DE602004004143T2 - Imidazopyrimidine und triazolopyrimidine: benzodiazepinrezeptorliganden - Google Patents

Info

Publication number

DE602004004143T2

DE602004004143T2 DE602004004143T DE602004004143T DE602004004143T2 DE 602004004143 T2 DE602004004143 T2 DE 602004004143T2 DE 602004004143 T DE602004004143 T DE 602004004143T DE 602004004143 T DE602004004143 T DE 602004004143T DE 602004004143 T2 DE602004004143 T2 DE 602004004143T2

Authority

DE

Germany

Prior art keywords

imidazol

triazolo

pyrimidine

ylmethyl

propyl

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

Links

• Espacenet
• Global Dossier
• DPMA
• Discuss

• 239000003446 ligand Substances 0.000 title description 16
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 2
• 102000004300 GABA-A Receptors Human genes 0.000 title description 2
• 108090000839 GABA-A Receptors Proteins 0.000 title description 2
• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 278
• -1 nitro, cyano, amino Chemical group 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 98
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• 229910052736 halogen Inorganic materials 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 62
• 150000002367 halogens Chemical class 0.000 claims description 61
• 238000002360 preparation method Methods 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 50
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 150000002431 hydrogen Chemical class 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 208000019901 Anxiety disease Diseases 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• 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 description 22
• 239000003814 drug Substances 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 208000019116 sleep disease Diseases 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 125000005518 carboxamido group Chemical group 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
• 230000036506 anxiety Effects 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 230000006403 short-term memory Effects 0.000 claims description 12
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 208000020685 sleep-wake disease Diseases 0.000 claims description 8
• 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 7
• 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 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 125000004648 C2-C8 alkenyl group Chemical group 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
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 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 6
• 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
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 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
• 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
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 206010012289 Dementia Diseases 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
• 230000006735 deficit Effects 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 239000007788 liquid Substances 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• ZFHXYIHQAPCFBD-UHFFFAOYSA-N 2-[7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]ethanol Chemical compound N1=CN2N=C(C)N=C2C(CCO)=C1CN1C=CN=C1C1=NC=CC=C1F ZFHXYIHQAPCFBD-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 3
• 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 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
• 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
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 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
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 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 2
• 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 2
• CELKOWQJPVJKIL-UHFFFAOYSA-N 3-fluoropyridine Chemical compound FC1=CC=CN=C1 CELKOWQJPVJKIL-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
• 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
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
• 239000002775 capsule Substances 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• AHLZHYYIYJLVNC-UHFFFAOYSA-N ethyl 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine-2-carboxylate Chemical compound N1=CN2C=C(C(=O)OCC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 AHLZHYYIYJLVNC-UHFFFAOYSA-N 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims 7
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 3
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 2
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 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 1
• 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 1
• 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 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
• 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
• 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
• 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
• 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
• 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
• 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
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• 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
• 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
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• 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
• 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
• 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
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• 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
• 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
• 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 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
• 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
• 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
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