JPWO2020005873A5 - - Google Patents
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- Publication number
- JPWO2020005873A5 JPWO2020005873A5 JP2020572895A JP2020572895A JPWO2020005873A5 JP WO2020005873 A5 JPWO2020005873 A5 JP WO2020005873A5 JP 2020572895 A JP2020572895 A JP 2020572895A JP 2020572895 A JP2020572895 A JP 2020572895A JP WO2020005873 A5 JPWO2020005873 A5 JP WO2020005873A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridazine
- triazolo
- phenol
- pyrazole
- tetramethylpiperidine
- Prior art date
- 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
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- -1 1,2,5,6-tetrahydropyridinyl Chemical group 0.000 claims 278
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 113
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 21
- ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 claims 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 7
- JELQZSVKOONUKD-UHFFFAOYSA-N phenol dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1.OC1=CC=CC=C1 JELQZSVKOONUKD-UHFFFAOYSA-N 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 4
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 3
- WFJZBOIOPMOUCB-UHFFFAOYSA-N pyridazine;hydrochloride Chemical compound Cl.C1=CC=NN=C1 WFJZBOIOPMOUCB-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- PUBSMDUBHLYMIX-UHFFFAOYSA-N phenol;dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1 PUBSMDUBHLYMIX-UHFFFAOYSA-N 0.000 claims 2
- DNRXKUPYJHTZJE-UHFFFAOYSA-N phenol;hydrobromide Chemical compound Br.OC1=CC=CC=C1 DNRXKUPYJHTZJE-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
- YOUQXTMNMLEWCM-UHFFFAOYSA-N 2-(1-piperidin-4-ylpyrazolo[3,4-c]pyridazin-5-yl)-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=NN=C2N(N=CC2=C1)C1CCNCC1 YOUQXTMNMLEWCM-UHFFFAOYSA-N 0.000 claims 1
- FVXQGVZLCVMFLE-UHFFFAOYSA-N 2-(1-piperidin-4-ylpyrazolo[3,4-c]pyridazin-5-yl)-5-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.Oc1cc(ccc1-c1cc2cnn(C3CCNCC3)c2nn1)-c1cn[nH]c1 FVXQGVZLCVMFLE-UHFFFAOYSA-N 0.000 claims 1
- OLYLBVGBSDAEHV-UHFFFAOYSA-N 2-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.Oc1ccccc1-c1cn[nH]c1 OLYLBVGBSDAEHV-UHFFFAOYSA-N 0.000 claims 1
- GDUVBKSVYWFWGV-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CNN=C1 GDUVBKSVYWFWGV-UHFFFAOYSA-N 0.000 claims 1
- NJYKXOJRBBASGJ-UHFFFAOYSA-N 2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]-5-(1,2,4-thiadiazol-5-yl)phenol Chemical compound CC1(NC(CC(C1)N1N=NC2=C1N=NC(=C2)C1=C(C=C(C=C1)C1=NC=NS1)O)(C)C)C NJYKXOJRBBASGJ-UHFFFAOYSA-N 0.000 claims 1
- QFFQDEGMTBBEMV-UHFFFAOYSA-N 2-methyl-6-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]-1H-benzimidazol-5-ol Chemical compound C1(NC(CC(N2C3=NN=C(C4=C(O)C=C5NC(=NC5=C4)C)C=C3N=N2)C1)(C)C)(C)C QFFQDEGMTBBEMV-UHFFFAOYSA-N 0.000 claims 1
- VTBHBWBXALXSJK-UHFFFAOYSA-N 3-methyl-6-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]benzimidazol-5-ol Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=C(O)C=C3N(C=NC3=C1)C)N=N2)(C)C VTBHBWBXALXSJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- YFWCCAXUEVEWBF-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazolo[3,4-c]pyridazin-5-yl]phenol Chemical compound CC1(NC(CC(C1)N1C2=C(C=N1)C=C(C1=CC=C(C=3C=NNC=3)C=C1O)N=N2)(C)C)C YFWCCAXUEVEWBF-UHFFFAOYSA-N 0.000 claims 1
- ZEZSKTLJQHOQSU-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethyl-1,3-dihydropyridin-4-yl)thieno[3,2-c]pyridazin-3-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)C(=CS2)C=1CC(NC(C=1)(C)C)(C)C ZEZSKTLJQHOQSU-UHFFFAOYSA-N 0.000 claims 1
- GIYSUKBTCIPXND-UHFFFAOYSA-N 5-(4-methylpyrazol-1-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound C1(C)(CC(N2C3=C(N=N2)C=C(C2=C(C=C(N4C=C(C=N4)C)C=C2)O)N=N3)CC(C)(C)N1)C GIYSUKBTCIPXND-UHFFFAOYSA-N 0.000 claims 1
- WLVVXZGHMCKLHT-UHFFFAOYSA-N Br.FC1=CC(=C(C=C1C1=CC=C(C=C1)O)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound Br.FC1=CC(=C(C=C1C1=CC=C(C=C1)O)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C WLVVXZGHMCKLHT-UHFFFAOYSA-N 0.000 claims 1
- PXVVRAVHOUCNOQ-UHFFFAOYSA-N BrC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound BrC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C PXVVRAVHOUCNOQ-UHFFFAOYSA-N 0.000 claims 1
- RMBKEKVHYKCBQU-UHFFFAOYSA-N C(=O)OC1=C(C=CC(=C1)C1=NC=C(C=C1)OC(F)F)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(=O)OC1=C(C=CC(=C1)C1=NC=C(C=C1)OC(F)F)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C RMBKEKVHYKCBQU-UHFFFAOYSA-N 0.000 claims 1
- IETUBBFAMCEKDY-UHFFFAOYSA-N C(C)N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(C)N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C IETUBBFAMCEKDY-UHFFFAOYSA-N 0.000 claims 1
- XXNQVQXOGYTQAO-UHFFFAOYSA-N C(CC)N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(CC)N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C XXNQVQXOGYTQAO-UHFFFAOYSA-N 0.000 claims 1
- WGGHKOLLPVNZPN-VPYROQPTSA-N C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C=1C=C2C(=NN=1)N(N=C2)C1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C=1C=C2C(=NN=1)N(N=C2)C1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] WGGHKOLLPVNZPN-VPYROQPTSA-N 0.000 claims 1
- AASTXZYIDCCVHJ-UHFFFAOYSA-N C1(C)(CC(N2C3=C(C=C2)N=C(C2=CC(F)=C(C4=CNN=C4)C=C2F)C=N3)CC(C)(C)N1)C Chemical compound C1(C)(CC(N2C3=C(C=C2)N=C(C2=CC(F)=C(C4=CNN=C4)C=C2F)C=N3)CC(C)(C)N1)C AASTXZYIDCCVHJ-UHFFFAOYSA-N 0.000 claims 1
- ZMKXJPXWSNQLIU-UHFFFAOYSA-N C1(CC1)N1C(C=C(C=C1)C1=CC(=C(C=C1)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)O)=O Chemical compound C1(CC1)N1C(C=C(C=C1)C1=CC(=C(C=C1)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)O)=O ZMKXJPXWSNQLIU-UHFFFAOYSA-N 0.000 claims 1
- MDLNGIZCASBHMN-UHFFFAOYSA-N C1(NC(CC(C1)N1C2=NN=C(C=C2N=N1)C1=CC=C(C=2C=CNC=2)C=C1O)(C)C)(C)C Chemical compound C1(NC(CC(C1)N1C2=NN=C(C=C2N=N1)C1=CC=C(C=2C=CNC=2)C=C1O)(C)C)(C)C MDLNGIZCASBHMN-UHFFFAOYSA-N 0.000 claims 1
- HGNVKFMIZLRXNG-UHFFFAOYSA-N C1(NC(CC(C2=CSC3=CC(C4=CC=C(C=5C=NNC=5)C=C4O)=NN=C23)C1)(C)C)(C)C Chemical compound C1(NC(CC(C2=CSC3=CC(C4=CC=C(C=5C=NNC=5)C=C4O)=NN=C23)C1)(C)C)(C)C HGNVKFMIZLRXNG-UHFFFAOYSA-N 0.000 claims 1
- DMSDXTCCTHPVTI-UHFFFAOYSA-N C1CN(CCN1)C1=CNC2=C1N=NC(=C2)C1=CC=C(C=2C=NNC=2)C=C1O Chemical compound C1CN(CCN1)C1=CNC2=C1N=NC(=C2)C1=CC=C(C=2C=NNC=2)C=C1O DMSDXTCCTHPVTI-UHFFFAOYSA-N 0.000 claims 1
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- AWMVRQRPJPJTOJ-UHFFFAOYSA-N CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3C=N2)C4=C(C=C(C=C4)C5=CN=CN=C5)O)C.Cl Chemical compound CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3C=N2)C4=C(C=C(C=C4)C5=CN=CN=C5)O)C.Cl AWMVRQRPJPJTOJ-UHFFFAOYSA-N 0.000 claims 1
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