JP2018512408A5 - - Google Patents
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- Publication number
- JP2018512408A5 JP2018512408A5 JP2017549107A JP2017549107A JP2018512408A5 JP 2018512408 A5 JP2018512408 A5 JP 2018512408A5 JP 2017549107 A JP2017549107 A JP 2017549107A JP 2017549107 A JP2017549107 A JP 2017549107A JP 2018512408 A5 JP2018512408 A5 JP 2018512408A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- pyridin
- benzonitrile
- cyano
- methyl
- 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.)
- Granted
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- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 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 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 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 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000033626 Renal failure acute Diseases 0.000 claims 2
- 201000011040 acute kidney failure Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000005475 oxolanyl group Chemical group 0.000 claims 2
- 208000030613 peripheral artery disease Diseases 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 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 1
- 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 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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
- 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 1
- 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 1
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 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 1
- VYXDUACUDNVIPB-UHFFFAOYSA-N 2-(dimethylamino)ethyl N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]carbamate Chemical compound CN(C)CCOC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N VYXDUACUDNVIPB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- UWZQEPNPYYQBNV-UHFFFAOYSA-N 2-fluoro-4-(6-methyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=C(N2N=CN=C2C=C1)C1=CC(F)=C(C=C1)C#N UWZQEPNPYYQBNV-UHFFFAOYSA-N 0.000 claims 1
- IGSPNUAJOLJAKK-UHFFFAOYSA-N 2-fluoro-4-(7-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)C1=CC(=CC=2N1N=CN=2)N1CCOCC1 IGSPNUAJOLJAKK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- TVVRDIWPFVHQAM-UHFFFAOYSA-N 2-fluoro-4-[7-(2-oxo-1,3-oxazolidin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=CC(=CC2=NC=NN12)N1CCOC1=O)C#N TVVRDIWPFVHQAM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MOVNZCBLDQVSLD-UHFFFAOYSA-N 2-fluoro-4-[7-(2-pyrrolidin-1-ylethoxy)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)C1=CC(=CC=2N1N=CN=2)OCCN1CCCC1 MOVNZCBLDQVSLD-UHFFFAOYSA-N 0.000 claims 1
- VGCGIXOMVFHOFE-UHFFFAOYSA-N 2-fluoro-4-[7-(3,3,3-trifluoropropylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=CC(NCCC(F)(F)F)=CC2=NC=NN12)C#N VGCGIXOMVFHOFE-UHFFFAOYSA-N 0.000 claims 1
- AMCNEQONGMDYSJ-UHFFFAOYSA-N 2-fluoro-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(F)=C(C=C1)C#N AMCNEQONGMDYSJ-UHFFFAOYSA-N 0.000 claims 1
- NYUBXXULNBLHOC-UHFFFAOYSA-N 2-fluoro-4-[7-(oxetan-3-ylmethylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)C1=CC(=CC=2N1N=CN=2)NCC1COC1 NYUBXXULNBLHOC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OVLYPFVIMFTQMP-UHFFFAOYSA-N 2-fluoro-4-[7-(oxolan-3-ylmethoxy)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C=CC(=C1)C1=CC(OCC2CCOC2)=CC2=NC=NN12)C#N OVLYPFVIMFTQMP-UHFFFAOYSA-N 0.000 claims 1
- RXMYAFFQPTUGQU-UHFFFAOYSA-N 2-fluoro-4-[7-[(3-methyloxetan-3-yl)methylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)C1=CC(=CC=2N1N=CN=2)NCC1(COC1)C RXMYAFFQPTUGQU-UHFFFAOYSA-N 0.000 claims 1
- GKXIHGMCEFJTEV-UHFFFAOYSA-N 2-fluoro-4-[7-[(3-phenyloxetan-3-yl)methylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)C1=CC(=CC=2N1N=CN=2)NCC1(COC1)C1=CC=CC=C1 GKXIHGMCEFJTEV-UHFFFAOYSA-N 0.000 claims 1
- DBZINLQIGIGBGR-UHFFFAOYSA-N 2-fluoro-4-[7-[2-(2-oxopyrrolidin-1-yl)ethoxy]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)C1=CC(=CC=2N1N=CN=2)OCCN1C(CCC1)=O DBZINLQIGIGBGR-UHFFFAOYSA-N 0.000 claims 1
- SILWQYKKPNLLJK-UHFFFAOYSA-N 2-fluoro-5-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=CC(C#N)=C(F)C=C1C1=CC=CC2=NC=NN12 SILWQYKKPNLLJK-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
- VWOHQDZHCQQGLW-UHFFFAOYSA-N 2-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=C(C=CC(=C1)C1=CC=CC2=NC=NN12)C#N VWOHQDZHCQQGLW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RKMWDUWATTXHKI-UHFFFAOYSA-N 3,5-dimethyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=CC(=CC(C)=C1C1=CC=CC2=NC=NN12)C#N RKMWDUWATTXHKI-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
- HBNUXWFTHWHLHL-UHFFFAOYSA-N 3-amino-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound NC1=C(C=CC(=C1)C#N)C1=CC=CC2=NC=NN12 HBNUXWFTHWHLHL-UHFFFAOYSA-N 0.000 claims 1
- RSEOIWHIXPKXNI-UHFFFAOYSA-N 3-bromo-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound BrC1=C(C=CC(=C1)C#N)C1=CC=CC2=NC=NN12 RSEOIWHIXPKXNI-UHFFFAOYSA-N 0.000 claims 1
- RTUWOCQLXWOWRJ-UHFFFAOYSA-N 3-chloro-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound ClC1=C(C=CC(=C1)C#N)C1=CC=CC2=NC=NN12 RTUWOCQLXWOWRJ-UHFFFAOYSA-N 0.000 claims 1
- WZNBZKZNQYRPKE-UHFFFAOYSA-N 3-ethyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CCC1=C(C=CC(=C1)C#N)C1=CC=CC2=NC=NN12 WZNBZKZNQYRPKE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KIMDFRBRYJBQCN-UHFFFAOYSA-N 3-fluoro-4-([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 KIMDFRBRYJBQCN-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
- SBAVDTSBJDDFOK-UHFFFAOYSA-N 3-fluoro-5-([1,2,4]triazolo[1,5-a]pyridin-5-yl)pyridine-2-carbonitrile Chemical compound FC=1C(=NC=C(C=1)C1=CC=CC=2N1N=CN=2)C#N SBAVDTSBJDDFOK-UHFFFAOYSA-N 0.000 claims 1
- GRRJHIVATRJJEV-UHFFFAOYSA-N 3-fluoro-5-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound CC1=CC(=CC(F)=C1C1=CC=CC2=NC=NN12)C#N GRRJHIVATRJJEV-UHFFFAOYSA-N 0.000 claims 1
- ZKWFDHAHAZNGPP-UHFFFAOYSA-N 3-methoxy-4-([1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound COC=1C=C(C#N)C=CC=1C1=CC=CC=2N1N=CN=2 ZKWFDHAHAZNGPP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- CXTIGGYEVMIHQJ-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]oxetane-2-carboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2CCO2)=CC2=NC=NN12)C#N CXTIGGYEVMIHQJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DUNVYKROXZDEGT-UHFFFAOYSA-N N-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3-methoxypropanamide Chemical compound COCCC(=O)NC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N DUNVYKROXZDEGT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- XITBTMQSRXIYDW-UHFFFAOYSA-N N-[5-(6-cyano-2-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]acetamide Chemical compound C(C)(=O)NC1=CC=2N(C(=C1)C=1C(=NC(=CC=1)C#N)C)N=CN=2 XITBTMQSRXIYDW-UHFFFAOYSA-N 0.000 claims 1
- GJELYERIEMVYBK-UHFFFAOYSA-N N-[5-(6-cyano-2-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanecarboxamide Chemical compound CC1=NC(=CC=C1C1=CC(NC(=O)C2CC2)=CC2=NC=NN12)C#N GJELYERIEMVYBK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- ZUGXFJNOSHGEMY-UHFFFAOYSA-N N-butyl-5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide Chemical compound CCCCNC(=O)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N ZUGXFJNOSHGEMY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- CIIIBQKLUPRIOO-UHFFFAOYSA-N OC1=CC=2N(C(=C1)C1=C(C=C(C#N)C=C1)C)N=CN=2 Chemical compound OC1=CC=2N(C(=C1)C1=C(C=C(C#N)C=C1)C)N=CN=2 CIIIBQKLUPRIOO-UHFFFAOYSA-N 0.000 claims 1
- DGAOSOHXOVJROD-UHFFFAOYSA-N OC1=CC=2N(C(=C1)C=1C=CC(=NC=1C)C#N)N=CN=2 Chemical compound OC1=CC=2N(C(=C1)C=1C=CC(=NC=1C)C#N)N=CN=2 DGAOSOHXOVJROD-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- HALMVMOOYFNWCX-UHFFFAOYSA-N cyclopropylmethyl N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]carbamate Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)OCC2CC2)=CC2=NC=NN12)C#N HALMVMOOYFNWCX-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 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 1
- RTVVXJLOUVJINV-UHFFFAOYSA-N methyl N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]carbamate Chemical compound COC(=O)NC1=CC2=NC=NN2C(=C1)C1=C(C)C=C(C=C1)C#N RTVVXJLOUVJINV-UHFFFAOYSA-N 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- OZDDETGHBHNVSA-UHFFFAOYSA-N tert-butyl 3-[[[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridine-7-carbonyl]amino]methyl]azetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(CNC(=O)C2=CC3=NC=NN3C(=C2)C2=CC=C(C=C2)C#N)C1 OZDDETGHBHNVSA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OPWBRHOZHVRWCU-UHFFFAOYSA-N tert-butyl 6-[5-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2,6-diazaspiro[3.3]heptane-2-carboxylate Chemical class CC(C)(C)OC(=O)N1CC2(C1)CN(C2)C1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N OPWBRHOZHVRWCU-UHFFFAOYSA-N 0.000 claims 1
- VDXFKQSWHPKREZ-UHFFFAOYSA-N tert-butyl N-[5-(4-cyano-2-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=C(F)C=C(C=C1)C#N VDXFKQSWHPKREZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PKJDSULXJCGSNH-UHFFFAOYSA-N tert-butyl N-[5-(4-cyanophenyl)-[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=C(C=C1)C#N PKJDSULXJCGSNH-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- OQNYMAJNLRQKJB-UHFFFAOYSA-N triazolo[1,5-a]pyridine-7-carboxamide Chemical compound NC(=O)C1=CC=CC2=CN=NN12 OQNYMAJNLRQKJB-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| PCT/JP2016/059782 WO2016148306A1 (en) | 2015-03-18 | 2016-03-17 | Fused bicyclic heteroaryl derivatives having activity as phd inhibitors |
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| EP3712153B1 (en) | 2016-02-24 | 2021-12-01 | Pfizer Inc. | Pyrazolo[1,5-a]pyrazin-4-yl derivatives as jak-inhibitors |
| US11254668B2 (en) | 2017-08-14 | 2022-02-22 | Pfizer Inc. | Pyrazolo[1,5-A]pyrazin-4-yl and related derivatives |
| MY207239A (en) * | 2018-09-13 | 2025-02-08 | Kissei Pharmaceutical | Imidazopyridinone compound |
| CN110950806A (zh) * | 2019-11-14 | 2020-04-03 | 安庆博曼生物技术有限公司 | 四乙基氯化铵催化嘧啶环羟基氯代制备方法 |
| JP7504822B2 (ja) * | 2020-03-12 | 2024-06-24 | キッセイ薬品工業株式会社 | イミダゾピリジノン化合物を含む医薬組成物 |
| US11718622B2 (en) | 2020-03-16 | 2023-08-08 | Exelixis Inc. | Heterocyclic adenosine receptor antagonists |
| WO2021213380A1 (zh) * | 2020-04-20 | 2021-10-28 | 深圳市塔吉瑞生物医药有限公司 | 吡嗪取代的烟酰胺的固体形式及其制备和用途 |
| TW202233629A (zh) * | 2020-10-20 | 2022-09-01 | 美商安進公司 | 雜環螺環化合物及使用方法 |
| US12492178B2 (en) | 2021-09-01 | 2025-12-09 | Empathbio, Inc. | Stable polymorph of R-MDMA HCl |
| CA3235718A1 (en) | 2021-10-28 | 2023-05-04 | Insilico Medicine Ip Limited | Prolyl hydroxylase domain-containing protein (phd) inhibitors and uses thereof |
| CN118715015A (zh) * | 2021-12-17 | 2024-09-27 | 阿克比治疗有限公司 | 选择性phd1抑制剂化合物、组合物和使用方法 |
| EP4457222A4 (en) | 2021-12-28 | 2025-12-24 | Empathbio Inc | MDA AND MDMA NITRIC OXIDE-RELEASING PROMEDICAMENTS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209621A (en) | 1979-04-27 | 1980-06-24 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines |
| US4572910A (en) * | 1983-03-03 | 1986-02-25 | Riker Laboratories, Inc. | Triazolo[1,5-c]pyrimidines substituted by nitrogen-containing heterocyclic rings |
| DK135184A (da) | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | Triazol(4,3-c)- og triazol(1,5-c)pyrimidiner |
| BR0112038A (pt) | 2000-06-30 | 2003-04-01 | Wyeth Corp | Triazolopirimidinas substituìdas como agentes anticâncer |
| JP2010065026A (ja) | 2008-08-13 | 2010-03-25 | Ishihara Sangyo Kaisha Ltd | ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤 |
| JP2010065024A (ja) | 2008-08-14 | 2010-03-25 | Ishihara Sangyo Kaisha Ltd | トリアゾロピリミジン誘導体又はその塩を含有する有害生物防除剤 |
| HRP20140705T1 (hr) * | 2009-07-17 | 2014-09-12 | Japan Tobacco, Inc. | Spoj triazolopiridina i njegovo djelovanje kao inhibitora prolil hidroksilaze i induktora proizvodnje eritropoetina |
| JP2011168582A (ja) | 2010-01-21 | 2011-09-01 | Ishihara Sangyo Kaisha Ltd | トリアゾロピリジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤 |
| US20150239889A1 (en) | 2012-08-23 | 2015-08-27 | Mitsubishi Tanabe Pharma Corporation | Pyrazolopyrimidine compound |
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