JP2007500130A5 - - Google Patents
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- JP2007500130A5 JP2007500130A5 JP2006521278A JP2006521278A JP2007500130A5 JP 2007500130 A5 JP2007500130 A5 JP 2007500130A5 JP 2006521278 A JP2006521278 A JP 2006521278A JP 2006521278 A JP2006521278 A JP 2006521278A JP 2007500130 A5 JP2007500130 A5 JP 2007500130A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazol
- triazolo
- pyrimidine
- ylmethyl
- propyl
- 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.)
- Pending
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- -1 nitro, cyano, amino Chemical group 0.000 claims 47
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- HMHIPFOQWVGGCP-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F HMHIPFOQWVGGCP-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- YMBCGEXQOACNHS-UHFFFAOYSA-N 2,8-diethyl-7-[[2-(5-fluoro-2-methylphenyl)imidazol-1-yl]methyl]-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(CC)N=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1C YMBCGEXQOACNHS-UHFFFAOYSA-N 0.000 claims 1
- GOPZZXGUDALQEB-UHFFFAOYSA-N 2-(cyclopentyloxymethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COC3CCCC3)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F GOPZZXGUDALQEB-UHFFFAOYSA-N 0.000 claims 1
- GKYYCIFMTQMTHX-UHFFFAOYSA-N 2-(difluoromethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C(F)F)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F GKYYCIFMTQMTHX-UHFFFAOYSA-N 0.000 claims 1
- IZSCGZKYJYEHCE-UHFFFAOYSA-N 2-(ethoxymethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COCC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F IZSCGZKYJYEHCE-UHFFFAOYSA-N 0.000 claims 1
- SCGMXMDBDVEBET-UHFFFAOYSA-N 2-(ethoxymethyl)-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COCC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 SCGMXMDBDVEBET-UHFFFAOYSA-N 0.000 claims 1
- XLBLTGCZHQLTHS-UHFFFAOYSA-N 2-(fluoromethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(CF)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F XLBLTGCZHQLTHS-UHFFFAOYSA-N 0.000 claims 1
- UUIOMTRXMKJVRQ-UHFFFAOYSA-N 2-[1-[(2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]-1,3-thiazole Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CS1 UUIOMTRXMKJVRQ-UHFFFAOYSA-N 0.000 claims 1
- HXQCURDPVMRVTF-UHFFFAOYSA-N 2-[1-[(2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1C#N HXQCURDPVMRVTF-UHFFFAOYSA-N 0.000 claims 1
- UYUZKXAGLYQINB-UHFFFAOYSA-N 2-[1-[(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1C#N UYUZKXAGLYQINB-UHFFFAOYSA-N 0.000 claims 1
- SQZVKGOCXXJDRW-UHFFFAOYSA-N 2-[1-[[8-(3-fluoropropyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound N1=CN2N=CN=C2C(CCCF)=C1CN1C=CN=C1C1=NC=CC=C1C#N SQZVKGOCXXJDRW-UHFFFAOYSA-N 0.000 claims 1
- DXFPPOJKGNNLKF-UHFFFAOYSA-N 2-[1-[[8-(3-fluoropropyl)-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound N1=CN2C=NN=C2C(CCCF)=C1CN1C=CN=C1C1=NC=CC=C1C#N DXFPPOJKGNNLKF-UHFFFAOYSA-N 0.000 claims 1
- JCUWOVITNZXHFK-UHFFFAOYSA-N 2-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]-1,3-thiazole Chemical compound N1=CN2N=C(C=3SC=CN=3)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F JCUWOVITNZXHFK-UHFFFAOYSA-N 0.000 claims 1
- ISAAPUBECZHBGQ-UHFFFAOYSA-N 2-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]propan-2-ol Chemical compound N1=CN2N=C(C(C)(C)O)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F ISAAPUBECZHBGQ-UHFFFAOYSA-N 0.000 claims 1
- JTXBWCRMHAVYJZ-UHFFFAOYSA-N 2-[7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]propan-2-ol Chemical compound N1=CN2N=C(C(C)(C)O)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 JTXBWCRMHAVYJZ-UHFFFAOYSA-N 0.000 claims 1
- AQQDLZIGRLPDMC-UHFFFAOYSA-N 2-chloro-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(Cl)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F AQQDLZIGRLPDMC-UHFFFAOYSA-N 0.000 claims 1
- MDMNLRIIJCLGPZ-UHFFFAOYSA-N 2-cyclobutyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C3CCC3)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 MDMNLRIIJCLGPZ-UHFFFAOYSA-N 0.000 claims 1
- LXWBGHJXKKIHGA-UHFFFAOYSA-N 2-ethoxy-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(OCC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F LXWBGHJXKKIHGA-UHFFFAOYSA-N 0.000 claims 1
- NERZUYNHTDRKCC-UHFFFAOYSA-N 2-ethyl-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(CC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F NERZUYNHTDRKCC-UHFFFAOYSA-N 0.000 claims 1
- SBAWYMUGSDAFIP-UHFFFAOYSA-N 2-ethyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=C(C)N2N=C(CC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 SBAWYMUGSDAFIP-UHFFFAOYSA-N 0.000 claims 1
- PGVWGWOXXXTRBI-UHFFFAOYSA-N 2-ethyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=C(CC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 PGVWGWOXXXTRBI-UHFFFAOYSA-N 0.000 claims 1
- OJGKSXCBHJNZDG-UHFFFAOYSA-N 2-methyl-8-propyl-7-[(2-pyridazin-3-ylimidazol-1-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CN=N1 OJGKSXCBHJNZDG-UHFFFAOYSA-N 0.000 claims 1
- MAMNCFUENSXJOF-UHFFFAOYSA-N 2-methyl-8-propyl-7-[(2-pyridin-2-ylimidazol-1-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC=N1 MAMNCFUENSXJOF-UHFFFAOYSA-N 0.000 claims 1
- LELCLASMDQWUKH-UHFFFAOYSA-N 3,8-diethyl-7-[[2-(5-fluoro-2-methylphenyl)imidazol-1-yl]methyl]-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(CC)=NN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1C LELCLASMDQWUKH-UHFFFAOYSA-N 0.000 claims 1
- VNRCPYKSCJJOCU-UHFFFAOYSA-N 3-(difluoromethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C(F)F)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F VNRCPYKSCJJOCU-UHFFFAOYSA-N 0.000 claims 1
- PLNOLJTZHMBVMG-UHFFFAOYSA-N 3-[1-[(8-ethyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]benzonitrile Chemical compound N1=CN2N=CN=C2C(CC)=C1CN1C=CN=C1C1=CC=CC(C#N)=C1 PLNOLJTZHMBVMG-UHFFFAOYSA-N 0.000 claims 1
- NZIZZDODSBLGRE-UHFFFAOYSA-N 3-cyclobutyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C3CCC3)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 NZIZZDODSBLGRE-UHFFFAOYSA-N 0.000 claims 1
- WRKXDSKCDCTVCJ-UHFFFAOYSA-N 3-ethyl-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(CC)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F WRKXDSKCDCTVCJ-UHFFFAOYSA-N 0.000 claims 1
- CGUKQGIMXXFLSP-UHFFFAOYSA-N 3-ethyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=C(C)N2C(CC)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 CGUKQGIMXXFLSP-UHFFFAOYSA-N 0.000 claims 1
- ISHJJXZEBIOQIF-UHFFFAOYSA-N 3-methyl-8-propyl-7-[(2-pyridazin-3-ylimidazol-1-yl)methyl]-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CN=N1 ISHJJXZEBIOQIF-UHFFFAOYSA-N 0.000 claims 1
- UERUEYQWZYJQJC-UHFFFAOYSA-N 3-methyl-8-propyl-7-[(2-pyridin-2-ylimidazol-1-yl)methyl]-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC=N1 UERUEYQWZYJQJC-UHFFFAOYSA-N 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
- ZBYGVHNGZCTZNX-UHFFFAOYSA-N 6-[1-[(2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 ZBYGVHNGZCTZNX-UHFFFAOYSA-N 0.000 claims 1
- NCLGCAXMIKOGKN-UHFFFAOYSA-N 6-[1-[(8-ethyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=CN=C2C(CC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 NCLGCAXMIKOGKN-UHFFFAOYSA-N 0.000 claims 1
- QPIDDKKIADXBRK-UHFFFAOYSA-N 6-[1-[(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]-1h-pyridin-2-one Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(O)=N1 QPIDDKKIADXBRK-UHFFFAOYSA-N 0.000 claims 1
- HRETYXMMIJBZRN-UHFFFAOYSA-N 6-[1-[(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 HRETYXMMIJBZRN-UHFFFAOYSA-N 0.000 claims 1
- MYVNHGGGZLUKTQ-UHFFFAOYSA-N 6-[1-[[2-(methoxymethyl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=C(COC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 MYVNHGGGZLUKTQ-UHFFFAOYSA-N 0.000 claims 1
- PDSVIKGHQBELEO-UHFFFAOYSA-N 6-[1-[[2-(propan-2-yloxymethyl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=C(COC(C)C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 PDSVIKGHQBELEO-UHFFFAOYSA-N 0.000 claims 1
- WCDKKXLFPLVUMO-UHFFFAOYSA-N 6-[1-[[8-(3-fluoropropyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=CN=C2C(CCCF)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 WCDKKXLFPLVUMO-UHFFFAOYSA-N 0.000 claims 1
- SEEDBSFYNSDULV-UHFFFAOYSA-N 6-[1-[[8-(3-fluoropropyl)-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2C=NN=C2C(CCCF)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 SEEDBSFYNSDULV-UHFFFAOYSA-N 0.000 claims 1
- ZVMBXSFOUZHVFX-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F ZVMBXSFOUZHVFX-UHFFFAOYSA-N 0.000 claims 1
- XNCYXJSDXIITFC-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-3-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F XNCYXJSDXIITFC-UHFFFAOYSA-N 0.000 claims 1
- OEXYXFNMBFRMHW-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-8-ethyl-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F OEXYXFNMBFRMHW-UHFFFAOYSA-N 0.000 claims 1
- BXLMLBMXACCJJC-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-8-ethyl-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F BXLMLBMXACCJJC-UHFFFAOYSA-N 0.000 claims 1
- CBFPVQBDUIONAG-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-8-ethyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F CBFPVQBDUIONAG-UHFFFAOYSA-N 0.000 claims 1
- LBBRUTMMONIDJW-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-8-ethyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F LBBRUTMMONIDJW-UHFFFAOYSA-N 0.000 claims 1
- CEEJHZQYRZHFJU-UHFFFAOYSA-N 7-[[2-(2,6-difluorophenyl)imidazol-1-yl]methyl]-8-propyl-2-(trifluoromethyl)imidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=C(C(F)(F)F)N=C2C(CCC)=C1CN1C=CN=C1C1=C(F)C=CC=C1F CEEJHZQYRZHFJU-UHFFFAOYSA-N 0.000 claims 1
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| DE60306918T2 (de) * | 2002-05-17 | 2007-03-01 | Neurogen Corp., Branford | Substituierte, ringkondensierte imidazolderivate: gabaa-rezeptorliganden |
| CN100579579C (zh) * | 2002-10-01 | 2010-01-13 | 诺华疫苗和诊断公司 | 抗癌及抗感染性疾病组合物及其使用方法 |
| ATE335732T1 (de) | 2002-11-08 | 2006-09-15 | Neurogen Corp | 4-imidazol-1-ylmethylpyrimidinderivate als liganden für gabaa-rezeptoren |
| CA2524376A1 (en) | 2003-05-05 | 2004-12-16 | Neurogen Corporation | Substituted imidazolopyrazine and triazolopyrazyne derivatives: gabaa receptor ligands |
-
2004
- 2004-07-23 WO PCT/US2004/023794 patent/WO2005012306A2/en not_active Ceased
- 2004-07-23 JP JP2006521278A patent/JP2007500130A/ja active Pending
- 2004-07-23 PT PT04779031T patent/PT1648899E/pt unknown
- 2004-07-23 MX MXPA06000887A patent/MXPA06000887A/es active IP Right Grant
- 2004-07-23 EP EP04779031A patent/EP1648899B1/en not_active Expired - Lifetime
- 2004-07-23 KR KR1020067001782A patent/KR20060098425A/ko not_active Ceased
- 2004-07-23 PL PL04779031T patent/PL1648899T3/pl unknown
- 2004-07-23 DE DE602004004143T patent/DE602004004143T2/de not_active Expired - Lifetime
- 2004-07-23 AU AU2004261591A patent/AU2004261591A1/en not_active Abandoned
- 2004-07-23 ES ES04779031T patent/ES2278345T3/es not_active Expired - Lifetime
- 2004-07-23 US US10/898,690 patent/US7271170B2/en not_active Expired - Lifetime
- 2004-07-23 AT AT04779031T patent/ATE350382T1/de not_active IP Right Cessation
- 2004-07-23 BR BRPI0412908-3A patent/BRPI0412908A/pt not_active IP Right Cessation
- 2004-07-23 DK DK04779031T patent/DK1648899T3/da active
- 2004-07-23 CA CA002537331A patent/CA2537331A1/en not_active Abandoned
- 2004-07-23 NZ NZ544262A patent/NZ544262A/xx unknown
- 2004-07-26 AR ARP040102649A patent/AR045117A1/es unknown
- 2004-07-26 TW TW093122247A patent/TW200524937A/zh unknown
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2006
- 2006-01-19 IL IL173265A patent/IL173265A0/en unknown
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2007
- 2007-02-26 CY CY20071100262T patent/CY1107565T1/el unknown
- 2007-09-14 US US11/855,386 patent/US20080139580A1/en not_active Abandoned
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