PT1648899E - Imidazo-pirimidinas e triazolo-pirimidinas: ligandos do receptor de benzodiazepina - Google Patents

Info

Publication number

PT1648899E

PT1648899E PT04779031T PT04779031T PT1648899E PT 1648899 E PT1648899 E PT 1648899E PT 04779031 T PT04779031 T PT 04779031T PT 04779031 T PT04779031 T PT 04779031T PT 1648899 E PT1648899 E PT 1648899E

Authority

PT

Portugal

Prior art keywords

imidazol

triazolo

pyrimidine

ylmethyl

propyl

Prior art date

2003-07-25

Links

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• Global Dossier
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• 239000003446 ligand Substances 0.000 title description 10
• 102000004300 GABA-A Receptors Human genes 0.000 title description 3
• 108090000839 GABA-A Receptors Proteins 0.000 title description 3
• 150000005237 imidazopyrimidines Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 299
• -1 nitro, cyano, amino Chemical group 0.000 claims description 208
• 239000000203 mixture Substances 0.000 claims description 78
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 238000002360 preparation method Methods 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 229910052736 halogen Inorganic materials 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 41
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 208000019901 Anxiety disease Diseases 0.000 claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• 208000019116 sleep disease Diseases 0.000 claims description 16
• 230000036506 anxiety Effects 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 9
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 9
• 208000024827 Alzheimer disease Diseases 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 208000000044 Amnesia Diseases 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000005518 carboxamido group Chemical group 0.000 claims description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• XQOLMNXEGDTGML-UHFFFAOYSA-N triazolo[1,5-c]pyrimidine Chemical compound C1=NC=CC2=CN=NN21 XQOLMNXEGDTGML-UHFFFAOYSA-N 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 208000020685 sleep-wake disease Diseases 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• QLOWGDIISXJREF-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=CN2N=CN=C21 QLOWGDIISXJREF-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
• IJZQSEGBLMAYSB-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(N3CCCC3)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F IJZQSEGBLMAYSB-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
• NUJDBYIZEFSXJP-UHFFFAOYSA-N 1-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]propan-1-ol Chemical compound N1=CN2N=C(C)N=C2C(C(O)CC)=C1CN1C=CN=C1C1=NC=CC=C1F NUJDBYIZEFSXJP-UHFFFAOYSA-N 0.000 claims description 2
• MEHYNRSHIWOOMA-UHFFFAOYSA-N 1-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]propan-1-ol Chemical compound N1=CN2C(C)=NN=C2C(C(O)CC)=C1CN1C=CN=C1C1=NC=CC=C1F MEHYNRSHIWOOMA-UHFFFAOYSA-N 0.000 claims description 2
• KDHJNMHGCNOHTL-UHFFFAOYSA-N 1-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]ethanol Chemical compound N1=CN2N=C(C(C)O)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F KDHJNMHGCNOHTL-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 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 description 2
• JFPWLZIMLNSFNL-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-(methoxymethyl)-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(COC)=C1CN1C=CN=C1C1=NC=CC=C1F JFPWLZIMLNSFNL-UHFFFAOYSA-N 0.000 claims description 2
• DCRXEJZBQJKWSR-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-(methoxymethyl)-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(COC)=C1CN1C=CN=C1C1=NC=CC=C1F DCRXEJZBQJKWSR-UHFFFAOYSA-N 0.000 claims description 2
• ZSMOLXAKLVEJMX-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-(methoxymethyl)-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(COC)=C1CN1C=CN=C1C1=NC=CC=C1F ZSMOLXAKLVEJMX-UHFFFAOYSA-N 0.000 claims description 2
• TZLOQVMITUMCFB-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-2-pyridin-3-yl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C=3C=NC=CC=3)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F TZLOQVMITUMCFB-UHFFFAOYSA-N 0.000 claims description 2
• NQNSKLMTADZAAD-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-3-pyridin-3-yl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C=3C=NC=CC=3)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F NQNSKLMTADZAAD-UHFFFAOYSA-N 0.000 claims description 2
• SRRFWMVLLFIYMM-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F SRRFWMVLLFIYMM-UHFFFAOYSA-N 0.000 claims description 2
• XROSGCBCSSJDSU-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3,5-dimethyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=C(C)N2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 XROSGCBCSSJDSU-UHFFFAOYSA-N 0.000 claims description 2
• VFIDEKLJABMLLR-UHFFFAOYSA-N 7-[[4-chloro-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=C(Cl)N=C1C1=NC=CC=C1F VFIDEKLJABMLLR-UHFFFAOYSA-N 0.000 claims description 2
• YBQFDTUPSVSURK-UHFFFAOYSA-N 8-(3-fluoropropyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CCCF)=C1CN1C=CN=C1C1=NC=CC=C1F YBQFDTUPSVSURK-UHFFFAOYSA-N 0.000 claims description 2
• NDLXWDICTXZBBF-UHFFFAOYSA-N 8-(3-fluoropropyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CCCF)=C1CN1C=CN=C1C1=NC=CC=C1F NDLXWDICTXZBBF-UHFFFAOYSA-N 0.000 claims description 2
• LBEFIEHEJIVHBB-UHFFFAOYSA-N 8-ethoxy-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(OCC)=C1CN1C=CN=C1C1=NC=CC=C1F LBEFIEHEJIVHBB-UHFFFAOYSA-N 0.000 claims description 2
• QLGKGVFMMHMEHO-UHFFFAOYSA-N 8-ethyl-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(CC)=C1CN1C=CN=C1C1=NC=CC=C1F QLGKGVFMMHMEHO-UHFFFAOYSA-N 0.000 claims description 2
• ITHWHVPDFQHQKS-UHFFFAOYSA-N 8-ethyl-7-[[2-(5-fluoro-2-methoxyphenyl)imidazol-1-yl]methyl]-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1OC ITHWHVPDFQHQKS-UHFFFAOYSA-N 0.000 claims description 2
• MBMGRIMXBHLVID-UHFFFAOYSA-N 8-propyl-7-[[2-[6-(trifluoromethyl)pyridin-2-yl]imidazol-1-yl]methyl]-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C(F)(F)F)=N1 MBMGRIMXBHLVID-UHFFFAOYSA-N 0.000 claims description 2
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
• 239000002775 capsule Substances 0.000 claims description 2
• 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 239000012530 fluid Substances 0.000 claims description 2
• 231100000863 loss of memory Toxicity 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
• 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
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
• ABHZXJAGIJWWEE-UHFFFAOYSA-N 1-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-yl]ethanol Chemical compound N1=CN2C(C(C)O)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F ABHZXJAGIJWWEE-UHFFFAOYSA-N 0.000 claims 1
• CQIVCBJKDYNCEP-UHFFFAOYSA-N 1-[7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]propan-1-ol Chemical compound N1=CN2N=C(C)N=C2C(C(O)CC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 CQIVCBJKDYNCEP-UHFFFAOYSA-N 0.000 claims 1
• IYGGACKRMNWBSI-UHFFFAOYSA-N 1-[7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]propan-1-ol Chemical compound N1=CN2C(C)=NN=C2C(C(O)CC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 IYGGACKRMNWBSI-UHFFFAOYSA-N 0.000 claims 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 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
• CQGORZBTKUXQKD-UHFFFAOYSA-N 2-[1-[(3-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl)methyl]imidazol-2-yl]-1,3-thiazole Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CS1 CQGORZBTKUXQKD-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
• RVXISMXQFQNUMO-UHFFFAOYSA-N 2-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]ethanol Chemical compound N1=CN2C(C)=NN=C2C(CCO)=C1CN1C=CN=C1C1=NC=CC=C1F RVXISMXQFQNUMO-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
• 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
• 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
• 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
• MQCVWBGSOPHZTF-UHFFFAOYSA-N 3-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]propan-1-ol Chemical compound N1=CN2C(C)=NN=C2C(CCCO)=C1CN1C=CN=C1C1=NC=CC=C1F MQCVWBGSOPHZTF-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
• 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
• FFLRKGVWGOSCAO-UHFFFAOYSA-N 6-[1-[(8-propyl-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl)methyl]imidazol-2-yl]-1h-pyridin-2-one Chemical compound N1=CN2C=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(O)=N1 FFLRKGVWGOSCAO-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
• 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
• MKVAHRVYXFGFIW-UHFFFAOYSA-N 7-[[2-(2,6-difluorophenyl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=C(F)C=CC=C1F MKVAHRVYXFGFIW-UHFFFAOYSA-N 0.000 claims 1
• GFWPDWYNKPMUCK-UHFFFAOYSA-N 7-[[2-(2,6-difluorophenyl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=C(F)C=CC=C1F GFWPDWYNKPMUCK-UHFFFAOYSA-N 0.000 claims 1
• WINNWQRJCGNPKH-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-1-methyl-8-propylimidazo[1,5-c]pyrimidine Chemical compound N1=CN2C=NC(C)=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F WINNWQRJCGNPKH-UHFFFAOYSA-N 0.000 claims 1
• GZJOODXEUFJDCY-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-(methoxymethyl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F GZJOODXEUFJDCY-UHFFFAOYSA-N 0.000 claims 1
• JTJGFFMMLFGUCS-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methoxy-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(OC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F JTJGFFMMLFGUCS-UHFFFAOYSA-N 0.000 claims 1
• AKGKQGXYMQRLOH-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-3-propyl-2h-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N(CCC)C(C)N=C2C=C1CN1C=CN=C1C1=NC=CC=C1F AKGKQGXYMQRLOH-UHFFFAOYSA-N 0.000 claims 1
• FFWKFXVAHOJBJD-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-8-(2-phenylmethoxyethyl)-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=C(C=2C(=CC=CN=2)F)N1CC=1N=CN2N=C(C)N=C2C=1CCOCC1=CC=CC=C1 FFWKFXVAHOJBJD-UHFFFAOYSA-N 0.000 claims 1
• ZEAWTFVUEKDYDK-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C=3C=CC=CC=3)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F ZEAWTFVUEKDYDK-UHFFFAOYSA-N 0.000 claims 1
• BRFPCEPJPXZGDA-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-propan-2-yl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C(C)C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F BRFPCEPJPXZGDA-UHFFFAOYSA-N 0.000 claims 1
• DQSXIULXVLEYIP-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-propan-2-yloxy-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(OC(C)C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DQSXIULXVLEYIP-UHFFFAOYSA-N 0.000 claims 1
• SPIKZNVEROZJMT-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methoxy-5-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=C(C)N2C(OC)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F SPIKZNVEROZJMT-UHFFFAOYSA-N 0.000 claims 1
• ITBPKDIWIVXDBB-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-8-prop-1-enyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(C=CC)=C1CN1C=CN=C1C1=NC=CC=C1F ITBPKDIWIVXDBB-UHFFFAOYSA-N 0.000 claims 1
• DNRXICIPOQCKBX-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)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=NC=CC=C1F DNRXICIPOQCKBX-UHFFFAOYSA-N 0.000 claims 1
• BSBGPAVQSMJLET-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-phenyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C=3C=CC=CC=3)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F BSBGPAVQSMJLET-UHFFFAOYSA-N 0.000 claims 1
• NBFWRPZRFCGSCI-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-propan-2-yl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C(C)C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F NBFWRPZRFCGSCI-UHFFFAOYSA-N 0.000 claims 1
• ZTBYDJXUPTZYBF-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C(F)(F)F)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F ZTBYDJXUPTZYBF-UHFFFAOYSA-N 0.000 claims 1
• YVNMREPZHJKGGJ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C(F)(F)F)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F YVNMREPZHJKGGJ-UHFFFAOYSA-N 0.000 claims 1
• SIFVDHWCLQHABA-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound N1=CN2N=C(N)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F SIFVDHWCLQHABA-UHFFFAOYSA-N 0.000 claims 1
• DUCQNVVDVIJXFQ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DUCQNVVDVIJXFQ-UHFFFAOYSA-N 0.000 claims 1
• JUXFIJBURSYEMS-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-carbonitrile Chemical compound N1=CN2N=C(C#N)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F JUXFIJBURSYEMS-UHFFFAOYSA-N 0.000 claims 1
• NLFNJZDYXHSTAE-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-carboxamide Chemical compound N1=CN2N=C(C(N)=O)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F NLFNJZDYXHSTAE-UHFFFAOYSA-N 0.000 claims 1
• DRLBVGSAXLSNEN-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-carboxylic acid Chemical compound N1=CN2N=C(C(O)=O)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DRLBVGSAXLSNEN-UHFFFAOYSA-N 0.000 claims 1
• MSAMDYNIRBHZAJ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine-3-carbonitrile Chemical compound N1=CN2C(C#N)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F MSAMDYNIRBHZAJ-UHFFFAOYSA-N 0.000 claims 1
• YLOQONJMXCYFRA-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine-3-carboxamide Chemical compound N1=CN2C(C(N)=O)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F YLOQONJMXCYFRA-UHFFFAOYSA-N 0.000 claims 1
• DDYKETUOYYATBU-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine-3-carboxylic acid Chemical compound N1=CN2C(C(O)=O)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DDYKETUOYYATBU-UHFFFAOYSA-N 0.000 claims 1
• JWGDOTNRVDLEMB-UHFFFAOYSA-N 7-[[2-(6-chloropyridin-2-yl)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=CC(Cl)=N1 JWGDOTNRVDLEMB-UHFFFAOYSA-N 0.000 claims 1
• UOFYVWZZEOSJGQ-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2,3-dimethyl-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C(C)=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 UOFYVWZZEOSJGQ-UHFFFAOYSA-N 0.000 claims 1
• ZSKRIUDQIWBRMG-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2,5-dimethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=C(C)N2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 ZSKRIUDQIWBRMG-UHFFFAOYSA-N 0.000 claims 1
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