KR101641596B1 - Ｐａｒｐ 억제제로서의 피리다지논 유도체 - Google Patents

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Publication number

KR101641596B1

KR101641596B1 KR1020107013113A KR20107013113A KR101641596B1 KR 101641596 B1 KR101641596 B1 KR 101641596B1 KR 1020107013113 A KR1020107013113 A KR 1020107013113A KR 20107013113 A KR20107013113 A KR 20107013113A KR 101641596 B1 KR101641596 B1 KR 101641596B1

Authority

KR

South Korea

Prior art keywords

carbonyl

oxo

trifluoroacetate

methyl

dihydropyridazin

Prior art date

2007-11-15

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.)

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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 15
• 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 275
• 238000011282 treatment Methods 0.000 claims abstract description 80
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 68
• 201000011510 cancer Diseases 0.000 claims abstract description 58
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 11
• 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 10
• 230000000302 ischemic effect Effects 0.000 claims abstract description 10
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 10
• 208000019553 vascular disease Diseases 0.000 claims abstract description 8
• 208000006011 Stroke Diseases 0.000 claims abstract description 7
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
• 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 6
• 206010038997 Retroviral infections Diseases 0.000 claims abstract description 6
• 201000006370 kidney failure Diseases 0.000 claims abstract description 6
• 206010057430 Retinal injury Diseases 0.000 claims abstract description 4
• 239000002534 radiation-sensitizing agent Substances 0.000 claims abstract description 4
• 230000009759 skin aging Effects 0.000 claims abstract description 4
• 230000037380 skin damage Effects 0.000 claims abstract description 4
• -1 bicyclo [1.1.1] pentyl Chemical group 0.000 claims description 310
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 278
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 234
• 125000000217 alkyl group Chemical group 0.000 claims description 144
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 96
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• 125000005843 halogen group Chemical group 0.000 claims description 76
• 238000000034 method Methods 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
• 150000002367 halogens Chemical class 0.000 claims description 55
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 125000005842 heteroatom Chemical group 0.000 claims description 43
• 229920006395 saturated elastomer Polymers 0.000 claims description 42
• 229910052717 sulfur Inorganic materials 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 33
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
• 230000002265 prevention Effects 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 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 27
• 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 27
• 239000003814 drug Substances 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 15
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 15
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000002393 azetidinyl group Chemical group 0.000 claims description 12
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000003566 oxetanyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
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• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
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• 238000011321 prophylaxis Methods 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 239000012458 free base Substances 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• FKRUSEKREOFROB-UHFFFAOYSA-N 4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC=1C=NNC(=O)C=1C FKRUSEKREOFROB-UHFFFAOYSA-N 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000004175 fluorobenzyl group Chemical group 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
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• ARBQQMHPEQJNID-UHFFFAOYSA-N 1-cyclopentylpiperazin-2-one Chemical compound O=C1CNCCN1C1CCCC1 ARBQQMHPEQJNID-UHFFFAOYSA-N 0.000 claims description 2
• LEOMFBHNMHBUOZ-UHFFFAOYSA-N 2-[[4-fluoro-3-[4-(2-hydroxy-2-methylpropyl)-3-oxopiperazine-1-carbonyl]phenyl]methyl]-4,5-dimethylpyridazin-3-one Chemical compound FC1=C(C=C(CN2N=CC(=C(C2=O)C)C)C=C1)C(=O)N1CC(N(CC1)CC(C)(C)O)=O LEOMFBHNMHBUOZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
• 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 description 2
• 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 2
• QQBHEBAZLOWBTG-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-5-ethyl-1h-pyridazin-1-ium-6-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH2+]1C(=O)C(CC)=CC(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCC3)CC2)=N1 QQBHEBAZLOWBTG-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 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 description 2
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