AU2011272787B2 - Fused heterocyclic compounds as ion channel modulators - Google Patents
Fused heterocyclic compounds as ion channel modulators Download PDFInfo
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- AU2011272787B2 AU2011272787B2 AU2011272787A AU2011272787A AU2011272787B2 AU 2011272787 B2 AU2011272787 B2 AU 2011272787B2 AU 2011272787 A AU2011272787 A AU 2011272787A AU 2011272787 A AU2011272787 A AU 2011272787A AU 2011272787 B2 AU2011272787 B2 AU 2011272787B2
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- Prior art keywords
- phenyl
- triazolo
- pyridin
- trifluoromethoxy
- aryl
- Prior art date
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- 102000004310 Ion Channels Human genes 0.000 title description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 255
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 201000010099 disease Diseases 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 11
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims description 359
- 125000001072 heteroaryl group Chemical group 0.000 claims description 321
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 310
- 125000000217 alkyl group Chemical group 0.000 claims description 296
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 275
- 125000000623 heterocyclic group Chemical group 0.000 claims description 275
- 125000001424 substituent group Chemical group 0.000 claims description 262
- 125000003545 alkoxy group Chemical group 0.000 claims description 251
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 235
- 125000005843 halogen group Chemical group 0.000 claims description 215
- 125000003342 alkenyl group Chemical group 0.000 claims description 136
- 125000000304 alkynyl group Chemical group 0.000 claims description 133
- -1 quinolonyl Chemical group 0.000 claims description 122
- 229910052739 hydrogen Inorganic materials 0.000 claims description 115
- 239000001257 hydrogen Substances 0.000 claims description 115
- LJRXNXBFJXXRNQ-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC=CN2C(=O)NN=C21 LJRXNXBFJXXRNQ-UHFFFAOYSA-N 0.000 claims description 110
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 104
- 239000011734 sodium Substances 0.000 claims description 104
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 99
- 150000002431 hydrogen Chemical class 0.000 claims description 88
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 32
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 29
- 229910052805 deuterium Inorganic materials 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 28
- 229910052799 carbon Inorganic materials 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 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 18
- 206010019280 Heart failures Diseases 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 13
- 208000028867 ischemia Diseases 0.000 claims description 13
- 206010002383 Angina Pectoris Diseases 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- WCKSPUOMUKLNAH-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)NN=C2C=C1 WCKSPUOMUKLNAH-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- 206010002388 Angina unstable Diseases 0.000 claims description 9
- 206010022562 Intermittent claudication Diseases 0.000 claims description 9
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 9
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 9
- 208000007814 Unstable Angina Diseases 0.000 claims description 9
- 125000001475 halogen functional group Chemical group 0.000 claims description 9
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 9
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 9
- 208000007718 Stable Angina Diseases 0.000 claims description 8
- 208000010125 myocardial infarction Diseases 0.000 claims description 8
- CIUYUJJQZDDGTM-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 CIUYUJJQZDDGTM-UHFFFAOYSA-N 0.000 claims description 6
- 206010007556 Cardiac failure acute Diseases 0.000 claims description 6
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims description 6
- 206010063837 Reperfusion injury Diseases 0.000 claims description 6
- 208000008253 Systolic Heart Failure Diseases 0.000 claims description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
- 230000000306 recurrent effect Effects 0.000 claims description 6
- ZOVVXDVDXFAXEL-UHFFFAOYSA-N 2-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)methyl]-6-[4-(4-fluorophenoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2=CN3C(=O)N(CC=4OC(=NN=4)C4CC4)N=C3C=C2)C=C1 ZOVVXDVDXFAXEL-UHFFFAOYSA-N 0.000 claims description 5
- FDRCWVQKOJFPSP-UHFFFAOYSA-N 2-[[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3ON=C(N=3)C=3C(=CC=CC=3Cl)Cl)N=C2C=C1 FDRCWVQKOJFPSP-UHFFFAOYSA-N 0.000 claims description 5
- FJMLVEMQSDYXRP-UHFFFAOYSA-N 6-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(F)C(OC(F)(F)F)=CC=2)=O)=N1 FJMLVEMQSDYXRP-UHFFFAOYSA-N 0.000 claims description 5
- VWQHRAHQPKHEDL-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)N=C2C=C1 VWQHRAHQPKHEDL-UHFFFAOYSA-N 0.000 claims description 5
- FZHYZEQARYMTOK-UHFFFAOYSA-N 8-methyl-6-[4-(trifluoromethoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N(C(NN=2)=O)C=2C(C)=CC=1C1=CC=C(OC(F)(F)F)C=C1 FZHYZEQARYMTOK-UHFFFAOYSA-N 0.000 claims description 5
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 5
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 5
- 206010010904 Convulsion Diseases 0.000 claims description 5
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
- 206010033799 Paralysis Diseases 0.000 claims description 5
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- JPBBULQEKZVHQV-UHFFFAOYSA-N 2-(3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C=CC=CC=3)N=C2C=C1 JPBBULQEKZVHQV-UHFFFAOYSA-N 0.000 claims description 4
- FLWDCZOHCTZLJQ-UHFFFAOYSA-N 2-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3SC(=NN=3)C3CC3)N=C2C=C1 FLWDCZOHCTZLJQ-UHFFFAOYSA-N 0.000 claims description 4
- FDGAKDDEXYYGQQ-UHFFFAOYSA-N 2-[2-(6-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CC(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 FDGAKDDEXYYGQQ-UHFFFAOYSA-N 0.000 claims description 4
- WJAPRRQAVZDFOB-UHFFFAOYSA-N 2-[2-[4-(cyclopropylmethoxy)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(OCC4CC4)C=CN=3)N=C2C=C1 WJAPRRQAVZDFOB-UHFFFAOYSA-N 0.000 claims description 4
- YLDVOFIKASMXON-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)-2-pyrimidin-2-yloxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC(COC=3C(=CC=CC=3)Cl)OC=3N=CC=CN=3)N=C2C=C1 YLDVOFIKASMXON-UHFFFAOYSA-N 0.000 claims description 4
- IBWDGDOOVUPPRH-UHFFFAOYSA-N 2-methyl-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(C)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 IBWDGDOOVUPPRH-UHFFFAOYSA-N 0.000 claims description 4
- UTIFATCBAZTAGS-UHFFFAOYSA-N 5-methyl-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C(C)=C(C=4C=CC(OC(F)(F)F)=CC=4)C=CC3=N2)=O)=N1 UTIFATCBAZTAGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- WVCRMSJBMLAUEK-UHFFFAOYSA-N 2-(1,2,4-oxadiazol-3-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC3=NOC=N3)N=C2C=C1 WVCRMSJBMLAUEK-UHFFFAOYSA-N 0.000 claims description 3
- OVXHQIODPLLPGS-UHFFFAOYSA-N 2-(2-hydroxy-3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(O)COC1=CC=CC=C1 OVXHQIODPLLPGS-UHFFFAOYSA-N 0.000 claims description 3
- JPLBWJUVLUAHER-UHFFFAOYSA-N 2-(2-pyrazin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=NC=3)N=C2C=C1 JPLBWJUVLUAHER-UHFFFAOYSA-N 0.000 claims description 3
- YFLRCGNFZGDKJZ-KRWDZBQOSA-N 2-[(2s)-3-methoxy-2-[3-(trifluoromethyl)pyridin-2-yl]oxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@@H](COC)OC=1C(=CC=CN=1)C(F)(F)F)N(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 YFLRCGNFZGDKJZ-KRWDZBQOSA-N 0.000 claims description 3
- CRTDEOBLJALPST-UHFFFAOYSA-N 2-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=CC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 CRTDEOBLJALPST-UHFFFAOYSA-N 0.000 claims description 3
- XODNHLRRHIVGBX-UHFFFAOYSA-N 2-[(5-methyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=CN=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 XODNHLRRHIVGBX-UHFFFAOYSA-N 0.000 claims description 3
- PBOLJUHFEBCLEW-UHFFFAOYSA-N 2-[2-(5-chloro-4-methoxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(OC)=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 PBOLJUHFEBCLEW-UHFFFAOYSA-N 0.000 claims description 3
- WVTQLJBWCSRDMW-UHFFFAOYSA-N 2-[2-hydroxy-3-(2-propan-2-yloxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC(C)OC1=CC=CC=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 WVTQLJBWCSRDMW-UHFFFAOYSA-N 0.000 claims description 3
- LOZNQJGOYFAIMZ-UHFFFAOYSA-N 2-[3-(4,5-dichloro-2-methoxyphenoxy)-2-hydroxypropyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC(Cl)=C(Cl)C=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(=CC=3)C(F)(F)F)C=CC2=N1 LOZNQJGOYFAIMZ-UHFFFAOYSA-N 0.000 claims description 3
- IISQOFPCGIIYLN-UHFFFAOYSA-N 2-[[3-(2-chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3ON=C(N=3)C=3C(=CC=CC=3)Cl)N=C2C=C1 IISQOFPCGIIYLN-UHFFFAOYSA-N 0.000 claims description 3
- QCHBVKBITVXFML-UHFFFAOYSA-N 2-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=CC=C1C1=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=NO1 QCHBVKBITVXFML-UHFFFAOYSA-N 0.000 claims description 3
- OGLVRRGTKNGIOF-UHFFFAOYSA-N 2-pyridin-2-yl-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(C=3N=CC=CC=3)N=C2C=C1 OGLVRRGTKNGIOF-UHFFFAOYSA-N 0.000 claims description 3
- AWBHWWVHNCWVBA-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(F)C(F)=CC=2)=O)=N1 AWBHWWVHNCWVBA-UHFFFAOYSA-N 0.000 claims description 3
- DTAYFBAOZRTZFV-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-2-[[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(CO)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=O)=N1 DTAYFBAOZRTZFV-UHFFFAOYSA-N 0.000 claims description 3
- COFSCJGADUHZIB-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[2-[3-(trifluoromethyl)pyridin-2-yl]oxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C(=CC=CN=3)C(F)(F)F)N=C2C=C1 COFSCJGADUHZIB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 claims description 3
- BMELULDLBXUUMQ-UHFFFAOYSA-N 1-[(3,4-difluorophenyl)methyl]-2-oxo-n-[[3-(3-oxo-2h-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl]methyl]pyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CN1C(=O)C(C(=O)NCC=2C=C(C=CC=2)C2=CN3C(=O)NN=C3C=C2)=CC=C1 BMELULDLBXUUMQ-UHFFFAOYSA-N 0.000 claims description 2
- YWZABFQZZGSQEQ-UHFFFAOYSA-N 2-(1,3-oxazol-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3OC=CN=3)N=C2C=C1 YWZABFQZZGSQEQ-UHFFFAOYSA-N 0.000 claims description 2
- OUOIJRKIRMVJNR-UHFFFAOYSA-N 2-(quinolin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C4C=CC=CC4=CC=3)N=C2C=C1 OUOIJRKIRMVJNR-UHFFFAOYSA-N 0.000 claims description 2
- KEJHEWPVIDRSDW-UHFFFAOYSA-N 2-[2-(3-methylpyrazin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NC=CN=C1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 KEJHEWPVIDRSDW-UHFFFAOYSA-N 0.000 claims description 2
- OMPOZZVWEMYHAA-UHFFFAOYSA-N 2-[2-[4-(3,3-difluoroazetidin-1-yl)-5-fluoropyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C(N2CC(F)(F)C2)C(F)=CN=C1OCCN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 OMPOZZVWEMYHAA-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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| US20120010192A1 (en) | 2012-01-12 |
| ES2529119T3 (es) | 2015-02-17 |
| IL223724A (en) | 2016-06-30 |
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| PT2588197E (pt) | 2015-02-09 |
| EA026385B9 (ru) | 2017-08-31 |
| EP2588197A1 (en) | 2013-05-08 |
| AU2011272787A1 (en) | 2013-01-10 |
| EA026385B1 (ru) | 2017-04-28 |
| EA201291272A1 (ru) | 2013-12-30 |
| CA2802288C (en) | 2018-08-21 |
| US9079901B2 (en) | 2015-07-14 |
| TW201215608A (en) | 2012-04-16 |
| BR112012033402A2 (pt) | 2017-01-24 |
| CN103096977B (zh) | 2017-02-15 |
| JP5858586B2 (ja) | 2016-02-10 |
| EP2588197B1 (en) | 2014-11-05 |
| HK1184092A1 (en) | 2014-01-17 |
| NZ604478A (en) | 2014-12-24 |
| JP2013535423A (ja) | 2013-09-12 |
| CN103096977A (zh) | 2013-05-08 |
| MX2012015096A (es) | 2013-05-28 |
| WO2012003392A1 (en) | 2012-01-05 |
| JP2016029107A (ja) | 2016-03-03 |
| US8703759B2 (en) | 2014-04-22 |
| TWI537266B (zh) | 2016-06-11 |
| CA2802288A1 (en) | 2012-01-05 |
| KR20130043158A (ko) | 2013-04-29 |
| KR101911560B1 (ko) | 2018-10-24 |
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