ES2278345T3 - Imidazo-pirimidinas y triazolo-pirimidinas: ligandos de receptores de benzodiazepinas. - Google Patents

Info

Publication number

ES2278345T3

ES2278345T3 ES04779031T ES04779031T ES2278345T3 ES 2278345 T3 ES2278345 T3 ES 2278345T3 ES 04779031 T ES04779031 T ES 04779031T ES 04779031 T ES04779031 T ES 04779031T ES 2278345 T3 ES2278345 T3 ES 2278345T3

Authority

ES

Spain

Prior art keywords

imidazol

triazolo

pyrimidine

propyl

ylmethyl

Prior art date

2003-07-25

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.)

Expired - Lifetime

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• 150000001875 compounds Chemical class 0.000 claims abstract description 287
• -1 nitro, cyano, amino Chemical group 0.000 claims abstract description 142
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 105
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 63
• 150000002367 halogens Chemical class 0.000 claims abstract description 60
• 125000001424 substituent group Chemical group 0.000 claims abstract description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
• 239000001257 hydrogen Substances 0.000 claims abstract description 53
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 46
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 36
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 13
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
• 239000000203 mixture Substances 0.000 claims description 95
• 125000003545 alkoxy group Chemical group 0.000 claims description 77
• 238000011282 treatment Methods 0.000 claims description 38
• 125000001188 haloalkyl group Chemical group 0.000 claims description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
• 125000004076 pyridyl group Chemical group 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 208000019901 Anxiety disease Diseases 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 150000005215 alkyl ethers Chemical class 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 208000019116 sleep disease Diseases 0.000 claims description 17
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 230000036506 anxiety Effects 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 9
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 8
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 8
• YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims description 8
• 125000004494 ethyl ester group Chemical group 0.000 claims description 8
• 208000020685 sleep-wake disease Diseases 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• UAMAIHOEGLEXSV-UHFFFAOYSA-N adipiplon Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F UAMAIHOEGLEXSV-UHFFFAOYSA-N 0.000 claims description 7
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
• 125000005518 carboxamido group Chemical group 0.000 claims description 7
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 7
• 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 description 6
• IPXNSCRXLXHBIZ-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=C(C)N2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 IPXNSCRXLXHBIZ-UHFFFAOYSA-N 0.000 claims description 6
• UWTLXBIEGTWTMZ-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine-2-carbonitrile Chemical compound N1=CN2C=C(C#N)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 UWTLXBIEGTWTMZ-UHFFFAOYSA-N 0.000 claims description 6
• 208000000044 Amnesia Diseases 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 206010012289 Dementia Diseases 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 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 description 5
• 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 5
• 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 description 5
• CIAROHKHYKMXOX-UHFFFAOYSA-N 7-[[2-(6-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=CC=CC(F)=N1 CIAROHKHYKMXOX-UHFFFAOYSA-N 0.000 claims description 5
• AFVWKPXVQGAVPE-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 AFVWKPXVQGAVPE-UHFFFAOYSA-N 0.000 claims description 5
• CDFFJLUXSUAEDN-UHFFFAOYSA-N 8-(2,2-difluoroethyl)-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(F)F)=C1CN1C=CN=C1C1=NC=CC=C1F CDFFJLUXSUAEDN-UHFFFAOYSA-N 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 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
• 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 description 4
• 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 description 4
• 208000026139 Memory disease Diseases 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 230000006984 memory degeneration Effects 0.000 claims description 4
• 208000023060 memory loss Diseases 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• JPOKMXYVDZDHCA-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine-3-carbonitrile Chemical compound N1=CN2C(C#N)=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 JPOKMXYVDZDHCA-UHFFFAOYSA-N 0.000 claims description 3
• GBQVPQANRQCFKU-UHFFFAOYSA-N 8-ethyl-7-[[2-[3-(trifluoromethyl)phenyl]imidazol-1-yl]methyl]-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CC)=C1CN1C=CN=C1C1=CC=CC(C(F)(F)F)=C1 GBQVPQANRQCFKU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• USNPJDROMQCDAO-UHFFFAOYSA-N [7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]methanol Chemical compound N1=CN2N=C(CO)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F USNPJDROMQCDAO-UHFFFAOYSA-N 0.000 claims description 2
• 239000002775 capsule Substances 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 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 3
• 125000001589 carboacyl group Chemical group 0.000 claims 3
• 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 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 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
• 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
• 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
• 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
• 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
• 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
• 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
• JSESSIYRQBVOJR-UHFFFAOYSA-N 6-[1-[[2-(ethoxymethyl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=C(COCC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 JSESSIYRQBVOJR-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
• 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
• ZYPLRHLOLLTGCF-UHFFFAOYSA-N 7-[[2-(2,6-difluorophenyl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CCC)=C1CN1C=CN=C1C1=C(F)C=CC=C1F ZYPLRHLOLLTGCF-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
• ZYNLZENDPKIIDI-UHFFFAOYSA-N 7-[[2-(2-chlorophenyl)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=C1Cl ZYNLZENDPKIIDI-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
• YTZNDNOKVZHSGN-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-(oxolan-2-yl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C3OCCC3)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F YTZNDNOKVZHSGN-UHFFFAOYSA-N 0.000 claims 1
• YFEYLPSLGVNYQR-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-(propan-2-yloxymethyl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COC(C)C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F YFEYLPSLGVNYQR-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
• 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
• QEWKYEIJIPNJHO-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-8-(3-phenylmethoxypropyl)-[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=1CCCOCC1=CC=CC=C1 QEWKYEIJIPNJHO-UHFFFAOYSA-N 0.000 claims 1
• ARGFLWAICIFABB-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-(methoxymethyl)-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(COC)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F ARGFLWAICIFABB-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
• 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
• 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 1
• 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 1
• PNFBLOLXFIYSFD-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-2-(2,2,2-trifluoroethoxymethyl)-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COCC(F)(F)F)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F PNFBLOLXFIYSFD-UHFFFAOYSA-N 0.000 claims 1
• TVWUSMPKIYMOFZ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-2-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(CC(F)(F)F)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F TVWUSMPKIYMOFZ-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
• 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 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
• 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 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
• 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
• 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 1
• MSHZCEXGMYQMCX-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-n,n,8-tripropyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound N1=CN2N=C(N(CCC)CCC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F MSHZCEXGMYQMCX-UHFFFAOYSA-N 0.000 claims 1
• VZJOLTPAOSKMGJ-UHFFFAOYSA-N 7-[[2-(5-fluoropyridin-2-yl)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=C(F)C=N1 VZJOLTPAOSKMGJ-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
• RBLGHXBHKAXSQT-UHFFFAOYSA-N 7-[[2-(6-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=CC=CC(F)=N1 RBLGHXBHKAXSQT-UHFFFAOYSA-N 0.000 claims 1
• GVXYGNNNENEIGC-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)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=CC(F)=N1 GVXYGNNNENEIGC-UHFFFAOYSA-N 0.000 claims 1
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