RU2490265C2 - Пиридазиноновые производные в качестве ингибиторов parp - Google Patents

Info

Publication number

RU2490265C2

RU2490265C2 RU2010123874/04A RU2010123874A RU2490265C2 RU 2490265 C2 RU2490265 C2 RU 2490265C2 RU 2010123874/04 A RU2010123874/04 A RU 2010123874/04A RU 2010123874 A RU2010123874 A RU 2010123874A RU 2490265 C2 RU2490265 C2 RU 2490265C2

Authority

RU

Russia

Prior art keywords

carbonyl

oxo

oxopiperazin

dihydropyridazin

trifluoroacetate

Prior art date

2007-11-15

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• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 10
• 239000012661 PARP inhibitor Substances 0.000 title description 23
• 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 title description 23
• 150000001875 compounds Chemical class 0.000 claims abstract description 308
• 150000003839 salts Chemical class 0.000 claims abstract description 58
• 239000003112 inhibitor Substances 0.000 claims abstract description 56
• 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 claims abstract description 32
• 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 claims abstract description 32
• 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims abstract description 29
• 239000003814 drug Substances 0.000 claims abstract description 25
• -1 bicyclo [1.1.1] pentyl Chemical group 0.000 claims description 439
• 125000000217 alkyl group Chemical group 0.000 claims description 141
• 239000000203 mixture Substances 0.000 claims description 111
• 229910052736 halogen Inorganic materials 0.000 claims description 93
• 150000002367 halogens Chemical class 0.000 claims description 91
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 84
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 81
• 238000000034 method Methods 0.000 claims description 73
• 238000011282 treatment Methods 0.000 claims description 73
• 206010028980 Neoplasm Diseases 0.000 claims description 68
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 65
• 201000011510 cancer Diseases 0.000 claims description 58
• 229910052760 oxygen Inorganic materials 0.000 claims description 50
• 229910052717 sulfur Inorganic materials 0.000 claims description 50
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 229920006395 saturated elastomer Polymers 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 32
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 230000002265 prevention Effects 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
• 206010012601 diabetes mellitus Diseases 0.000 claims description 9
• 239000011737 fluorine Substances 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 208000027866 inflammatory disease Diseases 0.000 claims description 9
• 230000000302 ischemic effect Effects 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• ZATJDLMIMGXSOJ-UHFFFAOYSA-N 2,4-dimethylpyridazin-3-one Chemical compound CC1=CC=NN(C)C1=O ZATJDLMIMGXSOJ-UHFFFAOYSA-N 0.000 claims description 8
• 206010063837 Reperfusion injury Diseases 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 230000001976 improved effect Effects 0.000 claims description 7
• 230000005764 inhibitory process Effects 0.000 claims description 7
• 230000004770 neurodegeneration Effects 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 238000011321 prophylaxis Methods 0.000 claims description 6
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
• 208000019553 vascular disease Diseases 0.000 claims description 6
• 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 description 5
• SGMOVYLUGVDSNT-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-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(=O)N(C3CCCC3)CC2)=N1 SGMOVYLUGVDSNT-UHFFFAOYSA-N 0.000 claims description 5
• RWJGRIHHRSKDDD-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4Cl)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4Cl)C RWJGRIHHRSKDDD-UHFFFAOYSA-N 0.000 claims description 5
• 206010038997 Retroviral infections Diseases 0.000 claims description 5
• QFLXYLHMJUPUTA-UHFFFAOYSA-N [3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-6-oxo-1,5-dihydropyridazin-2-yl] 2,2,2-trifluoroacetate Chemical compound FC(C(=O)ON1NC(C(C(=C1CC1=CC(=C(C=C1)F)C(=O)N1CC(N(CC1)C1CCCCC1)=O)C)C)=O)(F)F QFLXYLHMJUPUTA-UHFFFAOYSA-N 0.000 claims description 5
• AGZWIOIOHSYOBQ-UHFFFAOYSA-N [3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-6-oxo-5-(trifluoromethyl)-1,5-dihydropyridazin-2-yl] 2,2,2-trifluoroacetate Chemical compound FC(C(=O)ON1NC(C(C=C1CC1=CC(=C(C=C1)F)C(=O)N1CC(N(CC1)C1CCCC1)=O)C(F)(F)F)=O)(F)F AGZWIOIOHSYOBQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 208000015181 infectious disease Diseases 0.000 claims description 5
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000003003 spiro group Chemical group 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• CUVGGFVJAPAUTR-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3C)C4CCCCC4)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3C)C4CCCCC4)C CUVGGFVJAPAUTR-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000005972 dihydrochromenyl group Chemical group 0.000 claims description 4
• 201000006370 kidney failure Diseases 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 description 3
• 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 description 3
• WVLVNXURIODZRA-UHFFFAOYSA-N C1CCC(CC1)N2CCN(CC2=O)C(=O)C3=C(C=CC(=C3)CC4=CC(C(=O)NN4OC(=O)C(F)(F)F)C(F)(F)F)F Chemical compound C1CCC(CC1)N2CCN(CC2=O)C(=O)C3=C(C=CC(=C3)CC4=CC(C(=O)NN4OC(=O)C(F)(F)F)C(F)(F)F)F WVLVNXURIODZRA-UHFFFAOYSA-N 0.000 claims description 3
• RBHNOTMIJPRQBC-UHFFFAOYSA-N CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2C3CC4=CC=CC=C4CC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O Chemical compound CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2C3CC4=CC=CC=C4CC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O RBHNOTMIJPRQBC-UHFFFAOYSA-N 0.000 claims description 3
• LRWDEVQNGZXACC-UHFFFAOYSA-N CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2CC3C4=CC=CC=C4CCC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O Chemical compound CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2CC3C4=CC=CC=C4CCC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O LRWDEVQNGZXACC-UHFFFAOYSA-N 0.000 claims description 3
• DRNHVHQEQKZMAL-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=C(C=C4)Cl)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=C(C=C4)Cl)C DRNHVHQEQKZMAL-UHFFFAOYSA-N 0.000 claims description 3
• NWYXCXIBUKOTMG-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4)C NWYXCXIBUKOTMG-UHFFFAOYSA-N 0.000 claims description 3
• RSTCDRZGOWNHOF-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC(C)C(F)(F)F)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC(C)C(F)(F)F)C RSTCDRZGOWNHOF-UHFFFAOYSA-N 0.000 claims description 3
• NYNOMUZWNYLQOO-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC4(CCOCC4)C5=CC=CC=C5)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC4(CCOCC4)C5=CC=CC=C5)C NYNOMUZWNYLQOO-UHFFFAOYSA-N 0.000 claims description 3
• NHPHCISMLQIKKW-UHFFFAOYSA-N [3-[[3-(4-cyclobutyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-6-oxo-1,5-dihydropyridazin-2-yl] 2,2,2-trifluoroacetate Chemical compound FC(C(=O)ON1NC(C(C(=C1CC1=CC(=C(C=C1)F)C(=O)N1CC(N(CC1)C1CCC1)=O)C)C)=O)(F)F NHPHCISMLQIKKW-UHFFFAOYSA-N 0.000 claims description 3
• OUCZTXRPMSCINW-UHFFFAOYSA-N [3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-ethyl-5-methyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C)=C(CC)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 OUCZTXRPMSCINW-UHFFFAOYSA-N 0.000 claims description 3
• CIIXQFGFWXRNRU-UHFFFAOYSA-N [3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-methyl-6-oxo-5-(trifluoromethyl)pyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C(F)(F)F)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 CIIXQFGFWXRNRU-UHFFFAOYSA-N 0.000 claims description 3
• IQLJBFUYXUQJAH-UHFFFAOYSA-N [3-[[4-fluoro-3-(4-thiophen-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CCN(CC2)C2=CSC=C2)=N1 IQLJBFUYXUQJAH-UHFFFAOYSA-N 0.000 claims description 3
• IVDNZCSSHYLESM-UHFFFAOYSA-N [3-[[4-fluoro-3-[3-oxo-4-[4-(trifluoromethyl)pyridin-2-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=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 IVDNZCSSHYLESM-UHFFFAOYSA-N 0.000 claims description 3
• NRFNBNAZXMMBCV-UHFFFAOYSA-N [3-[[4-fluoro-3-[3-oxo-4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=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 NRFNBNAZXMMBCV-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 230000002207 retinal effect Effects 0.000 claims description 3
• 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 description 2
• 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 description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 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 description 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• QPMCMWZABOOUSH-CYBMUJFWSA-N 3-[[3-[(3r)-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-CYBMUJFWSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
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• 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 description 2
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• 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 description 2
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• 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 description 2
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