC=NN2C(=C1)C1=C(Cl)C=C(C=C1)C#N PHSYGPOCIUXUSY-UHFFFAOYSA-N 0.000 claims description 2
• GYZPCUWAXGVOOJ-UHFFFAOYSA-N N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2,2-difluorocyclopropane-1-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1)C1=CC(=CC=2N1N=CN=2)NC(=O)C1C(C1)(F)F)C GYZPCUWAXGVOOJ-UHFFFAOYSA-N 0.000 claims description 2
• SOADHZFGKVPPAW-UHFFFAOYSA-N N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound CC(=O)NC1=CC2=NC=NN2C(=C1)C1=C(C)C=C(C=C1)C#N SOADHZFGKVPPAW-UHFFFAOYSA-N 0.000 claims description 2
• RLQSXFUVONKDKB-UHFFFAOYSA-N N-[5-(4-cyano-5-fluoro-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound CC(=O)NC1=CC2=NC=NN2C(=C1)C1=C(C)C=C(C#N)C(F)=C1 RLQSXFUVONKDKB-UHFFFAOYSA-N 0.000 claims description 2
• KHDGSULFSVLOPM-UHFFFAOYSA-N oxane-3-carboxamide Chemical compound NC(=O)C1CCCOC1 KHDGSULFSVLOPM-UHFFFAOYSA-N 0.000 claims description 2
• LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 claims 3
• LNQCUTNLHUQZLR-OZJWLQQPSA-N iridin Chemical compound OC1=C(OC)C(OC)=CC(C=2C(C3=C(O)C(OC)=C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=C3OC=2)=O)=C1 LNQCUTNLHUQZLR-OZJWLQQPSA-N 0.000 claims 3
• QMZYXVFPQKWUCP-UHFFFAOYSA-N 1-cyano-N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropane-1-carboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2(CC2)C#N)=CC2=NC=NN12)C#N QMZYXVFPQKWUCP-UHFFFAOYSA-N 0.000 claims 1
• FEOUNFBJVTUVKJ-UHFFFAOYSA-N 2-methoxyethyl N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]carbamate Chemical compound COCCOC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N FEOUNFBJVTUVKJ-UHFFFAOYSA-N 0.000 claims 1
• GDKTZFXYPXBDTL-UHFFFAOYSA-N 3-(dimethylamino)propyl N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]carbamate Chemical compound CN(C)CCCOC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N GDKTZFXYPXBDTL-UHFFFAOYSA-N 0.000 claims 1
• DYBVVKHTQNXUPV-UHFFFAOYSA-N 3-fluoro-4-[7-(2-methoxyethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC=1C=C(C#N)C=CC=1C1=CC(=CC=2N1N=CN=2)NCCOC DYBVVKHTQNXUPV-UHFFFAOYSA-N 0.000 claims 1
• MQAXAPLBUHZTNL-UHFFFAOYSA-N 4-[7-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(=CC2=NC=NN12)N1CC2(COC2)C1 MQAXAPLBUHZTNL-UHFFFAOYSA-N 0.000 claims 1
• JHTDBBSCILMZHF-UHFFFAOYSA-N 4-[7-(3,3,3-trifluoropropylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC(F)(F)CCNC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N JHTDBBSCILMZHF-UHFFFAOYSA-N 0.000 claims 1
• IDORUDAREBTSMG-UHFFFAOYSA-N 4-[7-(3-methoxyazetidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound COC1CN(C1)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N IDORUDAREBTSMG-UHFFFAOYSA-N 0.000 claims 1
• AKEYSUXDCRNKMQ-UHFFFAOYSA-N 4-[7-(3-methoxypropylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound COCCCNC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N AKEYSUXDCRNKMQ-UHFFFAOYSA-N 0.000 claims 1
• PDUUXICHUULHEW-UHFFFAOYSA-N 4-[7-(oxan-4-ylmethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(NCC2CCOCC2)=CC2=NC=NN12 PDUUXICHUULHEW-UHFFFAOYSA-N 0.000 claims 1
• OKKZJSAGVOEQNC-UHFFFAOYSA-N 4-[7-(oxetan-3-ylmethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(NCC2COC2)=CC2=NC=NN12 OKKZJSAGVOEQNC-UHFFFAOYSA-N 0.000 claims 1
• ZZTSLNIRICVWLB-UHFFFAOYSA-N 4-[7-(oxolan-2-ylmethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound O1C(CCC1)CNC1=CC=2N(C(=C1)C1=CC=C(C#N)C=C1)N=CN=2 ZZTSLNIRICVWLB-UHFFFAOYSA-N 0.000 claims 1
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