JP2011503166A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011503166A5 JP2011503166A5 JP2010533666A JP2010533666A JP2011503166A5 JP 2011503166 A5 JP2011503166 A5 JP 2011503166A5 JP 2010533666 A JP2010533666 A JP 2010533666A JP 2010533666 A JP2010533666 A JP 2010533666A JP 2011503166 A5 JP2011503166 A5 JP 2011503166A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- oxo
- oxopiperazin
- fluoro
- dimethyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 46
- -1 bicyclo [1.1.1] pentyl Chemical group 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 229910052717 sulfur Inorganic materials 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000003566 oxetanyl group Chemical group 0.000 claims 4
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 claims 3
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 claims 3
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- ZSLJRVNJMQHIDL-UHFFFAOYSA-N 3-[[3-[4-(2-chlorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C)C(=O)N[NH+]=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(CC2)C=2C(=CC=CC=2)Cl)=C1 ZSLJRVNJMQHIDL-UHFFFAOYSA-N 0.000 claims 2
- KTMAUYPORXXOEN-DYVFJYSZSA-N 3-[[4-fluoro-3-[(3r)-3-methyl-5-oxo-4-[(3s)-oxolan-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1[C@H]1CCOC1 KTMAUYPORXXOEN-DYVFJYSZSA-N 0.000 claims 2
- KTMAUYPORXXOEN-GUYCJALGSA-N 3-[[4-fluoro-3-[(3s)-3-methyl-5-oxo-4-[(3s)-oxolan-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1[C@H]1CCOC1 KTMAUYPORXXOEN-GUYCJALGSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- AOSBZJAZXMKZKC-COBSGTNCSA-N (1s,4s)-5-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-phenyl-2,5-diazabicyclo[2.2.1]heptan-3-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@]1(C[C@@]2([H])C(=O)N1C=1C=CC=CC=1)[H])N2C(=O)C(C(=CC=1)F)=CC=1CC1=NNC(=O)C(C)=C1C AOSBZJAZXMKZKC-COBSGTNCSA-N 0.000 claims 1
- IVNDNVJERJOWTR-CXAGYDPISA-N (6r,9ar)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-6-methyl-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound C([C@H]1CCC[C@H](N1C(=O)C1)C)N1C(=O)C(C(=CC=1)F)=CC=1CC1=NNC(=O)C(C)=C1C IVNDNVJERJOWTR-CXAGYDPISA-N 0.000 claims 1
- NAWNZCRDVACEMZ-YLCXCWDSSA-N (6r,9as)-2-[2-fluoro-5-[[6-oxo-5-(trifluoromethyl)-1h-pyridazin-2-ium-3-yl]methyl]benzoyl]-6-methyl-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H]1CCC[C@H](N1C(=O)C1)C)N1C(=O)C(C(=CC=1)F)=CC=1CC=1C=C(C(F)(F)F)C(=O)N[NH+]=1 NAWNZCRDVACEMZ-YLCXCWDSSA-N 0.000 claims 1
- KOOMYNJXEUHAAR-YNDBEVAQSA-N (6r,9as)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-2-ium-3-yl)methyl]-2-fluorobenzoyl]-6-methyl-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H]1CCC[C@H](N1C(=O)C1)C)N1C(=O)C(C(=CC=1)F)=CC=1CC1=[NH+]NC(=O)C(C)=C1C KOOMYNJXEUHAAR-YNDBEVAQSA-N 0.000 claims 1
- IVNDNVJERJOWTR-GUYCJALGSA-N (6s,9as)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-6-methyl-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound C([C@@H]1CCC[C@@H](N1C(=O)C1)C)N1C(=O)C(C(=CC=1)F)=CC=1CC1=NNC(=O)C(C)=C1C IVNDNVJERJOWTR-GUYCJALGSA-N 0.000 claims 1
- MYYKSLDFPZKDHN-CQSZACIVSA-N (9ar)-2-[2-fluoro-5-[[6-oxo-5-(trifluoromethyl)-1h-pyridazin-3-yl]methyl]benzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound C1=C(C(=O)N2CC(=O)N3CCCC[C@@H]3C2)C(F)=CC=C1CC=1C=C(C(F)(F)F)C(=O)NN=1 MYYKSLDFPZKDHN-CQSZACIVSA-N 0.000 claims 1
- VJTRXXZCGWHXKE-MRXNPFEDSA-N (9ar)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCC[C@@H]3C2)=N1 VJTRXXZCGWHXKE-MRXNPFEDSA-N 0.000 claims 1
- IXLWKWHLDXINFB-PKLMIRHRSA-N (9ar)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCC[C@@H]3C2)=N1 IXLWKWHLDXINFB-PKLMIRHRSA-N 0.000 claims 1
- RLKKGLSAFARXAK-UQKRIMTDSA-N (9as)-2-[2-fluoro-5-[[4-methyl-6-oxo-5-(trifluoromethyl)-1h-pyridazin-1-ium-3-yl]methyl]benzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N3CCCC[C@H]3C2)=C1 RLKKGLSAFARXAK-UQKRIMTDSA-N 0.000 claims 1
- MYYKSLDFPZKDHN-AWEZNQCLSA-N (9as)-2-[2-fluoro-5-[[6-oxo-5-(trifluoromethyl)-1h-pyridazin-3-yl]methyl]benzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound C1=C(C(=O)N2CC(=O)N3CCCC[C@H]3C2)C(F)=CC=C1CC=1C=C(C(F)(F)F)C(=O)NN=1 MYYKSLDFPZKDHN-AWEZNQCLSA-N 0.000 claims 1
- VJTRXXZCGWHXKE-INIZCTEOSA-N (9as)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCC[C@H]3C2)=N1 VJTRXXZCGWHXKE-INIZCTEOSA-N 0.000 claims 1
- IXLWKWHLDXINFB-NTISSMGPSA-N (9as)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCC[C@H]3C2)=N1 IXLWKWHLDXINFB-NTISSMGPSA-N 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- UYJVDKNNVDGODK-UHFFFAOYSA-N 1-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-2-ium-3-yl)methyl]-2-fluorobenzoyl]-4-propan-2-yl-1,4-diazepan-5-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC(=O)N(C(C)C)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)N[NH+]=2)C)=CC=C1F UYJVDKNNVDGODK-UHFFFAOYSA-N 0.000 claims 1
- XGPUZFFYLPSQGR-UHFFFAOYSA-N 1-cyclohexyl-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-2-ium-3-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-2-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CCC2)=[NH+]1 XGPUZFFYLPSQGR-UHFFFAOYSA-N 0.000 claims 1
- HYCAGUHRBSKSLG-UHFFFAOYSA-N 1-cyclopropyl-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-2-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC3)CCC2)=N1 HYCAGUHRBSKSLG-UHFFFAOYSA-N 0.000 claims 1
- MYYKSLDFPZKDHN-UHFFFAOYSA-N 2-[2-fluoro-5-[[6-oxo-5-(trifluoromethyl)-1h-pyridazin-3-yl]methyl]benzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound C1=C(C(=O)N2CC(=O)N3CCCCC3C2)C(F)=CC=C1CC=1C=C(C(F)(F)F)C(=O)NN=1 MYYKSLDFPZKDHN-UHFFFAOYSA-N 0.000 claims 1
- IXLWKWHLDXINFB-UHFFFAOYSA-N 2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-2-ium-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCCC3C2)=[NH+]1 IXLWKWHLDXINFB-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- OFRDHELOEGITNL-CQSZACIVSA-N 3-[(2r)-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-methyl-6-oxopiperazin-1-yl]-5-fluorobenzonitrile Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC(F)=CC(C#N)=C1 OFRDHELOEGITNL-CQSZACIVSA-N 0.000 claims 1
- KUAYOHCIBZUBSQ-UHFFFAOYSA-N 3-[[2-bromo-5-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1=C(C)C(=O)NN=C1CC1=CC(C(=O)N2CC(=O)N(C3CCCC3)CC2)=C(F)C=C1Br KUAYOHCIBZUBSQ-UHFFFAOYSA-N 0.000 claims 1
- LOVPKEGVBQPBKX-UHFFFAOYSA-N 3-[[3-(3,3-dimethyl-5-oxo-4-phenylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(C)(C)N(C=3C=CC=CC=3)C(=O)C2)=N1 LOVPKEGVBQPBKX-UHFFFAOYSA-N 0.000 claims 1
- COACDFVSJZKJQH-UHFFFAOYSA-N 3-[[3-(4-butyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(=O)N(CCCC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F COACDFVSJZKJQH-UHFFFAOYSA-N 0.000 claims 1
- HKCNWPZOGXXWCQ-UHFFFAOYSA-N 3-[[3-(4-cyclobutyl-3-ethyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CCC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 HKCNWPZOGXXWCQ-UHFFFAOYSA-N 0.000 claims 1
- QPMCMWZABOOUSH-UHFFFAOYSA-N 3-[[3-(4-cyclobutyl-3-methyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 QPMCMWZABOOUSH-UHFFFAOYSA-N 0.000 claims 1
- XNDNKVJVVFHDDV-UHFFFAOYSA-N 3-[[3-(4-cyclobutyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCC3)CC2)=[NH+]1 XNDNKVJVVFHDDV-UHFFFAOYSA-N 0.000 claims 1
- PCJPQCDNNKQSTD-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-2,2-dimethyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2C(C(=O)N(C3CCCCC3)CC2)(C)C)=N1 PCJPQCDNNKQSTD-UHFFFAOYSA-N 0.000 claims 1
- QOMHXKYAOKTISN-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-2,2-dimethyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2C(CN(C(=O)C2)C2CCCCC2)(C)C)=N1 QOMHXKYAOKTISN-UHFFFAOYSA-N 0.000 claims 1
- JFUFSFAORCRIIJ-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-2-methyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O=C1C(C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)N[NH+]=3)C)C=2)F)CCN1C1CCCCC1 JFUFSFAORCRIIJ-UHFFFAOYSA-N 0.000 claims 1
- HZEUKGTVBAQKDU-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-ethyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CCC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCCC1 HZEUKGTVBAQKDU-UHFFFAOYSA-N 0.000 claims 1
- BVGFIJPNSZVWGK-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-methyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)[NH2+]N=3)C)C=2)F)CC(=O)N1C1CCCCC1 BVGFIJPNSZVWGK-UHFFFAOYSA-N 0.000 claims 1
- YVVYCBBBSDGTLV-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=[NH+]1 YVVYCBBBSDGTLV-UHFFFAOYSA-N 0.000 claims 1
- FABNTBHOPIPFBX-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-ethyl-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C(C(F)(F)F)=C(CC)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 FABNTBHOPIPFBX-UHFFFAOYSA-N 0.000 claims 1
- YQYUDVHOZVXQSI-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-ethyl-5-methyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CCC1=C(C)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(C3CCCCC3)CC2)=C1 YQYUDVHOZVXQSI-UHFFFAOYSA-N 0.000 claims 1
- VOGJKJAPBSYXQI-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(C3CCCCC3)CC2)=C1 VOGJKJAPBSYXQI-UHFFFAOYSA-N 0.000 claims 1
- WVMRNUDBPVLKHH-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=C(C(=O)N2CC(=O)N(C3CCCCC3)CC2)C(F)=CC=C1CC=1C=C(C(F)(F)F)C(=O)N[NH+]=1 WVMRNUDBPVLKHH-UHFFFAOYSA-N 0.000 claims 1
- CZQUMIARIUPLMB-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-ethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 CZQUMIARIUPLMB-UHFFFAOYSA-N 0.000 claims 1
- DDUVVTVKVNGTJL-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-ethyl-4-methyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(CC)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 DDUVVTVKVNGTJL-UHFFFAOYSA-N 0.000 claims 1
- XTZZUUYOYNMEEQ-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-ethyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CCC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCC1 XTZZUUYOYNMEEQ-UHFFFAOYSA-N 0.000 claims 1
- ITKKLIWBRDSPFE-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-methyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)N[NH+]=3)C)C=2)F)CC(=O)N1C1CCCC1 ITKKLIWBRDSPFE-UHFFFAOYSA-N 0.000 claims 1
- BUBGQZGDPNUYFT-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-(1,1,2,2,2-pentafluoroethyl)-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=C(C(=O)N2CC(=O)N(C3CCCC3)CC2)C(F)=CC=C1CC=1C=C(C(F)(F)C(F)(F)F)C(=O)N[NH+]=1 BUBGQZGDPNUYFT-UHFFFAOYSA-N 0.000 claims 1
- RTWRQZMYIKICPE-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-(1,1,2,2,2-pentafluoroethyl)-1h-pyridazin-6-one Chemical compound C1=C(C(=O)N2CC(=O)N(C3CCCC3)CC2)C(F)=CC=C1CC=1C=C(C(F)(F)C(F)(F)F)C(=O)NN=1 RTWRQZMYIKICPE-UHFFFAOYSA-N 0.000 claims 1
- VXOAPGOXHBTEME-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=C(C(=O)N2CC(=O)N(C3CCCC3)CC2)C(F)=CC=C1CC=1C=C(C(F)(F)F)C(=O)N[NH+]=1 VXOAPGOXHBTEME-UHFFFAOYSA-N 0.000 claims 1
- HYRWEVBMZNIWBD-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-ethyl-1H-pyridazin-6-one Chemical compound N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCC3)CC2)=N1 HYRWEVBMZNIWBD-UHFFFAOYSA-N 0.000 claims 1
- YXTQYXBZLZLWQX-UHFFFAOYSA-N 3-[[3-(4-ethyl-3-methyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N(CC)C(C)CN1C(=O)C1=CC(CC=2C(=C(C)C(=O)N[NH+]=2)C)=CC=C1F YXTQYXBZLZLWQX-UHFFFAOYSA-N 0.000 claims 1
- FLSNNVYIUJBKNC-UHFFFAOYSA-N 3-[[3-(4-ethyl-3-methyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N(CC)C(C)CN1C(=O)C1=CC(CC=2C(=C(C(=O)[NH2+]N=2)C(F)(F)F)C)=CC=C1F FLSNNVYIUJBKNC-UHFFFAOYSA-N 0.000 claims 1
- XXMHLYAIPBTIMO-UHFFFAOYSA-N 3-[[3-(4-ethyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(=O)N(CC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F XXMHLYAIPBTIMO-UHFFFAOYSA-N 0.000 claims 1
- FQNRUQXXGXFMIP-UHFFFAOYSA-N 3-[[3-(4-ethyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N(CC)CCN1C(=O)C1=CC(CC=2C(=C(C(=O)[NH2+]N=2)C(F)(F)F)C)=CC=C1F FQNRUQXXGXFMIP-UHFFFAOYSA-N 0.000 claims 1
- NDQANTXTPTWCLI-UHFFFAOYSA-N 3-[[3-(4-ethyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C1C(=O)N(CC)CCN1C(=O)C1=CC(CC=2C(=C(C(=O)NN=2)C(F)(F)F)C)=CC=C1F NDQANTXTPTWCLI-UHFFFAOYSA-N 0.000 claims 1
- NLSUARWHLBXYJY-GFCCVEGCSA-N 3-[[3-[(3r)-4-(3,3-difluorocyclobutyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CC(F)(F)C1 NLSUARWHLBXYJY-GFCCVEGCSA-N 0.000 claims 1
- UXRAOAPQRGYPDA-CYBMUJFWSA-N 3-[[3-[(3r)-4-(3,4-difluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(F)C(F)=C1 UXRAOAPQRGYPDA-CYBMUJFWSA-N 0.000 claims 1
- NBSQPZYCIZDIFX-CYBMUJFWSA-N 3-[[3-[(3r)-4-(3,5-difluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC(F)=CC(F)=C1 NBSQPZYCIZDIFX-CYBMUJFWSA-N 0.000 claims 1
- SHPVVKUVNDZXES-CYBMUJFWSA-N 3-[[3-[(3r)-4-(3-chloro-2-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=CC(Cl)=C1F SHPVVKUVNDZXES-CYBMUJFWSA-N 0.000 claims 1
- CONQVQRNADZQIF-CYBMUJFWSA-N 3-[[3-[(3r)-4-(3-chloro-4-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(F)C(Cl)=C1 CONQVQRNADZQIF-CYBMUJFWSA-N 0.000 claims 1
- SULIUWKSJYODEG-CYBMUJFWSA-N 3-[[3-[(3r)-4-(3-chloro-5-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC(F)=CC(Cl)=C1 SULIUWKSJYODEG-CYBMUJFWSA-N 0.000 claims 1
- JEEITVVSQRSAGI-CYBMUJFWSA-N 3-[[3-[(3r)-4-(4-chloro-2-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(Cl)C=C1F JEEITVVSQRSAGI-CYBMUJFWSA-N 0.000 claims 1
- JZYJNTVTLDMUNI-CYBMUJFWSA-N 3-[[3-[(3r)-4-(4-chloro-3-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(Cl)C(F)=C1 JZYJNTVTLDMUNI-CYBMUJFWSA-N 0.000 claims 1
- HETXTLWLCXWMEI-CYBMUJFWSA-N 3-[[3-[(3r)-4-(5-chloro-2-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC(Cl)=CC=C1F HETXTLWLCXWMEI-CYBMUJFWSA-N 0.000 claims 1
- HKCNWPZOGXXWCQ-QGZVFWFLSA-N 3-[[3-[(3r)-4-cyclobutyl-3-ethyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1CC)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 HKCNWPZOGXXWCQ-QGZVFWFLSA-N 0.000 claims 1
- JNLAUAOSNHRVNX-CQSZACIVSA-N 3-[[3-[(3r)-4-cyclopentyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCC1 JNLAUAOSNHRVNX-CQSZACIVSA-N 0.000 claims 1
- AKIGDHHFVMHBQD-CYBMUJFWSA-N 3-[[3-[(3r)-4-cyclopentyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC3=NNC(=O)C(=C3)C(F)(F)F)C=2)F)CC(=O)N1C1CCCC1 AKIGDHHFVMHBQD-CYBMUJFWSA-N 0.000 claims 1
- DTRVINCMYIVRML-LLVKDONJSA-N 3-[[3-[(3r)-4-ethyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C1C(=O)N(CC)[C@H](C)CN1C(=O)C1=CC(CC=2C(=C(C(=O)NN=2)C(F)(F)F)C)=CC=C1F DTRVINCMYIVRML-LLVKDONJSA-N 0.000 claims 1
- NLSUARWHLBXYJY-LBPRGKRZSA-N 3-[[3-[(3s)-4-(3,3-difluorocyclobutyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CC(F)(F)C1 NLSUARWHLBXYJY-LBPRGKRZSA-N 0.000 claims 1
- JZYJNTVTLDMUNI-ZDUSSCGKSA-N 3-[[3-[(3s)-4-(4-chloro-3-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(Cl)C(F)=C1 JZYJNTVTLDMUNI-ZDUSSCGKSA-N 0.000 claims 1
- HKCNWPZOGXXWCQ-KRWDZBQOSA-N 3-[[3-[(3s)-4-cyclobutyl-3-ethyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1CC)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 HKCNWPZOGXXWCQ-KRWDZBQOSA-N 0.000 claims 1
- QPMCMWZABOOUSH-ZDUSSCGKSA-N 3-[[3-[(3s)-4-cyclobutyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 QPMCMWZABOOUSH-ZDUSSCGKSA-N 0.000 claims 1
- AKIGDHHFVMHBQD-ZDUSSCGKSA-N 3-[[3-[(3s)-4-cyclopentyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC3=NNC(=O)C(=C3)C(F)(F)F)C=2)F)CC(=O)N1C1CCCC1 AKIGDHHFVMHBQD-ZDUSSCGKSA-N 0.000 claims 1
- DTRVINCMYIVRML-NSHDSACASA-N 3-[[3-[(3s)-4-ethyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C1C(=O)N(CC)[C@@H](C)CN1C(=O)C1=CC(CC=2C(=C(C(=O)NN=2)C(F)(F)F)C)=CC=C1F DTRVINCMYIVRML-NSHDSACASA-N 0.000 claims 1
- RHYKAJQGNSJSMC-QHCPKHFHSA-N 3-[[3-[(5r)-4-cyclopentyl-3-oxo-5-propan-2-ylpiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C(C)C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCC1 RHYKAJQGNSJSMC-QHCPKHFHSA-N 0.000 claims 1
- NDMNGRRBMZDFDQ-UHFFFAOYSA-N 3-[[3-[4-(1-benzothiophen-3-yl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C=3C4=CC=CC=C4SC=3)CC2)=N1 NDMNGRRBMZDFDQ-UHFFFAOYSA-N 0.000 claims 1
- YTTDJMQEUGJITH-UHFFFAOYSA-N 3-[[3-[4-(2,2-difluoro-1-phenylethyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C(C(F)F)C1=CC=CC=C1 YTTDJMQEUGJITH-UHFFFAOYSA-N 0.000 claims 1
- DYHOWDCVECDOGP-UHFFFAOYSA-N 3-[[3-[4-(2,2-difluoro-1-phenylethyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C(C(F)F)C=3C=CC=CC=3)CC2)=[NH+]1 DYHOWDCVECDOGP-UHFFFAOYSA-N 0.000 claims 1
- KVNMRNNXCRCGQC-UHFFFAOYSA-N 3-[[3-[4-(2,2-difluoro-1-pyridin-3-ylethyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C(C(F)F)C=3C=NC=CC=3)CC2)=[NH+]1 KVNMRNNXCRCGQC-UHFFFAOYSA-N 0.000 claims 1
- CIXPEFLLCZOCJM-UHFFFAOYSA-N 3-[[3-[4-(2,2-dimethyloxan-4-yl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(C)(C)OCC3)CC2)=N1 CIXPEFLLCZOCJM-UHFFFAOYSA-N 0.000 claims 1
- GQJFXNDYYVTQDS-UHFFFAOYSA-N 3-[[3-[4-(2,3-dihydro-1h-inden-1-yl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3C4=CC=CC=C4CC3)CC2)=[NH+]1 GQJFXNDYYVTQDS-UHFFFAOYSA-N 0.000 claims 1
- MCZJWKOHNDFCQW-UHFFFAOYSA-N 3-[[3-[4-(2,3-dihydro-1h-inden-2-yl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC4=CC=CC=C4C3)CC2)=[NH+]1 MCZJWKOHNDFCQW-UHFFFAOYSA-N 0.000 claims 1
- AIZFFKSDBAYRPO-UHFFFAOYSA-N 3-[[3-[4-(2,4-dimethyl-1,3-thiazol-5-yl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.S1C(C)=NC(C)=C1N1C(=O)CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)[NH2+]N=3)C)C=2)F)CC1 AIZFFKSDBAYRPO-UHFFFAOYSA-N 0.000 claims 1
- BFUFUMUHQSNMQR-UHFFFAOYSA-N 3-[[3-[4-(2-chloro-4-fluorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C)C(=O)N[NH+]=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(CC2)C=2C(=CC(F)=CC=2)Cl)=C1 BFUFUMUHQSNMQR-UHFFFAOYSA-N 0.000 claims 1
- CFMQCEXSKNCLPQ-UHFFFAOYSA-N 3-[[3-[4-(2-ethoxyethyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N(CCOCC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F CFMQCEXSKNCLPQ-UHFFFAOYSA-N 0.000 claims 1
- JZJBCNYIOFDYFD-UHFFFAOYSA-N 3-[[3-[4-(3,3-difluorocyclobutyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(F)(F)C3)CC2)=[NH+]1 JZJBCNYIOFDYFD-UHFFFAOYSA-N 0.000 claims 1
- WVKHPKGBHKGYMA-UHFFFAOYSA-N 3-[[3-[4-(3,3-difluorocyclopentyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC(F)(F)C1 WVKHPKGBHKGYMA-UHFFFAOYSA-N 0.000 claims 1
- YGLADTWFVZYKJZ-UHFFFAOYSA-N 3-[[3-[4-(3,3-difluorocyclopentyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(F)(F)CC3)CC2)=[NH+]1 YGLADTWFVZYKJZ-UHFFFAOYSA-N 0.000 claims 1
- RKCXUBQSYFIFRN-UHFFFAOYSA-N 3-[[3-[4-(3,3-dimethylcyclohexyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(C)(C)CCC3)CC2)=[NH+]1 RKCXUBQSYFIFRN-UHFFFAOYSA-N 0.000 claims 1
- LSFAVCKASMXLEM-UHFFFAOYSA-N 3-[[3-[4-(3,4-difluorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=C(F)C(F)=CC=2)=[NH+]1 LSFAVCKASMXLEM-UHFFFAOYSA-N 0.000 claims 1
- YRMMOMGGIRFWMP-UHFFFAOYSA-N 3-[[3-[4-(3,4-difluorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(CC2)C=2C=C(F)C(F)=CC=2)=C1 YRMMOMGGIRFWMP-UHFFFAOYSA-N 0.000 claims 1
- DPVHLXQMOUPZAV-UHFFFAOYSA-N 3-[[3-[4-(3,4-dihydro-2h-chromen-3-yl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC4=CC=CC=C4OC3)CC2)=[NH+]1 DPVHLXQMOUPZAV-UHFFFAOYSA-N 0.000 claims 1
- PZEHSYUACPPZRB-UHFFFAOYSA-N 3-[[3-[4-(3,5-difluorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=C(F)C=C(F)C=2)=[NH+]1 PZEHSYUACPPZRB-UHFFFAOYSA-N 0.000 claims 1
- FWGQWEKLYCBSKT-UHFFFAOYSA-N 3-[[3-[4-(3-bicyclo[1.1.1]pentanyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C23CC(C2)C3)=[NH+]1 FWGQWEKLYCBSKT-UHFFFAOYSA-N 0.000 claims 1
- PNMQKDLDCTUGSA-UHFFFAOYSA-N 3-[[3-[4-(3-chloro-4-fluorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C)C(=O)N[NH+]=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(CC2)C=2C=C(Cl)C(F)=CC=2)=C1 PNMQKDLDCTUGSA-UHFFFAOYSA-N 0.000 claims 1
- RZQBHUQBYPLUFP-UHFFFAOYSA-N 3-[[3-[4-(3-chlorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=CC(Cl)=C1 RZQBHUQBYPLUFP-UHFFFAOYSA-N 0.000 claims 1
- AECZUGZEZGMLDV-UHFFFAOYSA-N 3-[[3-[4-(4,4-difluorocyclohexyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC(F)(F)CC1 AECZUGZEZGMLDV-UHFFFAOYSA-N 0.000 claims 1
- FQJYZXJEBGUVHW-UHFFFAOYSA-N 3-[[3-[4-(4,4-difluorocyclohexyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCC(F)(F)CC3)CC2)=[NH+]1 FQJYZXJEBGUVHW-UHFFFAOYSA-N 0.000 claims 1
- SYTSOEDYTBZWEC-UHFFFAOYSA-N 3-[[3-[4-(4,4-dimethylcyclohexyl)-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC(C)(C)CC1 SYTSOEDYTBZWEC-UHFFFAOYSA-N 0.000 claims 1
- NCWHOPXUKIXJHF-UHFFFAOYSA-N 3-[[3-[4-(4,4-dimethylcyclohexyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCC(C)(C)CC3)CC2)=[NH+]1 NCWHOPXUKIXJHF-UHFFFAOYSA-N 0.000 claims 1
- HOMZMKASHNWOGC-UHFFFAOYSA-N 3-[[3-[4-(4-chlorophenyl)-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C)C(=O)N[NH+]=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(CC2)C=2C=CC(Cl)=CC=2)=C1 HOMZMKASHNWOGC-UHFFFAOYSA-N 0.000 claims 1
- DYHOWDCVECDOGP-GNAFDRTKSA-N 3-[[3-[4-[(1r)-2,2-difluoro-1-phenylethyl]-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@@H](C(F)F)C=3C=CC=CC=3)CC2)=[NH+]1 DYHOWDCVECDOGP-GNAFDRTKSA-N 0.000 claims 1
- DTQWKAUAWUSUJC-DZVWYLRVSA-N 3-[[3-[4-[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N([C@H]2[C@]3([H])CC[C@@](C3)(C2)[H])CCN1C(=O)C(C(=CC=1)F)=CC=1CC1=[NH+]NC(=O)C(C)=C1C DTQWKAUAWUSUJC-DZVWYLRVSA-N 0.000 claims 1
- UMKDRINYHNEBAU-CFUKEOEUSA-N 3-[[3-[4-[(1s,4r)-3-bicyclo[2.2.1]heptanyl]-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@]2([H])CC[C@@](C2)(C1)[H])N(C(C1)=O)C(C)CN1C(=O)C(C(=CC=1)F)=CC=1CC1=[NH+]NC(=O)C(C)=C1C UMKDRINYHNEBAU-CFUKEOEUSA-N 0.000 claims 1
- XCJBAFXZFIDPBT-CYBMUJFWSA-N 3-[[3-[4-[(2r)-butan-2-yl]-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@H](C)CC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F XCJBAFXZFIDPBT-CYBMUJFWSA-N 0.000 claims 1
- XCJBAFXZFIDPBT-ZDUSSCGKSA-N 3-[[3-[4-[(2s)-butan-2-yl]-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@@H](C)CC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F XCJBAFXZFIDPBT-ZDUSSCGKSA-N 0.000 claims 1
- RMZCLRKLTJKPTI-UHFFFAOYSA-N 3-[[3-[4-[2,2-difluoro-1-(4-fluorophenyl)ethyl]-3-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C(C(F)F)C=3C=CC(F)=CC=3)CC2)=[NH+]1 RMZCLRKLTJKPTI-UHFFFAOYSA-N 0.000 claims 1
- MJLUTWLXYFNUCQ-UHFFFAOYSA-N 3-[[3-[4-cyclopentyl-3-(2-methylpropyl)-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC(C)CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCC1 MJLUTWLXYFNUCQ-UHFFFAOYSA-N 0.000 claims 1
- ILHSHXNNHWRAAT-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-methyl-5-oxo-4-phenylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)[NH2+]N=3)C)C=2)F)CC(=O)N1C1=CC=CC=C1 ILHSHXNNHWRAAT-UHFFFAOYSA-N 0.000 claims 1
- UHQDWRATAUWPNG-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-pentan-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N(C(CC)CC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F UHQDWRATAUWPNG-UHFFFAOYSA-N 0.000 claims 1
- YDCLYRYQZDYKML-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-phenylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=CC=CC=2)=[NH+]1 YDCLYRYQZDYKML-UHFFFAOYSA-N 0.000 claims 1
- RIPHLUZLPYKOAM-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-phenylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;hydrochloride Chemical compound Cl.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=CC=CC=2)=N1 RIPHLUZLPYKOAM-UHFFFAOYSA-N 0.000 claims 1
- ZBTVZZWZEZODAK-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-propan-2-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N(C(C)C)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F ZBTVZZWZEZODAK-UHFFFAOYSA-N 0.000 claims 1
- BSKHSVKUAAOHDS-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-pyridin-2-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2N=CC=CC=2)=N1 BSKHSVKUAAOHDS-UHFFFAOYSA-N 0.000 claims 1
- MMYQUKVDUAHGLE-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-pyridin-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=NC=CC=2)=N1 MMYQUKVDUAHGLE-UHFFFAOYSA-N 0.000 claims 1
- KFSQMTKYNDZSDO-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-pyrimidin-5-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=NC=NC=2)=N1 KFSQMTKYNDZSDO-UHFFFAOYSA-N 0.000 claims 1
- NPRRPYUSGSZKOW-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-quinolin-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=C3C=CC=CC3=NC=2)=N1 NPRRPYUSGSZKOW-UHFFFAOYSA-N 0.000 claims 1
- ODMWRARXNMMZTO-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-thiophen-2-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C=3SC=CC=3)CC2)=N1 ODMWRARXNMMZTO-UHFFFAOYSA-N 0.000 claims 1
- XAUREGQHZUPQFT-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-methyl-3-oxopiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N(C)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)[NH2+]N=2)C)=CC=C1F XAUREGQHZUPQFT-UHFFFAOYSA-N 0.000 claims 1
- NQUKMVBTVQWLIT-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-naphthalen-1-yl-3-oxopiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C3=CC=CC=C3C=CC=2)=N1 NQUKMVBTVQWLIT-UHFFFAOYSA-N 0.000 claims 1
- OQLGYBKBFICAJW-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-thiophen-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CCN(CC2)C2=CSC=C2)=N1 OQLGYBKBFICAJW-UHFFFAOYSA-N 0.000 claims 1
- XCSZRHUVMAAQPI-OAHLLOKOSA-N 3-[[4-fluoro-3-[(3r)-3-methyl-5-oxo-4-phenylpiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=CC=C1 XCSZRHUVMAAQPI-OAHLLOKOSA-N 0.000 claims 1
- PSRWAQWJJCWYLR-CQSZACIVSA-N 3-[[4-fluoro-3-[(3r)-4-(4-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(F)C=C1 PSRWAQWJJCWYLR-CQSZACIVSA-N 0.000 claims 1
- XCSZRHUVMAAQPI-HNNXBMFYSA-N 3-[[4-fluoro-3-[(3s)-3-methyl-5-oxo-4-phenylpiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=CC=C1 XCSZRHUVMAAQPI-HNNXBMFYSA-N 0.000 claims 1
- PSRWAQWJJCWYLR-AWEZNQCLSA-N 3-[[4-fluoro-3-[(3s)-4-(4-fluorophenyl)-3-methyl-5-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(F)C=C1 PSRWAQWJJCWYLR-AWEZNQCLSA-N 0.000 claims 1
- ZMYCFZSIBHQTOU-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-methyl-4-(oxan-3-yl)-5-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCOC1 ZMYCFZSIBHQTOU-UHFFFAOYSA-N 0.000 claims 1
- KHMAGPKLZLHOFR-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-methyl-5-oxo-4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N(CC(F)(F)F)C(C)CN1C(=O)C1=CC(CC=2C(=C(C)C(=O)N[NH+]=2)C)=CC=C1F KHMAGPKLZLHOFR-UHFFFAOYSA-N 0.000 claims 1
- SEOXIPMYMQUKCU-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-methyl-5-oxo-4-(oxolan-3-yl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCOC1 SEOXIPMYMQUKCU-UHFFFAOYSA-N 0.000 claims 1
- NAHYIGQTRRTVLZ-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3C4=CC=CC=C4CCC3)CC2)=[NH+]1 NAHYIGQTRRTVLZ-UHFFFAOYSA-N 0.000 claims 1
- AKXHIHZBJKPCDB-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC3C4=CC=CC=C4CCC3)CC2)=[NH+]1 AKXHIHZBJKPCDB-UHFFFAOYSA-N 0.000 claims 1
- FGNLCPCLFXXXNQ-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(1,2,3,4-tetrahydronaphthalen-2-yl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC4=CC=CC=C4CC3)CC2)=[NH+]1 FGNLCPCLFXXXNQ-UHFFFAOYSA-N 0.000 claims 1
- BCGSMEMPZPAUDA-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(1,3-thiazol-5-yl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C=3SC=NC=3)CC2)=N1 BCGSMEMPZPAUDA-UHFFFAOYSA-N 0.000 claims 1
- BZUYIWRKDNXMJE-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC(F)(F)F)CC2)=[NH+]1 BZUYIWRKDNXMJE-UHFFFAOYSA-N 0.000 claims 1
- CKSIYQFJGXHJRG-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(2-phenylethyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CCC=3C=CC=CC=3)CC2)=N1 CKSIYQFJGXHJRG-UHFFFAOYSA-N 0.000 claims 1
- QHQSGCUCHJABPV-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(2-propan-2-yloxyethyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N(CCOC(C)C)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F QHQSGCUCHJABPV-UHFFFAOYSA-N 0.000 claims 1
- WDOYCQLRMZEAKV-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(3,3,3-trifluoro-2-methylpropyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N(CC(C)C(F)(F)F)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)N[NH+]=2)C)=CC=C1F WDOYCQLRMZEAKV-UHFFFAOYSA-N 0.000 claims 1
- MPPDWKHMUWHBCY-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(3-phenylcyclohexyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(CCC3)C=3C=CC=CC=3)CC2)=[NH+]1 MPPDWKHMUWHBCY-UHFFFAOYSA-N 0.000 claims 1
- MCHPSKRHDCTEAS-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(3-phenylcyclopentyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(CC3)C=3C=CC=CC=3)CC2)=[NH+]1 MCHPSKRHDCTEAS-UHFFFAOYSA-N 0.000 claims 1
- MZBVUUKRWNXOPG-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(4-phenylcyclohexyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCC(CC3)C=3C=CC=CC=3)CC2)=[NH+]1 MZBVUUKRWNXOPG-UHFFFAOYSA-N 0.000 claims 1
- XZYVELVEQSTFOE-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(oxolan-3-yl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3COCC3)CC2)=[NH+]1 XZYVELVEQSTFOE-UHFFFAOYSA-N 0.000 claims 1
- KWWDAHYOTNBCLC-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-(oxolan-3-yl)piperazine-1-carbonyl]phenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(C3COCC3)CC2)=C1 KWWDAHYOTNBCLC-UHFFFAOYSA-N 0.000 claims 1
- QMSVLWQYYBKAJU-GMUIIQOCSA-N 3-[[4-fluoro-3-[3-oxo-4-[(1r)-1-phenylethyl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N([C@H](C)C=2C=CC=CC=2)CCN1C(=O)C(C(=CC=1)F)=CC=1CC1=[NH+]NC(=O)C(C)=C1C QMSVLWQYYBKAJU-GMUIIQOCSA-N 0.000 claims 1
- GXABFHPWVUYENG-UETCURACSA-N 3-[[4-fluoro-3-[3-oxo-4-[(1r,2s)-2-phenylcyclohexyl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@H]3[C@@H](CCCC3)C=3C=CC=CC=3)CC2)=[NH+]1 GXABFHPWVUYENG-UETCURACSA-N 0.000 claims 1
- QMSVLWQYYBKAJU-FERBBOLQSA-N 3-[[4-fluoro-3-[3-oxo-4-[(1s)-1-phenylethyl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C(=O)N([C@@H](C)C=2C=CC=CC=2)CCN1C(=O)C(C(=CC=1)F)=CC=1CC1=[NH+]NC(=O)C(C)=C1C QMSVLWQYYBKAJU-FERBBOLQSA-N 0.000 claims 1
- RBIDHRPLGJIYIO-CYBMUJFWSA-N 3-[[4-fluoro-3-[3-oxo-4-[(2r)-1,1,1-trifluoropropan-2-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@H](C)C(F)(F)F)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F RBIDHRPLGJIYIO-CYBMUJFWSA-N 0.000 claims 1
- RBIDHRPLGJIYIO-ZDUSSCGKSA-N 3-[[4-fluoro-3-[3-oxo-4-[(2s)-1,1,1-trifluoropropan-2-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@@H](C)C(F)(F)F)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F RBIDHRPLGJIYIO-ZDUSSCGKSA-N 0.000 claims 1
- HJHLXEKGUKMDQL-MRXNPFEDSA-N 3-[[4-fluoro-3-[3-oxo-4-[(3r)-oxolan-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@H]3COCC3)CC2)=N1 HJHLXEKGUKMDQL-MRXNPFEDSA-N 0.000 claims 1
- HJHLXEKGUKMDQL-INIZCTEOSA-N 3-[[4-fluoro-3-[3-oxo-4-[(3s)-oxolan-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@@H]3COCC3)CC2)=N1 HJHLXEKGUKMDQL-INIZCTEOSA-N 0.000 claims 1
- PRNPGVVXMORTJI-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-[(4-phenyloxan-4-yl)methyl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC3(CCOCC3)C=3C=CC=CC=3)CC2)=[NH+]1 PRNPGVVXMORTJI-UHFFFAOYSA-N 0.000 claims 1
- XRKVDNLCUZLYOQ-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-[1-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)ethyl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC(C)C1=NOC(C(C)N2C(CN(CC2)C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)N[NH+]=3)C)C=2)F)=O)=N1 XRKVDNLCUZLYOQ-UHFFFAOYSA-N 0.000 claims 1
- DGSXTGROUQTHNH-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-[2-(trifluoromethyl)phenyl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C(=CC=CC=2)C(F)(F)F)=[NH+]1 DGSXTGROUQTHNH-UHFFFAOYSA-N 0.000 claims 1
- RDCDYRISWMDBOT-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-[4-(trifluoromethyl)pyridin-2-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2N=CC=C(C=2)C(F)(F)F)=N1 RDCDYRISWMDBOT-UHFFFAOYSA-N 0.000 claims 1
- HINAILSCOFMNGQ-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-oxo-4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=C(C=NC=2)C(F)(F)F)=N1 HINAILSCOFMNGQ-UHFFFAOYSA-N 0.000 claims 1
- JFGGGQCMHZYTBT-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(1-methoxypropan-2-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N(C(C)COC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F JFGGGQCMHZYTBT-UHFFFAOYSA-N 0.000 claims 1
- PUNUAMNHUCPYIT-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(1-methylcyclohexyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C2(C)CCCCC2)=[NH+]1 PUNUAMNHUCPYIT-UHFFFAOYSA-N 0.000 claims 1
- YZJFAQXROBHKKD-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(1-methylsulfonylpiperidin-4-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCN(CC3)S(C)(=O)=O)CC2)=[NH+]1 YZJFAQXROBHKKD-UHFFFAOYSA-N 0.000 claims 1
- QLXDFJWTIZFLTD-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(1-oxaspiro[4.4]nonan-3-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC4(CCCC4)OC3)CC2)=N1 QLXDFJWTIZFLTD-UHFFFAOYSA-N 0.000 claims 1
- FFJXXTYZBJSRHP-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(1-oxaspiro[4.5]decan-3-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC4(OC3)CCCCC4)CC2)=N1 FFJXXTYZBJSRHP-UHFFFAOYSA-N 0.000 claims 1
- SKERQAYTHYIDTP-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(2-fluoroethyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CCF)CC2)=[NH+]1 SKERQAYTHYIDTP-UHFFFAOYSA-N 0.000 claims 1
- WVJDJAQMMBKNAZ-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(2-hydroxy-2-methylpropyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1=C(C)C(=O)NN=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(CC(C)(C)O)CC2)=C1 WVJDJAQMMBKNAZ-UHFFFAOYSA-N 0.000 claims 1
- JSWMKEIDYDXTAO-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(2-methoxyethyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N(CCOC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F JSWMKEIDYDXTAO-UHFFFAOYSA-N 0.000 claims 1
- DZIQYFKXWINRRF-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(3-fluorocyclopentyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC(F)CC3)CC2)=N1 DZIQYFKXWINRRF-UHFFFAOYSA-N 0.000 claims 1
- QAXDPQDCOQARJZ-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(3-methylimidazol-4-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C=3N(C=NC=3)C)CC2)=N1 QAXDPQDCOQARJZ-UHFFFAOYSA-N 0.000 claims 1
- WSUQZLGABPPDSI-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(4-fluorophenyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=CC(F)=CC=2)=[NH+]1 WSUQZLGABPPDSI-UHFFFAOYSA-N 0.000 claims 1
- KZNMUYHPNSTUAG-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(4-methylsulfonylphenyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 KZNMUYHPNSTUAG-UHFFFAOYSA-N 0.000 claims 1
- JMNXBHGYTOGYLY-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(oxan-3-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3COCCC3)CC2)=[NH+]1 JMNXBHGYTOGYLY-UHFFFAOYSA-N 0.000 claims 1
- ABZAVRRSYRUWKS-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(oxan-3-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(C3COCCC3)CC2)=C1 ABZAVRRSYRUWKS-UHFFFAOYSA-N 0.000 claims 1
- DDAKMYLARCUAHD-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(oxan-4-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCOCC3)CC2)=[NH+]1 DDAKMYLARCUAHD-UHFFFAOYSA-N 0.000 claims 1
- MXWYZZAJGMLHOT-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(oxan-4-yl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4-methyl-5-(trifluoromethyl)-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N(C3CCOCC3)CC2)=C1 MXWYZZAJGMLHOT-UHFFFAOYSA-N 0.000 claims 1
- DZIQYFKXWINRRF-IRXDYDNUSA-N 3-[[4-fluoro-3-[4-[(1s,3s)-3-fluorocyclopentyl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@@H]3C[C@@H](F)CC3)CC2)=N1 DZIQYFKXWINRRF-IRXDYDNUSA-N 0.000 claims 1
- BLNRWQUAKGQDGV-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-[(2-methyloxolan-2-yl)methyl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC3(C)OCCC3)CC2)=[NH+]1 BLNRWQUAKGQDGV-UHFFFAOYSA-N 0.000 claims 1
- JFGGGQCMHZYTBT-CYBMUJFWSA-N 3-[[4-fluoro-3-[4-[(2r)-1-methoxypropan-2-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@H](C)COC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F JFGGGQCMHZYTBT-CYBMUJFWSA-N 0.000 claims 1
- JULQVEYDKOIUEA-MRXNPFEDSA-N 3-[[4-fluoro-3-[4-[(2r)-3-methylbutan-2-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@H](C)C(C)C)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F JULQVEYDKOIUEA-MRXNPFEDSA-N 0.000 claims 1
- JFGGGQCMHZYTBT-ZDUSSCGKSA-N 3-[[4-fluoro-3-[4-[(2s)-1-methoxypropan-2-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@@H](C)COC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F JFGGGQCMHZYTBT-ZDUSSCGKSA-N 0.000 claims 1
- JULQVEYDKOIUEA-INIZCTEOSA-N 3-[[4-fluoro-3-[4-[(2s)-3-methylbutan-2-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound C1C(=O)N([C@@H](C)C(C)C)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F JULQVEYDKOIUEA-INIZCTEOSA-N 0.000 claims 1
- PNJSMHXQEMZWQR-QGZVFWFLSA-N 3-[[4-fluoro-3-[4-[(3r)-oxan-3-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@H]3COCCC3)CC2)=N1 PNJSMHXQEMZWQR-QGZVFWFLSA-N 0.000 claims 1
- JWXCIHPTKKTFAN-OAHLLOKOSA-N 3-[[4-fluoro-3-[4-[(3r)-oxan-3-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C1=C(C(=O)N2CC(=O)N([C@H]3COCCC3)CC2)C(F)=CC=C1CC=1C=C(C(F)(F)F)C(=O)NN=1 JWXCIHPTKKTFAN-OAHLLOKOSA-N 0.000 claims 1
- PNJSMHXQEMZWQR-KRWDZBQOSA-N 3-[[4-fluoro-3-[4-[(3s)-oxan-3-yl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@@H]3COCCC3)CC2)=N1 PNJSMHXQEMZWQR-KRWDZBQOSA-N 0.000 claims 1
- NRKPNLGUOVMBNG-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-[(4-fluorophenyl)methyl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC=3C=CC(F)=CC=3)CC2)=N1 NRKPNLGUOVMBNG-UHFFFAOYSA-N 0.000 claims 1
- BYGFTTRBCBZENQ-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-[(4-methoxyphenyl)methyl]-3-methyl-5-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1CN1C(=O)CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)N[NH+]=3)C)C=2)F)CC1C BYGFTTRBCBZENQ-UHFFFAOYSA-N 0.000 claims 1
- BUCZBDUYMUHPQP-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-[(4-methoxyphenyl)methyl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1CN1C(=O)CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC1 BUCZBDUYMUHPQP-UHFFFAOYSA-N 0.000 claims 1
- IZKRXZMGIVNOLU-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-[2-(3-fluorophenyl)ethyl]-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CCC=3C=C(F)C=CC=3)CC2)=[NH+]1 IZKRXZMGIVNOLU-UHFFFAOYSA-N 0.000 claims 1
- AGPDETWRZWGUNQ-CQSZACIVSA-N 4-[(2r)-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-methyl-6-oxopiperazin-1-yl]-3-fluorobenzonitrile Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(C#N)C=C1F AGPDETWRZWGUNQ-CQSZACIVSA-N 0.000 claims 1
- JEXXGVBJWUHYIQ-OAHLLOKOSA-N 4-[(2r)-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-methyl-6-oxopiperazin-1-yl]benzonitrile Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(C#N)C=C1 JEXXGVBJWUHYIQ-OAHLLOKOSA-N 0.000 claims 1
- FTIWFHUIKFYQLP-AWEZNQCLSA-N 4-[(2s)-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-methyl-6-oxopiperazin-1-yl]-2-fluorobenzonitrile Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(C#N)C(F)=C1 FTIWFHUIKFYQLP-AWEZNQCLSA-N 0.000 claims 1
- JEXXGVBJWUHYIQ-HNNXBMFYSA-N 4-[(2s)-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-methyl-6-oxopiperazin-1-yl]benzonitrile Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC=C(C#N)C=C1 JEXXGVBJWUHYIQ-HNNXBMFYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- UYTNEUKDYZHXLW-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-(3-oxo-4-phenylpiperazine-1-carbonyl)phenyl]methyl]-1h-pyridazin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=CC=CC=2)=N1 UYTNEUKDYZHXLW-UHFFFAOYSA-N 0.000 claims 1
- FFJYTJUSVLWQAX-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-[3-oxo-4-(1,2,3,4-tetrahydronaphthalen-2-yl)piperazine-1-carbonyl]phenyl]methyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC4=CC=CC=C4CC3)CC2)=N1 FFJYTJUSVLWQAX-UHFFFAOYSA-N 0.000 claims 1
- AEVPSIRVWFVTGU-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-[3-oxo-4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]methyl]-1h-pyridazin-2-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC(F)(F)F)CC2)=[NH+]1 AEVPSIRVWFVTGU-UHFFFAOYSA-N 0.000 claims 1
- FFJYTJUSVLWQAX-HSZRJFAPSA-N 5-ethyl-3-[[4-fluoro-3-[3-oxo-4-[(2r)-1,2,3,4-tetrahydronaphthalen-2-yl]piperazine-1-carbonyl]phenyl]methyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@H]3CC4=CC=CC=C4CC3)CC2)=N1 FFJYTJUSVLWQAX-HSZRJFAPSA-N 0.000 claims 1
- FFJYTJUSVLWQAX-QHCPKHFHSA-N 5-ethyl-3-[[4-fluoro-3-[3-oxo-4-[(2s)-1,2,3,4-tetrahydronaphthalen-2-yl]piperazine-1-carbonyl]phenyl]methyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N([C@@H]3CC4=CC=CC=C4CC3)CC2)=N1 FFJYTJUSVLWQAX-QHCPKHFHSA-N 0.000 claims 1
- VSXMOKYRIMPJSM-UHFFFAOYSA-N 8-[2-fluoro-5-[[4-methyl-6-oxo-5-(trifluoromethyl)-1h-pyridazin-1-ium-3-yl]methyl]benzoyl]-1,3,4,7,9,9a-hexahydropyrazino[2,1-c][1,4]oxazin-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(C(F)(F)F)C(=O)[NH2+]N=C1CC1=CC=C(F)C(C(=O)N2CC(=O)N3CCOCC3C2)=C1 VSXMOKYRIMPJSM-UHFFFAOYSA-N 0.000 claims 1
- GSRINRJKGQSOHR-UHFFFAOYSA-N 8-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-2-ium-3-yl)methyl]-2-fluorobenzoyl]-1,3,4,7,9,9a-hexahydropyrazino[2,1-c][1,4]oxazin-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCOCC3C2)=[NH+]1 GSRINRJKGQSOHR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 108091026813 Poly(ADPribose) Proteins 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010057430 Retinal injury Diseases 0.000 claims 1
- 206010038997 Retroviral infections Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000005972 dihydrochromenyl group Chemical group 0.000 claims 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- KNPBKKLNMDSNPI-UHFFFAOYSA-N pyridazin-1-ium 2,2,2-trifluoroacetate Chemical compound C1=CN=NC=C1.OC(=O)C(F)(F)F KNPBKKLNMDSNPI-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000002534 radiation-sensitizing agent Substances 0.000 claims 1
- 230000009759 skin aging Effects 0.000 claims 1
- 230000037380 skin damage Effects 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0722401.7 | 2007-11-15 | ||
| GB0722401A GB0722401D0 (en) | 2007-11-15 | 2007-11-15 | Therapeutic compounds |
| GB0816707.4 | 2008-09-12 | ||
| GB0816707A GB0816707D0 (en) | 2008-09-12 | 2008-09-12 | Therapeutic compounds |
| PCT/GB2008/051063 WO2009063244A1 (en) | 2007-11-15 | 2008-11-14 | Pyridazinone derivatives as parp inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011503166A JP2011503166A (ja) | 2011-01-27 |
| JP2011503166A5 true JP2011503166A5 (show.php) | 2011-12-15 |
| JP5758630B2 JP5758630B2 (ja) | 2015-08-05 |
Family
ID=40427149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010533666A Active JP5758630B2 (ja) | 2007-11-15 | 2008-11-14 | Ｐａｒｐ阻害剤としてのピリダジノン誘導体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8268827B2 (show.php) |
| EP (1) | EP2220073B1 (show.php) |
| JP (1) | JP5758630B2 (show.php) |
| KR (1) | KR101641596B1 (show.php) |
| CN (1) | CN101855221B (show.php) |
| AU (1) | AU2008322676B9 (show.php) |
| CA (1) | CA2704714C (show.php) |
| ES (1) | ES2524787T3 (show.php) |
| IL (1) | IL205142A (show.php) |
| MX (1) | MX2010005070A (show.php) |
| NZ (1) | NZ585395A (show.php) |
| RU (1) | RU2490265C2 (show.php) |
| WO (1) | WO2009063244A1 (show.php) |
| ZA (1) | ZA201002466B (show.php) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2422718T3 (es) * | 2009-04-02 | 2013-09-13 | Merck Patent Gmbh | Derivados de piperidina y piperazina como inhibidores de la autotaxina |
| WO2012027495A1 (en) | 2010-08-27 | 2012-03-01 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
| CA2829123C (en) * | 2011-03-14 | 2016-04-12 | Eternity Bioscience Inc. | Quinazolinediones and their use |
| JP5960253B2 (ja) | 2011-05-31 | 2016-08-02 | ニューゲン セラピューティクス， インコーポレイテッド | ポリ（ａｄｐ−リボース）ポリメラーゼの三環系阻害剤 |
| CN104169283B (zh) | 2011-12-31 | 2016-05-18 | 百济神州有限公司 | 作为parp抑制剂的稠合的四元或五元环吡啶并酞嗪酮类化合物 |
| JP6034877B2 (ja) | 2011-12-31 | 2016-11-30 | ベイジーン リミテッド | Ｐａｒｐ阻害剤としての縮合四環式または縮合五環式ジヒドロジアゼピノカルバゾロン |
| CN104427984A (zh) | 2012-01-20 | 2015-03-18 | D·布朗 | 包括二脱水半乳糖醇和类似物的经取代的己糖醇类于治疗包括多形性胶质母细胞瘤和成神经管细胞瘤的肿瘤疾病和癌症干细胞的用途 |
| EP2872161B1 (en) | 2012-06-26 | 2020-12-16 | Del Mar Pharmaceuticals | Dianhydrogalactitol for use in treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations |
| CN103570725B (zh) * | 2012-08-01 | 2017-03-22 | 中国科学院上海药物研究所 | 哌嗪并三唑类化合物及其制备方法和用途 |
| MX2015006780A (es) * | 2012-12-31 | 2015-08-06 | Cadila Healthcare Ltd | Derivados de ftalazin-1-(2h)-ona sustituida. |
| AU2014251038A1 (en) | 2013-04-08 | 2015-11-26 | Dennis M. Brown | Therapeutic benefit of suboptimally administered chemical compounds |
| US9993460B2 (en) | 2013-07-26 | 2018-06-12 | Race Oncology Ltd. | Compositions to improve the therapeutic benefit of bisantrene and analogs and derivatives thereof |
| KR101670126B1 (ko) | 2013-09-13 | 2016-10-27 | 일동제약(주) | 신규 프탈라지논 유도체 및 그 제조방법 |
| JP6783224B2 (ja) | 2014-04-04 | 2020-11-11 | デル マー ファーマシューティカルズ | 肺の非小細胞癌腫及び卵巣癌を処置するためのジアンヒドロガラクチトール及びその類縁体又は誘導体の使用 |
| FR3027901B1 (fr) * | 2014-10-31 | 2018-03-16 | Universite De Reims Champagne Ardenne | Nouveaux procedes appartenant a la famille des pyridazinones. |
| WO2016096709A1 (en) | 2014-12-16 | 2016-06-23 | Eudendron S.R.L. | Heterocyclic derivatives modulating activity of certain protein kinases |
| CN107820494B (zh) * | 2015-06-09 | 2020-10-16 | 艾伯维公司 | 核受体调节剂 |
| WO2017037116A1 (en) * | 2015-09-02 | 2017-03-09 | Glaxosmithkline Intellectual Property (No.2) Limited | Pyridinone dicarboxamide for use as bromodomain inhibitors |
| WO2017059080A1 (en) | 2015-10-01 | 2017-04-06 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| KR102030016B1 (ko) | 2016-09-05 | 2019-10-08 | 충남대학교산학협력단 | 신규한 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 폴리(adp-리보스)폴리머라제-1(parp-1) 관련 질환의 예방 또는 치료용 약학적 조성물 |
| SMT201900517T1 (it) | 2017-03-20 | 2019-11-13 | Forma Therapeutics Inc | Composizioni di pirrolopirrolo come attivatori di piruvato chinasi (pkr) |
| CN108383837B (zh) * | 2018-02-09 | 2020-08-11 | 福建医科大学 | 一种氨基取代四氢吡啶并嘧啶类化合物或其可用盐及其制备方法与应用 |
| HRP20230458T1 (hr) * | 2018-04-30 | 2023-07-21 | Ribon Therapeutics Inc. | Piridazinoni kao inhibitori parp7 |
| WO2019212946A1 (en) | 2018-04-30 | 2019-11-07 | Ribon Therapeutics Inc. | Screening methods for parp modulators |
| KR102017115B1 (ko) | 2018-05-15 | 2019-09-02 | 충남대학교산학협력단 | 폴리(adp-리보스)폴리머라제-1(parp-1) 관련 질환의 예방 또는 치료용 약학적 조성물 |
| CN113166060B (zh) | 2018-09-19 | 2024-01-09 | 诺沃挪第克健康护理股份公司 | 用丙酮酸激酶激活化合物治疗镰状细胞病 |
| US11001588B2 (en) | 2018-09-19 | 2021-05-11 | Forma Therapeutics, Inc. | Activating pyruvate kinase R and mutants thereof |
| WO2020223229A1 (en) | 2019-04-29 | 2020-11-05 | Ribon Therapeutics, Inc. | Solid forms of a parp7 inhibitor |
| CN110818908B (zh) * | 2019-08-29 | 2021-12-17 | 杭州市富阳区浙工大银湖创新创业研究院 | 一种用于检测氧化气体的金属有机骨架材料的制备方法 |
| CA3151612A1 (en) | 2019-09-19 | 2021-03-25 | George P. Luke | Pyruvate kinase r (pkr) activating compositions |
| US20240190844A1 (en) * | 2019-10-30 | 2024-06-13 | Ribon Therapeutics, Inc. | Pyridazinones as parp7 inhibitors |
| KR20220109401A (ko) | 2019-10-30 | 2022-08-04 | 리본 테라퓨틱스 인코포레이티드 | Parp7 억제제로서의 피리다진온 |
| US12459899B2 (en) | 2019-10-30 | 2025-11-04 | DIGMBIO, Inc. | Isoquinolinone derivatives, method for preparing the same, and pharmaceutical composition for preventing or treating poly(ADP-ribose) polymerase-1-related diseases, comprising the same as active ingredient |
| CN115702151B (zh) | 2020-04-21 | 2025-03-11 | 伊迪恩斯股份有限公司 | 酞嗪酮化合物的结晶形式 |
| KR20230004724A (ko) | 2020-04-21 | 2023-01-06 | 아이디언스 주식회사 | 프탈라지논 유도체 및 이의 중간체의 제조 방법 |
| WO2021224186A1 (en) * | 2020-05-04 | 2021-11-11 | Institut Curie | New pyridine derivatives as radiosensitizers |
| US12059419B2 (en) | 2020-10-16 | 2024-08-13 | Idience Co., Ltd. | Pharmaceutical composition comprising phthalazinone derivatives |
| WO2022188889A1 (zh) * | 2021-03-12 | 2022-09-15 | 杭州英创医药科技有限公司 | 作为parp7抑制剂的化合物 |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
| KR20240021751A (ko) | 2021-03-27 | 2024-02-19 | 티알엑스 바이오사이언시스 리미티드 | 치료제의 생체 이용률이 향상된 조성물 |
| CN115477640A (zh) * | 2021-05-31 | 2022-12-16 | 由理生物医药（上海）有限公司 | 作为parp7抑制剂的哒嗪酮类化合物 |
| CN117751108A (zh) * | 2021-07-21 | 2024-03-22 | 南京明德新药研发有限公司 | 哒嗪酮类化合物 |
| CN117642393A (zh) * | 2021-07-29 | 2024-03-01 | 上海齐鲁制药研究中心有限公司 | 新型parp7抑制剂及其应用 |
| WO2023011629A1 (zh) * | 2021-08-06 | 2023-02-09 | 成都百裕制药股份有限公司 | 吡咯烷酮衍生物及其在医药上的应用 |
| WO2023076983A1 (en) | 2021-10-28 | 2023-05-04 | Gilead Sciences, Inc. | Pyridizin-3(2h)-one derivatives |
| CN115745971B (zh) * | 2021-12-20 | 2024-07-30 | 北京华森英诺生物科技有限公司 | Parp7抑制剂及其应用 |
| CN116375688B (zh) * | 2021-12-23 | 2025-04-11 | 中国药科大学 | 哒嗪酮类化合物及其制备方法、药物组合物和应用 |
| JP2025509680A (ja) * | 2022-03-14 | 2025-04-11 | ティーアールエックス バイオサイエンシズ リミテッド | 治療薬のバイオアベイラビリティを改善した組成物およびその使用 |
| US20240336596A1 (en) * | 2022-04-01 | 2024-10-10 | Novostar Pharmaceuticals, Ltd. | Parp7 inhibitor and use thereof |
| WO2024073133A1 (en) * | 2022-09-30 | 2024-04-04 | Azkarra Therapeutics, Inc. | Pyridazin-3(2h)-one and pyridin-2(1h)-one parp inhibitor compounds |
| WO2024229406A1 (en) | 2023-05-04 | 2024-11-07 | Revolution Medicines, Inc. | Combination therapy for a ras related disease or disorder |
| US20250049810A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025080946A2 (en) | 2023-10-12 | 2025-04-17 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025087383A1 (zh) * | 2023-10-26 | 2025-05-01 | 深圳众格生物科技有限公司 | 作为parp7抑制剂的化合物 |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025217307A1 (en) | 2024-04-09 | 2025-10-16 | Revolution Medicines, Inc. | Methods for predicting response to a ras(on) inhibitor and combination therapies |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras inhibitors |
| US20250375445A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5622948A (en) | 1994-12-01 | 1997-04-22 | Syntex (U.S.A.) Inc. | Pyrrole pyridazine and pyridazinone anti-inflammatory agents |
| IL118631A (en) * | 1995-06-27 | 2002-05-23 | Tanabe Seiyaku Co | History of pyridazinone and processes for their preparation |
| CN1136197C (zh) * | 1996-05-30 | 2004-01-28 | 霍夫曼-拉罗奇有限公司 | 新的哒嗪酮衍生物 |
| CA2423279C (en) | 2000-10-30 | 2011-07-05 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| EP1397350B1 (en) | 2001-05-08 | 2007-02-28 | Kudos Pharmaceuticals Limited | Isoquinolinone derivatives as parp inhibitors |
| WO2003093261A1 (en) | 2002-04-30 | 2003-11-13 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| KR101146806B1 (ko) * | 2003-03-12 | 2012-05-22 | 메이브릿지 리미티드 | 프탈라지논 유도체 |
| CA2518823A1 (en) * | 2003-03-24 | 2004-10-07 | F.Hoffmann-La Roche Ag | Benzyl-pyridazinons as reverse transcriptase inhibitors |
| CA2557547A1 (en) | 2004-02-26 | 2005-09-09 | Inotek Pharmaceuticals Corporation | Isoquinoline derivatives and methods of use thereof |
| EP1730120A1 (en) | 2004-03-23 | 2006-12-13 | F.Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| PE20060285A1 (es) | 2004-03-30 | 2006-05-08 | Aventis Pharma Inc | Piridonas sustituidas como inhibidores de pol(adp-ribosa)-polimerasa (parp) |
| CN1942449A (zh) * | 2004-04-15 | 2007-04-04 | 弗·哈夫曼-拉罗切有限公司 | 制备哒嗪酮化合物的方法 |
| BRPI0514632A (pt) | 2004-08-26 | 2008-06-17 | Kudos Pharm Ltd | derivados de ftalazinona 4-heteroarilmetila substituìdos |
| WO2007009913A1 (en) | 2005-07-21 | 2007-01-25 | F. Hoffmann-La Roche Ag | Pyridazinone derivatives as thyroid hormone receptor agonists |
| GB0610680D0 (en) * | 2006-05-31 | 2006-07-12 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| PT2698062E (pt) * | 2006-12-28 | 2015-10-19 | Abbvie Inc | Inibidores da poli (adp-ribose) polimerase |
| US8466150B2 (en) * | 2006-12-28 | 2013-06-18 | Abbott Laboratories | Inhibitors of poly(ADP-ribose)polymerase |
| US20080280910A1 (en) | 2007-03-22 | 2008-11-13 | Keith Allan Menear | Phthalazinone derivatives |
| TW200900396A (en) | 2007-04-10 | 2009-01-01 | Kudos Pharm Ltd | Phthalazinone derivatives |
| US20090023727A1 (en) | 2007-07-05 | 2009-01-22 | Muhammad Hashim Javaid | Phthalazinone derivatives |
-
2008
- 2008-11-14 EP EP08850429.5A patent/EP2220073B1/en active Active
- 2008-11-14 WO PCT/GB2008/051063 patent/WO2009063244A1/en not_active Ceased
- 2008-11-14 KR KR1020107013113A patent/KR101641596B1/ko active Active
- 2008-11-14 RU RU2010123874/04A patent/RU2490265C2/ru active
- 2008-11-14 NZ NZ585395A patent/NZ585395A/en unknown
- 2008-11-14 AU AU2008322676A patent/AU2008322676B9/en active Active
- 2008-11-14 JP JP2010533666A patent/JP5758630B2/ja active Active
- 2008-11-14 US US12/739,262 patent/US8268827B2/en active Active
- 2008-11-14 MX MX2010005070A patent/MX2010005070A/es active IP Right Grant
- 2008-11-14 CA CA2704714A patent/CA2704714C/en active Active
- 2008-11-14 ES ES08850429.5T patent/ES2524787T3/es active Active
- 2008-11-14 CN CN2008801155905A patent/CN101855221B/zh active Active
-
2010
- 2010-04-08 ZA ZA2010/02466A patent/ZA201002466B/en unknown
- 2010-04-15 IL IL205142A patent/IL205142A/en active IP Right Grant
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011503166A5 (show.php) | ||
| RU2010123874A (ru) | Пиридазиноновые производные в качестве ингибиторов parp | |
| RU2396269C2 (ru) | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1) | |
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| JP2007510689A5 (show.php) | ||
| RU2008141761A (ru) | ИНГИБИТОРЫ с-МЕТ ПРОТЕИНКИНАЗЫ | |
| JP2008513514A5 (show.php) | ||
| JP2019077725A5 (show.php) | ||
| RU2017124425A (ru) | Производные 2,4-диоксо-хиназолин-6-сульфонамида в качестве ингибиторов parg | |
| RU2019132212A (ru) | Селективные ингибиторы hdac6 | |
| RU2016124178A (ru) | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет | |
| JP2018530591A5 (show.php) | ||
| JP2020515575A5 (show.php) | ||
| RU2010137300A (ru) | Модуляторы бета-амилоида | |
| JP2016523911A5 (show.php) | ||
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| JP2014062093A5 (show.php) | ||
| RU2016102137A (ru) | Первичные карбоксамиды в качестве ингибиторов bik | |
| JP2017502049A5 (show.php) | ||
| IL277579B (en) | Piperidinone derivatives as mdm2 inhibitors for cancer therapy | |
| JP2011500806A5 (show.php) | ||
| RU2016141646A (ru) | Ингибиторы trka киназы, основанные на них композиции и способы | |
| JP2014517833A5 (show.php) | ||
| JP2007523182A5 (show.php) | ||
| JP2013533868A5 (show.php) |