JP2007506749A5 - - Google Patents
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- Publication number
- JP2007506749A5 JP2007506749A5 JP2006528111A JP2006528111A JP2007506749A5 JP 2007506749 A5 JP2007506749 A5 JP 2007506749A5 JP 2006528111 A JP2006528111 A JP 2006528111A JP 2006528111 A JP2006528111 A JP 2006528111A JP 2007506749 A5 JP2007506749 A5 JP 2007506749A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- dihydroisoquinoline
- carbonitrile
- methoxy
- fluorophenyl
- 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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- -1 R 46 Chemical compound 0.000 claims 28
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 206010003119 arrhythmia Diseases 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 208000024891 symptom Diseases 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 4
- BUXRKQONBGINRO-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-4-(3-fluorophenyl)-6-methoxy-1-oxoisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(O)CO)C=2C#N)=O)C=1C=2C1=CC=CC(F)=C1 BUXRKQONBGINRO-UHFFFAOYSA-N 0.000 claims 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 101150065749 Churc1 gene Proteins 0.000 claims 3
- 102100038239 Protein Churchill Human genes 0.000 claims 3
- 239000002464 receptor antagonist Substances 0.000 claims 3
- 229940044551 receptor antagonist Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- JEADZHWYHZOCKD-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-6-methoxy-1-oxo-4-pyridin-2-ylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(O)CO)C=2C#N)=O)C=1C=2C1=CC=CC=N1 JEADZHWYHZOCKD-UHFFFAOYSA-N 0.000 claims 2
- TVUAYFVGQJIYGX-UHFFFAOYSA-N 6-methoxy-1-oxo-4-phenyl-2h-isoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(NC=2C#N)=O)C=1C=2C1=CC=CC=C1 TVUAYFVGQJIYGX-UHFFFAOYSA-N 0.000 claims 2
- BBEKWMYOCKGLPU-UHFFFAOYSA-N 6-methoxy-2-methyl-4-(2-methylphenyl)-1-oxoisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(C)C=2C#N)=O)C=1C=2C1=CC=CC=C1C BBEKWMYOCKGLPU-UHFFFAOYSA-N 0.000 claims 2
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims 2
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 2
- 206010003662 Atrial flutter Diseases 0.000 claims 2
- 208000005189 Embolism Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000003734 Supraventricular Tachycardia Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- MTGHYRYGOGTOGP-UHFFFAOYSA-N 1-(3-cyano-2-methyl-1-oxo-4-phenylisoquinolin-6-yl)ethylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(C([NH3+])C)=CC=C(C(N(C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 MTGHYRYGOGTOGP-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 1
- YSTSFONVAHVOGJ-UHFFFAOYSA-N 2,5-dimethyl-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound CC1=CC=CC(C(N(C)C=2C#N)=O)=C1C=2C1=CC=CC=C1 YSTSFONVAHVOGJ-UHFFFAOYSA-N 0.000 claims 1
- IYRROYDOVNAQSO-UHFFFAOYSA-N 2,6-dimethyl-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(C)=CC=C(C(N(C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 IYRROYDOVNAQSO-UHFFFAOYSA-N 0.000 claims 1
- XPACVYBEBXYWLW-UHFFFAOYSA-N 2-(1h-benzimidazol-1-ium-2-ylmethyl)-4-(3-fluorophenyl)-6-methoxy-1-oxoisoquinoline-3-carbonitrile;chloride Chemical compound [Cl-].C=1C(OC)=CC=C(C(N(CC=2[NH2+]C3=CC=CC=C3N=2)C=2C#N)=O)C=1C=2C1=CC=CC(F)=C1 XPACVYBEBXYWLW-UHFFFAOYSA-N 0.000 claims 1
- LBUCEXRLZYOTOS-UHFFFAOYSA-N 2-(2,2-diethoxyethyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2C(=O)N(CC(OCC)OCC)C(C#N)=C1C1=CC=CC=C1 LBUCEXRLZYOTOS-UHFFFAOYSA-N 0.000 claims 1
- DZUOMKVEIAWBCD-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-4-(2-fluorophenyl)-6-methoxy-1-oxoisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(O)CO)C=2C#N)=O)C=1C=2C1=CC=CC=C1F DZUOMKVEIAWBCD-UHFFFAOYSA-N 0.000 claims 1
- PNAGDVNLGQNAEQ-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-4-(3-fluorophenyl)-1-oxo-6-thiophen-3-ylisoquinoline-3-carbonitrile Chemical compound C12=CC(C3=CSC=C3)=CC=C2C(=O)N(CC(O)CO)C(C#N)=C1C1=CC=CC(F)=C1 PNAGDVNLGQNAEQ-UHFFFAOYSA-N 0.000 claims 1
- BSNAQOSFWPLXJW-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-4-(3-fluorophenyl)-6-(6-methylpyridin-1-ium-2-yl)-1-oxoisoquinoline-3-carbonitrile;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=CC=CC(C=2C=C3C(C(N(CC(O)CO)C(C#N)=C3C=3C=C(F)C=CC=3)=O)=CC=2)=[NH+]1 BSNAQOSFWPLXJW-UHFFFAOYSA-N 0.000 claims 1
- VAQYNLLDOFFRIT-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-4-(3-fluorophenyl)-6-(furan-3-yl)-1-oxoisoquinoline-3-carbonitrile Chemical compound C12=CC(C3=COC=C3)=CC=C2C(=O)N(CC(O)CO)C(C#N)=C1C1=CC=CC(F)=C1 VAQYNLLDOFFRIT-UHFFFAOYSA-N 0.000 claims 1
- BWXGEBUBIIIAGP-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-6-methoxy-1-oxo-4-[3-(trifluoromethyl)phenyl]isoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(O)CO)C=2C#N)=O)C=1C=2C1=CC=CC(C(F)(F)F)=C1 BWXGEBUBIIIAGP-UHFFFAOYSA-N 0.000 claims 1
- IHNXTAHQOZPVBI-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(O)CO)C=2C#N)=O)C=1C=2C1=CC=CC=C1 IHNXTAHQOZPVBI-UHFFFAOYSA-N 0.000 claims 1
- PMJGWQCJPZIABM-UHFFFAOYSA-N 2-(2-amino-3-hydroxypropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(N)CO)C=2C#N)=O)C=1C=2C1=CC=CC=C1 PMJGWQCJPZIABM-UHFFFAOYSA-N 0.000 claims 1
- XDVBFZHCFHQUMC-UHFFFAOYSA-N 2-(2-chloroethyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CCCl)C=2C#N)=O)C=1C=2C1=CC=CC=C1 XDVBFZHCFHQUMC-UHFFFAOYSA-N 0.000 claims 1
- IBHZMWNAYLULPE-UHFFFAOYSA-N 2-(2-hydroxy-2-methylpropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(C)(C)O)C=2C#N)=O)C=1C=2C1=CC=CC=C1 IBHZMWNAYLULPE-UHFFFAOYSA-N 0.000 claims 1
- HNMTZCXVAMYMAA-UHFFFAOYSA-N 2-(2-hydroxy-3-methoxypropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2C(=O)N(CC(O)COC)C(C#N)=C1C1=CC=CC=C1 HNMTZCXVAMYMAA-UHFFFAOYSA-N 0.000 claims 1
- WVLLEUJMEPOPDR-UHFFFAOYSA-N 2-(2-hydroxy-3-propan-2-yloxypropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(O)COC(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 WVLLEUJMEPOPDR-UHFFFAOYSA-N 0.000 claims 1
- QZOKTARRUCMUBQ-UHFFFAOYSA-N 2-(2-hydroxybutyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2C(=O)N(CC(O)CC)C(C#N)=C1C1=CC=CC=C1 QZOKTARRUCMUBQ-UHFFFAOYSA-N 0.000 claims 1
- GSSPZJUNXYDOFO-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CCO)C=2C#N)=O)C=1C=2C1=CC=CC=C1 GSSPZJUNXYDOFO-UHFFFAOYSA-N 0.000 claims 1
- FZYGFZVYIBYUGE-UHFFFAOYSA-N 2-(2-hydroxypropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(C)O)C=2C#N)=O)C=1C=2C1=CC=CC=C1 FZYGFZVYIBYUGE-UHFFFAOYSA-N 0.000 claims 1
- CVISLNLWUDOHMX-UHFFFAOYSA-N 2-(3-cyano-2-methyl-1-oxo-4-phenylisoquinolin-6-yl)oxyacetic acid Chemical compound C12=CC(OCC(O)=O)=CC=C2C(=O)N(C)C(C#N)=C1C1=CC=CC=C1 CVISLNLWUDOHMX-UHFFFAOYSA-N 0.000 claims 1
- PWFJMVNRTDRVTH-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(2,3-dihydro-1h-inden-2-yl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]C2CC3=CC=CC=C3C2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 PWFJMVNRTDRVTH-UHFFFAOYSA-N 0.000 claims 1
- OLNHALBUWYKULQ-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(2-methyl-2-phenylpropyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CC(C)(C)C=2C=CC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 OLNHALBUWYKULQ-UHFFFAOYSA-N 0.000 claims 1
- KBEGAXDKWDRFFY-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(2-phenylbutyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C=CC=CC=1C(CC)C[NH2+]CCN(C(C1=CC=C(OC)C=C11)=O)C(C#N)=C1C1=CC=CC=C1 KBEGAXDKWDRFFY-UHFFFAOYSA-N 0.000 claims 1
- RODDIPKQBRVCEV-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(2-phenylethyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CCC=2C=CC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 RODDIPKQBRVCEV-UHFFFAOYSA-N 0.000 claims 1
- BWNDLOZMGMCRNS-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(3,3-dimethylbutyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CCC(C)(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 BWNDLOZMGMCRNS-UHFFFAOYSA-N 0.000 claims 1
- RMPALOMHHBAGSM-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(3-phenylpropyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CCCC=2C=CC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 RMPALOMHHBAGSM-UHFFFAOYSA-N 0.000 claims 1
- QLPQDDVDSCBHDG-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(4-phenylbutyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CCCCC=2C=CC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 QLPQDDVDSCBHDG-UHFFFAOYSA-N 0.000 claims 1
- SDSJTOYQVOBAIG-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(cyclohexylmethyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CC2CCCCC2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 SDSJTOYQVOBAIG-UHFFFAOYSA-N 0.000 claims 1
- KPGNSRPEHCSXFW-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(cyclopropylmethyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CC2CC2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 KPGNSRPEHCSXFW-UHFFFAOYSA-N 0.000 claims 1
- SCDODIGEWJLAGB-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-(thiophen-2-ylmethyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]CC=2SC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 SCDODIGEWJLAGB-UHFFFAOYSA-N 0.000 claims 1
- OPSLVJLGYQYNIH-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-cyclohexyl-methylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH+](C)C2CCCCC2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 OPSLVJLGYQYNIH-UHFFFAOYSA-N 0.000 claims 1
- GRYJZHAUBYMNNX-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-cyclohexylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]C2CCCCC2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 GRYJZHAUBYMNNX-UHFFFAOYSA-N 0.000 claims 1
- VYKDWZPHYXGCQL-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-phenylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]C=2C=CC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 VYKDWZPHYXGCQL-UHFFFAOYSA-N 0.000 claims 1
- PPHBLAIFFMGXAK-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-propan-2-ylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]C(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 PPHBLAIFFMGXAK-UHFFFAOYSA-N 0.000 claims 1
- BRKOFYGSWAHUAC-UHFFFAOYSA-N 2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl-pyridin-2-ylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]C=2N=CC=CC=2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 BRKOFYGSWAHUAC-UHFFFAOYSA-N 0.000 claims 1
- WRGOTNPGTPGJFD-UHFFFAOYSA-N 2-(3-ethoxy-2-hydroxypropyl)-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2C(=O)N(CC(O)COCC)C(C#N)=C1C1=CC=CC=C1 WRGOTNPGTPGJFD-UHFFFAOYSA-N 0.000 claims 1
- IHNXTAHQOZPVBI-CQSZACIVSA-N 2-[(2r)-2,3-dihydroxypropyl]-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(C[C@@H](O)CO)C=2C#N)=O)C=1C=2C1=CC=CC=C1 IHNXTAHQOZPVBI-CQSZACIVSA-N 0.000 claims 1
- IHNXTAHQOZPVBI-AWEZNQCLSA-N 2-[(2s)-2,3-dihydroxypropyl]-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(C[C@H](O)CO)C=2C#N)=O)C=1C=2C1=CC=CC=C1 IHNXTAHQOZPVBI-AWEZNQCLSA-N 0.000 claims 1
- PKARHDFDQSIJEZ-UHFFFAOYSA-N 2-[2-(3-imidazol-1-ylpropylamino)ethyl]-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CCNCCCN2C=NC=C2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 PKARHDFDQSIJEZ-UHFFFAOYSA-N 0.000 claims 1
- AMHYZUBOGOAFNU-UHFFFAOYSA-N 2-[2-(4-benzylpiperazin-1-yl)ethyl]-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CCN2CCN(CC=3C=CC=CC=3)CC2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 AMHYZUBOGOAFNU-UHFFFAOYSA-N 0.000 claims 1
- SJYRYEVCAXJCBP-UHFFFAOYSA-N 2-[2-(cyclopropylamino)ethyl]-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CCNC2CC2)C=2C#N)=O)C=1C=2C1=CC=CC=C1 SJYRYEVCAXJCBP-UHFFFAOYSA-N 0.000 claims 1
- JLMVIMFBTPSZMF-UHFFFAOYSA-N 2-[2-(dimethylamino)-3-hydroxypropyl]-6-methoxy-1-oxo-4-phenylisoquinoline-3-carbonitrile Chemical compound C=1C(OC)=CC=C(C(N(CC(CO)N(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 JLMVIMFBTPSZMF-UHFFFAOYSA-N 0.000 claims 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229930002534 steroid glycoside Natural products 0.000 claims 1
- BXLXWNNXZWCCLV-UHFFFAOYSA-N tert-butyl 4-[(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)methyl]piperidine-1-carboxylate Chemical compound C=1C(OC)=CC=C(C(N(CC2CCN(CC2)C(=O)OC(C)(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 BXLXWNNXZWCCLV-UHFFFAOYSA-N 0.000 claims 1
- QWSZPQXTBHJUJM-UHFFFAOYSA-N tert-butyl n-[2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl]carbamate Chemical compound C=1C(OC)=CC=C(C(N(CCNC(=O)OC(C)(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 QWSZPQXTBHJUJM-UHFFFAOYSA-N 0.000 claims 1
- IUTANHWQTPRAPI-UHFFFAOYSA-N tert-butyl-[2-(3-cyano-6-methoxy-1-oxo-4-phenylisoquinolin-2-yl)ethyl]azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C(OC)=CC=C(C(N(CC[NH2+]C(C)(C)C)C=2C#N)=O)C=1C=2C1=CC=CC=C1 IUTANHWQTPRAPI-UHFFFAOYSA-N 0.000 claims 1
- 239000003868 thrombin inhibitor Substances 0.000 claims 1
- 239000002396 thromboxane receptor blocking agent Substances 0.000 claims 1
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- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 claims 1
- 229960005080 warfarin Drugs 0.000 claims 1
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| US50521603P | 2003-09-23 | 2003-09-23 | |
| US60/505,216 | 2003-09-23 | ||
| PCT/US2004/030945 WO2005030729A1 (en) | 2003-09-23 | 2004-09-22 | Isoquinoline potassium channel inhibitors |
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| JP2007506749A JP2007506749A (ja) | 2007-03-22 |
| JP2007506749A5 true JP2007506749A5 (https=) | 2007-09-06 |
| JP4824563B2 JP4824563B2 (ja) | 2011-11-30 |
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| EP (1) | EP1667981A4 (https=) |
| JP (1) | JP4824563B2 (https=) |
| CN (1) | CN1856477A (https=) |
| AU (1) | AU2004276268B2 (https=) |
| CA (1) | CA2539546C (https=) |
| WO (1) | WO2005030729A1 (https=) |
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| JP4719151B2 (ja) * | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | イソキノリノンカリウムチャネル阻害剤 |
| WO2005030791A2 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinolinone potassium channel inhibitors |
| CN1856473A (zh) * | 2003-09-23 | 2006-11-01 | 默克公司 | 异喹啉酮钾通道抑制剂 |
| WO2005030726A1 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinolinone potassium channel inhibitors |
| US7569589B2 (en) | 2004-07-29 | 2009-08-04 | Merck & Co., Inc. | Potassium channel inhibitors |
| US7879839B2 (en) | 2004-07-29 | 2011-02-01 | Merck Sharp & Dohme Corp. | Potassium channel inhibitors |
| EP1922311A2 (en) | 2005-09-09 | 2008-05-21 | Brystol-Myers Squibb Company | Acyclic ikur inhibitors |
| KR101682058B1 (ko) * | 2008-12-11 | 2016-12-02 | 비이브 헬쓰케어 컴퍼니 | 카르바모일피리돈 ｈｉｖ 인테그라제 억제제를 위한 제조방법 및 중간체 |
| US8232273B2 (en) * | 2008-12-19 | 2012-07-31 | Genentech, Inc. | Heterocyclic compounds and methods of use |
| GB0909671D0 (en) * | 2009-06-04 | 2009-07-22 | Xention Discovery Ltd | Compounds |
| GB0909672D0 (en) * | 2009-06-04 | 2009-07-22 | Xention Discovery Ltd | Compounds |
| US8940737B2 (en) | 2011-10-14 | 2015-01-27 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| CN103987711B (zh) | 2011-10-14 | 2016-08-24 | 艾伯维公司 | 作为用于治疗癌症和免疫性和自身免疫性疾病的凋亡诱导剂的8-氨基甲酰基-2-(2,3-二取代吡啶-6-基)-1,2,3,4-四氢异喹啉衍生物 |
| CN103922952A (zh) * | 2014-05-07 | 2014-07-16 | 宁夏宝马药业有限公司 | 用羟基乙腈制取环丙基甘氨酸的方法 |
| AR104259A1 (es) | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| WO2017003723A1 (en) | 2015-07-01 | 2017-01-05 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| US11028068B2 (en) | 2017-07-25 | 2021-06-08 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| CN114728177B (zh) * | 2019-10-07 | 2025-06-24 | D·E·萧尔研究有限责任公司 | 作为Kv1.3钾Shaker通道阻滞剂的芳基杂二环化合物 |
| BR112022006292A2 (pt) * | 2019-10-07 | 2022-06-28 | De Shaw Res Llc | Compostos heterobicílicos de arila como bloqueadores de canais de agitador de potássio kv1.3 |
| CN116693456A (zh) * | 2022-02-28 | 2023-09-05 | 复旦大学 | 异喹啉酮类化合物及其制备方法和应用 |
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| DE287032C (https=) | ||||
| DD287032A5 (de) * | 1989-07-28 | 1991-02-14 | Karl-Marx-Universitaet Leipzig,De | Verfahren zur herstellung von 3-carbamoyl-4-aryl-1,2-di-hydro-isochinolin-1h-onen |
| TW241258B (https=) * | 1992-04-15 | 1995-02-21 | Takeda Pharm Industry Co Ltd | |
| EP0585913B1 (en) * | 1992-09-04 | 1997-12-29 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic compounds, their production and use |
| EP1322619B1 (en) | 2000-09-20 | 2008-01-23 | Merck & Co., Inc. | Isoquinolinone potassium channel inhibitors |
| CN1500080A (zh) | 2001-02-02 | 2004-05-26 | ����ҩƷ��ҵ��ʽ���� | 稠合杂环化合物 |
| JP4719151B2 (ja) * | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | イソキノリノンカリウムチャネル阻害剤 |
| WO2005030791A2 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinolinone potassium channel inhibitors |
| CN1856473A (zh) * | 2003-09-23 | 2006-11-01 | 默克公司 | 异喹啉酮钾通道抑制剂 |
| WO2005030726A1 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinolinone potassium channel inhibitors |
-
2004
- 2004-09-22 EP EP04784700A patent/EP1667981A4/en not_active Withdrawn
- 2004-09-22 WO PCT/US2004/030945 patent/WO2005030729A1/en not_active Ceased
- 2004-09-22 US US10/572,236 patent/US7763614B2/en not_active Expired - Fee Related
- 2004-09-22 CN CNA2004800274862A patent/CN1856477A/zh active Pending
- 2004-09-22 JP JP2006528111A patent/JP4824563B2/ja not_active Expired - Fee Related
- 2004-09-22 AU AU2004276268A patent/AU2004276268B2/en not_active Ceased
- 2004-09-22 CA CA2539546A patent/CA2539546C/en not_active Expired - Fee Related
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