BR112017019653B1 - Composto de formula i e composição farmaceutica - Google Patents

Info

Publication number

BR112017019653B1

BR112017019653B1 BR112017019653-0A BR112017019653A BR112017019653B1 BR 112017019653 B1 BR112017019653 B1 BR 112017019653B1 BR 112017019653 A BR112017019653 A BR 112017019653A BR 112017019653 B1 BR112017019653 B1 BR 112017019653B1

Authority

BR

Brazil

Prior art keywords

triazolo

pyridin

benzonitrile

cyano

methyl

Prior art date

2015-03-18

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 217
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 24
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 125000001424 substituent group Chemical group 0.000 claims description 115
• 229910052757 nitrogen Inorganic materials 0.000 claims description 89
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
• 125000000623 heterocyclic group Chemical group 0.000 claims description 82
• -1 NR9R10 Chemical group 0.000 claims description 65
• 229910052736 halogen Inorganic materials 0.000 claims description 57
• 150000002367 halogens Chemical group 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 48
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 42
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 40
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 125000004043 oxo group Chemical group O=* 0.000 claims description 37
• 239000011737 fluorine Substances 0.000 claims description 36
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 150000002431 hydrogen Chemical group 0.000 claims description 31
• 229910052801 chlorine Inorganic materials 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 239000000460 chlorine Substances 0.000 claims description 25
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 239000001301 oxygen Substances 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 12
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 11
• 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 11
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 125000005843 halogen group 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
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group 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 9
• FKAGHRYUKLRFOX-UHFFFAOYSA-N 5-(4-cyanophenyl)-N-(cyclopropylmethyl)-[1,2,4]triazolo[1,5-a]pyridine-7-sulfonamide Chemical compound O=S(=O)(NCC1CC1)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N FKAGHRYUKLRFOX-UHFFFAOYSA-N 0.000 claims description 9
• 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 8
• 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 8
• 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 8
• 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 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• ZPSOTUXICABJJK-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3,5-difluorobenzonitrile Chemical compound NC1=CC2=NC=NN2C(=C1)C1=C(F)C=C(C=C1F)C#N ZPSOTUXICABJJK-UHFFFAOYSA-N 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
• NFWRDVSLYMEJFZ-UHFFFAOYSA-N 5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid Chemical compound OC(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N NFWRDVSLYMEJFZ-UHFFFAOYSA-N 0.000 claims description 7
• 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 7
• GVFTZNIEVIEAGU-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanesulfonamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NS(=O)(=O)C2CC2)=CC2=NC=NN12)C#N GVFTZNIEVIEAGU-UHFFFAOYSA-N 0.000 claims description 7
• 239000002671 adjuvant Substances 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• 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 6
• 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 6
• 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 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 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 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
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• PHEQNCKVSGNNQD-UHFFFAOYSA-N tert-butyl N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N PHEQNCKVSGNNQD-UHFFFAOYSA-N 0.000 claims description 6
• 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 5
• HFHKVUPJAOIPSX-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-chlorobenzonitrile Chemical compound NC1=CC2=NC=NN2C(=C1)C1=C(Cl)C=C(C=C1)C#N HFHKVUPJAOIPSX-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 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
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• KXWCZFKMDQFKHV-UHFFFAOYSA-N N-[5-(6-cyano-4-methylpyridin-3-yl)-[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(N=C1)C#N KXWCZFKMDQFKHV-UHFFFAOYSA-N 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
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• DOALMKSXYREJPI-UHFFFAOYSA-N tert-butyl 4-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC1)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N DOALMKSXYREJPI-UHFFFAOYSA-N 0.000 claims description 5
• 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 4
• 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
• 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
• 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
• 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 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
• 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 4
• BOCBZMIXGXBPRK-UHFFFAOYSA-N 4,6-dimethyl-5-([1,2,4]triazolo[1,5-a]pyridin-5-yl)pyrimidine-2-carbonitrile Chemical compound CC1=NC(=NC(C)=C1C1=CC=CC2=NC=NN12)C#N BOCBZMIXGXBPRK-UHFFFAOYSA-N 0.000 claims description 4
• JQSPRHORZWCDKZ-UHFFFAOYSA-N 4-(6-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound NC1=C(N2N=CN=C2C=C1)C1=CC=C(C=C1)C#N JQSPRHORZWCDKZ-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
• JFPRQLNDBOCDKC-UHFFFAOYSA-N 4-(6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=C(N2N=CN=C2C=C1)C1=CC=C(C=C1)C#N JFPRQLNDBOCDKC-UHFFFAOYSA-N 0.000 claims description 4
• QMHVUOAGWLRDPP-UHFFFAOYSA-N 4-(7-amino-6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound NC1=CC=2N(C(=C1F)C1=CC=C(C#N)C=C1)N=CN=2 QMHVUOAGWLRDPP-UHFFFAOYSA-N 0.000 claims description 4
• DICBKTZZIMWZTR-UHFFFAOYSA-N 4-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2,3-difluorobenzonitrile Chemical compound NC1=CC2=NC=NN2C(=C1)C1=C(F)C(F)=C(C=C1)C#N DICBKTZZIMWZTR-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
• 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
• BTGQGTQMHPRCBE-UHFFFAOYSA-N 4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)piperazine-1-carbonitrile Chemical compound N#CN1CCN(CC1)C1=CC=CC2=NC=NN12 BTGQGTQMHPRCBE-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• COLMJYBVAGMECJ-UHFFFAOYSA-N 4-[7-(4-acetylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound CC(=O)N1CCN(CC1)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N COLMJYBVAGMECJ-UHFFFAOYSA-N 0.000 claims description 4
• AYDGFDAMRGQULT-UHFFFAOYSA-N 4-[7-(methoxymethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound COCC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N AYDGFDAMRGQULT-UHFFFAOYSA-N 0.000 claims description 4
• QNDWEZDBQKXRCL-UHFFFAOYSA-N 5-(4-chloro-3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=C(Cl)C=CC(=C1)C1=CC=CC2=NC=NN12 QNDWEZDBQKXRCL-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
• SSHKMJBQTVEESP-UHFFFAOYSA-N 5-(6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-6-methylpyridine-2-carbonitrile Chemical compound CC1=C(C=CC(=N1)C#N)C1=C(F)C=CC2=NC=NN12 SSHKMJBQTVEESP-UHFFFAOYSA-N 0.000 claims description 4
• ZECDLNVIDWWXMH-UHFFFAOYSA-N 6-amino-5-([1,2,4]triazolo[1,5-a]pyridin-5-yl)pyridine-2-carbonitrile Chemical compound NC1=C(C=CC(=N1)C#N)C1=CC=CC2=NC=NN12 ZECDLNVIDWWXMH-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
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• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
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