JP2013535423A5 - - Google Patents
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- JP2013535423A5 JP2013535423A5 JP2013518741A JP2013518741A JP2013535423A5 JP 2013535423 A5 JP2013535423 A5 JP 2013535423A5 JP 2013518741 A JP2013518741 A JP 2013518741A JP 2013518741 A JP2013518741 A JP 2013518741A JP 2013535423 A5 JP2013535423 A5 JP 2013535423A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- triazolo
- trifluoromethoxy
- pyridin
- aryl
- 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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- 125000003118 aryl group Chemical group 0.000 claims description 254
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 229
- 125000001072 heteroaryl group Chemical group 0.000 claims description 213
- 125000003545 alkoxy group Chemical group 0.000 claims description 210
- 125000000217 alkyl group Chemical group 0.000 claims description 203
- 125000000623 heterocyclic group Chemical group 0.000 claims description 202
- 125000001424 substituent group Chemical group 0.000 claims description 191
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 175
- 125000000304 alkynyl group Chemical group 0.000 claims description 103
- 125000003342 alkenyl group Chemical group 0.000 claims description 102
- 125000001475 halogen functional group Chemical group 0.000 claims description 94
- -1 —CF 3 Chemical group 0.000 claims description 93
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 86
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 70
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 52
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 20
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- SOPXTTHIOLOJNS-UHFFFAOYSA-N 2-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 SOPXTTHIOLOJNS-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 208000028867 ischemia Diseases 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 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 2
- LJSSRJKRLOGJFW-UHFFFAOYSA-N 2-(1,3-benzothiazol-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=3SC4=CC=CC=C4N=3)N=C2C=C1 LJSSRJKRLOGJFW-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
- XOBKXZRZGDWUJA-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(CC(F)(F)F)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 XOBKXZRZGDWUJA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- QFDHIAJTTBECEF-UHFFFAOYSA-N 2-(2-imidazo[1,2-a]pyrazin-8-yloxyethyl)-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=3C4=NC=CN4C=CN=3)N=C2C=C1 QFDHIAJTTBECEF-UHFFFAOYSA-N 0.000 claims description 2
- WJWGCBXJYLKGEI-UHFFFAOYSA-N 2-(2-isoquinolin-1-yloxyethyl)-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=3C4=CC=CC=C4C=CN=3)N=C2C=C1 WJWGCBXJYLKGEI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- VQMSMAKRFVGWKP-UHFFFAOYSA-N 2-(2-pyrazol-1-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(CCN3N=CC=C3)N=C2C=C1 VQMSMAKRFVGWKP-UHFFFAOYSA-N 0.000 claims description 2
- FGLZQEQLYKFHCZ-UHFFFAOYSA-N 2-(2-pyridazin-3-yloxyethyl)-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=NC=CC=3)N=C2C=C1 FGLZQEQLYKFHCZ-UHFFFAOYSA-N 0.000 claims description 2
- VECCJOMKYSSSIJ-UHFFFAOYSA-N 2-(2-pyridin-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=CC=3)N=C2C=C1 VECCJOMKYSSSIJ-UHFFFAOYSA-N 0.000 claims description 2
- KPSXKNBCIVEAPH-UHFFFAOYSA-N 2-(2-pyridin-2-yloxyethyl)-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=CC=CC=3)N=C2C=C1 KPSXKNBCIVEAPH-UHFFFAOYSA-N 0.000 claims description 2
- BULIWKSBFXZAGF-UHFFFAOYSA-N 2-(2-pyridin-2-ylpropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1C=CC=NC=1C(C)CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 BULIWKSBFXZAGF-UHFFFAOYSA-N 0.000 claims description 2
- NJSCGQIPYJCGEK-UHFFFAOYSA-N 2-(2-pyridin-3-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=3C=NC=CC=3)N=C2C=C1 NJSCGQIPYJCGEK-UHFFFAOYSA-N 0.000 claims description 2
- HCIVEOQQCFYJPE-UHFFFAOYSA-N 2-(2-pyrimidin-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=CN=3)N=C2C=C1 HCIVEOQQCFYJPE-UHFFFAOYSA-N 0.000 claims description 2
- BDNLOHSMZUXJNE-UHFFFAOYSA-N 2-(2-pyrimidin-2-yloxyethyl)-6-(4-trimethylsilylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC([Si](C)(C)C)=CC=C1C1=CN2C(=O)N(CCOC=3N=CC=CN=3)N=C2C=C1 BDNLOHSMZUXJNE-UHFFFAOYSA-N 0.000 claims description 2
- BCMKIAFOKMLLCY-UHFFFAOYSA-N 2-(2-pyrimidin-4-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=CN=CC=3)N=C2C=C1 BCMKIAFOKMLLCY-UHFFFAOYSA-N 0.000 claims description 2
- LVDLJZHEVASLAG-UHFFFAOYSA-N 2-(2-pyrrolo[1,2-a]pyrazin-1-yloxyethyl)-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=3C4=CC=CN4C=CN=3)N=C2C=C1 LVDLJZHEVASLAG-UHFFFAOYSA-N 0.000 claims description 2
- OSQKXFGNSNWFOT-UHFFFAOYSA-N 2-(3,4-dihydro-2h-chromen-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(CC3OC4=CC=CC=C4CC3)N=C2C=C1 OSQKXFGNSNWFOT-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- SIASCGMZXFPZNB-UHFFFAOYSA-N 2-(3-phenylprop-2-enyl)-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=CC=3C=CC=CC=3)N=C2C=C1 SIASCGMZXFPZNB-UHFFFAOYSA-N 0.000 claims description 2
- RIONBHYBBHCCBB-UHFFFAOYSA-N 2-(3-pyridazin-3-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(CCCOC=3N=NC=CC=3)N=C2C=C1 RIONBHYBBHCCBB-UHFFFAOYSA-N 0.000 claims description 2
- JOABKTNOERGASJ-UHFFFAOYSA-N 2-(pyridin-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=CC=CC=3)N=C2C=C1 JOABKTNOERGASJ-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
- MZBYMEWBOVJKJG-UHFFFAOYSA-N 2-[(1-methylpyrazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CN1C=CC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 MZBYMEWBOVJKJG-UHFFFAOYSA-N 0.000 claims description 2
- AVSQLPAJCOPVGM-UHFFFAOYSA-N 2-[(1-methylpyrazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=NN(C)C=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 AVSQLPAJCOPVGM-UHFFFAOYSA-N 0.000 claims description 2
- ULZDGJTZMAKGPD-UHFFFAOYSA-N 2-[(2-methyl-1,3-oxazol-5-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC=C1CN1C(=O)N2C=C(C=3C=CC(=CC=3)C(F)(F)F)C=CC2=N1 ULZDGJTZMAKGPD-UHFFFAOYSA-N 0.000 claims description 2
- YWPYCDLKADHMCQ-GOSISDBHSA-N 2-[(2r)-3-(2-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@H](OC)CN1C(N2C=C(C=CC2=N1)C=1C=CC(OC(F)(F)F)=CC=1)=O)OC1=CC=CC=C1Cl YWPYCDLKADHMCQ-GOSISDBHSA-N 0.000 claims description 2
- YFLRCGNFZGDKJZ-QGZVFWFLSA-N 2-[(2r)-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-QGZVFWFLSA-N 0.000 claims description 2
- YWPYCDLKADHMCQ-SFHVURJKSA-N 2-[(2s)-3-(2-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@@H](OC)CN1C(N2C=C(C=CC2=N1)C=1C=CC(OC(F)(F)F)=CC=1)=O)OC1=CC=CC=C1Cl YWPYCDLKADHMCQ-SFHVURJKSA-N 0.000 claims description 2
- 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 2
- HVBIGQNMFRGYHK-UHFFFAOYSA-N 2-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 HVBIGQNMFRGYHK-UHFFFAOYSA-N 0.000 claims description 2
- NGXPLUHGOPEZPQ-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-trimethylsilylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)[Si](C)(C)C)=O)=N1 NGXPLUHGOPEZPQ-UHFFFAOYSA-N 0.000 claims description 2
- DCUSGGLEJVNADI-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[2-methyl-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)C)=O)=N1 DCUSGGLEJVNADI-UHFFFAOYSA-N 0.000 claims description 2
- PYCKDNAEOSDPSW-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(2,2,2-trifluoroethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OCC(F)(F)F)=CC=2)=O)=N1 PYCKDNAEOSDPSW-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LVIVCBYJGVUQAJ-UHFFFAOYSA-N 2-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NON=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 LVIVCBYJGVUQAJ-UHFFFAOYSA-N 0.000 claims description 2
- WKKLMCJUZVSRLP-UHFFFAOYSA-N 2-[(4-methyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=COC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 WKKLMCJUZVSRLP-UHFFFAOYSA-N 0.000 claims description 2
- RPOMDDHFVCHVKW-UHFFFAOYSA-N 2-[(4-methyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=COC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 RPOMDDHFVCHVKW-UHFFFAOYSA-N 0.000 claims description 2
- CRLVACGUSHLQEQ-UHFFFAOYSA-N 2-[(5-cyclopropyl-1,2,4-oxadiazol-3-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=3N=C(ON=3)C3CC3)N=C2C=C1 CRLVACGUSHLQEQ-UHFFFAOYSA-N 0.000 claims description 2
- RRAJQAYXEXKFHG-UHFFFAOYSA-N 2-[(5-cyclopropyl-2-methylpyrazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CN1N=C(C2CC2)C=C1CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 RRAJQAYXEXKFHG-UHFFFAOYSA-N 0.000 claims description 2
- NGBGOTULLHICLU-UHFFFAOYSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-(3-phenoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)=O)=N1 NGBGOTULLHICLU-UHFFFAOYSA-N 0.000 claims description 2
- MGKQMRGQRNCSMN-UHFFFAOYSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 MGKQMRGQRNCSMN-UHFFFAOYSA-N 0.000 claims description 2
- CPZBZRZORXDGGZ-UHFFFAOYSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 CPZBZRZORXDGGZ-UHFFFAOYSA-N 0.000 claims description 2
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- JMCLXORBNBWOEO-UHFFFAOYSA-N 2-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 JMCLXORBNBWOEO-UHFFFAOYSA-N 0.000 claims description 2
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- YXIXQPPNKVUIRT-UHFFFAOYSA-N 2-[2-(5-pyridin-3-ylpyridin-2-yl)ethyl]-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(=CC=3)C=3C=NC=CC=3)N=C2C=C1 YXIXQPPNKVUIRT-UHFFFAOYSA-N 0.000 claims description 2
- HGTRMKUOOYDDBC-JOCHJYFZSA-N 2-[2-[(3r)-3-(4-fluorophenoxy)pyrrolidin-1-yl]ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1O[C@H]1CN(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)CC1 HGTRMKUOOYDDBC-JOCHJYFZSA-N 0.000 claims description 2
- NNXWYNPCXFMLPG-UHFFFAOYSA-N 2-[2-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(COCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 NNXWYNPCXFMLPG-UHFFFAOYSA-N 0.000 claims description 2
- YBXKMLYTHQBHJQ-UHFFFAOYSA-N 2-[2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(C=2C(=CC=CC=2)OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 YBXKMLYTHQBHJQ-UHFFFAOYSA-N 0.000 claims description 2
- FIUJLHZTQNKDDW-UHFFFAOYSA-N 2-[2-[4-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC(F)(F)COC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 FIUJLHZTQNKDDW-UHFFFAOYSA-N 0.000 claims description 2
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- FINVLTBKFNUEGB-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenoxy)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(OC=4C=CC(Cl)=CC=4)C=CN=3)N=C2C=C1 FINVLTBKFNUEGB-UHFFFAOYSA-N 0.000 claims description 2
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- IDVVEYCFEYNEGJ-UHFFFAOYSA-N 2-[2-[4-(dimethylamino)-5-fluoropyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(F)C(N(C)C)=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 IDVVEYCFEYNEGJ-UHFFFAOYSA-N 0.000 claims description 2
- RQALVPINBQGMCE-UHFFFAOYSA-N 2-[2-ethoxy-3-(4-fluoro-2-methoxyphenoxy)propyl]-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(OCC)COC1=CC=C(F)C=C1OC RQALVPINBQGMCE-UHFFFAOYSA-N 0.000 claims description 2
- ACSLOAIBGIAKBZ-UHFFFAOYSA-N 2-[2-ethoxy-3-[(2-methyl-1,3-benzothiazol-6-yl)oxy]propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1C=C2N=C(C)SC2=CC=1OCC(OCC)CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 ACSLOAIBGIAKBZ-UHFFFAOYSA-N 0.000 claims description 2
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2011
- 2011-06-30 BR BR112012033402A patent/BR112012033402A2/pt not_active Application Discontinuation
- 2011-06-30 JP JP2013518741A patent/JP5858586B2/ja not_active Expired - Fee Related
- 2011-06-30 ES ES11732540.7T patent/ES2529119T3/es active Active
- 2011-06-30 CA CA2802288A patent/CA2802288C/en not_active Expired - Fee Related
- 2011-06-30 WO PCT/US2011/042700 patent/WO2012003392A1/en not_active Ceased
- 2011-06-30 PT PT117325407T patent/PT2588197E/pt unknown
- 2011-06-30 KR KR1020137001153A patent/KR101911560B1/ko not_active Expired - Fee Related
- 2011-06-30 AU AU2011272787A patent/AU2011272787B2/en not_active Ceased
- 2011-06-30 US US13/174,587 patent/US8703759B2/en active Active
- 2011-06-30 CN CN201180042654.5A patent/CN103096977B/zh not_active Expired - Fee Related
- 2011-06-30 EA EA201291272A patent/EA026385B9/ru not_active IP Right Cessation
- 2011-06-30 NZ NZ604478A patent/NZ604478A/en not_active IP Right Cessation
- 2011-06-30 EP EP11732540.7A patent/EP2588197B1/en active Active
- 2011-06-30 MX MX2012015096A patent/MX2012015096A/es active IP Right Grant
- 2011-07-01 TW TW100123352A patent/TWI537266B/zh not_active IP Right Cessation
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2012
- 2012-12-18 IL IL223724A patent/IL223724A/en active IP Right Grant
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