JP2016512259A5 - - Google Patents

Info

Publication number

JP2016512259A5

JP2016512259A5 JP2016500760A JP2016500760A JP2016512259A5 JP 2016512259 A5 JP2016512259 A5 JP 2016512259A5 JP 2016500760 A JP2016500760 A JP 2016500760A JP 2016500760 A JP2016500760 A JP 2016500760A JP 2016512259 A5 JP2016512259 A5 JP 2016512259A5

Authority

JP

Japan

Prior art keywords

methyl

chlorophenyl

difluoromethoxy

methoxypyridin

triazol

Prior art date

2014-03-06

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

• Espacenet
• Global Dossier
• Discuss

• 125000000217 alkyl group Chemical group 0.000 claims 25
• -1 -NHCOCH 3 Chemical group 0.000 claims 20
• 239000000126 substance Substances 0.000 claims 16
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
• 125000001188 haloalkyl group Chemical group 0.000 claims 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
• 229910052757 nitrogen Inorganic materials 0.000 claims 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
• KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 3
• GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims 3
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
• 125000005843 halogen group Chemical group 0.000 claims 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
• 125000002757 morpholinyl group Chemical group 0.000 claims 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 3
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
• 210000003169 central nervous system Anatomy 0.000 claims 2
• 150000001875 compounds Chemical class 0.000 claims 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
• 208000035475 disorder Diseases 0.000 claims 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
• 150000003839 salts Chemical class 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
• CTAPFRYPJLPFDF-HQMMCQRPSA-N 1,2-oxazole Chemical group C1=CON=[14CH]1 CTAPFRYPJLPFDF-HQMMCQRPSA-N 0.000 claims 1
• WFFBPHABLYPNGS-UHFFFAOYSA-N 1-[4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(CC=2C=C(C(OC(F)F)=NC=2)C=2C=C(Cl)C=CC=2)C=CC=1C1(C(=O)N)CC1 WFFBPHABLYPNGS-UHFFFAOYSA-N 0.000 claims 1
• OFCZUXNREAJCGY-UHFFFAOYSA-N 1-[4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC(C=C1)=CC=C1NC(=O)NC1COC1 OFCZUXNREAJCGY-UHFFFAOYSA-N 0.000 claims 1
• FHYGJJCXJHUKMB-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]-1-(4-fluorophenyl)-n,n-dimethylmethanamine Chemical compound COC1=NC=C(C(N(C)C)C=2C=CC(F)=CC=2)C=C1C1=CC=CC(Cl)=C1 FHYGJJCXJHUKMB-UHFFFAOYSA-N 0.000 claims 1
• LRAUSXLDNRDNDN-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]-1-(4-fluorophenyl)-n-methylmethanamine Chemical compound C=1N=C(OC)C(C=2C=C(Cl)C=CC=2)=CC=1C(NC)C1=CC=C(F)C=C1 LRAUSXLDNRDNDN-UHFFFAOYSA-N 0.000 claims 1
• OXNNOFNFBRDTEB-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]-1-(4-fluorophenyl)ethanol Chemical compound COC1=NC=C(C(C)(O)C=2C=CC(F)=CC=2)C=C1C1=CC=CC(Cl)=C1 OXNNOFNFBRDTEB-UHFFFAOYSA-N 0.000 claims 1
• FLNYWZLLWZUYIT-UHFFFAOYSA-N 1-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]azetidin-3-ol Chemical compound COc1ncc(Cc2cnc(nc2)N2CC(O)C2)cc1-c1cccc(Cl)c1 FLNYWZLLWZUYIT-UHFFFAOYSA-N 0.000 claims 1
• OTFHWUFFRQTBSQ-UHFFFAOYSA-N 1-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]oxy-2-methylpropan-2-ol Chemical compound COc1ncc(Cc2cnc(OCC(C)(C)O)nc2)cc1-c1cccc(Cl)c1 OTFHWUFFRQTBSQ-UHFFFAOYSA-N 0.000 claims 1
• PWUNXNJMFBEGSY-UHFFFAOYSA-N 1-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]pyrrolidin-3-ol Chemical compound COc1ncc(Cc2cnc(nc2)N2CCC(O)C2)cc1-c1cccc(Cl)c1 PWUNXNJMFBEGSY-UHFFFAOYSA-N 0.000 claims 1
• NDEYKHHAHOWQJJ-UHFFFAOYSA-N 1-[[5-(2-cyanopyridin-4-yl)-6-methoxypyridin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound COc1ncc(Cn2ccc(n2)C(N)=O)cc1-c1ccnc(c1)C#N NDEYKHHAHOWQJJ-UHFFFAOYSA-N 0.000 claims 1
• NAMMXWFMSXYGJJ-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound N1=C(N)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 NAMMXWFMSXYGJJ-UHFFFAOYSA-N 0.000 claims 1
• LCFPWVKRPYXRSS-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,2,4-triazole-3-carbonitrile Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CN1C=NC(C#N)=N1 LCFPWVKRPYXRSS-UHFFFAOYSA-N 0.000 claims 1
• QSCHSVKARQAZEN-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-n,n-dimethyl-1,2,4-triazol-3-amine Chemical compound N1=C(N(C)C)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 QSCHSVKARQAZEN-UHFFFAOYSA-N 0.000 claims 1
• ONOVBFYIDFDASD-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-n-methyl-1,2,4-triazol-3-amine Chemical compound N1=C(NC)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 ONOVBFYIDFDASD-UHFFFAOYSA-N 0.000 claims 1
• HLLUQQJOZVJAMZ-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]imidazole-4-carboxamide Chemical compound C1=NC(C(=O)N)=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 HLLUQQJOZVJAMZ-UHFFFAOYSA-N 0.000 claims 1
• WCBUBYPUPPRXKZ-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-5-methylpyrazol-3-amine Chemical compound CCOc1ncc(Cn2nc(N)cc2C)cc1-c1cccc(Cl)c1 WCBUBYPUPPRXKZ-UHFFFAOYSA-N 0.000 claims 1
• BBOQXRXQMIMFNU-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]imidazole-4-carboxamide Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OCC)CN1C=NC(=C1)C(=O)N BBOQXRXQMIMFNU-UHFFFAOYSA-N 0.000 claims 1
• MTZNSFQMEALNDI-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=CC(C(N)=O)=N1 MTZNSFQMEALNDI-UHFFFAOYSA-N 0.000 claims 1
• RLVWEHSOSQAUHM-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(N)=N1 RLVWEHSOSQAUHM-UHFFFAOYSA-N 0.000 claims 1
• SDDXXTVLFKHFAJ-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazole-3-carboxamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(C(N)=O)=N1 SDDXXTVLFKHFAJ-UHFFFAOYSA-N 0.000 claims 1
• UUPRCZKKDHEWPD-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CN1N=C(C=C1)C(=O)N UUPRCZKKDHEWPD-UHFFFAOYSA-N 0.000 claims 1
• ZMCNYJJKJRQBIR-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazole-4-carbonitrile Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(C#N)C=N1 ZMCNYJJKJRQBIR-UHFFFAOYSA-N 0.000 claims 1
• IGSZLPAKCFFFMM-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(C(N)=O)C=N1 IGSZLPAKCFFFMM-UHFFFAOYSA-N 0.000 claims 1
• CITDHBYWOOKXEA-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(C(O)=O)C=N1 CITDHBYWOOKXEA-UHFFFAOYSA-N 0.000 claims 1
• XBPIJKUWLMOAAC-UHFFFAOYSA-N 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridin-2-one Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=CC=CC1=O XBPIJKUWLMOAAC-UHFFFAOYSA-N 0.000 claims 1
• REEWTTQHHGCBSV-UHFFFAOYSA-N 1-[[5-(3-cyclopropyloxyphenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(OC3CC3)C=CC=2)C(OC)=NC=C1CN1C=NC(N)=N1 REEWTTQHHGCBSV-UHFFFAOYSA-N 0.000 claims 1
• PDARERDSRBORCH-UHFFFAOYSA-N 1-[[5-(3-ethoxyphenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound CCOC1=CC=CC(C=2C(=NC=C(CN3N=C(N)N=C3)C=2)OC)=C1 PDARERDSRBORCH-UHFFFAOYSA-N 0.000 claims 1
• ONOOZODGEYTMLP-UHFFFAOYSA-N 1-[[5-(3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC)=NC=C1CN1C=NC(N)=N1 ONOOZODGEYTMLP-UHFFFAOYSA-N 0.000 claims 1
• QWXJFGVUTZLFLR-UHFFFAOYSA-N 1-[[5-(4-fluoro-3-methoxyphenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound COc1cc(ccc1F)-c1cc(Cn2cnc(N)n2)cnc1OC QWXJFGVUTZLFLR-UHFFFAOYSA-N 0.000 claims 1
• HSSCUFYRANNIFY-UHFFFAOYSA-N 1-[[5-(5-chloropyridin-3-yl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(Cl)C=NC=2)C(OC)=NC=C1CN1C=NC(N)=N1 HSSCUFYRANNIFY-UHFFFAOYSA-N 0.000 claims 1
• VESZJPIWQCNBKC-UHFFFAOYSA-N 1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OCC)=NC=C1CN1C=NC(N)=N1 VESZJPIWQCNBKC-UHFFFAOYSA-N 0.000 claims 1
• JKZONBFNPZGABR-UHFFFAOYSA-N 1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-ethoxypyridin-3-yl]methyl]imidazole-4-carboxamide Chemical compound FC(OC1=NC=CC(=C1)C=1C=C(C=NC1OCC)CN1C=NC(=C1)C(=O)N)F JKZONBFNPZGABR-UHFFFAOYSA-N 0.000 claims 1
• HGGIGEBBJRSVQX-UHFFFAOYSA-N 1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OC)=NC=C1CN1C=NC(N)=N1 HGGIGEBBJRSVQX-UHFFFAOYSA-N 0.000 claims 1
• ISCVOEJGPJEUQY-UHFFFAOYSA-N 1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound FC(OC1=NC=CC(=C1)C=1C=C(C=NC1OC)CN1N=C(C=C1)C(=O)N)F ISCVOEJGPJEUQY-UHFFFAOYSA-N 0.000 claims 1
• QHTXAKIYTAQAQA-UHFFFAOYSA-N 1-[[5-[3-(difluoromethoxy)phenyl]-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(N)=N1 QHTXAKIYTAQAQA-UHFFFAOYSA-N 0.000 claims 1
• NYKYTPMWHSOXOH-UHFFFAOYSA-N 1-[[5-[3-(difluoromethoxy)phenyl]-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC(N)=N1 NYKYTPMWHSOXOH-UHFFFAOYSA-N 0.000 claims 1
• INPWUVJJQLVCAB-UHFFFAOYSA-N 1-[[6-(3,4-difluorophenyl)-5-ethoxypyrazin-2-yl]methyl]imidazole-4-carboxamide Chemical compound FC=1C=C(C=CC1F)C1=C(N=CC(=N1)CN1C=NC(=C1)C(=O)N)OCC INPWUVJJQLVCAB-UHFFFAOYSA-N 0.000 claims 1
• XDXZEFJWUKOSIY-UHFFFAOYSA-N 1-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]imidazole-4-carboxamide Chemical compound CCOc1ncc(Cn2cnc(c2)C(N)=O)nc1-c1cccc(Cl)c1 XDXZEFJWUKOSIY-UHFFFAOYSA-N 0.000 claims 1
• ACFXPNWMZSRQPP-UHFFFAOYSA-N 1-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]pyrazole-3-carboxamide Chemical compound CCOc1ncc(Cn2ccc(n2)C(N)=O)nc1-c1cccc(Cl)c1 ACFXPNWMZSRQPP-UHFFFAOYSA-N 0.000 claims 1
• ITYHDMDZQWUSDK-UHFFFAOYSA-N 1-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]pyrazol-4-amine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(N)C=N1 ITYHDMDZQWUSDK-UHFFFAOYSA-N 0.000 claims 1
• IUOUJOFKRLYMJK-UHFFFAOYSA-N 1-[[6-(difluoromethoxy)-5-(3-methoxyphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound COC1=CC=CC(C=2C(=NC=C(CN3N=C(N)N=C3)C=2)OC(F)F)=C1 IUOUJOFKRLYMJK-UHFFFAOYSA-N 0.000 claims 1
• DMMXKKBVJDVPSH-UHFFFAOYSA-N 1-[[6-(difluoromethoxy)-5-[2-(difluoromethoxy)pyridin-4-yl]pyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound N1=C(N)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(OC(F)F)N=CC=2)=C1 DMMXKKBVJDVPSH-UHFFFAOYSA-N 0.000 claims 1
• WSOLCFWMDIZQKZ-UHFFFAOYSA-N 1-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-amine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(N)=N1 WSOLCFWMDIZQKZ-UHFFFAOYSA-N 0.000 claims 1
• PWLLDJZVHBZBND-UHFFFAOYSA-N 1-[[6-methoxy-5-(3-methoxyphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound COC1=CC=CC(C=2C(=NC=C(CN3N=C(N)N=C3)C=2)OC)=C1 PWLLDJZVHBZBND-UHFFFAOYSA-N 0.000 claims 1
• MQLWWOOWVBXIIR-UHFFFAOYSA-N 1-[[6-methoxy-5-(3-methylphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-amine Chemical compound C1=C(C=2C=C(C)C=CC=2)C(OC)=NC=C1CN1C=NC(N)=N1 MQLWWOOWVBXIIR-UHFFFAOYSA-N 0.000 claims 1
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
• GUSIVYFGMPZMKT-UHFFFAOYSA-N 2-(difluoromethoxy)-3-(3-ethoxyphenyl)-5-[[3-(fluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound CCOC1=CC=CC(C=2C(=NC=C(CN3N=C(CF)N=C3)C=2)OC(F)F)=C1 GUSIVYFGMPZMKT-UHFFFAOYSA-N 0.000 claims 1
• FVQLXOOKSSLEKN-UHFFFAOYSA-N 2-(difluoromethoxy)-3-(3-fluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC(F)F)=NC=C1CN1C=NC=N1 FVQLXOOKSSLEKN-UHFFFAOYSA-N 0.000 claims 1
• USWXVRXVJRPUSW-UHFFFAOYSA-N 2-(difluoromethoxy)-3-(3-methoxyphenyl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound COC1=CC=CC(C=2C(=NC=C(CN3N=CN=C3)C=2)OC(F)F)=C1 USWXVRXVJRPUSW-UHFFFAOYSA-N 0.000 claims 1
• FBAWTFIVPCZFFX-UHFFFAOYSA-N 2-(difluoromethoxy)-3-(3-methylphenyl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound CC1=CC=CC(C=2C(=NC=C(CN3N=CN=C3)C=2)OC(F)F)=C1 FBAWTFIVPCZFFX-UHFFFAOYSA-N 0.000 claims 1
• QETYSEUWFLEXAS-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(1,2,4-triazol-1-ylmethyl)-3-[3-(trifluoromethoxy)phenyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)(F)F)C=CC=2)C(OC(F)F)=NC=C1CN1C=NC=N1 QETYSEUWFLEXAS-UHFFFAOYSA-N 0.000 claims 1
• KRARMLZLFIVZMH-UHFFFAOYSA-N 2-[1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]acetonitrile Chemical compound FC(F)Oc1ncc(Cn2cnc(CC#N)n2)cc1-c1cccc(Cl)c1 KRARMLZLFIVZMH-UHFFFAOYSA-N 0.000 claims 1
• BMJCSQNTMVWGHX-UHFFFAOYSA-N 2-[1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]propan-2-ol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(C(C)(C)O)=N1 BMJCSQNTMVWGHX-UHFFFAOYSA-N 0.000 claims 1
• OEVADVXPBXQANH-UHFFFAOYSA-N 2-[1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]ethanol Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CN1N=NN=C1CCO OEVADVXPBXQANH-UHFFFAOYSA-N 0.000 claims 1
• JOZIAIBFNHKNFN-UHFFFAOYSA-N 2-[2-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]propan-2-ol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1N=CN=C1C(C)(C)O JOZIAIBFNHKNFN-UHFFFAOYSA-N 0.000 claims 1
• BCCHULUYHWZWMO-UHFFFAOYSA-N 2-[4-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]acetamide Chemical compound COc1ncc(Cc2ccc(CC(N)=O)cc2)cc1-c1ccc(F)c(F)c1 BCCHULUYHWZWMO-UHFFFAOYSA-N 0.000 claims 1
• PSGPDKALYSLNFX-UHFFFAOYSA-N 2-[4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]phenyl]acetamide Chemical compound C1=CC(CC(=O)N)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 PSGPDKALYSLNFX-UHFFFAOYSA-N 0.000 claims 1
• IMVYDCJRAAGWFW-UHFFFAOYSA-N 2-[4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]acetamide Chemical compound COc1ncc(Cc2ccc(CC(N)=O)cc2)cc1-c1cccc(Cl)c1 IMVYDCJRAAGWFW-UHFFFAOYSA-N 0.000 claims 1
• VDSMDFFQVTYLGR-UHFFFAOYSA-N 2-[4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]propan-2-ol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(C)(C)O)C=C1 VDSMDFFQVTYLGR-UHFFFAOYSA-N 0.000 claims 1
• DINGIKXXEOELPN-UHFFFAOYSA-N 2-[4-[[5-(4-chloro-3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]acetamide Chemical compound COc1ncc(Cc2ccc(CC(N)=O)cc2)cc1-c1ccc(Cl)c(F)c1 DINGIKXXEOELPN-UHFFFAOYSA-N 0.000 claims 1
• AFJSRPQUCRIGSZ-UHFFFAOYSA-N 2-[4-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]acetamide Chemical compound COc1ncc(Cc2ccc(CC(N)=O)cc2)cc1-c1ccc(F)cc1 AFJSRPQUCRIGSZ-UHFFFAOYSA-N 0.000 claims 1
• JZSVWUWCCAJQOM-UHFFFAOYSA-N 2-[5-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound COc1ncc(Cc2cnc(CC(N)=O)nc2)cc1-c1ccc(F)c(F)c1 JZSVWUWCCAJQOM-UHFFFAOYSA-N 0.000 claims 1
• GAIZHSNKCLHDSE-UHFFFAOYSA-N 2-[5-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]acetonitrile Chemical compound COc1ncc(Cc2cnc(CC#N)nc2)cc1-c1ccc(F)c(F)c1 GAIZHSNKCLHDSE-UHFFFAOYSA-N 0.000 claims 1
• BTJBNXMJBYZNJE-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound NC(=O)Cc1ncc(Cc2cnc(OCC(F)(F)F)c(c2)-c2cccc(Cl)c2)cn1 BTJBNXMJBYZNJE-UHFFFAOYSA-N 0.000 claims 1
• PEOZQRAOPUPUOX-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-(2,2-difluoroethoxy)pyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound NC(=O)Cc1ncc(Cc2cnc(OCC(F)F)c(c2)-c2cccc(Cl)c2)cn1 PEOZQRAOPUPUOX-UHFFFAOYSA-N 0.000 claims 1
• ZHLYSSNGAXYWFF-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-(2,2-difluoroethoxy)pyridin-3-yl]methyl]pyrimidin-2-yl]acetonitrile Chemical compound FC(F)COc1ncc(Cc2cnc(CC#N)nc2)cc1-c1cccc(Cl)c1 ZHLYSSNGAXYWFF-UHFFFAOYSA-N 0.000 claims 1
• AADZWWTZZYAPEJ-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridin-2-yl]propan-2-ol Chemical compound C1=NC(C(C)(O)C)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 AADZWWTZZYAPEJ-UHFFFAOYSA-N 0.000 claims 1
• ILZKAGCTILMZHF-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridin-2-yl]propan-2-ol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(C)(C)O)N=C1 ILZKAGCTILMZHF-UHFFFAOYSA-N 0.000 claims 1
• OESWFORUESMPGO-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]-2-methylpropanamide Chemical compound COc1ncc(Cc2cnc(nc2)C(C)(C)C(N)=O)cc1-c1cccc(Cl)c1 OESWFORUESMPGO-UHFFFAOYSA-N 0.000 claims 1
• BJCQRPKSPCRZSX-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]-2-methylpropanenitrile Chemical compound COc1ncc(Cc2cnc(nc2)C(C)(C)C#N)cc1-c1cccc(Cl)c1 BJCQRPKSPCRZSX-UHFFFAOYSA-N 0.000 claims 1
• RRTYMSRFHWUHMD-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound COc1ncc(Cc2cnc(CC(N)=O)nc2)cc1-c1cccc(Cl)c1 RRTYMSRFHWUHMD-UHFFFAOYSA-N 0.000 claims 1
• DPHMXSREBFHLQO-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]oxyacetamide Chemical compound COc1ncc(Cc2cnc(OCC(N)=O)nc2)cc1-c1cccc(Cl)c1 DPHMXSREBFHLQO-UHFFFAOYSA-N 0.000 claims 1
• VQWGPVJNZPZYGM-UHFFFAOYSA-N 2-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]oxyethanol Chemical compound COc1ncc(Cc2cnc(OCCO)nc2)cc1-c1cccc(Cl)c1 VQWGPVJNZPZYGM-UHFFFAOYSA-N 0.000 claims 1
• BNISOGCJGZLCQQ-UHFFFAOYSA-N 2-[5-[[5-(4-chloro-3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound COc1ncc(Cc2cnc(CC(N)=O)nc2)cc1-c1ccc(Cl)c(F)c1 BNISOGCJGZLCQQ-UHFFFAOYSA-N 0.000 claims 1
• FJRBABJASLJMSY-UHFFFAOYSA-N 2-[5-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound COc1ncc(Cc2cnc(CC(N)=O)nc2)cc1-c1ccc(F)cc1 FJRBABJASLJMSY-UHFFFAOYSA-N 0.000 claims 1
• QIDSVKGYXKKBEN-UHFFFAOYSA-N 2-[5-[[5-[3-(difluoromethoxy)phenyl]-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]propan-2-ol Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CC1=CN=C(C(C)(C)O)N=C1 QIDSVKGYXKKBEN-UHFFFAOYSA-N 0.000 claims 1
• RYHAFVPEYSMOTO-UHFFFAOYSA-N 2-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,3-thiazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC1=NC=CS1 RYHAFVPEYSMOTO-UHFFFAOYSA-N 0.000 claims 1
• MSPXDFCQFGOETD-UHFFFAOYSA-N 2-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyrazine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC1=CN=CC=N1 MSPXDFCQFGOETD-UHFFFAOYSA-N 0.000 claims 1
• HHSBNJJLYZSZPL-UHFFFAOYSA-N 2-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-5-ethoxypyrazine Chemical compound CCOc1cnc(Cc2cnc(OC)c(c2)-c2cccc(Cl)c2)cn1 HHSBNJJLYZSZPL-UHFFFAOYSA-N 0.000 claims 1
• XHQCOTDUVCLORQ-UHFFFAOYSA-N 2-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-5-methylpyrazine Chemical compound COc1ncc(Cc2cnc(C)cn2)cc1-c1cccc(Cl)c1 XHQCOTDUVCLORQ-UHFFFAOYSA-N 0.000 claims 1
• QOXFHQDYZZOGMN-UHFFFAOYSA-N 2-[[5-[3-(difluoromethoxy)phenyl]-6-methoxypyridin-3-yl]methyl]pyrazol-3-amine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1N=CC=C1N QOXFHQDYZZOGMN-UHFFFAOYSA-N 0.000 claims 1
• KHWGLFDEIQCWIL-UHFFFAOYSA-N 2-[[5-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]amino]ethanol Chemical compound COc1ncc(Cc2cnc(NCCO)nc2)cc1-c1ccc(F)c(F)c1 KHWGLFDEIQCWIL-UHFFFAOYSA-N 0.000 claims 1
• ZVXJNJFBQJCLKG-UHFFFAOYSA-N 2-[[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazin-2-yl]amino]ethanol Chemical compound COc1ncc(Cc2cnc(NCCO)cn2)cc1-c1cccc(Cl)c1 ZVXJNJFBQJCLKG-UHFFFAOYSA-N 0.000 claims 1
• DSFNYLMBJJSVOL-UHFFFAOYSA-N 2-[[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]amino]ethanol Chemical compound COc1ncc(Cc2cnc(NCCO)nc2)cc1-c1cccc(Cl)c1 DSFNYLMBJJSVOL-UHFFFAOYSA-N 0.000 claims 1
• OQJJUBWGNKNMHD-UHFFFAOYSA-N 2-[[5-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]amino]ethanol Chemical compound COc1ncc(Cc2cnc(NCCO)nc2)cc1-c1ccc(F)cc1 OQJJUBWGNKNMHD-UHFFFAOYSA-N 0.000 claims 1
• GVYVAXZOPSUMJG-UHFFFAOYSA-N 2-[[5-[[6-(3,4-difluorophenyl)-5-ethoxypyrazin-2-yl]methyl]pyrimidin-2-yl]amino]ethanol Chemical compound FC=1C=C(C=CC1F)C1=C(N=CC(=N1)CC=1C=NC(=NC1)NCCO)OCC GVYVAXZOPSUMJG-UHFFFAOYSA-N 0.000 claims 1
• ZXEYNIZZNOXRIX-UHFFFAOYSA-N 2-chloro-5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(Cl)N=C1 ZXEYNIZZNOXRIX-UHFFFAOYSA-N 0.000 claims 1
• JVTUMKVPJWABLJ-UHFFFAOYSA-N 2-ethoxy-3-(2-ethoxypyridin-4-yl)-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1cc(ccn1)-c1cc(Cn2nnnc2C)cnc1OCC JVTUMKVPJWABLJ-UHFFFAOYSA-N 0.000 claims 1
• VOPIGWZCFANWFQ-UHFFFAOYSA-N 2-ethoxy-3-(3-ethoxyphenyl)-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1cccc(c1)-c1cc(Cn2nnnc2C)cnc1OCC VOPIGWZCFANWFQ-UHFFFAOYSA-N 0.000 claims 1
• LKCNYNPGFSXCPZ-UHFFFAOYSA-N 2-ethoxy-3-(3-fluoro-5-methoxyphenyl)-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnnc2C)cc1-c1cc(F)cc(OC)c1 LKCNYNPGFSXCPZ-UHFFFAOYSA-N 0.000 claims 1
• QSQSXSYWCUEOQA-UHFFFAOYSA-N 2-ethoxy-3-(4-fluorophenyl)-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnnc2C)cc1-c1ccc(F)cc1 QSQSXSYWCUEOQA-UHFFFAOYSA-N 0.000 claims 1
• MHFCRWJMDFQTFU-UHFFFAOYSA-N 2-ethoxy-3-(4-fluorophenyl)-5-[(5-methyltetrazol-2-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnc(C)n2)cc1-c1ccc(F)cc1 MHFCRWJMDFQTFU-UHFFFAOYSA-N 0.000 claims 1
• MLKWBELCBCEZEX-UHFFFAOYSA-N 2-methoxy-3-(2-methylpyridin-4-yl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(C)N=CC=2)C(OC)=NC=C1CN1C=NC=N1 MLKWBELCBCEZEX-UHFFFAOYSA-N 0.000 claims 1
• NUNXRAIYMRYLGJ-UHFFFAOYSA-N 2-methoxy-3-(3-methylphenyl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(C)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 NUNXRAIYMRYLGJ-UHFFFAOYSA-N 0.000 claims 1
• NLFDESPHTWAAGI-UHFFFAOYSA-N 2-methoxy-3-(3-methylsulfonylphenyl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(C=CC=2)S(C)(=O)=O)C(OC)=NC=C1CN1C=NC=N1 NLFDESPHTWAAGI-UHFFFAOYSA-N 0.000 claims 1
• MLPHDVGWJDSAFJ-UHFFFAOYSA-N 2-methoxy-3-(4-methylpyridin-2-yl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2N=CC=C(C)C=2)C(OC)=NC=C1CN1C=NC=N1 MLPHDVGWJDSAFJ-UHFFFAOYSA-N 0.000 claims 1
• BGPVFPJEQUFYJG-UHFFFAOYSA-N 2-methoxy-3-(5-methylpyridin-3-yl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(C)C=NC=2)C(OC)=NC=C1CN1C=NC=N1 BGPVFPJEQUFYJG-UHFFFAOYSA-N 0.000 claims 1
• LAXWTMJBXOIIBZ-UHFFFAOYSA-N 2-methoxy-3-(6-methoxypyridin-2-yl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound COC1=CC=CC(C=2C(=NC=C(CN3N=CN=C3)C=2)OC)=N1 LAXWTMJBXOIIBZ-UHFFFAOYSA-N 0.000 claims 1
• VUEMIQQIHHXGLI-UHFFFAOYSA-N 2-methoxy-3-(6-methylpyridin-2-yl)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2N=C(C)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 VUEMIQQIHHXGLI-UHFFFAOYSA-N 0.000 claims 1
• RCLKUADNPHYXGN-UHFFFAOYSA-N 2-methoxy-3-pyridin-4-yl-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=CN=CC=2)C(OC)=NC=C1CN1C=NC=N1 RCLKUADNPHYXGN-UHFFFAOYSA-N 0.000 claims 1
• QYISCWDKBRWXJZ-UHFFFAOYSA-N 2-methoxy-5-(1,2,4-triazol-1-ylmethyl)-3-[3-(trifluoromethoxy)phenyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 QYISCWDKBRWXJZ-UHFFFAOYSA-N 0.000 claims 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
• WJGHPYNTAJYETH-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-ethoxy-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnnc2C)cc1-c1ccc(F)c(F)c1 WJGHPYNTAJYETH-UHFFFAOYSA-N 0.000 claims 1
• JBMGENCVWCEMGO-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-ethoxy-5-[(5-methyltetrazol-2-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnc(C)n2)cc1-c1ccc(F)c(F)c1 JBMGENCVWCEMGO-UHFFFAOYSA-N 0.000 claims 1
• APHGLZFERIOTRI-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(F)C=C(F)C=2)C(OC)=NC=C1CN1C=NC=N1 APHGLZFERIOTRI-UHFFFAOYSA-N 0.000 claims 1
• CEGZMWMIAACRCX-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-2-ethoxy-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound ClC=1C=C(C=CC1F)C=1C(=NC=C(C1)CN1N=NN=C1C)OCC CEGZMWMIAACRCX-UHFFFAOYSA-N 0.000 claims 1
• VOVOFQFBKRYHPJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CN1C=NC=N1 VOVOFQFBKRYHPJ-UHFFFAOYSA-N 0.000 claims 1
• UUDMLPSBHATPJT-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-(1h-pyrazol-4-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC=1C=NNC=1 UUDMLPSBHATPJT-UHFFFAOYSA-N 0.000 claims 1
• UNXOANBCRTYSCI-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-(pyridin-2-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC1=CC=CC=N1 UNXOANBCRTYSCI-UHFFFAOYSA-N 0.000 claims 1
• IXGKWIMXOFNUGV-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-(tetrazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CN1C=NN=N1 IXGKWIMXOFNUGV-UHFFFAOYSA-N 0.000 claims 1
• NTXMGTYNKRTQGK-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-(tetrazol-2-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CN1N=CN=N1 NTXMGTYNKRTQGK-UHFFFAOYSA-N 0.000 claims 1
• SJKWHBWZBOEWPN-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(3-ethoxy-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound N1=C(OCC)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 SJKWHBWZBOEWPN-UHFFFAOYSA-N 0.000 claims 1
• RMPKVVCDMROFFU-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(3-methoxy-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound N1=C(OC)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 RMPKVVCDMROFFU-UHFFFAOYSA-N 0.000 claims 1
• MIRFIHHHXUIEDX-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(3-methyl-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound N1=C(C)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 MIRFIHHHXUIEDX-UHFFFAOYSA-N 0.000 claims 1
• CUNRTMIBGRQUTK-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(4-methylimidazol-1-yl)methyl]pyridine Chemical compound C1=NC(C)=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 CUNRTMIBGRQUTK-UHFFFAOYSA-N 0.000 claims 1
• PAENXFIGMCXPSQ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(4-methylsulfonylphenyl)methyl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 PAENXFIGMCXPSQ-UHFFFAOYSA-N 0.000 claims 1
• PUAWCIQXYQFACS-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(5-methoxy-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound COC1=NC=NN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 PUAWCIQXYQFACS-UHFFFAOYSA-N 0.000 claims 1
• UVZFPKKCTFUSOS-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(6-methylpyridin-3-yl)methyl]pyridine Chemical compound C1=NC(C)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 UVZFPKKCTFUSOS-UHFFFAOYSA-N 0.000 claims 1
• SBWLVQYKOUJOGW-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(6-propan-2-yloxypyridin-3-yl)methyl]pyridine Chemical compound C1=NC(OC(C)C)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 SBWLVQYKOUJOGW-UHFFFAOYSA-N 0.000 claims 1
• BXXQORISXTVKBJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[(6-propoxypyridin-3-yl)methyl]pyridine Chemical compound C1=NC(OCCC)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 BXXQORISXTVKBJ-UHFFFAOYSA-N 0.000 claims 1
• LXDVSQVTWVZOAH-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[1-(1,2,4-triazol-1-yl)ethyl]pyridine Chemical compound C1=NC=NN1C(C)C(C=1)=CN=C(OC(F)F)C=1C1=CC=CC(Cl)=C1 LXDVSQVTWVZOAH-UHFFFAOYSA-N 0.000 claims 1
• QFLNFQJRALCQJT-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[[3-(difluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CN1C=NC(C(F)F)=N1 QFLNFQJRALCQJT-UHFFFAOYSA-N 0.000 claims 1
• WDJRUBWKDKUUGI-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[[3-(methoxymethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound N1=C(COC)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 WDJRUBWKDKUUGI-UHFFFAOYSA-N 0.000 claims 1
• FHAFGFQTDQUXOV-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(difluoromethoxy)-5-[[5-(methoxymethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound COCC1=NC=NN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 FHAFGFQTDQUXOV-UHFFFAOYSA-N 0.000 claims 1
• MYJZQYADCGGLCH-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-ethoxy-5-[[3-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=NC(C(F)(F)F)=N1 MYJZQYADCGGLCH-UHFFFAOYSA-N 0.000 claims 1
• PKIFTQFDXPWYRS-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-ethoxy-5-[[5-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1C(F)(F)F PKIFTQFDXPWYRS-UHFFFAOYSA-N 0.000 claims 1
• BJNRQUDKDCVCMR-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 BJNRQUDKDCVCMR-UHFFFAOYSA-N 0.000 claims 1
• STKFPMKFCHDHGD-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 STKFPMKFCHDHGD-UHFFFAOYSA-N 0.000 claims 1
• WEMDGLQZGZKIBX-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(1h-pyrazol-4-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C=NNC=1 WEMDGLQZGZKIBX-UHFFFAOYSA-N 0.000 claims 1
• QBNMSGRGXNXHKZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(pyrazol-1-ylmethyl)pyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=CC=N1 QBNMSGRGXNXHKZ-UHFFFAOYSA-N 0.000 claims 1
• HIFQXTGXOAVHRO-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(pyrazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=CC=N1 HIFQXTGXOAVHRO-UHFFFAOYSA-N 0.000 claims 1
• HTVYSFBAYPWVLW-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(pyridin-3-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=CN=C1 HTVYSFBAYPWVLW-UHFFFAOYSA-N 0.000 claims 1
• RFAFHNFWVRZTJL-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(pyridin-4-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=NC=C1 RFAFHNFWVRZTJL-UHFFFAOYSA-N 0.000 claims 1
• SVBABBWDTSAPCN-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-(triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=CN=N1 SVBABBWDTSAPCN-UHFFFAOYSA-N 0.000 claims 1
• IFZYXQCYLBJOTR-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(1-methylpyrazol-4-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C=NN(C)C=1 IFZYXQCYLBJOTR-UHFFFAOYSA-N 0.000 claims 1
• RKXTXCGDFTZHSJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(1-methylpyrazol-4-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C=NN(C)C=1 RKXTXCGDFTZHSJ-UHFFFAOYSA-N 0.000 claims 1
• UXUBTQXUNXZMCI-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(2-methoxypyrimidin-5-yl)methyl]pyrazine Chemical compound C1=NC(OC)=NC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=N1 UXUBTQXUNXZMCI-UHFFFAOYSA-N 0.000 claims 1
• DEIPAAPVNHAOPB-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(3-methoxy-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound N1=C(OC)N=CN1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 DEIPAAPVNHAOPB-UHFFFAOYSA-N 0.000 claims 1
• RTNVSFFAEQNTLX-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(3-methyl-1,2,4-triazol-1-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(C)=N1 RTNVSFFAEQNTLX-UHFFFAOYSA-N 0.000 claims 1
• MZBLCEFGXKPSMY-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(3-methyl-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(C)=N1 MZBLCEFGXKPSMY-UHFFFAOYSA-N 0.000 claims 1
• FLZUMXLCLRTUKZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(3-methyl-1,2,4-triazol-4-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NN=C1C FLZUMXLCLRTUKZ-UHFFFAOYSA-N 0.000 claims 1
• OJZWYHDYPCCTNO-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(4-methylpyrazol-1-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(C)C=N1 OJZWYHDYPCCTNO-UHFFFAOYSA-N 0.000 claims 1
• RFYQDHDRIISTIM-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(4-methylpyrazol-1-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(C)C=N1 RFYQDHDRIISTIM-UHFFFAOYSA-N 0.000 claims 1
• HXXJPXYSBPLQNT-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(4-nitropyrazol-1-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C([N+]([O-])=O)C=N1 HXXJPXYSBPLQNT-UHFFFAOYSA-N 0.000 claims 1
• NPDVCWQOJFBTKC-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(4-nitropyrazol-1-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C([N+]([O-])=O)C=N1 NPDVCWQOJFBTKC-UHFFFAOYSA-N 0.000 claims 1
• RRUDKNWBVHATBN-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound ClC=1C=C(C=CC1)C=1C(=NC=C(C1)CN1N=NN=C1C)OC RRUDKNWBVHATBN-UHFFFAOYSA-N 0.000 claims 1
• XGSQZZKVYJURNU-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(6-methoxy-5-methylpyridin-3-yl)methyl]pyridine Chemical compound C1=C(C)C(OC)=NC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 XGSQZZKVYJURNU-UHFFFAOYSA-N 0.000 claims 1
• RVTNIGSWRHPHPC-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[(6-methoxypyridin-3-yl)methyl]pyridine Chemical compound C1=NC(OC)=CC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 RVTNIGSWRHPHPC-UHFFFAOYSA-N 0.000 claims 1
• CKNQNXPUKOWLDK-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[[3-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(C(F)(F)F)=N1 CKNQNXPUKOWLDK-UHFFFAOYSA-N 0.000 claims 1
• IASCIRBDFFAQPJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[[4-(trifluoromethyl)imidazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(C(F)(F)F)=C1 IASCIRBDFFAQPJ-UHFFFAOYSA-N 0.000 claims 1
• OQCRAIRTAGWAJO-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-5-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(F)(F)F)N=C1 OQCRAIRTAGWAJO-UHFFFAOYSA-N 0.000 claims 1
• CEEAKFAOCSYHLR-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methoxy-6-methyl-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC(C)=C1CN1C=NC=N1 CEEAKFAOCSYHLR-UHFFFAOYSA-N 0.000 claims 1
• IJEGKXMNRKZAKZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-propan-2-yloxy-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(C)C)=NC=C1CN1C=NC=N1 IJEGKXMNRKZAKZ-UHFFFAOYSA-N 0.000 claims 1
• KXMCZBZDGOBVQN-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(imidazol-1-ylmethyl)-2-methoxypyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=CN=C1 KXMCZBZDGOBVQN-UHFFFAOYSA-N 0.000 claims 1
• ZPQBQXRMFFWYTH-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(imidazol-1-ylmethyl)-2-methoxypyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=CN=C1 ZPQBQXRMFFWYTH-UHFFFAOYSA-N 0.000 claims 1
• YHGMDKBESVZRPP-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(2,6-dimethylpyridin-4-yl)methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC(C)=NC(C)=C1 YHGMDKBESVZRPP-UHFFFAOYSA-N 0.000 claims 1
• YDOYZDHJPMERJW-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(3-cyclopropyl-1,2,4-triazol-1-yl)methyl]-2-(difluoromethoxy)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CN(N=1)C=NC=1C1CC1 YDOYZDHJPMERJW-UHFFFAOYSA-N 0.000 claims 1
• JDMMOVAENYNRCT-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(3-cyclopropyl-1,2,4-triazol-1-yl)methyl]-2-methoxypyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN(N=1)C=NC=1C1CC1 JDMMOVAENYNRCT-UHFFFAOYSA-N 0.000 claims 1
• FRAPBDWCEDFTRQ-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(3-cyclopropyl-1,2,4-triazol-1-yl)methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN(N=1)C=NC=1C1CC1 FRAPBDWCEDFTRQ-UHFFFAOYSA-N 0.000 claims 1
• PJYFXODYNCDEQV-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-chloropyrazol-1-yl)methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(Cl)C=N1 PJYFXODYNCDEQV-UHFFFAOYSA-N 0.000 claims 1
• NPOUGRPJBAGGCM-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-fluorophenyl)methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(F)C=C1 NPOUGRPJBAGGCM-UHFFFAOYSA-N 0.000 claims 1
• WIRMSDVCCHNIMR-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(5-ethoxypyridin-2-yl)methyl]-2-methoxypyridine Chemical compound CCOc1ccc(Cc2cnc(OC)c(c2)-c2cccc(Cl)c2)nc1 WIRMSDVCCHNIMR-UHFFFAOYSA-N 0.000 claims 1
• KDISUTZASQWHQI-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[3-(fluoromethyl)-1,2,4-triazol-1-yl]methyl]-2-methoxypyrazine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(CF)=N1 KDISUTZASQWHQI-UHFFFAOYSA-N 0.000 claims 1
• KOTZWJRUXYFGKP-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-(difluoromethyl)-2-methylimidazol-1-yl]methyl]-2-ethoxypyrazine Chemical compound CCOc1ncc(Cn2cc(nc2C)C(F)F)nc1-c1cccc(Cl)c1 KOTZWJRUXYFGKP-UHFFFAOYSA-N 0.000 claims 1
• ABTOYSXYGWEPCZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[6-(cyclopropylmethoxy)pyridin-3-yl]methyl]-2-(difluoromethoxy)pyridine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC(C=N1)=CC=C1OCC1CC1 ABTOYSXYGWEPCZ-UHFFFAOYSA-N 0.000 claims 1
• KBLPURBTTMOTOM-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[fluoro-(4-fluorophenyl)methyl]-2-methoxypyridine Chemical compound COC1=NC=C(C(F)C=2C=CC(F)=CC=2)C=C1C1=CC=CC(Cl)=C1 KBLPURBTTMOTOM-UHFFFAOYSA-N 0.000 claims 1
• HYGULAQNBJFHHR-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 HYGULAQNBJFHHR-UHFFFAOYSA-N 0.000 claims 1
• SOGZCHYVKYBPQP-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-methoxy-5-[(3-methyl-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC)=NC=C1CN1C=NC(C)=N1 SOGZCHYVKYBPQP-UHFFFAOYSA-N 0.000 claims 1
• SNALNLAUPLLWEK-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-2-ethoxy-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnnc2C)cc1-c1ccc(Cl)c(F)c1 SNALNLAUPLLWEK-UHFFFAOYSA-N 0.000 claims 1
• BDQIQXJBSQMODW-UHFFFAOYSA-N 3-[2-(difluoromethoxy)pyridin-4-yl]-2-ethoxy-5-[(5-fluoropyridin-3-yl)methyl]pyridine Chemical compound CCOc1ncc(Cc2cncc(F)c2)cc1-c1ccnc(OC(F)F)c1 BDQIQXJBSQMODW-UHFFFAOYSA-N 0.000 claims 1
• SQWYBWKXNIZMLT-UHFFFAOYSA-N 3-[2-(difluoromethoxy)pyridin-4-yl]-2-ethoxy-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnnc2C)cc1-c1ccnc(OC(F)F)c1 SQWYBWKXNIZMLT-UHFFFAOYSA-N 0.000 claims 1
• WQTGGDAZGCIUBL-UHFFFAOYSA-N 3-[2-(difluoromethoxy)pyridin-4-yl]-2-ethoxy-5-[(5-methyltetrazol-2-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnc(C)n2)cc1-c1ccnc(OC(F)F)c1 WQTGGDAZGCIUBL-UHFFFAOYSA-N 0.000 claims 1
• PQRLVNUDQSWTID-UHFFFAOYSA-N 3-[2-(difluoromethoxy)pyridin-4-yl]-5-[[3-(difluoromethyl)-1,2,4-triazol-1-yl]methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OC)=NC=C1CN1C=NC(C(F)F)=N1 PQRLVNUDQSWTID-UHFFFAOYSA-N 0.000 claims 1
• KETQZKJOZLLKCO-UHFFFAOYSA-N 3-[2-(difluoromethoxy)pyridin-4-yl]-5-[[3-(fluoromethyl)-1,2,4-triazol-1-yl]methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OC)=NC=C1CN1C=NC(CF)=N1 KETQZKJOZLLKCO-UHFFFAOYSA-N 0.000 claims 1
• JINKSJWWYJZKGZ-UHFFFAOYSA-N 3-[2-(difluoromethoxy)pyridin-4-yl]-5-[[4-(difluoromethyl)-2-methylimidazol-1-yl]methyl]-2-methoxypyridine Chemical compound COc1ncc(Cn2cc(nc2C)C(F)F)cc1-c1ccnc(OC(F)F)c1 JINKSJWWYJZKGZ-UHFFFAOYSA-N 0.000 claims 1
• XFGQFUPMKUCQHL-UHFFFAOYSA-N 3-[2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyridin-3-yl]benzonitrile Chemical compound C1=C(C=2C=C(C=CC=2)C#N)C(OC)=NC=C1CN1C=NC=N1 XFGQFUPMKUCQHL-UHFFFAOYSA-N 0.000 claims 1
• RASKUSUJNHVWNX-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[(3-methyl-1,2,4-triazol-1-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(C)=N1 RASKUSUJNHVWNX-UHFFFAOYSA-N 0.000 claims 1
• WTZIWBZTQDBGOS-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[(3-nitro-1,2,4-triazol-1-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC([N+]([O-])=O)=N1 WTZIWBZTQDBGOS-UHFFFAOYSA-N 0.000 claims 1
• LXJCCUKXHFCMCI-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[(5-methyltetrazol-1-yl)methyl]pyridine Chemical compound CCOc1ncc(Cn2nnnc2C)cc1-c1cccc(OC(F)F)c1 LXJCCUKXHFCMCI-UHFFFAOYSA-N 0.000 claims 1
• SWFCCEYKQIAPHR-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[(5-nitro-1,2,4-triazol-1-yl)methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1[N+]([O-])=O SWFCCEYKQIAPHR-UHFFFAOYSA-N 0.000 claims 1
• NVHRFIDJWMNLDW-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[3-(fluoromethyl)-1,2,4-triazol-1-yl]methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(CF)=N1 NVHRFIDJWMNLDW-UHFFFAOYSA-N 0.000 claims 1
• QRVDMZJFHORLEL-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[3-(methoxymethyl)-1,2,4-triazol-1-yl]methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(COC)=N1 QRVDMZJFHORLEL-UHFFFAOYSA-N 0.000 claims 1
• KMODMVWYRYSLAO-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[3-(methoxymethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(COC)=N1 KMODMVWYRYSLAO-UHFFFAOYSA-N 0.000 claims 1
• CYWUSYJSEQURJU-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[3-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(C(F)(F)F)=N1 CYWUSYJSEQURJU-UHFFFAOYSA-N 0.000 claims 1
• YFZOBGQLXMDPKD-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[3-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(C(F)(F)F)=N1 YFZOBGQLXMDPKD-UHFFFAOYSA-N 0.000 claims 1
• FTBMGSHGXBFWLB-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[4-(fluoromethyl)triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=C(CF)N=N1 FTBMGSHGXBFWLB-UHFFFAOYSA-N 0.000 claims 1
• CDSKFCDWJDVAQB-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[5-(methoxymethyl)-1,2,4-triazol-1-yl]methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1COC CDSKFCDWJDVAQB-UHFFFAOYSA-N 0.000 claims 1
• WMXKZWAHPJENGY-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[5-(methoxymethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1COC WMXKZWAHPJENGY-UHFFFAOYSA-N 0.000 claims 1
• VFDFHDSTAFPLQP-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[5-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1C(F)(F)F VFDFHDSTAFPLQP-UHFFFAOYSA-N 0.000 claims 1
• UZVAEDHFMRRXKI-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-ethoxy-5-[[5-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1C(F)(F)F UZVAEDHFMRRXKI-UHFFFAOYSA-N 0.000 claims 1
• ACYQOTQNCWBNPX-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-methoxy-5-[(3-methyl-1,2,4-triazol-1-yl)methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC(C)=N1 ACYQOTQNCWBNPX-UHFFFAOYSA-N 0.000 claims 1
• SCCLHDMIOSQXNC-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-2-methoxy-5-[[3-(trifluoromethyl)-1,2,4-triazol-1-yl]methyl]pyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC(C(F)(F)F)=N1 SCCLHDMIOSQXNC-UHFFFAOYSA-N 0.000 claims 1
• PRZWVNVAMOKFFC-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-5-[[3-(difluoromethyl)-1,2,4-triazol-1-yl]methyl]-2-ethoxypyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(C(F)F)=N1 PRZWVNVAMOKFFC-UHFFFAOYSA-N 0.000 claims 1
• MNBGIXIOQGGDGG-UHFFFAOYSA-N 3-[3-(difluoromethoxy)phenyl]-5-[[3-(fluoromethyl)-1,2,4-triazol-1-yl]methyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC(CF)=N1 MNBGIXIOQGGDGG-UHFFFAOYSA-N 0.000 claims 1
• RWYITOASPDXUGT-UHFFFAOYSA-N 3-[3-(difluoromethyl)phenyl]-2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyridine Chemical compound C1=C(C=2C=C(C=CC=2)C(F)F)C(OC)=NC=C1CN1C=NC=N1 RWYITOASPDXUGT-UHFFFAOYSA-N 0.000 claims 1
• JPBPMDGPJIOJIU-UHFFFAOYSA-N 3-[4-[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]pyrimidin-2-yl]morpholine Chemical compound COc1ncc(cc1-c1cccc(Cl)c1)-c1ccnc(n1)C1COCCN1 JPBPMDGPJIOJIU-UHFFFAOYSA-N 0.000 claims 1
• RYQIITIQSYDMGE-UHFFFAOYSA-N 3-[5-[(2-aminopyrimidin-5-yl)methyl]-2-methoxypyridin-3-yl]benzonitrile Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1cccc(c1)C#N RYQIITIQSYDMGE-UHFFFAOYSA-N 0.000 claims 1
• MDFGCWQPXKMIHK-UHFFFAOYSA-N 3-[5-[(3-amino-1,2,4-triazol-1-yl)methyl]-2-methoxypyridin-3-yl]benzonitrile Chemical compound C1=C(C=2C=C(C=CC=2)C#N)C(OC)=NC=C1CN1C=NC(N)=N1 MDFGCWQPXKMIHK-UHFFFAOYSA-N 0.000 claims 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• MROPHBWWMYOIRQ-UHFFFAOYSA-N 4-[5-[(2-aminopyrimidin-5-yl)methyl]-2-methoxypyridin-3-yl]pyridine-2-carbonitrile Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1ccnc(c1)C#N MROPHBWWMYOIRQ-UHFFFAOYSA-N 0.000 claims 1
• BCQYICJKUOADKD-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,2-oxazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC=1C=NOC=1 BCQYICJKUOADKD-UHFFFAOYSA-N 0.000 claims 1
• UNCPGPNSPYWCRP-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-3,5-dimethyl-1,2-oxazole Chemical compound CC1=NOC(C)=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 UNCPGPNSPYWCRP-UHFFFAOYSA-N 0.000 claims 1
• NKDWWNQULCBSKV-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 NKDWWNQULCBSKV-UHFFFAOYSA-N 0.000 claims 1
• MUQUEKAAAYLTMS-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2-oxazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C=NOC=1 MUQUEKAAAYLTMS-UHFFFAOYSA-N 0.000 claims 1
• TZGPNAJUGJQGON-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-n-(oxetan-3-yl)benzamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC(C=C1)=CC=C1C(=O)NC1COC1 TZGPNAJUGJQGON-UHFFFAOYSA-N 0.000 claims 1
• JWBZBNMXSATIJF-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]benzamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(N)=O)C=C1 JWBZBNMXSATIJF-UHFFFAOYSA-N 0.000 claims 1
• AXMWRPFFWLXKBK-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]benzoic acid Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(O)=O)C=C1 AXMWRPFFWLXKBK-UHFFFAOYSA-N 0.000 claims 1
• XSPOBUOUTQPQTC-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=NC(N)=C1 XSPOBUOUTQPQTC-UHFFFAOYSA-N 0.000 claims 1
• JPYSDHXQGKLLJJ-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridine-2-carbonitrile Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=NC(C#N)=C1 JPYSDHXQGKLLJJ-UHFFFAOYSA-N 0.000 claims 1
• MGHRKPHGSDLODO-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridine-2-carboxamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=NC(C(N)=O)=C1 MGHRKPHGSDLODO-UHFFFAOYSA-N 0.000 claims 1
• SHRHJCAUNYVDOA-UHFFFAOYSA-N 4-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-1,2-oxazole Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C=NOC=1 SHRHJCAUNYVDOA-UHFFFAOYSA-N 0.000 claims 1
• RGFNZTAROCMGER-UHFFFAOYSA-N 4-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-3,5-dimethyl-1,2-oxazole Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C(C)=NOC=1C RGFNZTAROCMGER-UHFFFAOYSA-N 0.000 claims 1
• AVVDRNJGDXTKQZ-UHFFFAOYSA-N 4-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(N)=O)C=C1 AVVDRNJGDXTKQZ-UHFFFAOYSA-N 0.000 claims 1
• USCXCTBEBGCVMW-UHFFFAOYSA-N 4-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]benzonitrile Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C#N)C=C1 USCXCTBEBGCVMW-UHFFFAOYSA-N 0.000 claims 1
• XKTQURBHIFZABA-UHFFFAOYSA-N 4-chloro-1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrazol-3-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=C(Cl)C(N)=N1 XKTQURBHIFZABA-UHFFFAOYSA-N 0.000 claims 1
• XHDGCONRZQPVLQ-UHFFFAOYSA-N 4-chloro-2-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrazol-3-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1N=CC(Cl)=C1N XHDGCONRZQPVLQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• JKGJPSGNNASHSZ-UHFFFAOYSA-N 5-[(3-cyclopropyl-1,2,4-triazol-1-yl)methyl]-3-[3-(difluoromethoxy)phenyl]-2-ethoxypyrazine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN(N=1)C=NC=1C1CC1 JKGJPSGNNASHSZ-UHFFFAOYSA-N 0.000 claims 1
• TYILFLWSMXYWLH-UHFFFAOYSA-N 5-[(4-chloropyrazol-1-yl)methyl]-3-[3-(difluoromethoxy)phenyl]-2-methoxypyridine Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=C(Cl)C=N1 TYILFLWSMXYWLH-UHFFFAOYSA-N 0.000 claims 1
• RHYSKZLZPLNJDP-UHFFFAOYSA-N 5-[[5-(2-ethoxypyridin-4-yl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1cc(ccn1)-c1cc(Cc2cnc(N)nc2)cnc1OC RHYSKZLZPLNJDP-UHFFFAOYSA-N 0.000 claims 1
• AVRJOAUKWBHOPZ-UHFFFAOYSA-N 5-[[5-(3,4-difluorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(F)c1 AVRJOAUKWBHOPZ-UHFFFAOYSA-N 0.000 claims 1
• ZOKBZPMGSHJWTJ-UHFFFAOYSA-N 5-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(F)c1 ZOKBZPMGSHJWTJ-UHFFFAOYSA-N 0.000 claims 1
• JYVRJAVIULOTNV-UHFFFAOYSA-N 5-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound COc1ncc(Cc2cnc(nc2)C(N)=O)cc1-c1ccc(F)c(F)c1 JYVRJAVIULOTNV-UHFFFAOYSA-N 0.000 claims 1
• YGUIYFSQNPZXFL-UHFFFAOYSA-N 5-[[5-(3,4-difluorophenyl)-6-propoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCCOc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(F)c1 YGUIYFSQNPZXFL-UHFFFAOYSA-N 0.000 claims 1
• GRHFTJCXTFSEDL-UHFFFAOYSA-N 5-[[5-(3-chloro-4-fluorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(Cl)c1 GRHFTJCXTFSEDL-UHFFFAOYSA-N 0.000 claims 1
• XBLBTZIEOOYKNI-UHFFFAOYSA-N 5-[[5-(3-chloro-4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazin-2-amine Chemical compound COc1ncc(Cc2cnc(N)cn2)cc1-c1ccc(F)c(Cl)c1 XBLBTZIEOOYKNI-UHFFFAOYSA-N 0.000 claims 1
• YHQJAOBPSSAWBE-UHFFFAOYSA-N 5-[[5-(3-chloro-4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(Cl)c1 YHQJAOBPSSAWBE-UHFFFAOYSA-N 0.000 claims 1
• GHQXXAVBQQOWAR-UHFFFAOYSA-N 5-[[5-(3-chloro-4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound COc1ncc(Cc2cnc(nc2)C(N)=O)cc1-c1ccc(F)c(Cl)c1 GHQXXAVBQQOWAR-UHFFFAOYSA-N 0.000 claims 1
• YWOXQRKKAZEHGS-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 YWOXQRKKAZEHGS-UHFFFAOYSA-N 0.000 claims 1
• AFRQLTCOUKTTTF-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,3-thiazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC1=CN=CS1 AFRQLTCOUKTTTF-UHFFFAOYSA-N 0.000 claims 1
• LSPXYMMBXWQBAM-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-2,4-dimethyl-1,3-thiazole Chemical compound S1C(C)=NC(C)=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 LSPXYMMBXWQBAM-UHFFFAOYSA-N 0.000 claims 1
• RXNORFHBZQAQJS-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-2-methoxypyrimidine Chemical compound C1=NC(OC)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 RXNORFHBZQAQJS-UHFFFAOYSA-N 0.000 claims 1
• GTIVKIFPHBERBD-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 GTIVKIFPHBERBD-UHFFFAOYSA-N 0.000 claims 1
• MCKKZNZNHUCXJV-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-n-(2,2,2-trifluoroethyl)pyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC1=CN=C(NCC(F)(F)F)N=C1 MCKKZNZNHUCXJV-UHFFFAOYSA-N 0.000 claims 1
• QUVQTIHSMPEMIK-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-n-cyclopropylpyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC(C=N1)=CN=C1NC1CC1 QUVQTIHSMPEMIK-UHFFFAOYSA-N 0.000 claims 1
• BFLYAOTUKJQFQU-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 BFLYAOTUKJQFQU-UHFFFAOYSA-N 0.000 claims 1
• YHIMURCGIQFUOA-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 YHIMURCGIQFUOA-UHFFFAOYSA-N 0.000 claims 1
• XQVQFNFLKKEEJK-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 XQVQFNFLKKEEJK-UHFFFAOYSA-N 0.000 claims 1
• HIJLLFATNWZLSL-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 HIJLLFATNWZLSL-UHFFFAOYSA-N 0.000 claims 1
• SSXVIABOYAOBOU-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 SSXVIABOYAOBOU-UHFFFAOYSA-N 0.000 claims 1
• OWMVVICJFUCXQR-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(CC=2C=C(C(OC(F)F)=NC=2)C=2C=C(Cl)C=CC=2)=C1 OWMVVICJFUCXQR-UHFFFAOYSA-N 0.000 claims 1
• JTENYBOSQDMVFS-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 JTENYBOSQDMVFS-UHFFFAOYSA-N 0.000 claims 1
• WXCPJBQEKYBFFB-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyrimidine-2-carbonitrile Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(F)F)=NC=C1CC1=CN=C(C#N)N=C1 WXCPJBQEKYBFFB-UHFFFAOYSA-N 0.000 claims 1
• ZFDJIVHQMPQZCR-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound C1=NC(C(=O)N)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 ZFDJIVHQMPQZCR-UHFFFAOYSA-N 0.000 claims 1
• QZULMEPRRKFUTB-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CC1=CN=C(N)N=C1 QZULMEPRRKFUTB-UHFFFAOYSA-N 0.000 claims 1
• VPYFDMBSXDWRPC-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,3-thiazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=CS1 VPYFDMBSXDWRPC-UHFFFAOYSA-N 0.000 claims 1
• BUBHQWUSUQUIBN-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1-methylpyridin-2-one Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1C=CC(=O)N(C)C=1 BUBHQWUSUQUIBN-UHFFFAOYSA-N 0.000 claims 1
• WYHDDJZTYLNKGZ-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1H-pyrimidin-2-one Chemical compound COc1ncc(Cc2cnc(O)nc2)cc1-c1cccc(Cl)c1 WYHDDJZTYLNKGZ-UHFFFAOYSA-N 0.000 claims 1
• HTWHAUMIUDQCSZ-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-2,4-dimethyl-1,3-thiazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC=1SC(C)=NC=1C HTWHAUMIUDQCSZ-UHFFFAOYSA-N 0.000 claims 1
• MQGLLXXIMRFWMO-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-2-(difluoromethoxy)pyrimidine Chemical compound COc1ncc(Cc2cnc(OC(F)F)nc2)cc1-c1cccc(Cl)c1 MQGLLXXIMRFWMO-UHFFFAOYSA-N 0.000 claims 1
• OOQHRLAMRNCORE-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-2-methoxypyrimidine Chemical compound C1=NC(OC)=NC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 OOQHRLAMRNCORE-UHFFFAOYSA-N 0.000 claims 1
• LKIPHULPCRKTOK-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-2-methylpyrimidine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(C)N=C1 LKIPHULPCRKTOK-UHFFFAOYSA-N 0.000 claims 1
• CRXLUEYZIUZTOJ-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-3-methylpyridazine Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CC=1C=C(N=NC1)C CRXLUEYZIUZTOJ-UHFFFAOYSA-N 0.000 claims 1
• LOPNDRLPELQGJA-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-n,n-dimethylpyridin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(N(C)C)N=C1 LOPNDRLPELQGJA-UHFFFAOYSA-N 0.000 claims 1
• GOGNQIWHNXOXEX-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-n,n-dimethylpyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(N(C)C)N=C1 GOGNQIWHNXOXEX-UHFFFAOYSA-N 0.000 claims 1
• JNCBBUDAAIZANF-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-n-(2,2,2-trifluoroethyl)pyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(NCC(F)(F)F)N=C1 JNCBBUDAAIZANF-UHFFFAOYSA-N 0.000 claims 1
• SDOWXWMEXAKNJJ-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 SDOWXWMEXAKNJJ-UHFFFAOYSA-N 0.000 claims 1
• ZIJRLRCNXBPSRP-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-n-propan-2-ylpyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(NC(C)C)N=C1 ZIJRLRCNXBPSRP-UHFFFAOYSA-N 0.000 claims 1
• ITTOUFNXXNCHES-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazin-2-amine Chemical compound COc1ncc(Cc2cnc(N)cn2)cc1-c1cccc(Cl)c1 ITTOUFNXXNCHES-UHFFFAOYSA-N 0.000 claims 1
• IUVCRRODMWIHDK-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(N)N=C1 IUVCRRODMWIHDK-UHFFFAOYSA-N 0.000 claims 1
• QRSUGSQRLYUKMV-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridine-2-carboxamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(N)=O)N=C1 QRSUGSQRLYUKMV-UHFFFAOYSA-N 0.000 claims 1
• KTEHACJOUKAWSI-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(N)N=C1 KTEHACJOUKAWSI-UHFFFAOYSA-N 0.000 claims 1
• SWCDBOGUGHOMLF-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=CN=C1 SWCDBOGUGHOMLF-UHFFFAOYSA-N 0.000 claims 1
• GVTUUEVGWFKAJX-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(C(N)=O)N=C1 GVTUUEVGWFKAJX-UHFFFAOYSA-N 0.000 claims 1
• KCBUBQXGRDWWDM-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxylic acid Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(C(O)=O)N=C1 KCBUBQXGRDWWDM-UHFFFAOYSA-N 0.000 claims 1
• FJSOXGKQCIGAIS-UHFFFAOYSA-N 5-[[5-(3-chlorophenyl)-6-propan-2-yloxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC(C)C)=NC=C1CC1=CN=C(N)N=C1 FJSOXGKQCIGAIS-UHFFFAOYSA-N 0.000 claims 1
• WZWDBLUDODMWIG-UHFFFAOYSA-N 5-[[5-(3-ethoxy-4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1cc(ccc1F)-c1cc(Cc2cnc(N)nc2)cnc1OC WZWDBLUDODMWIG-UHFFFAOYSA-N 0.000 claims 1
• KEPMVERLVIYVTQ-UHFFFAOYSA-N 5-[[5-(3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC)=NC=C1CC1=CN=C(N)N=C1 KEPMVERLVIYVTQ-UHFFFAOYSA-N 0.000 claims 1
• ZINMHWDRFNTEET-UHFFFAOYSA-N 5-[[5-(3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carbonitrile Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC)=NC=C1CC1=CN=C(C#N)N=C1 ZINMHWDRFNTEET-UHFFFAOYSA-N 0.000 claims 1
• RAWAZGIXEVBPGS-UHFFFAOYSA-N 5-[[5-(3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound C1=C(C=2C=C(F)C=CC=2)C(OC)=NC=C1CC1=CN=C(C(N)=O)N=C1 RAWAZGIXEVBPGS-UHFFFAOYSA-N 0.000 claims 1
• XQKREHRAKCZGGD-UHFFFAOYSA-N 5-[[5-(4-chloro-3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(Cl)c(F)c1 XQKREHRAKCZGGD-UHFFFAOYSA-N 0.000 claims 1
• MOGVTQANMPNWBT-UHFFFAOYSA-N 5-[[5-(4-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(Cl)cc1 MOGVTQANMPNWBT-UHFFFAOYSA-N 0.000 claims 1
• SYIAYRYVHVIRAD-UHFFFAOYSA-N 5-[[5-(4-fluoro-3-methoxyphenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COc1cc(ccc1F)-c1cc(Cc2cnc(N)nc2)cnc1OC SYIAYRYVHVIRAD-UHFFFAOYSA-N 0.000 claims 1
• PMVMYJHIMNRROC-UHFFFAOYSA-N 5-[[5-(4-fluoro-3-methylphenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(C)c1 PMVMYJHIMNRROC-UHFFFAOYSA-N 0.000 claims 1
• JDESNMUBTYEMIT-UHFFFAOYSA-N 5-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)cc1 JDESNMUBTYEMIT-UHFFFAOYSA-N 0.000 claims 1
• GUPQYETZODSLKM-UHFFFAOYSA-N 5-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound COc1ncc(Cc2cnc(nc2)C(N)=O)cc1-c1ccc(F)cc1 GUPQYETZODSLKM-UHFFFAOYSA-N 0.000 claims 1
• CDSJCCIJTSGJOV-UHFFFAOYSA-N 5-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-ethoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OCC)=NC=C1CC1=CN=C(C(N)=O)N=C1 CDSJCCIJTSGJOV-UHFFFAOYSA-N 0.000 claims 1
• OMGARGSFJXSCRR-UHFFFAOYSA-N 5-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]-3-fluoropyridin-2-amine Chemical compound COc1ncc(Cc2cnc(N)c(F)c2)cc1-c1ccnc(OC(F)F)c1 OMGARGSFJXSCRR-UHFFFAOYSA-N 0.000 claims 1
• QDKZLTBMNHUIAC-UHFFFAOYSA-N 5-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OC)=NC=C1CC1=CN=C(N)N=C1 QDKZLTBMNHUIAC-UHFFFAOYSA-N 0.000 claims 1
• PSSAMOZEUWUYBF-UHFFFAOYSA-N 5-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OC)=NC=C1CC1=CN=C(C(N)=O)N=C1 PSSAMOZEUWUYBF-UHFFFAOYSA-N 0.000 claims 1
• FPCOYIKYVJDXLJ-UHFFFAOYSA-N 5-[[5-[3-(difluoromethoxy)phenyl]-6-ethoxypyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CC1=CN=C(C(N)=O)N=C1 FPCOYIKYVJDXLJ-UHFFFAOYSA-N 0.000 claims 1
• VVPCYHBTPJJDSV-UHFFFAOYSA-N 5-[[6-(3,4-difluorophenyl)-5-ethoxypyrazin-2-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1ncc(Cc2cnc(N)nc2)nc1-c1ccc(F)c(F)c1 VVPCYHBTPJJDSV-UHFFFAOYSA-N 0.000 claims 1
• YGCQENJEYMSJHD-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]pyrimidin-2-amine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CC1=CN=C(N)N=C1 YGCQENJEYMSJHD-UHFFFAOYSA-N 0.000 claims 1
• VETMQTLBBADPEG-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]pyrimidine-2-carbonitrile Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CC1=CN=C(C#N)N=C1 VETMQTLBBADPEG-UHFFFAOYSA-N 0.000 claims 1
• HKSQYRKWRWNXNB-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]pyrimidine-2-carboxamide Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CC1=CN=C(C(N)=O)N=C1 HKSQYRKWRWNXNB-UHFFFAOYSA-N 0.000 claims 1
• QOCAQSQGHRRDCD-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-n-cyclopropylpyrimidin-2-amine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC(C=N1)=CN=C1NC1CC1 QOCAQSQGHRRDCD-UHFFFAOYSA-N 0.000 claims 1
• GDNIQXRPTMMTRI-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=N1 GDNIQXRPTMMTRI-UHFFFAOYSA-N 0.000 claims 1
• YVVRYTPAANHPFB-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]pyridine-2-carboxamide Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(C(N)=O)N=C1 YVVRYTPAANHPFB-UHFFFAOYSA-N 0.000 claims 1
• NEBNNGNQRRQRQN-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]pyrimidin-2-amine Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(N)N=C1 NEBNNGNQRRQRQN-UHFFFAOYSA-N 0.000 claims 1
• ZNQRJZYTVNHUEN-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]pyrimidine-2-carbonitrile Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(C#N)N=C1 ZNQRJZYTVNHUEN-UHFFFAOYSA-N 0.000 claims 1
• ZDISZORVQNFBIW-UHFFFAOYSA-N 5-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]pyrimidine-2-carboxamide Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(C(N)=O)N=C1 ZDISZORVQNFBIW-UHFFFAOYSA-N 0.000 claims 1
• SKOFVLFUTPJZML-UHFFFAOYSA-N 5-[[6-(difluoromethoxy)-5-(2-methoxypyridin-4-yl)pyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=C(CC=3C=NC(N)=NC=3)C=2)OC(F)F)=C1 SKOFVLFUTPJZML-UHFFFAOYSA-N 0.000 claims 1
• CAUQPZIRJMHLEN-UHFFFAOYSA-N 5-[[6-(difluoromethoxy)-5-(3-methoxyphenyl)pyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound COC1=CC=CC(C=2C(=NC=C(CC=3C=NC(N)=NC=3)C=2)OC(F)F)=C1 CAUQPZIRJMHLEN-UHFFFAOYSA-N 0.000 claims 1
• RVMKRADJUFAZQQ-UHFFFAOYSA-N 5-[[6-(difluoromethoxy)-5-(3-methoxyphenyl)pyridin-3-yl]methyl]pyrimidine-2-carboxamide Chemical compound COC1=CC=CC(C=2C(=NC=C(CC=3C=NC(=NC=3)C(N)=O)C=2)OC(F)F)=C1 RVMKRADJUFAZQQ-UHFFFAOYSA-N 0.000 claims 1
• QDPFRHOPGGJXLD-UHFFFAOYSA-N 5-[[6-(difluoromethoxy)-5-[3-(oxetan-3-yloxy)phenyl]pyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1CC1=CN=C(OC(F)F)C(C=2C=C(OC3COC3)C=CC=2)=C1 QDPFRHOPGGJXLD-UHFFFAOYSA-N 0.000 claims 1
• HNCGDIATXIDSDR-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]pyridine-2-carbonitrile Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CC1=CC=C(C#N)N=C1 HNCGDIATXIDSDR-UHFFFAOYSA-N 0.000 claims 1
• RDBLVGMTJOIWMZ-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]pyridine-2-carboxamide Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CC1=CC=C(C(N)=O)N=C1 RDBLVGMTJOIWMZ-UHFFFAOYSA-N 0.000 claims 1
• VGYUSEZOPWNWOL-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]pyrimidin-2-amine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CC1=CN=C(N)N=C1 VGYUSEZOPWNWOL-UHFFFAOYSA-N 0.000 claims 1
• YHXBKJIPLMOOIO-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]pyrimidine-2-carbonitrile Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CC1=CN=C(C#N)N=C1 YHXBKJIPLMOOIO-UHFFFAOYSA-N 0.000 claims 1
• YNXDWRHAKAMDCU-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]pyrimidine-2-carboxamide Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CC1=CN=C(C(N)=O)N=C1 YNXDWRHAKAMDCU-UHFFFAOYSA-N 0.000 claims 1
• UTIGMQBCVIBUOG-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-methoxypyrazin-2-yl]methyl]pyrimidin-2-amine Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CC1=CN=C(N)N=C1 UTIGMQBCVIBUOG-UHFFFAOYSA-N 0.000 claims 1
• HJSHJWHDFDLCSA-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-methoxypyrazin-2-yl]methyl]pyrimidine-2-carbonitrile Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CC1=CN=C(C#N)N=C1 HJSHJWHDFDLCSA-UHFFFAOYSA-N 0.000 claims 1
• LSBUIVVYLFRXIZ-UHFFFAOYSA-N 5-[[6-[3-(difluoromethoxy)phenyl]-5-methoxypyrazin-2-yl]methyl]pyrimidine-2-carboxamide Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CC1=CN=C(C(N)=O)N=C1 LSBUIVVYLFRXIZ-UHFFFAOYSA-N 0.000 claims 1
• CVOHJEVOGBKMTC-UHFFFAOYSA-N 5-[[6-ethoxy-5-(4-fluoro-3-methylphenyl)pyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)c(C)c1 CVOHJEVOGBKMTC-UHFFFAOYSA-N 0.000 claims 1
• XMPFOKQFTROFHP-UHFFFAOYSA-N 5-[[6-ethoxy-5-(4-fluorophenyl)pyridin-3-yl]methyl]pyrimidin-2-amine Chemical compound CCOc1ncc(Cc2cnc(N)nc2)cc1-c1ccc(F)cc1 XMPFOKQFTROFHP-UHFFFAOYSA-N 0.000 claims 1
• LWSUSPDGAICGSP-UHFFFAOYSA-N 6-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridazin-3-amine Chemical compound N1=NC(N)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 LWSUSPDGAICGSP-UHFFFAOYSA-N 0.000 claims 1
• VHERCFDERVDJPL-UHFFFAOYSA-N 6-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyridine-3-carbonitrile Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CC1=CC=C(C=N1)C#N VHERCFDERVDJPL-UHFFFAOYSA-N 0.000 claims 1
• 208000012239 Developmental disease Diseases 0.000 claims 1
• 208000030814 Eating disease Diseases 0.000 claims 1
• 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
• 208000012902 Nervous system disease Diseases 0.000 claims 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
• 208000027520 Somatoform disease Diseases 0.000 claims 1
• GSQWODXSIGSVCG-UHFFFAOYSA-N [1-[[5-(3,4-dichlorophenyl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1ccc(Cl)c(Cl)c1 GSQWODXSIGSVCG-UHFFFAOYSA-N 0.000 claims 1
• FMWNWYOREROOLP-UHFFFAOYSA-N [1-[[5-(3,4-difluorophenyl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1ccc(F)c(F)c1 FMWNWYOREROOLP-UHFFFAOYSA-N 0.000 claims 1
• MSAHDYAANNXWMD-UHFFFAOYSA-N [1-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound COc1ncc(Cn2cc(CO)nc2C)cc1-c1ccc(F)c(F)c1 MSAHDYAANNXWMD-UHFFFAOYSA-N 0.000 claims 1
• QYEFMLFKAZSDLB-UHFFFAOYSA-N [1-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnnc2CO)cc1-c1ccc(F)c(F)c1 QYEFMLFKAZSDLB-UHFFFAOYSA-N 0.000 claims 1
• IEPSIXMFQTXQGD-UHFFFAOYSA-N [1-[[5-(3,5-difluorophenyl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1cc(F)cc(F)c1 IEPSIXMFQTXQGD-UHFFFAOYSA-N 0.000 claims 1
• OQNLHPKDRFLJEU-UHFFFAOYSA-N [1-[[5-(3-chloro-4-fluorophenyl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound ClC=1C=C(C=CC1F)C=1C=C(C=NC1OCC)CN1N=C(N=C1)CO OQNLHPKDRFLJEU-UHFFFAOYSA-N 0.000 claims 1
• MMXKTJHLRNTRGZ-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound OCc1ncn(Cc2cnc(OCC(F)(F)F)c(c2)-c2cccc(Cl)c2)n1 MMXKTJHLRNTRGZ-UHFFFAOYSA-N 0.000 claims 1
• SIUFDBPXXAOKBR-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-(2,2-difluoroethoxy)pyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OCC(F)F)CN1C(=NC(=C1)CO)C SIUFDBPXXAOKBR-UHFFFAOYSA-N 0.000 claims 1
• WLGIMISBEJTKIG-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanamine Chemical compound N1=C(CN)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 WLGIMISBEJTKIG-UHFFFAOYSA-N 0.000 claims 1
• CSGQUVIHJDXMRI-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(CO)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 CSGQUVIHJDXMRI-UHFFFAOYSA-N 0.000 claims 1
• DOMPYGDOHITEJG-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound Cc1nc(CO)cn1Cc1cnc(OC(F)F)c(c1)-c1cccc(Cl)c1 DOMPYGDOHITEJG-UHFFFAOYSA-N 0.000 claims 1
• UBXPGACEJDLJLC-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 UBXPGACEJDLJLC-UHFFFAOYSA-N 0.000 claims 1
• CKCXNXMVKJDKFY-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=NC(CO)=N1 CKCXNXMVKJDKFY-UHFFFAOYSA-N 0.000 claims 1
• OEEZQHBKTFAAAO-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound CCOc1ncc(Cn2cc(CO)nc2C)cc1-c1cccc(Cl)c1 OEEZQHBKTFAAAO-UHFFFAOYSA-N 0.000 claims 1
• CLKDLGPLWDWVRS-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-5-methylpyrazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2nc(CO)cc2C)cc1-c1cccc(Cl)c1 CLKDLGPLWDWVRS-UHFFFAOYSA-N 0.000 claims 1
• OVNRBVJEBUJRLY-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrazol-4-yl]methanol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=C(CO)C=N1 OVNRBVJEBUJRLY-UHFFFAOYSA-N 0.000 claims 1
• RLBPYDJTUQSNQG-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound COc1ncc(Cn2cnc(CO)n2)cc1-c1cccc(Cl)c1 RLBPYDJTUQSNQG-UHFFFAOYSA-N 0.000 claims 1
• UZTNJBZICDOZKP-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound COc1ncc(Cn2cc(CO)nc2C)cc1-c1cccc(Cl)c1 UZTNJBZICDOZKP-UHFFFAOYSA-N 0.000 claims 1
• ZSMGZUOJPXEBLY-UHFFFAOYSA-N [1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnnc2CO)cc1-c1cccc(Cl)c1 ZSMGZUOJPXEBLY-UHFFFAOYSA-N 0.000 claims 1
• DCEGOGUCAHHWBZ-UHFFFAOYSA-N [1-[[5-(4-chloro-3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound ClC1=C(C=C(C=C1)C=1C=C(C=NC1OC)CN1N=NN=C1CO)F DCEGOGUCAHHWBZ-UHFFFAOYSA-N 0.000 claims 1
• WEFBDGNVCXXOCY-UHFFFAOYSA-N [1-[[5-(4-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1ccc(Cl)cc1 WEFBDGNVCXXOCY-UHFFFAOYSA-N 0.000 claims 1
• SCBMNZNOXSUJMW-UHFFFAOYSA-N [1-[[5-(4-fluoro-3-methoxyphenyl)-6-methoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound FC1=C(C=C(C=C1)C=1C=C(C=NC1OC)CN1C(=NC(=C1)CO)C)OC SCBMNZNOXSUJMW-UHFFFAOYSA-N 0.000 claims 1
• DBTGPZHKBMWISZ-UHFFFAOYSA-N [1-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound COc1ncc(Cn2cc(CO)nc2C)cc1-c1ccc(F)cc1 DBTGPZHKBMWISZ-UHFFFAOYSA-N 0.000 claims 1
• BJMJXTAIBGCKFH-UHFFFAOYSA-N [1-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnnc2CO)cc1-c1ccc(F)cc1 BJMJXTAIBGCKFH-UHFFFAOYSA-N 0.000 claims 1
• UIRNVBHUWLEDMN-UHFFFAOYSA-N [1-[[5-(5-chloropyridin-3-yl)-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1cncc(Cl)c1 UIRNVBHUWLEDMN-UHFFFAOYSA-N 0.000 claims 1
• ZXDYFTOBZHRKJY-UHFFFAOYSA-N [1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OCC)=NC=C1CN1C=NC(CO)=N1 ZXDYFTOBZHRKJY-UHFFFAOYSA-N 0.000 claims 1
• BMNIXJPVEXAXGI-UHFFFAOYSA-N [1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)N=CC=2)C(OC)=NC=C1CN1C=NC(CO)=N1 BMNIXJPVEXAXGI-UHFFFAOYSA-N 0.000 claims 1
• NEVJPKGLAOMDNF-UHFFFAOYSA-N [1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound FC(OC1=NC=CC(=C1)C=1C=C(C=NC1OC)CN1C(=NC(=C1)CO)C)F NEVJPKGLAOMDNF-UHFFFAOYSA-N 0.000 claims 1
• VYBGGOJUICIMLS-UHFFFAOYSA-N [1-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-methoxypyridin-3-yl]methyl]-5-methylpyrazol-3-yl]methanol Chemical compound FC(OC1=NC=CC(=C1)C=1C=C(C=NC1OC)CN1N=C(C=C1C)CO)F VYBGGOJUICIMLS-UHFFFAOYSA-N 0.000 claims 1
• WFTWMBGLRLMVKG-UHFFFAOYSA-N [1-[[5-[3-(difluoromethoxy)phenyl]-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(CO)=N1 WFTWMBGLRLMVKG-UHFFFAOYSA-N 0.000 claims 1
• GJFRTDDJDSJCFD-UHFFFAOYSA-N [1-[[5-[3-(difluoromethoxy)phenyl]-6-ethoxypyridin-3-yl]methyl]triazol-4-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=C(CO)N=N1 GJFRTDDJDSJCFD-UHFFFAOYSA-N 0.000 claims 1
• LDJMXEAQDMTKBZ-UHFFFAOYSA-N [1-[[5-[3-(difluoromethoxy)phenyl]-6-methoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC(CO)=N1 LDJMXEAQDMTKBZ-UHFFFAOYSA-N 0.000 claims 1
• GJCJNYVMICOOLM-UHFFFAOYSA-N [1-[[5-[3-(difluoromethoxy)phenyl]-6-methoxypyridin-3-yl]methyl]pyrazol-3-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=CC(CO)=N1 GJCJNYVMICOOLM-UHFFFAOYSA-N 0.000 claims 1
• ISUXIOSHYZLQNV-UHFFFAOYSA-N [1-[[5-[3-(difluoromethoxy)phenyl]-6-methoxypyridin-3-yl]methyl]pyrazol-4-yl]methanol Chemical compound C1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=C(CO)C=N1 ISUXIOSHYZLQNV-UHFFFAOYSA-N 0.000 claims 1
• KKPWJKCWALSRJQ-UHFFFAOYSA-N [1-[[5-[3-(dimethylamino)phenyl]-6-ethoxypyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1cccc(c1)N(C)C KKPWJKCWALSRJQ-UHFFFAOYSA-N 0.000 claims 1
• XRTYNXVJMJUMOR-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=NC(CO)=N1 XRTYNXVJMJUMOR-UHFFFAOYSA-N 0.000 claims 1
• OWYRDYUUPQXVHL-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound CCOc1ncc(Cn2cc(CO)nc2C)nc1-c1cccc(Cl)c1 OWYRDYUUPQXVHL-UHFFFAOYSA-N 0.000 claims 1
• HYLSCXIEWREKFB-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]-5-methylpyrazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2nc(CO)cc2C)nc1-c1cccc(Cl)c1 HYLSCXIEWREKFB-UHFFFAOYSA-N 0.000 claims 1
• GRCJTFGBOLWWMO-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-ethoxypyrazin-2-yl]methyl]triazol-4-yl]methanol Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=C(CO)N=N1 GRCJTFGBOLWWMO-UHFFFAOYSA-N 0.000 claims 1
• AIRSRIABGPKLOI-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=NC(CO)=N1 AIRSRIABGPKLOI-UHFFFAOYSA-N 0.000 claims 1
• IQRROQGKNQZUBC-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound COc1ncc(Cn2cc(CO)nc2C)nc1-c1cccc(Cl)c1 IQRROQGKNQZUBC-UHFFFAOYSA-N 0.000 claims 1
• MCGYWZBWIMWTOP-UHFFFAOYSA-N [1-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]triazol-4-yl]methanol Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(CO)N=N1 MCGYWZBWIMWTOP-UHFFFAOYSA-N 0.000 claims 1
• METDTSFRMZVUDY-UHFFFAOYSA-N [1-[[6-(difluoromethoxy)-5-(3-ethoxyphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOC1=CC=CC(C=2C(=NC=C(CN3N=C(CO)N=C3)C=2)OC(F)F)=C1 METDTSFRMZVUDY-UHFFFAOYSA-N 0.000 claims 1
• WNXBKEKWXUZJKQ-UHFFFAOYSA-N [1-[[6-(difluoromethoxy)-5-(3-ethoxyphenyl)pyridin-3-yl]methyl]triazol-4-yl]methanol Chemical compound CCOC1=CC=CC(C=2C(=NC=C(CN3N=NC(CO)=C3)C=2)OC(F)F)=C1 WNXBKEKWXUZJKQ-UHFFFAOYSA-N 0.000 claims 1
• YWCBKWDUAHSEGD-UHFFFAOYSA-N [1-[[6-(difluoromethoxy)-5-[2-(difluoromethoxy)pyridin-4-yl]pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(CO)N=CN1CC1=CN=C(OC(F)F)C(C=2C=C(OC(F)F)N=CC=2)=C1 YWCBKWDUAHSEGD-UHFFFAOYSA-N 0.000 claims 1
• ZCOYRXOAZRILBK-UHFFFAOYSA-N [1-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(CO)=N1 ZCOYRXOAZRILBK-UHFFFAOYSA-N 0.000 claims 1
• PERPQYIAHQMZLV-UHFFFAOYSA-N [1-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]triazol-4-yl]methanol Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=C(CO)N=N1 PERPQYIAHQMZLV-UHFFFAOYSA-N 0.000 claims 1
• KWUDZNVKMKBTCQ-UHFFFAOYSA-N [1-[[6-[3-(difluoromethoxy)phenyl]-5-methoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=NC(CO)=N1 KWUDZNVKMKBTCQ-UHFFFAOYSA-N 0.000 claims 1
• UUANGSQZTAISDN-UHFFFAOYSA-N [1-[[6-[3-(difluoromethoxy)phenyl]-5-methoxypyrazin-2-yl]methyl]triazol-4-yl]methanol Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OC)=NC=C1CN1C=C(CO)N=N1 UUANGSQZTAISDN-UHFFFAOYSA-N 0.000 claims 1
• KPHWMPVCOCFKPP-UHFFFAOYSA-N [1-[[6-ethoxy-5-(2-fluorophenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1ccccc1F KPHWMPVCOCFKPP-UHFFFAOYSA-N 0.000 claims 1
• SGUXRCGACDPOOO-UHFFFAOYSA-N [1-[[6-ethoxy-5-(3-ethoxyphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1cccc(c1)-c1cc(Cn2cnc(CO)n2)cnc1OCC SGUXRCGACDPOOO-UHFFFAOYSA-N 0.000 claims 1
• ZIHUJZXGRSKFDV-UHFFFAOYSA-N [1-[[6-ethoxy-5-(3-fluorophenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1cccc(F)c1 ZIHUJZXGRSKFDV-UHFFFAOYSA-N 0.000 claims 1
• CSCFODIXFNNYNX-UHFFFAOYSA-N [1-[[6-ethoxy-5-(3-methoxyphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1cccc(OC)c1 CSCFODIXFNNYNX-UHFFFAOYSA-N 0.000 claims 1
• MQLTZQAENPFCQL-UHFFFAOYSA-N [1-[[6-ethoxy-5-(4-fluoro-3-methylphenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C(C)OC1=C(C=C(C=N1)CN1N=C(N=C1)CO)C1=CC(=C(C=C1)F)C MQLTZQAENPFCQL-UHFFFAOYSA-N 0.000 claims 1
• KSTUJRAQGGKYBT-UHFFFAOYSA-N [1-[[6-ethoxy-5-(4-fluorophenyl)pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2cnc(CO)n2)cc1-c1ccc(F)cc1 KSTUJRAQGGKYBT-UHFFFAOYSA-N 0.000 claims 1
• JXINBVJXEKHOHL-UHFFFAOYSA-N [1-[[6-ethoxy-5-[2-(trifluoromethyl)pyridin-4-yl]pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C(C)OC1=C(C=C(C=N1)CN1N=C(N=C1)CO)C1=CC(=NC=C1)C(F)(F)F JXINBVJXEKHOHL-UHFFFAOYSA-N 0.000 claims 1
• NTIVZIKBKKIMLU-UHFFFAOYSA-N [1-[[6-ethoxy-5-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C(C)OC1=C(C=C(C=N1)CN1N=C(N=C1)CO)C1=CC(=CC=C1)OC(F)(F)F NTIVZIKBKKIMLU-UHFFFAOYSA-N 0.000 claims 1
• WCELYXKDNRVSQX-UHFFFAOYSA-N [1-[[6-ethoxy-5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound C(C)OC1=C(C=C(C=N1)CN1N=C(N=C1)CO)C1=CC(=CC=C1)C(F)(F)F WCELYXKDNRVSQX-UHFFFAOYSA-N 0.000 claims 1
• AZDCGVSZAWYEOG-UHFFFAOYSA-N [2-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnc(CO)n2)cc1-c1ccc(F)c(F)c1 AZDCGVSZAWYEOG-UHFFFAOYSA-N 0.000 claims 1
• NZCNXUDBNWBNAF-UHFFFAOYSA-N [2-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-5-methylpyrazol-3-yl]methanol Chemical compound CCOc1ncc(Cn2nc(C)cc2CO)cc1-c1cccc(Cl)c1 NZCNXUDBNWBNAF-UHFFFAOYSA-N 0.000 claims 1
• AZNOOWJCLXJQED-UHFFFAOYSA-N [2-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]methanol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=CC=C1CO AZNOOWJCLXJQED-UHFFFAOYSA-N 0.000 claims 1
• VQTGHDNQHCCZQG-UHFFFAOYSA-N [2-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnc(CO)n2)cc1-c1cccc(Cl)c1 VQTGHDNQHCCZQG-UHFFFAOYSA-N 0.000 claims 1
• FWSDZLMKGUWINI-UHFFFAOYSA-N [2-[[5-(4-chloro-3-fluorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnc(CO)n2)cc1-c1ccc(Cl)c(F)c1 FWSDZLMKGUWINI-UHFFFAOYSA-N 0.000 claims 1
• GIEFYQBIIOWCNO-UHFFFAOYSA-N [2-[[5-(4-fluorophenyl)-6-methoxypyridin-3-yl]methyl]tetrazol-5-yl]methanol Chemical compound COc1ncc(Cn2nnc(CO)n2)cc1-c1ccc(F)cc1 GIEFYQBIIOWCNO-UHFFFAOYSA-N 0.000 claims 1
• GJOIKXIQIAOZQQ-UHFFFAOYSA-N [2-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1N=CN=C1CO GJOIKXIQIAOZQQ-UHFFFAOYSA-N 0.000 claims 1
• CYFYHXFTYSSCOA-UHFFFAOYSA-N [2-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]-1,2,4-triazol-3-yl]methanol Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1CO CYFYHXFTYSSCOA-UHFFFAOYSA-N 0.000 claims 1
• GVHKVPJYGOFOIP-UHFFFAOYSA-N [3-[2-methoxy-5-(1,2,4-triazol-1-ylmethyl)pyridin-3-yl]phenyl]methanol Chemical compound C1=C(C=2C=C(CO)C=CC=2)C(OC)=NC=C1CN1C=NC=N1 GVHKVPJYGOFOIP-UHFFFAOYSA-N 0.000 claims 1
• WSINRNLYWYFMTD-UHFFFAOYSA-N [3-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]imidazol-4-yl]methanol Chemical compound OCC1=CN=CN1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 WSINRNLYWYFMTD-UHFFFAOYSA-N 0.000 claims 1
• PATYCFWJJPPBGV-UHFFFAOYSA-N [3-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]-2-methylimidazol-4-yl]methanol Chemical compound CCOc1ncc(Cn2c(C)ncc2CO)cc1-c1cccc(Cl)c1 PATYCFWJJPPBGV-UHFFFAOYSA-N 0.000 claims 1
• FVXFBANCKRJRLJ-UHFFFAOYSA-N [4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]methanamine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(CN)C=C1 FVXFBANCKRJRLJ-UHFFFAOYSA-N 0.000 claims 1
• FZPUZCDCMKYUIL-UHFFFAOYSA-N [4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]urea Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CC=C(NC(N)=O)C=C1 FZPUZCDCMKYUIL-UHFFFAOYSA-N 0.000 claims 1
• IBNOLHYKCLVONK-UHFFFAOYSA-N [4-chloro-1-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrazol-3-yl]methanol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1C=C(Cl)C(CO)=N1 IBNOLHYKCLVONK-UHFFFAOYSA-N 0.000 claims 1
• ZXCCGHMDXRCISU-UHFFFAOYSA-N [4-chloro-2-[[5-(3-chlorophenyl)-6-ethoxypyridin-3-yl]methyl]pyrazol-3-yl]methanol Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OCC)=NC=C1CN1N=CC(Cl)=C1CO ZXCCGHMDXRCISU-UHFFFAOYSA-N 0.000 claims 1
• QFQOBRMNLWFLOW-UHFFFAOYSA-N [5-(3-chlorophenyl)-6-methoxypyridin-3-yl]-(4-fluorophenyl)methanamine Chemical compound COC1=NC=C(C(N)C=2C=CC(F)=CC=2)C=C1C1=CC=CC(Cl)=C1 QFQOBRMNLWFLOW-UHFFFAOYSA-N 0.000 claims 1
• UKXSBPLHYKLZQV-UHFFFAOYSA-N [5-(3-chlorophenyl)-6-methoxypyridin-3-yl]-(4-fluorophenyl)methanol Chemical compound COC1=NC=C(C(O)C=2C=CC(F)=CC=2)C=C1C1=CC=CC(Cl)=C1 UKXSBPLHYKLZQV-UHFFFAOYSA-N 0.000 claims 1
• QZIXORRWSXAKCD-UHFFFAOYSA-N [5-(3-chlorophenyl)-6-methoxypyridin-3-yl]-(5-fluoropyridin-2-yl)methanol Chemical compound COC1=NC=C(C(O)C=2N=CC(F)=CC=2)C=C1C1=CC=CC(Cl)=C1 QZIXORRWSXAKCD-UHFFFAOYSA-N 0.000 claims 1
• NVSIMQJXPQVMIQ-UHFFFAOYSA-N [5-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]pyridin-3-yl]methanamine Chemical compound NCC1=CN=CC(CC=2C=C(C(OC(F)F)=NC=2)C=2C=C(Cl)C=CC=2)=C1 NVSIMQJXPQVMIQ-UHFFFAOYSA-N 0.000 claims 1
• AVEICUKDOANRFC-UHFFFAOYSA-N [5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazin-2-yl]methanol Chemical compound ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CC=1N=CC(=NC1)CO AVEICUKDOANRFC-UHFFFAOYSA-N 0.000 claims 1
• RJHMFTGBUHHTFT-UHFFFAOYSA-N [5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]methanol Chemical compound COc1ncc(Cc2cnc(CO)nc2)cc1-c1cccc(Cl)c1 RJHMFTGBUHHTFT-UHFFFAOYSA-N 0.000 claims 1
• ZODOPTYMUJTIHK-UHFFFAOYSA-N [5-[[5-[2-(difluoromethoxy)pyridin-4-yl]-6-ethoxypyridin-3-yl]methyl]-3-fluoropyridin-2-yl]methanol Chemical compound CCOc1ncc(Cc2cnc(CO)c(F)c2)cc1-c1ccnc(OC(F)F)c1 ZODOPTYMUJTIHK-UHFFFAOYSA-N 0.000 claims 1
• SUFNJYFECMOTCD-UHFFFAOYSA-N [5-[[6-(2,2-difluoroethoxy)-5-(2-ethoxypyridin-4-yl)pyridin-3-yl]methyl]-3-fluoropyridin-2-yl]methanol Chemical compound CCOc1cc(ccn1)-c1cc(Cc2cnc(CO)c(F)c2)cnc1OCC(F)F SUFNJYFECMOTCD-UHFFFAOYSA-N 0.000 claims 1
• 208000010877 cognitive disease Diseases 0.000 claims 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
• 235000014632 disordered eating Nutrition 0.000 claims 1
• 208000018459 dissociative disease Diseases 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• GLONARDOUQTWDU-UHFFFAOYSA-N ethyl 1-[4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(CC=2C=C(C(OC(F)F)=NC=2)C=2C=C(Cl)C=CC=2)C=CC=1C1(C(=O)OCC)CC1 GLONARDOUQTWDU-UHFFFAOYSA-N 0.000 claims 1
• KJVHHMOHNWRQFO-UHFFFAOYSA-N ethyl 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 KJVHHMOHNWRQFO-UHFFFAOYSA-N 0.000 claims 1
• HTHCNXXGOXUVCK-UHFFFAOYSA-N ethyl 2-[4-[[5-(3,4-difluorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]acetate Chemical compound CCOC(=O)Cc1ccc(Cc2cnc(OC)c(c2)-c2ccc(F)c(F)c2)cc1 HTHCNXXGOXUVCK-UHFFFAOYSA-N 0.000 claims 1
• FGRALLPFZIPSSD-UHFFFAOYSA-N ethyl 2-[4-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]phenyl]acetate Chemical compound CCOC(=O)Cc1ccc(Cc2cnc(OC)c(c2)-c2cccc(Cl)c2)cc1 FGRALLPFZIPSSD-UHFFFAOYSA-N 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 208000014674 injury Diseases 0.000 claims 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• NMPACWKNXWZELH-UHFFFAOYSA-N methyl 1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=CN1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 NMPACWKNXWZELH-UHFFFAOYSA-N 0.000 claims 1
• UHEXQOVRZKPGMK-UHFFFAOYSA-N methyl 1-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=CN1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=N1 UHEXQOVRZKPGMK-UHFFFAOYSA-N 0.000 claims 1
• FLWQPITYTVPAIC-UHFFFAOYSA-N methyl 1-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1C=NC(C(=O)OC)=N1 FLWQPITYTVPAIC-UHFFFAOYSA-N 0.000 claims 1
• ICRTXOGGMDLCAV-UHFFFAOYSA-N methyl 1-[[6-[3-(difluoromethoxy)phenyl]-5-methoxypyrazin-2-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=CN1CC1=CN=C(OC)C(C=2C=C(OC(F)F)C=CC=2)=N1 ICRTXOGGMDLCAV-UHFFFAOYSA-N 0.000 claims 1
• LLZFDLXRWFKWQN-UHFFFAOYSA-N methyl 2-[4-[[5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl]methyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1CC1=CN=C(OC(F)F)C(C=2C=C(Cl)C=CC=2)=C1 LLZFDLXRWFKWQN-UHFFFAOYSA-N 0.000 claims 1
• KRYTUJDAOYTAHM-UHFFFAOYSA-N methyl 2-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound COC(=O)C1=NC=NN1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=C1 KRYTUJDAOYTAHM-UHFFFAOYSA-N 0.000 claims 1
• AZGJERSRQXFOQG-UHFFFAOYSA-N methyl 2-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound COC(=O)C1=NC=NN1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=N1 AZGJERSRQXFOQG-UHFFFAOYSA-N 0.000 claims 1
• ATNHFUHXQZXGSQ-UHFFFAOYSA-N methyl 2-[[6-[3-(difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl]methyl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C(OCC)=NC=C1CN1N=CN=C1C(=O)OC ATNHFUHXQZXGSQ-UHFFFAOYSA-N 0.000 claims 1
• RNDJTZBPTYZCKK-UHFFFAOYSA-N methyl 4-[[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CC1=CN=C(OC)C(C=2C=C(Cl)C=CC=2)=N1 RNDJTZBPTYZCKK-UHFFFAOYSA-N 0.000 claims 1
• 125000002950 monocyclic group Chemical group 0.000 claims 1
• NYXAFZBXCCMRDJ-UHFFFAOYSA-N n-[1-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrazol-4-yl]acetamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CN1C=C(NC(C)=O)C=N1 NYXAFZBXCCMRDJ-UHFFFAOYSA-N 0.000 claims 1
• DNWVPGPSMLMPAD-UHFFFAOYSA-N n-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(NCCN(C)C)N=C1 DNWVPGPSMLMPAD-UHFFFAOYSA-N 0.000 claims 1
• DGOHWAGCGMYARB-UHFFFAOYSA-N n-[5-[[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl]pyrimidin-2-yl]acetamide Chemical compound C1=C(C=2C=C(Cl)C=CC=2)C(OC)=NC=C1CC1=CN=C(NC(C)=O)N=C1 DGOHWAGCGMYARB-UHFFFAOYSA-N 0.000 claims 1
• 230000004770 neurodegeneration Effects 0.000 claims 1
• 208000015122 neurodegenerative disease Diseases 0.000 claims 1
• 201000001119 neuropathy Diseases 0.000 claims 1
• 230000007823 neuropathy Effects 0.000 claims 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
• 208000027753 pain disease Diseases 0.000 claims 1
• 208000033808 peripheral neuropathy Diseases 0.000 claims 1
• 208000022821 personality disease Diseases 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 208000020016 psychiatric disease Diseases 0.000 claims 1
• XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims 1
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
• FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims 1
• 208000019116 sleep disease Diseases 0.000 claims 1
• 208000020685 sleep-wake disease Diseases 0.000 claims 1
• 208000011117 substance-related disease Diseases 0.000 claims 1
• 150000003536 tetrazoles Chemical class 0.000 claims 1
• 230000008733 trauma Effects 0.000 claims 1
• 150000003852 triazoles Chemical class 0.000 claims 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
• 0 CC*c1ccc(*)cc1 Chemical compound CC*c1ccc(*)cc1 0.000 description 12
• XIHLHJOMGBHGOB-UHFFFAOYSA-N C[n](cn1)nc1[Rh] Chemical compound C[n](cn1)nc1[Rh] XIHLHJOMGBHGOB-UHFFFAOYSA-N 0.000 description 2