CA2260774C - Derives de triazolo-pyridazine substitues servant de ligands pour recepteurs de gaba - Google Patents

Info

Publication number

CA2260774C

CA2260774C CA002260774A CA2260774A CA2260774C CA 2260774 C CA2260774 C CA 2260774C CA 002260774 A CA002260774 A CA 002260774A CA 2260774 A CA2260774 A CA 2260774A CA 2260774 C CA2260774 C CA 2260774C

Authority

CA

Canada

Prior art keywords

triazolo

phenyl

pyridazine

methyl

ylmethoxy

Prior art date

1996-07-25

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

Expired - Fee Related

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• 239000003446 ligand Substances 0.000 title abstract description 7
• CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical class N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 title description 7
• 102000005915 GABA Receptors Human genes 0.000 title description 2
• 108010005551 GABA Receptors Proteins 0.000 title description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
• 230000002265 prevention Effects 0.000 claims abstract description 23
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 16
• 230000036506 anxiety Effects 0.000 claims abstract description 14
• 206010010904 Convulsion Diseases 0.000 claims abstract description 13
• 230000036461 convulsion Effects 0.000 claims abstract description 12
• 102000004300 GABA-A Receptors Human genes 0.000 claims abstract 7
• 108090000839 GABA-A Receptors Proteins 0.000 claims abstract 7
• 150000001875 compounds Chemical class 0.000 claims description 523
• -1 C6-10 bicycloalkenyl Chemical group 0.000 claims description 311
• 238000000034 method Methods 0.000 claims description 227
• 239000000203 mixture Substances 0.000 claims description 135
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 76
• 150000003839 salts Chemical class 0.000 claims description 51
• 239000000651 prodrug Substances 0.000 claims description 43
• 229940002612 prodrug Drugs 0.000 claims description 43
• 125000004076 pyridyl group Chemical group 0.000 claims description 35
• 125000003118 aryl group Chemical group 0.000 claims description 27
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 230000027455 binding Effects 0.000 claims description 21
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 20
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 15
• 230000004044 response Effects 0.000 claims description 15
• 125000000335 thiazolyl group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 11
• 238000012360 testing method Methods 0.000 claims description 11
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 10
• 229940049706 benzodiazepine Drugs 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
• 239000002249 anxiolytic agent Substances 0.000 claims description 7
• 230000000949 anxiolytic effect Effects 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
• 206010039897 Sedation Diseases 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 230000036280 sedation Effects 0.000 claims description 6
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
• ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• NAHDCPURDJHFAG-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-3-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2SC=CC=2)C=2C=CC=CC=2)=N1 NAHDCPURDJHFAG-UHFFFAOYSA-N 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• 239000003054 catalyst Substances 0.000 claims description 4
• 230000001624 sedative effect Effects 0.000 claims description 4
• 229910001961 silver nitrate Inorganic materials 0.000 claims description 4
• STZAMPDZKQQFBF-UHFFFAOYSA-N 2-[(7-cyclobutyl-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxy]acetonitrile Chemical compound N#CCOC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1CCC1 STZAMPDZKQQFBF-UHFFFAOYSA-N 0.000 claims description 3
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 3
• WEJVWILDQNWNJW-UHFFFAOYSA-N 3,7-diphenyl-6-(2h-triazol-4-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=NNN=C1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 WEJVWILDQNWNJW-UHFFFAOYSA-N 0.000 claims description 3
• QLJFGMLCGLIGSZ-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-7-(1-methylcyclopentyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC(F)=CC=2)F)C2(C)CCCC2)=N1 QLJFGMLCGLIGSZ-UHFFFAOYSA-N 0.000 claims description 3
• GQZORSSJIAKBEJ-UHFFFAOYSA-N 3-(2-fluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC=CC=2)F)C=2C=CC=CC=2)=N1 GQZORSSJIAKBEJ-UHFFFAOYSA-N 0.000 claims description 3
• DKJVVUVRFFFLLC-UHFFFAOYSA-N 4-[6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]morpholine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2SC=CC=2)N2CCOCC2)=N1 DKJVVUVRFFFLLC-UHFFFAOYSA-N 0.000 claims description 3
• ZQTRFFPESLNLHA-UHFFFAOYSA-N 6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-pyrrolidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)N2CCCC2)=NN2C1=NN=C2C1=CC=CC=C1 ZQTRFFPESLNLHA-UHFFFAOYSA-N 0.000 claims description 3
• OTYBGZZAPBCLPB-UHFFFAOYSA-N 6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C=2SC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 OTYBGZZAPBCLPB-UHFFFAOYSA-N 0.000 claims description 3
• HOCBROYEBQFDGA-UHFFFAOYSA-N 7-cyclobutyl-3-phenyl-6-prop-2-ynoxy-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C#CCOC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1CCC1 HOCBROYEBQFDGA-UHFFFAOYSA-N 0.000 claims description 3
• VACJUKKURQMWHE-UHFFFAOYSA-N 7-cyclobutyl-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2CCC2)=NN2C1=NN=C2C1=CC=CC=C1 VACJUKKURQMWHE-UHFFFAOYSA-N 0.000 claims description 3
• GFMZKHHVXNWGOW-UHFFFAOYSA-N 7-methyl-3-phenyl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N12N=C(OCC=3N=CC=CC=3)C(C)=CC2=NN=C1C1=CC=CC=C1 GFMZKHHVXNWGOW-UHFFFAOYSA-N 0.000 claims description 3
• 239000004160 Ammonium persulphate Substances 0.000 claims description 3
• 235000019395 ammonium persulphate Nutrition 0.000 claims description 3
• 238000010561 standard procedure Methods 0.000 claims description 3
• 229910052723 transition metal Inorganic materials 0.000 claims description 3
• 150000003624 transition metals Chemical class 0.000 claims description 3
• MMDIHJNGUCQPFF-UHFFFAOYSA-N 2-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-5-methyl-1,3-thiazole Chemical compound S1C(C)=CN=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 MMDIHJNGUCQPFF-UHFFFAOYSA-N 0.000 claims description 2
• VNAOXTIBJQHVRM-UHFFFAOYSA-N 2-[3-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-1,2,4-triazol-1-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 VNAOXTIBJQHVRM-UHFFFAOYSA-N 0.000 claims description 2
• HWGNAWBPLYPUJG-UHFFFAOYSA-N 2-[3-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-1,2,4-triazol-1-yl]-n,n-dimethylethanamine Chemical compound CN(C)CCN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 HWGNAWBPLYPUJG-UHFFFAOYSA-N 0.000 claims description 2
• GIUNTDNEYLMTBV-UHFFFAOYSA-N 2-[3-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-1,2,4-triazol-1-yl]acetonitrile Chemical compound N#CCN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 GIUNTDNEYLMTBV-UHFFFAOYSA-N 0.000 claims description 2
• YPYNGKVFEWEQPN-UHFFFAOYSA-N 2-[3-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-1,2,4-triazol-1-yl]ethanamine Chemical compound NCCN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 YPYNGKVFEWEQPN-UHFFFAOYSA-N 0.000 claims description 2
• AAFRVZSZEIHNAI-UHFFFAOYSA-N 3,7-diphenyl-6-(1h-1,2,4-triazol-5-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1C=NNC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 AAFRVZSZEIHNAI-UHFFFAOYSA-N 0.000 claims description 2
• WOLTXCLEGCMVNA-UHFFFAOYSA-N 3,7-diphenyl-6-(pyrazin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1N=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 WOLTXCLEGCMVNA-UHFFFAOYSA-N 0.000 claims description 2
• DHVVPBUFVXPPMP-UHFFFAOYSA-N 3,7-diphenyl-6-(pyridazin-3-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C=CN=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 DHVVPBUFVXPPMP-UHFFFAOYSA-N 0.000 claims description 2
• OIVNHVRINWMDTH-UHFFFAOYSA-N 3,7-diphenyl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 OIVNHVRINWMDTH-UHFFFAOYSA-N 0.000 claims description 2
• RCAREXJZVVHPHV-UHFFFAOYSA-N 3,7-diphenyl-6-(pyrimidin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1C=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 RCAREXJZVVHPHV-UHFFFAOYSA-N 0.000 claims description 2
• MYJSELOFPLYFEG-UHFFFAOYSA-N 3,7-diphenyl-6-(pyrimidin-4-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C=NC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 MYJSELOFPLYFEG-UHFFFAOYSA-N 0.000 claims description 2
• DQPAAFTXZFHSMD-UHFFFAOYSA-N 3,7-diphenyl-6-(pyrimidin-5-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1N=CN=CC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 DQPAAFTXZFHSMD-UHFFFAOYSA-N 0.000 claims description 2
• LYGWGPHLTGKDDZ-UHFFFAOYSA-N 3,7-diphenyl-6-[(1-propyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CCCN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 LYGWGPHLTGKDDZ-UHFFFAOYSA-N 0.000 claims description 2
• WRWXYWQNZNBPRI-UHFFFAOYSA-N 3,7-diphenyl-6-[[1-(2-piperazin-1-ylethyl)-1,2,4-triazol-3-yl]methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1CNCCN1CCN(N=1)C=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 WRWXYWQNZNBPRI-UHFFFAOYSA-N 0.000 claims description 2
• KCSTVGDYVKXIJT-UHFFFAOYSA-N 3,7-diphenyl-6-[[1-(2-pyrrolidin-1-ylethyl)-1,2,4-triazol-3-yl]methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1CCCN1CCN(N=1)C=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 KCSTVGDYVKXIJT-UHFFFAOYSA-N 0.000 claims description 2
• VXIUXRNTQNASBZ-UHFFFAOYSA-N 3,7-diphenyl-6-[[1-(pyridin-2-ylmethyl)-1,2,4-triazol-3-yl]methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N1=CN(CC=2N=CC=CC=2)N=C1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 VXIUXRNTQNASBZ-UHFFFAOYSA-N 0.000 claims description 2
• BFUOYOXAUFRHJA-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-7-(1-methylcyclopentyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2(C)CCCC2)=NN2C1=NN=C2C1=CC=C(F)C=C1F BFUOYOXAUFRHJA-UHFFFAOYSA-N 0.000 claims description 2
• RFHYKWWROVNBBX-UHFFFAOYSA-N 3-(2-fluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-thiophen-3-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC=CC=2)F)C2=CSC=C2)=N1 RFHYKWWROVNBBX-UHFFFAOYSA-N 0.000 claims description 2
• WBGFZYZIMGCWRS-UHFFFAOYSA-N 3-(2-fluorophenyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1F WBGFZYZIMGCWRS-UHFFFAOYSA-N 0.000 claims description 2
• MCASNKXBBBTTOS-UHFFFAOYSA-N 3-(2-fluorophenyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-7-thiophen-3-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2=CSC=C2)=NN2C1=NN=C2C1=CC=CC=C1F MCASNKXBBBTTOS-UHFFFAOYSA-N 0.000 claims description 2
• PCWJWLZHLADFLD-UHFFFAOYSA-N 3-(2-fluorophenyl)-7-(1-methylcyclobutyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC=CC=2)F)C2(C)CCC2)=N1 PCWJWLZHLADFLD-UHFFFAOYSA-N 0.000 claims description 2
• UFULYACRJFODBY-UHFFFAOYSA-N 3-(2-fluorophenyl)-7-(1-methylcyclobutyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2(C)CCC2)=NN2C1=NN=C2C1=CC=CC=C1F UFULYACRJFODBY-UHFFFAOYSA-N 0.000 claims description 2
• ZBPFNELZLABPJO-UHFFFAOYSA-N 3-(2-fluorophenyl)-7-(1-methylcyclopentyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC=CC=2)F)C2(C)CCCC2)=N1 ZBPFNELZLABPJO-UHFFFAOYSA-N 0.000 claims description 2
• FRXCYAPNCVFQCR-UHFFFAOYSA-N 3-(2-fluorophenyl)-7-(1-methylcyclopentyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2(C)CCCC2)=NN2C1=NN=C2C1=CC=CC=C1F FRXCYAPNCVFQCR-UHFFFAOYSA-N 0.000 claims description 2
• MEVOCWHZYRHURQ-UHFFFAOYSA-N 3-(3-fluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=C(F)C=CC=2)C=2C=CC=CC=2)=N1 MEVOCWHZYRHURQ-UHFFFAOYSA-N 0.000 claims description 2
• IKZGGLQQGAJSRM-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)=N1 IKZGGLQQGAJSRM-UHFFFAOYSA-N 0.000 claims description 2
• KQYHETYQOIUNLY-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-7-thiophen-3-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2=CSC=C2)=NN2C1=NN=C2C1=CC=C(F)C=C1 KQYHETYQOIUNLY-UHFFFAOYSA-N 0.000 claims description 2
• FRDBGMYFMSVJDR-UHFFFAOYSA-N 3-(4-methoxyphenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(OCC1=NN(C)C=N1)C(C=1C=CC=CC=1)=C2 FRDBGMYFMSVJDR-UHFFFAOYSA-N 0.000 claims description 2
• HPHNQRHXQRLRLZ-UHFFFAOYSA-N 3-(4-methylphenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(C)=CC=C1C1=NN=C2N1N=C(OCC1=NN(C)C=N1)C(C=1C=CC=CC=1)=C2 HPHNQRHXQRLRLZ-UHFFFAOYSA-N 0.000 claims description 2
• REJBYWVLGVSIGN-UHFFFAOYSA-N 3-(4-methylphenyl)-6-[(3-methylpyridin-2-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(C)=CC=C1C1=NN=C2N1N=C(OCC=1C(=CC=CN=1)C)C(C=1C=CC=CC=1)=C2 REJBYWVLGVSIGN-UHFFFAOYSA-N 0.000 claims description 2
• UHJNPZTZEYIENC-UHFFFAOYSA-N 3-(4-methylphenyl)-7-phenyl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(C)=CC=C1C1=NN=C2N1N=C(OCC=1N=CC=CC=1)C(C=1C=CC=CC=1)=C2 UHJNPZTZEYIENC-UHFFFAOYSA-N 0.000 claims description 2
• RRAWTSZJLAMHFE-UHFFFAOYSA-N 3-(furan-2-yl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2OC=CC=2)C=2C=CC=CC=2)=N1 RRAWTSZJLAMHFE-UHFFFAOYSA-N 0.000 claims description 2
• ZBIZEDUBXBVVDX-UHFFFAOYSA-N 3-(furan-3-yl)-6-(pyridin-2-ylmethoxy)-7,8,9,10-tetrahydro-[1,2,4]triazolo[3,4-a]phthalazine Chemical compound C=1C=CC=NC=1COC(C=1CCCCC=1C1=NN=2)=NN1C=2C=1C=COC=1 ZBIZEDUBXBVVDX-UHFFFAOYSA-N 0.000 claims description 2
• CRFYXSJVEFOVJZ-UHFFFAOYSA-N 3-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-5-methyl-1,2-oxazole Chemical compound O1C(C)=CC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 CRFYXSJVEFOVJZ-UHFFFAOYSA-N 0.000 claims description 2
• FCFAREUMSQVSLJ-UHFFFAOYSA-N 3-cyclopropyl-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C2CC2)C=2C=CC=CC=2)=N1 FCFAREUMSQVSLJ-UHFFFAOYSA-N 0.000 claims description 2
• ZPSBXQBYCQOCEU-UHFFFAOYSA-N 3-phenyl-6-(pyridin-2-ylmethoxy)-7,8,9,10-tetrahydro-[1,2,4]triazolo[3,4-a]phthalazine Chemical compound C=1C=CC=NC=1COC(C=1CCCCC=1C1=NN=2)=NN1C=2C1=CC=CC=C1 ZPSBXQBYCQOCEU-UHFFFAOYSA-N 0.000 claims description 2
• AVDYSIRPQQXPMM-UHFFFAOYSA-N 3-phenyl-6-(pyridin-2-ylmethoxy)-7-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CS1 AVDYSIRPQQXPMM-UHFFFAOYSA-N 0.000 claims description 2
• NCBOIASFLNJMTE-UHFFFAOYSA-N 3-phenyl-7-piperidin-1-yl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1N1CCCCC1 NCBOIASFLNJMTE-UHFFFAOYSA-N 0.000 claims description 2
• CEKCQRZLMWJFHB-UHFFFAOYSA-N 3-phenyl-7-pyridin-3-yl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CN=C1 CEKCQRZLMWJFHB-UHFFFAOYSA-N 0.000 claims description 2
• IDEZPOJTOXGVQI-UHFFFAOYSA-N 3-phenyl-7-thiophen-3-yl-6-(1h-1,2,4-triazol-5-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1C=NNC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C=1C=CSC=1 IDEZPOJTOXGVQI-UHFFFAOYSA-N 0.000 claims description 2
• JQSZTNICLOUIPD-UHFFFAOYSA-N 4-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-1,3-thiazole Chemical compound C=1SC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 JQSZTNICLOUIPD-UHFFFAOYSA-N 0.000 claims description 2
• LZRYKBWTOGDZRQ-UHFFFAOYSA-N 4-[2-[3-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxymethyl]-1,2,4-triazol-1-yl]ethyl]morpholine Chemical compound C1COCCN1CCN(N=1)C=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 LZRYKBWTOGDZRQ-UHFFFAOYSA-N 0.000 claims description 2
• UALFGPVTWGMBCB-UHFFFAOYSA-N 4-[3-(3-fluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]morpholine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=C(F)C=CC=2)N2CCOCC2)=N1 UALFGPVTWGMBCB-UHFFFAOYSA-N 0.000 claims description 2
• GSQTYKQADBTZAF-UHFFFAOYSA-N 4-[3-phenyl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]morpholine Chemical compound C=1C=CC=NC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1N1CCOCC1 GSQTYKQADBTZAF-UHFFFAOYSA-N 0.000 claims description 2
• LTMYXBJRKUILMN-UHFFFAOYSA-N 4-[4-[(7-cyclobutyl-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxy]but-2-ynyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CC#CCOC(C(=C1)C2CCC2)=NN2C1=NN=C2C1=CC=CC=C1 LTMYXBJRKUILMN-UHFFFAOYSA-N 0.000 claims description 2
• IUEGWDIGIFAMBR-UHFFFAOYSA-N 4-[6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]morpholine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)N2CCOCC2)=N1 IUEGWDIGIFAMBR-UHFFFAOYSA-N 0.000 claims description 2
• VDORHDUUIQZRDL-UHFFFAOYSA-N 5-[2-[(3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxy]ethyl]-4-methyl-1,3-thiazole Chemical compound N1=CSC(CCOC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C VDORHDUUIQZRDL-UHFFFAOYSA-N 0.000 claims description 2
• SIYUIIGNHRAJJA-UHFFFAOYSA-N 6-(1h-benzimidazol-2-ylmethoxy)-3-(2,4-difluorophenyl)-7-(1-methylcyclopentyl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C=1C2=NN=C(C=3C(=CC(F)=CC=3)F)N2N=C(OCC=2NC3=CC=CC=C3N=2)C=1C1(C)CCCC1 SIYUIIGNHRAJJA-UHFFFAOYSA-N 0.000 claims description 2
• MDTDCBJLYUNWJT-UHFFFAOYSA-N 6-[(1-benzyl-1,2,4-triazol-3-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N1=CN(CC=2C=CC=CC=2)N=C1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1=CC=CC=C1 MDTDCBJLYUNWJT-UHFFFAOYSA-N 0.000 claims description 2
• LDIXKOVZSSLYMJ-UHFFFAOYSA-N 6-[(1-ethylimidazol-2-yl)methoxy]-3-(4-methylphenyl)-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CCN1C=CN=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=C(C)C=C1 LDIXKOVZSSLYMJ-UHFFFAOYSA-N 0.000 claims description 2
• RIXHBDMRLPVSEE-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 RIXHBDMRLPVSEE-UHFFFAOYSA-N 0.000 claims description 2
• VJYHJBZTXOLVMU-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-propan-2-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N12N=C(OCC3=NN(C)C=N3)C(C(C)C)=CC2=NN=C1C1=CC=CC=C1 VJYHJBZTXOLVMU-UHFFFAOYSA-N 0.000 claims description 2
• JKWLECBCROPOMV-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CN=CC=2)=N1 JKWLECBCROPOMV-UHFFFAOYSA-N 0.000 claims description 2
• NABBTMMFXIVNLD-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-pyrrolidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)N2CCCC2)=N1 NABBTMMFXIVNLD-UHFFFAOYSA-N 0.000 claims description 2
• DEEIDXBPQNUNGZ-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2SC=CC=2)=N1 DEEIDXBPQNUNGZ-UHFFFAOYSA-N 0.000 claims description 2
• RYHZVZSDMUNURQ-UHFFFAOYSA-N 6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-thiophen-3-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C2=CSC=C2)=N1 RYHZVZSDMUNURQ-UHFFFAOYSA-N 0.000 claims description 2
• SSQNGBXFKQFNSC-UHFFFAOYSA-N 6-[(1-methylimidazol-4-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SSQNGBXFKQFNSC-UHFFFAOYSA-N 0.000 claims description 2
• LHMYCKKRCBXCBI-UHFFFAOYSA-N 6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 LHMYCKKRCBXCBI-UHFFFAOYSA-N 0.000 claims description 2
• VBIUWFXJSGIEKL-UHFFFAOYSA-N 6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-7-propan-2-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N12N=C(OCC=3N(N=CN=3)C)C(C(C)C)=CC2=NN=C1C1=CC=CC=C1 VBIUWFXJSGIEKL-UHFFFAOYSA-N 0.000 claims description 2
• NJSIZMUEMYUQFZ-UHFFFAOYSA-N 6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-7-phenyl-3-pyridin-3-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=CN=C1 NJSIZMUEMYUQFZ-UHFFFAOYSA-N 0.000 claims description 2
• FLWIFTLBIHIEOW-UHFFFAOYSA-N 6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-7-thiophen-3-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2=CSC=C2)=NN2C1=NN=C2 FLWIFTLBIHIEOW-UHFFFAOYSA-N 0.000 claims description 2
• CXJRNDIMOTWWJA-UHFFFAOYSA-N 6-[(2-methyltetrazol-5-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 CXJRNDIMOTWWJA-UHFFFAOYSA-N 0.000 claims description 2
• GCVRJJZTGPVPAD-UHFFFAOYSA-N 6-[(3-methylimidazol-4-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 GCVRJJZTGPVPAD-UHFFFAOYSA-N 0.000 claims description 2
• LKJQVAJICVZOQT-UHFFFAOYSA-N 6-[(3-methylpyridin-2-yl)methoxy]-3-phenyl-7-piperidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CC1=CC=CN=C1COC(C(=C1)N2CCCCC2)=NN2C1=NN=C2C1=CC=CC=C1 LKJQVAJICVZOQT-UHFFFAOYSA-N 0.000 claims description 2
• LTHHNAJLVMPSRA-UHFFFAOYSA-N 6-[(4-methyl-1,2,4-triazol-3-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NN=C1COC(C(=C1)C=2C=CC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 LTHHNAJLVMPSRA-UHFFFAOYSA-N 0.000 claims description 2
• MGIHNTDQHRDPQF-UHFFFAOYSA-N 6-[(5-methyl-1h-1,2,4-triazol-3-yl)methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CC1=NNC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 MGIHNTDQHRDPQF-UHFFFAOYSA-N 0.000 claims description 2
• USZJBAPIJYTILI-UHFFFAOYSA-N 6-[[1-(1-methylpiperidin-4-yl)-1,2,4-triazol-3-yl]methoxy]-3,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1CN(C)CCC1N1N=C(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)N=C1 USZJBAPIJYTILI-UHFFFAOYSA-N 0.000 claims description 2
• YIXXOJVMOQDGNI-UHFFFAOYSA-N 7,8-dimethyl-3-phenyl-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1N2C(C=3C=CC=CC=3)=NN=C2C(C)=C(C)C=1OCC1=CC=CC=N1 YIXXOJVMOQDGNI-UHFFFAOYSA-N 0.000 claims description 2
• OXPVLJHRJBFDQB-UHFFFAOYSA-N 7-(1-methylcyclobutyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C2(C)CCC2)=N1 OXPVLJHRJBFDQB-UHFFFAOYSA-N 0.000 claims description 2
• CFOOYYMKAMEJBL-UHFFFAOYSA-N 7-(1-methylcyclobutyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2(C)CCC2)=NN2C1=NN=C2C1=CC=CC=C1 CFOOYYMKAMEJBL-UHFFFAOYSA-N 0.000 claims description 2
• XMTHRPGPSUJCCG-UHFFFAOYSA-N 7-(1-methylcyclopentyl)-6-[(3-methylpyridin-2-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CC1=CC=CN=C1COC(C(=C1)C2(C)CCCC2)=NN2C1=NN=C2C1=CC=CC=C1 XMTHRPGPSUJCCG-UHFFFAOYSA-N 0.000 claims description 2
• KRNIZJFCJNEAMC-UHFFFAOYSA-N 7-(1-methylcyclopropyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C2(C)CC2)=N1 KRNIZJFCJNEAMC-UHFFFAOYSA-N 0.000 claims description 2
• YUNYEPKAWNWTCM-UHFFFAOYSA-N 7-(2-methylbutan-2-yl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N12N=C(OCC3=NN(C)C=N3)C(C(C)(C)CC)=CC2=NN=C1C1=CC=CC=C1 YUNYEPKAWNWTCM-UHFFFAOYSA-N 0.000 claims description 2
• XPMNJDCXQMPCIO-UHFFFAOYSA-N 7-(5-chlorothiophen-2-yl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C=2SC(Cl)=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 XPMNJDCXQMPCIO-UHFFFAOYSA-N 0.000 claims description 2
• YTVKHJZQLGIKCE-UHFFFAOYSA-N 7-(furan-2-yl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C=2OC=CC=2)=N1 YTVKHJZQLGIKCE-UHFFFAOYSA-N 0.000 claims description 2
• QUDANIBRZAJEHA-UHFFFAOYSA-N 7-(furan-2-yl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C=2OC=CC=2)=NN2C1=NN=C2C1=CC=CC=C1 QUDANIBRZAJEHA-UHFFFAOYSA-N 0.000 claims description 2
• WFQGCGNGOVKICN-UHFFFAOYSA-N 7-cyclobutyl-3-phenyl-6-(1h-1,2,4-triazol-5-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1C=NNC=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C=C1C1CCC1 WFQGCGNGOVKICN-UHFFFAOYSA-N 0.000 claims description 2
• RJTIKEAHSDDBFU-UHFFFAOYSA-N 7-cyclobutyl-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C2CCC2)=N1 RJTIKEAHSDDBFU-UHFFFAOYSA-N 0.000 claims description 2
• NRVMDUPYHCGRQW-UHFFFAOYSA-N 7-cyclobutyl-8-methyl-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N1=CN(C)N=C1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C(C)=C1C1CCC1 NRVMDUPYHCGRQW-UHFFFAOYSA-N 0.000 claims description 2
• FFPOLBVOCSSYCJ-UHFFFAOYSA-N 7-cyclobutyl-8-methyl-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1C=NN(C)C=1COC1=NN2C(C=3C=CC=CC=3)=NN=C2C(C)=C1C1CCC1 FFPOLBVOCSSYCJ-UHFFFAOYSA-N 0.000 claims description 2
• XXDJXHYFDGGRRZ-UHFFFAOYSA-N 7-cyclohexyl-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C=CC=CC=2)C2CCCCC2)=N1 XXDJXHYFDGGRRZ-UHFFFAOYSA-N 0.000 claims description 2
• YLPHFEFMBAMSKS-UHFFFAOYSA-N 7-cyclohexyl-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2CCCCC2)=NN2C1=NN=C2C1=CC=CC=C1 YLPHFEFMBAMSKS-UHFFFAOYSA-N 0.000 claims description 2
• FPKLVZXGBZJJNX-UHFFFAOYSA-N 7-cyclopentyl-3-(2,4-difluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC(F)=CC=2)F)C2CCCC2)=N1 FPKLVZXGBZJJNX-UHFFFAOYSA-N 0.000 claims description 2
• SXFKAOHJTVSOPJ-UHFFFAOYSA-N 7-cyclopentyl-3-(2,4-difluorophenyl)-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C2CCCC2)=NN2C1=NN=C2C1=CC=C(F)C=C1F SXFKAOHJTVSOPJ-UHFFFAOYSA-N 0.000 claims description 2
• OHSIIKNYYFSTJF-UHFFFAOYSA-N 7-cyclopentyl-3-(2-fluorophenyl)-6-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1C=NC(COC=2C(=CC3=NN=C(N3N=2)C=2C(=CC=CC=2)F)C2CCCC2)=N1 OHSIIKNYYFSTJF-UHFFFAOYSA-N 0.000 claims description 2
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