JP2009538896A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009538896A5 JP2009538896A5 JP2009512681A JP2009512681A JP2009538896A5 JP 2009538896 A5 JP2009538896 A5 JP 2009538896A5 JP 2009512681 A JP2009512681 A JP 2009512681A JP 2009512681 A JP2009512681 A JP 2009512681A JP 2009538896 A5 JP2009538896 A5 JP 2009538896A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- methyl
- dihydropyridazin
- fluorobenzoyl
- alkyl
- 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
- -1 4- {5-[(5-ethyl-6-oxo-1,6-dihydropyridazin-3-yl) methyl] -2-fluorobenzoyl} -1,4-diazepan-1-ium trifluoroacetic acid Chemical compound 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- NWOWTFJZANGFLS-UHFFFAOYSA-N 3-[[3-(4-acetyl-1,4-diazepane-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)N2CCN(CCC2)C(C)=O)=N1 NWOWTFJZANGFLS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 69
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 37
- 229910052760 oxygen Inorganic materials 0.000 claims 36
- 229910052717 sulfur Inorganic materials 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000005842 heteroatoms Chemical group 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 18
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
- 125000004429 atoms Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N Decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 6
- NVSPJDGXKBDYIZ-UHFFFAOYSA-O N=1[NH+]=CN2C=1C=NC=C2 Chemical compound N=1[NH+]=CN2C=1C=NC=C2 NVSPJDGXKBDYIZ-UHFFFAOYSA-O 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-O pyrrolidinium Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N Nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O Pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 2
- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- MBCLRULCFCYDDQ-UHFFFAOYSA-N 3-[5-[(4,5-dimethyl-6-oxo-1H-pyridazin-2-ium-3-yl)methyl]-2-fluorophenyl]-5-methylimidazolidine-2,4-dione;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O=C1C(C)NC(=O)N1C1=CC(CC=2C(=C(C)C(=O)N[NH+]=2)C)=CC=C1F MBCLRULCFCYDDQ-UHFFFAOYSA-N 0.000 claims 1
- FLXPTVMDSSTTNP-UHFFFAOYSA-N 3-[[3-(2-benzylpiperazin-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-5-ethyl-1H-pyridazin-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)N2C(C[NH2+]CC2)CC=2C=CC=CC=2)=N1 FLXPTVMDSSTTNP-UHFFFAOYSA-N 0.000 claims 1
- FTHGVCLKCHMPSX-UHFFFAOYSA-N 3-[[3-[4-(1-aminocyclopentanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1H-pyridazin-6-one Chemical compound CC1=C(C)C(=O)NN=C1CC1=CC=C(F)C(C(=O)N2CCN(CC2)C(=O)C2(N)CCCC2)=C1 FTHGVCLKCHMPSX-UHFFFAOYSA-N 0.000 claims 1
- JBRLKAQINFPJGH-UHFFFAOYSA-N 3-[[3-[4-(1-anilinocyclopentanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-4,5-dimethyl-1H-pyridazin-6-one Chemical compound CC1=C(C)C(=O)NN=C1CC1=CC=C(F)C(C(=O)N2CCN(CC2)C(=O)C2(CCCC2)NC=2C=CC=CC=2)=C1 JBRLKAQINFPJGH-UHFFFAOYSA-N 0.000 claims 1
- WFWMSFWIVZDZPJ-UHFFFAOYSA-N 3-[[3-[4-(2,2-difluoroacetyl)piperazine-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)N2CCN(CC2)C(=O)C(F)F)=N1 WFWMSFWIVZDZPJ-UHFFFAOYSA-N 0.000 claims 1
- NYVWAIBLKVQKAZ-UHFFFAOYSA-N 3-[[3-[4-(cyclopentanecarbonyl)-1,4-diazepane-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)N2CCN(CCC2)C(=O)C2CCCC2)=N1 NYVWAIBLKVQKAZ-UHFFFAOYSA-N 0.000 claims 1
- OJFJYYSYBAGJCD-UHFFFAOYSA-N 3-[[3-[4-(cyclopentanecarbonyl)-1,4-diazepane-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)N2CCN(CCC2)C(=O)C2CCCC2)=N1 OJFJYYSYBAGJCD-UHFFFAOYSA-N 0.000 claims 1
- ZNTLEPDPODEOGR-UQIIZPHYSA-N 3-[[3-[4-[(2S)-2-ethylpyrrolidine-2-carbonyl]piperazine-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.C1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CCN1C(=O)[C@]1(CC)CCCN1 ZNTLEPDPODEOGR-UQIIZPHYSA-N 0.000 claims 1
- MSBJGCGKVWLBNJ-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-piperidin-1-ium-1-ylpiperidine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1H-pyridazin-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)N2CCC(CC2)[NH+]2CCCCC2)=N1 MSBJGCGKVWLBNJ-UHFFFAOYSA-N 0.000 claims 1
- VLZAESAXVDBRFX-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-propanoylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1H-pyridazin-6-one Chemical compound C1CN(C(=O)CC)CCN1C(=O)C1=CC(CC=2C(=C(C)C(=O)NN=2)C)=CC=C1F VLZAESAXVDBRFX-UHFFFAOYSA-N 0.000 claims 1
- JDKJFVFQAKJLFZ-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-pyrimidin-1-ium-2-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1H-pyridazin-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)N2CCN(CC2)C=2[NH+]=CC=CN=2)=N1 JDKJFVFQAKJLFZ-UHFFFAOYSA-N 0.000 claims 1
- SOOQWALEZNJUSY-UHFFFAOYSA-N 3-[[4-fluoro-3-(4-quinazolin-3-ium-4-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1H-pyridazin-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)N2CCN(CC2)C=2C3=CC=CC=C3[NH+]=CN=2)=N1 SOOQWALEZNJUSY-UHFFFAOYSA-N 0.000 claims 1
- WAZSTEZQSPJVPM-UHFFFAOYSA-N 3-[[4-fluoro-3-(piperazin-4-ium-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1H-pyridazin-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[NH2+]CC2)=N1 WAZSTEZQSPJVPM-UHFFFAOYSA-N 0.000 claims 1
- UYJWVMZRCGZZEK-UHFFFAOYSA-N 3-[[4-fluoro-3-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-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=3N(C(=NN=3)C(F)(F)F)CC2)=N1 UYJWVMZRCGZZEK-UHFFFAOYSA-N 0.000 claims 1
- OAPNPJLTWTUAJF-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(2-methylpyrrolidin-1-ium-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-1H-pyridazin-6-one;chloride Chemical compound [Cl-].CC1=C(O)N=NC(CC=2C=C(C(F)=CC=2)C(=O)N2CCN(CC2)C(=O)C2(C)[NH2+]CCC2)=C1C OAPNPJLTWTUAJF-UHFFFAOYSA-N 0.000 claims 1
- PRWUSOQACLUHCV-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(3,3,3-trifluoropropanoyl)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)N2CCN(CC2)C(=O)CC(F)(F)F)=N1 PRWUSOQACLUHCV-UHFFFAOYSA-N 0.000 claims 1
- JHSBRKCIIORYOE-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-(oxolane-2-carbonyl)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)N2CCN(CC2)C(=O)C2OCCC2)=N1 JHSBRKCIIORYOE-UHFFFAOYSA-N 0.000 claims 1
- NLDJQNDOIRHNPD-DEOSSOPVSA-N 3-[[4-fluoro-3-[4-[(2S)-2-methylpyrrolidine-2-carbonyl]piperazine-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)N2CCN(CC2)C(=O)[C@@]2(C)NCCC2)=C1 NLDJQNDOIRHNPD-DEOSSOPVSA-N 0.000 claims 1
- BCVHULSKBSQLBH-UHFFFAOYSA-N 3-[[4-fluoro-3-[4-[1-(2-methylpropylamino)cyclopentanecarbonyl]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.C1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CCN1C(=O)C1(NCC(C)C)CCCC1 BCVHULSKBSQLBH-UHFFFAOYSA-N 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- VJYYYWFCYKMFCQ-UHFFFAOYSA-N 4,5-dimethyl-3-[[3-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-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=CC=2)C(=O)N2CC=3N(C(=NN=3)C(F)(F)F)CC2)=N1 VJYYYWFCYKMFCQ-UHFFFAOYSA-N 0.000 claims 1
- MBEWIDXCHBWSMZ-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-(3-pyridin-1-ium-4-ylpyrrolidine-1-carbonyl)phenyl]methyl]-1H-pyridazin-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(CC2)C=2C=C[NH+]=CC=2)=N1 MBEWIDXCHBWSMZ-UHFFFAOYSA-N 0.000 claims 1
- WPLGERDSVRSDJR-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-(4-pyridin-1-ium-4-ylpiperidine-1-carbonyl)phenyl]methyl]-1H-pyridazin-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)N2CCC(CC2)C=2C=C[NH+]=CC=2)=N1 WPLGERDSVRSDJR-UHFFFAOYSA-N 0.000 claims 1
- GAYNDBFEKBRCAV-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-(piperazin-4-ium-1-carbonyl)phenyl]methyl]-1H-pyridazin-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[NH2+]CC2)=N1 GAYNDBFEKBRCAV-UHFFFAOYSA-N 0.000 claims 1
- VFBMYVYSPOZAGE-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-[1-(2,2,2-trifluoroethyl)-6,7-dihydro-4H-triazolo[4,5-c]pyridine-5-carbonyl]phenyl]methyl]-1H-pyridazin-6-one Chemical compound N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC3=C(N(N=N3)CC(F)(F)F)CC2)=N1 VFBMYVYSPOZAGE-UHFFFAOYSA-N 0.000 claims 1
- KTISWWKDSHPNGQ-UHFFFAOYSA-N 5-ethyl-3-[[4-fluoro-3-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-1H-pyridazin-6-one Chemical compound N1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC=3N(C(=NN=3)C(F)(F)F)CC2)=N1 KTISWWKDSHPNGQ-UHFFFAOYSA-N 0.000 claims 1
- YZOGLGWPRZWVAL-UHFFFAOYSA-O C(C)C1=C(C(=NNC1=O)CC=1C=CC(=C(C(=O)N2CC[NH2+]CCC2)C=1)F)C Chemical compound C(C)C1=C(C(=NNC1=O)CC=1C=CC(=C(C(=O)N2CC[NH2+]CCC2)C=1)F)C YZOGLGWPRZWVAL-UHFFFAOYSA-O 0.000 claims 1
- JZYMFDWSMWCQOZ-UHFFFAOYSA-O C(C)C=1C(=NNC(C=1C)=O)CC=1C=CC(=C(C(=O)N2CC[NH2+]CCC2)C=1)F Chemical compound C(C)C=1C(=NNC(C=1C)=O)CC=1C=CC(=C(C(=O)N2CC[NH2+]CCC2)C=1)F JZYMFDWSMWCQOZ-UHFFFAOYSA-O 0.000 claims 1
- YYBMHFGIFYHINS-UHFFFAOYSA-O CC=1C(=NNC(C=1C)=O)CC=1C=CC(=C(C(=O)N2CC=3N(CC2)C(=N[NH+]=3)NC2=CC=C(C=C2)C(F)(F)F)C=1)F Chemical compound CC=1C(=NNC(C=1C)=O)CC=1C=CC(=C(C(=O)N2CC=3N(CC2)C(=N[NH+]=3)NC2=CC=C(C=C2)C(F)(F)F)C=1)F YYBMHFGIFYHINS-UHFFFAOYSA-O 0.000 claims 1
- GUWQTVXBNQHPSD-UHFFFAOYSA-N CCC1=CC(CC2=CC(C(=O)N3CCC4(COC5=CC=CC=C45)CC3)=C(F)C=C2)=NNC1=O Chemical compound CCC1=CC(CC2=CC(C(=O)N3CCC4(COC5=CC=CC=C45)CC3)=C(F)C=C2)=NNC1=O GUWQTVXBNQHPSD-UHFFFAOYSA-N 0.000 claims 1
- ZRSSQNHNGDXNIB-UHFFFAOYSA-O CN(C(C)(C)C1=NN=C2N1CCN(C2)C(=O)C=1C=C(CC=2C(=C(C(N[NH+]=2)=O)C)C)C=CC=1F)C Chemical compound CN(C(C)(C)C1=NN=C2N1CCN(C2)C(=O)C=1C=C(CC=2C(=C(C(N[NH+]=2)=O)C)C)C=CC=1F)C ZRSSQNHNGDXNIB-UHFFFAOYSA-O 0.000 claims 1
- GWAIYUUSEQXTAB-UHFFFAOYSA-N OC(=O)C(F)(F)F.Cc1c(C)c(=O)[nH]nc1Cc1ccc(F)c(c1)C(=O)N1CCN(CC1)C(=O)C1(CCCC1)NCc1ccccc1 Chemical compound OC(=O)C(F)(F)F.Cc1c(C)c(=O)[nH]nc1Cc1ccc(F)c(c1)C(=O)N1CCN(CC1)C(=O)C1(CCCC1)NCc1ccccc1 GWAIYUUSEQXTAB-UHFFFAOYSA-N 0.000 claims 1
- ODCOTZAEOSDYAF-UHFFFAOYSA-N [O-]C(=O)C(F)(F)F.O=C1[NH2+]N=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.O=C1[NH2+]N=CC=C1 ODCOTZAEOSDYAF-UHFFFAOYSA-N 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N ethyl 2,2,2-trifluoroacetate Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UQORINXZBNKHDW-UHFFFAOYSA-N 1-[4-[5-[(6-chloro-4-ethylpyridazin-3-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-1-yl]ethanone Chemical compound CCC1=CC(Cl)=NN=C1CC1=CC=C(F)C(C(=O)N2CCN(CCC2)C(C)=O)=C1 UQORINXZBNKHDW-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0610680.1A GB0610680D0 (en) | 2006-05-31 | 2006-05-31 | Therapeutic compounds |
GB0610680.1 | 2006-05-31 | ||
PCT/GB2007/050295 WO2007138351A2 (en) | 2006-05-31 | 2007-05-25 | Pyridinone and pyridazinone derivatives as inhibitors of poly(adp-ribose)polymerase (parp) |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009538896A JP2009538896A (ja) | 2009-11-12 |
JP2009538896A5 true JP2009538896A5 (pt-PT) | 2013-08-22 |
JP5351755B2 JP5351755B2 (ja) | 2013-11-27 |
Family
ID=36694627
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009512681A Active JP5351755B2 (ja) | 2006-05-31 | 2007-05-25 | ポリ(adp−リボース)ポリメラーゼ(parp)インヒビターとしてのピリジノン及びピリダジノン誘導体 |
Country Status (16)
Country | Link |
---|---|
US (1) | US8188084B2 (pt-PT) |
EP (1) | EP2029551B1 (pt-PT) |
JP (1) | JP5351755B2 (pt-PT) |
KR (1) | KR101529891B1 (pt-PT) |
CN (2) | CN103420988A (pt-PT) |
AU (1) | AU2007266836B2 (pt-PT) |
BR (1) | BRPI0711741B8 (pt-PT) |
CA (1) | CA2653529C (pt-PT) |
ES (1) | ES2702781T3 (pt-PT) |
GB (1) | GB0610680D0 (pt-PT) |
IL (1) | IL195113A (pt-PT) |
MX (1) | MX2008015014A (pt-PT) |
NO (1) | NO343950B1 (pt-PT) |
NZ (1) | NZ572815A (pt-PT) |
WO (1) | WO2007138351A2 (pt-PT) |
ZA (1) | ZA200809238B (pt-PT) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0622195D0 (en) * | 2006-11-08 | 2006-12-20 | Angeletti P Ist Richerche Bio | Therapeutic agents |
ES2524787T3 (es) * | 2007-11-15 | 2014-12-12 | Msd Italia S.R.L. | Derivados de piridazinona como inhibidores de PARP |
DE102008019907A1 (de) * | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
US8501946B2 (en) * | 2009-04-29 | 2013-08-06 | Glaxo Group Limited | 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine derivatives as P2X7 modulators |
GB0907515D0 (en) * | 2009-04-30 | 2009-06-10 | Glaxo Group Ltd | Compounds |
AU2011234398B8 (en) * | 2010-04-02 | 2015-03-05 | Ogeda Sa | Novel NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders |
US10065960B2 (en) * | 2010-04-02 | 2018-09-04 | Ogeda Sa | NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders |
US20130116284A1 (en) | 2010-05-10 | 2013-05-09 | Radikal Therapeutics Inc. | Lipoic acid and nitroxide derivatives and uses thereof |
CN102372716A (zh) * | 2010-08-09 | 2012-03-14 | 江苏恒瑞医药股份有限公司 | 酞嗪酮类衍生物、其制备方法及其在医药上的应用 |
EP3925962A1 (en) | 2011-05-31 | 2021-12-22 | Rakovina Therapeutics Inc. | Tricyclic inhibitors of poly(adp-ribose) polymerase |
MX367774B (es) | 2011-10-03 | 2019-09-04 | Ogeda S A | N-ACIL-5,6,7, (8-SUSTITUIDO)-TETRAHIDRO- [1,2,4] TRIAZOLO [4,3-a] PIRAZINAS QUIRALES, NOVEDOSAS, COMO ANTAGONISTAS SELECTIVOS DE RECEPTOR DE NK-3; COMPOSICIÓN FARMACÉUTICA, MÉTODOS PARA USO EN TRASTORNOS MEDIADOS POR RECEPTOR DE NK-3 Y SU SÍNTESIS QUIRAL. |
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 |
CN103833756B (zh) * | 2012-11-26 | 2016-12-21 | 中国科学院上海药物研究所 | 一类哒嗪酮类化合物及其制备方法和用途 |
ES2469990B1 (es) * | 2012-12-19 | 2015-01-26 | Universidade De Vigo | Compuestos de estructura híbrida piridazinona ditiocarbamato con actividad antineoplásica |
WO2014102817A1 (en) * | 2012-12-31 | 2014-07-03 | Cadila Healthcare Limited | Substituted phthalazin-1 (2h)-one derivatives as selective inhibitors of poly (adp-ribose) polymerase-1 |
DK2968316T3 (da) | 2013-03-13 | 2019-10-07 | Forma Therapeutics Inc | 2-hydroxy-1-{4-[(4-phenylphenyl)carbonyl]piperazin-1-yl}ethan-1-on-derivater og relaterede forbindelser som fedtsyresyntase (fasn)-inhibitorer til behandlingen af cancer |
KR102072268B1 (ko) * | 2013-03-13 | 2020-01-31 | 추가이 세이야쿠 가부시키가이샤 | 디하이드로피리다진-3,5-디온 유도체 |
US10183948B2 (en) | 2013-03-29 | 2019-01-22 | Ogeda Sa | N-acyl-(3-substituted)-(8-substituted)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists |
LT2948455T (lt) | 2013-03-29 | 2017-11-27 | Ogeda S.A. | N-acil-(3-pakeisto)-(8-pakeisto)-5,6-dihidro- [1,2,4]triazol[4,3-a]pirazinai, kaip selektyvūs nk-3 receptorių antagonistai, farmacinė kompozicija, būdai, skirti naudoti nk-3 receptoriaus sąlygotų sutrikimų gydymui |
CA2907813C (en) | 2013-03-29 | 2021-09-07 | Euroscreen Sa | Novel n-acyl-(3-substituted)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective nk-3 receptor antagonists, pharmaceutical composition, methods for use in nk-3 receptor-mediated disorders |
AU2014242908B2 (en) | 2013-03-29 | 2018-07-19 | Ogeda Sa | Novel N-acyl-(3-substituted)-(8-methyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor-mediated disorders |
KR101670126B1 (ko) | 2013-09-13 | 2016-10-27 | 일동제약(주) | 신규 프탈라지논 유도체 및 그 제조방법 |
ES2544869B2 (es) * | 2014-03-04 | 2016-01-18 | Universidade De Vigo | Derivados de piridazin-3(2H)-ona inhibidores selectivos de la isoforma B de la monoaminooxidasa |
US10550108B2 (en) | 2014-10-03 | 2020-02-04 | Institute For Cancer Research | Poly(ADP-ribose) polymerase 1 inhibitors structurally unrelated to NAD |
US10472664B2 (en) | 2014-10-03 | 2019-11-12 | Institute For Cancer Research | Screening assay for identification of poly(ADP-ribose) polymerase 1 inhibitors |
CA2977685C (en) | 2015-03-02 | 2024-02-20 | Sinai Health System | Homologous recombination factors |
EP3325623B3 (en) | 2015-07-23 | 2021-01-20 | Institut Curie | Use of a combination of dbait molecule and parp inhibitors to treat cancer |
CN106749261A (zh) * | 2015-11-23 | 2017-05-31 | 中国科学院上海药物研究所 | 一类取代三唑并哌嗪类parp抑制剂及其制备方法和用途 |
WO2018162439A1 (en) | 2017-03-08 | 2018-09-13 | Onxeo | New predictive biomarker for the sensitivity to a treatment of cancer with a dbait molecule |
KR102296703B1 (ko) | 2017-03-20 | 2021-09-01 | 포르마 세라퓨틱스 인크. | 피루베이트 키나제 (pkr) 활성화제로서의 피롤로피롤 조성물 |
CN109232575B (zh) * | 2017-07-10 | 2022-01-25 | 中国科学院上海药物研究所 | 吡咯[1,2-b]哒嗪类化合物或其可药用盐及它们的用途 |
WO2019175132A1 (en) | 2018-03-13 | 2019-09-19 | Onxeo | A dbait molecule against acquired resistance in the treatment of cancer |
PT3788040T (pt) | 2018-04-30 | 2023-07-12 | Ribon Therapeutics Inc | Piridazinonas como inibidores de parp7 |
BR112021005188A2 (pt) | 2018-09-19 | 2021-06-08 | Forma Therapeutics, Inc. | tratamento de anemia falciforme com um composto de ativação de piruvato cinase r |
US20230055923A1 (en) | 2018-09-19 | 2023-02-23 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
US10793554B2 (en) | 2018-10-29 | 2020-10-06 | Forma Therapeutics, Inc. | Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone |
AU2020375821A1 (en) | 2019-10-30 | 2022-06-02 | Ribon Therapeutics, Inc. | Pyridazinones as PARP7 inhibitors |
WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
MX2022013304A (es) | 2020-04-21 | 2022-12-15 | Idience Co Ltd | Formas cristalinas de compuesto de ftalazinona. |
WO2022223022A1 (zh) * | 2021-04-23 | 2022-10-27 | 四川海思科制药有限公司 | 一种并环杂环衍生物及其在医药上的应用 |
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 |
CA3234909A1 (en) | 2021-10-28 | 2023-05-04 | Gilead Sciences, Inc. | Pyridizin-3(2h)-one derivatives |
CN115745971A (zh) * | 2021-12-20 | 2023-03-07 | 重庆华森制药股份有限公司 | Parp7抑制剂及其应用 |
CN115785074B (zh) * | 2022-04-01 | 2024-05-07 | 诺沃斯达药业(上海)有限公司 | Parp7抑制剂及其用途 |
Family Cites Families (23)
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 |
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 |
EA006300B1 (ru) | 2000-10-30 | 2005-10-27 | Кудос Фармасеутикалс Лимитед | Производные фталазинона |
DE60218458T2 (de) | 2001-05-08 | 2007-11-15 | Kudos Pharmaceuticals Ltd. | Isochinolinon derivate als parp inhibitoren |
JP2005504034A (ja) * | 2001-08-02 | 2005-02-10 | ニューロクライン バイオサイエンシーズ, インコーポレイテッド | ゴナドトロピン放出性ホルモンレセプターアンタゴニストとしてのピリジノン誘導体およびピリダジノン誘導体 |
US7211779B2 (en) | 2001-08-14 | 2007-05-01 | Transchip, Inc. | Pixel sensor with charge evacuation element and systems and methods for using such |
JP4500161B2 (ja) | 2002-04-30 | 2010-07-14 | クドス ファーマシューティカルズ リミテッド | フタラジノン誘導体 |
GB2415430B (en) * | 2003-03-12 | 2006-07-12 | Kudos Pharm Ltd | Phthalazinone derivatives |
AU2004224191A1 (en) * | 2003-03-24 | 2004-10-07 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
CN1934092A (zh) * | 2004-03-23 | 2007-03-21 | 弗·哈夫曼-拉罗切有限公司 | 非核苷逆转录酶抑制剂 |
PE20060285A1 (es) | 2004-03-30 | 2006-05-08 | Aventis Pharma Inc | Piridonas sustituidas como inhibidores de pol(adp-ribosa)-polimerasa (parp) |
JP2007532592A (ja) * | 2004-04-15 | 2007-11-15 | エフ.ホフマン−ラ ロシュ アーゲー | ピリダジノン化合物の製造方法 |
MX2007002318A (es) | 2004-08-26 | 2007-04-17 | Kudos Pharm Ltd | Derivados de ftalazinona substituidos con 4-heteroarilmetilo. |
DK1919878T3 (da) * | 2005-07-21 | 2010-10-25 | Hoffmann La Roche | Pyridazinonderivater som thyroidhormonreceptoragonister |
AU2006298853A1 (en) * | 2005-09-30 | 2007-04-12 | F. Hoffmann-La Roche Ag | NNRT inhibitors |
JP4611441B2 (ja) * | 2006-04-03 | 2011-01-12 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | ポリ(adp−リボース)ポリメラーゼ(parp)阻害剤としてのアミド置換インダゾール及びベンゾトリアゾール誘導体 |
JP5271897B2 (ja) * | 2006-05-31 | 2013-08-21 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・エルレ・エルレ | ポリ(ADP−リボース)ポリメラーゼ(PARP)の阻害剤としての、ピロロ[1,2−a]ピラジン−1(2H)−オン及びピロロ[1,2−d][1,2,4]トリアジン−1(2H)−オン誘導体 |
US8466150B2 (en) | 2006-12-28 | 2013-06-18 | Abbott Laboratories | Inhibitors of poly(ADP-ribose)polymerase |
KR101491998B1 (ko) | 2006-12-28 | 2015-02-10 | 애브비 인코포레이티드 | 폴리(adp-리보스)폴리머라제 억제제 |
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 |
WO2011055270A1 (en) * | 2009-11-04 | 2011-05-12 | Wyeth Llc | Indole based receptor crth2 antagonists |
-
2006
- 2006-05-31 GB GBGB0610680.1A patent/GB0610680D0/en not_active Ceased
-
2007
- 2007-05-25 AU AU2007266836A patent/AU2007266836B2/en active Active
- 2007-05-25 ES ES07733716T patent/ES2702781T3/es active Active
- 2007-05-25 CN CN2013103167261A patent/CN103420988A/zh active Pending
- 2007-05-25 MX MX2008015014A patent/MX2008015014A/es active IP Right Grant
- 2007-05-25 NZ NZ572815A patent/NZ572815A/en unknown
- 2007-05-25 CA CA2653529A patent/CA2653529C/en active Active
- 2007-05-25 EP EP07733716.0A patent/EP2029551B1/en active Active
- 2007-05-25 US US12/227,513 patent/US8188084B2/en active Active
- 2007-05-25 WO PCT/GB2007/050295 patent/WO2007138351A2/en active Application Filing
- 2007-05-25 BR BRPI0711741A patent/BRPI0711741B8/pt active IP Right Grant
- 2007-05-25 KR KR1020087029132A patent/KR101529891B1/ko active IP Right Grant
- 2007-05-25 CN CNA2007800201367A patent/CN101501006A/zh active Pending
- 2007-05-25 JP JP2009512681A patent/JP5351755B2/ja active Active
-
2008
- 2008-10-27 ZA ZA200809238A patent/ZA200809238B/xx unknown
- 2008-11-04 IL IL195113A patent/IL195113A/en active IP Right Grant
- 2008-12-29 NO NO20085397A patent/NO343950B1/no unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2009538896A5 (pt-PT) | ||
RU2405771C2 (ru) | Гетероциклические замещенные фенилметаноны в качестве ингибиторов переносчика глицина 1 | |
JP7418395B2 (ja) | Shp2ホスファターゼ阻害剤およびこれらの使用方法 | |
RU2503676C2 (ru) | Пирролопиразиновые ингибиторы киназы | |
ES2805087T3 (es) | Compuestos de pirazolo[1,5-a]piridina sustituidos como inhibidores de la cinasa RET | |
JP2014506929A5 (pt-PT) | ||
ES2778700T3 (es) | Nuevos derivados de piperidinilo sustituidos con (hetero)arilo, un proceso para su preparación y composiciones farmacéuticas que los contienen | |
RU2005117383A (ru) | Производные фенилаланина в качестве ингибиторов дипептидилпептидазы для лечения или профилактики диабета | |
BR112021001292A2 (pt) | compostos heterobicíclicos para inibir a atividade de shp2 | |
AU2011253057B2 (en) | Nitrogen heterocyclic compounds useful as PDE10 inhibitors | |
JP2011500774A5 (pt-PT) | ||
JP2011516512A5 (ja) | 新規な置換スピロ[シクロアルキル−1,3'−インドール]−2'(1'H)−オン誘導体およびp38マイトジェン活性化タンパク質キナーゼ阻害剤としてのそれらの使用 | |
HRP20120105T1 (hr) | Aminoheterociklički spojevi | |
JP2020522570A5 (pt-PT) | ||
JP2009507758A5 (pt-PT) | ||
JP2018522046A5 (pt-PT) | ||
JP2012510998A5 (pt-PT) | ||
RU2014123316A (ru) | Ингибиторы фосфодиэстеразы типа 10а | |
JP2010524984A5 (pt-PT) | ||
JP2018529725A (ja) | キナーゼ阻害剤としての縮合ピラゾール誘導体 | |
RU2008145660A (ru) | Фармацевтические соединения | |
JP2015522002A5 (pt-PT) | ||
JP2013522238A5 (pt-PT) | ||
JP2014534976A5 (pt-PT) | ||
HRP20140796T1 (hr) | Spoj benzodiazepina i farmaceutski sastav |