KR20130002317A - Ｎａｄｐｈ 옥시다아제 억제제인 피라졸로 피페리딘 유도체 - Google Patents

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Publication number

KR20130002317A

KR20130002317A KR1020127021663A KR20127021663A KR20130002317A KR 20130002317 A KR20130002317 A KR 20130002317A KR 1020127021663 A KR1020127021663 A KR 1020127021663A KR 20127021663 A KR20127021663 A KR 20127021663A KR 20130002317 A KR20130002317 A KR 20130002317A

Authority

KR

South Korea

Prior art keywords

pyrazolo

hexahydro

pyridin

optionally substituted

benzyl

Prior art date

2010-02-18

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.)

Withdrawn

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• RTTBBADOMOOPTQ-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-b]pyridine Chemical class C1CCNC2=C1NN=C2 RTTBBADOMOOPTQ-UHFFFAOYSA-N 0.000 title claims abstract description 37
• 108010002998 NADPH Oxidases Proteins 0.000 title claims abstract description 37
• 102000004722 NADPH Oxidases Human genes 0.000 title claims abstract description 37
• 239000003112 inhibitor Substances 0.000 title description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 101000968308 Homo sapiens Dual oxidase 1 Proteins 0.000 claims abstract description 7
• 101000968305 Homo sapiens Dual oxidase 2 Proteins 0.000 claims abstract description 7
• 102100021217 Dual oxidase 2 Human genes 0.000 claims abstract description 4
• -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims description 151
• 150000001875 compounds Chemical class 0.000 claims description 98
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 96
• 201000010099 disease Diseases 0.000 claims description 87
• 125000001072 heteroaryl group Chemical group 0.000 claims description 62
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 56
• 206010028980 Neoplasm Diseases 0.000 claims description 54
• 230000033115 angiogenesis Effects 0.000 claims description 52
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 42
• 238000000034 method Methods 0.000 claims description 40
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 39
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 37
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 36
• 201000011510 cancer Diseases 0.000 claims description 35
• 208000024891 symptom Diseases 0.000 claims description 33
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000003107 substituted aryl group Chemical group 0.000 claims description 28
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
• 208000014674 injury Diseases 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 208000023504 respiratory system disease Diseases 0.000 claims description 17
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 15
• 208000020084 Bone disease Diseases 0.000 claims description 14
• 208000022555 Genital disease Diseases 0.000 claims description 14
• 208000027866 inflammatory disease Diseases 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 230000004770 neurodegeneration Effects 0.000 claims description 14
• 208000017169 kidney disease Diseases 0.000 claims description 13
• 208000017520 skin disease Diseases 0.000 claims description 13
• 208000002193 Pain Diseases 0.000 claims description 12
• 208000026935 allergic disease Diseases 0.000 claims description 12
• 230000036407 pain Effects 0.000 claims description 12
• 210000003027 ear inner Anatomy 0.000 claims description 11
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 11
• 230000002008 hemorrhagic effect Effects 0.000 claims description 11
• 208000019423 liver disease Diseases 0.000 claims description 11
• 208000030159 metabolic disease Diseases 0.000 claims description 11
• 230000035939 shock Effects 0.000 claims description 11
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 11
• 230000008736 traumatic injury Effects 0.000 claims description 11
• 230000001419 dependent effect Effects 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 208000016097 disease of metabolism Diseases 0.000 claims description 9
• 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• XDDWGECWOBJRNT-UHFFFAOYSA-N 6-benzyl-2,4,5,7-tetrahydro-1h-pyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)NNC=2CN1CC1=CC=CC=C1 XDDWGECWOBJRNT-UHFFFAOYSA-N 0.000 claims description 7
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
• 230000002314 neuroinflammatory effect Effects 0.000 claims description 7
• GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 6
• ADAIEKAITRRAEN-UHFFFAOYSA-N 6-benzyl-3a,4,5,7-tetrahydro-2h-pyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC2C(=O)NN=C2CN1CC1=CC=CC=C1 ADAIEKAITRRAEN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 230000002491 angiogenic effect Effects 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000004453 alkoxycarbonyl 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
• 238000001959 radiotherapy Methods 0.000 claims description 5
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 4
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 4
• VXBVYYQZHZRYQU-UHFFFAOYSA-N 6-methyl-2-phenyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1N(C)CCC(C2=O)=C1NN2C1=CC=CC=C1 VXBVYYQZHZRYQU-UHFFFAOYSA-N 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
• 206010029240 Neuritis Diseases 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• CFRBCNVIUKICRC-UHFFFAOYSA-N 2,6-dibenzyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(CC=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CC=C1 CFRBCNVIUKICRC-UHFFFAOYSA-N 0.000 claims description 2
• QNQQRYAZASXZDH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(C=3C=C4OCOC4=CC=3)C(=O)C=2CCN1CC1=CC=CN=C1 QNQQRYAZASXZDH-UHFFFAOYSA-N 0.000 claims description 2
• GOHBSBGXDWUZNP-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-[(6-chloropyridin-3-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=NC(Cl)=CC=C1CN1CC(NN(C=2C=C3OCOC3=CC=2)C2=O)=C2CC1 GOHBSBGXDWUZNP-UHFFFAOYSA-N 0.000 claims description 2
• MVCZHMANIKWGLT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(CN2CC3=C(C(N(C=4C=C5OCOC5=CC=4)N3)=O)CC2)=C1 MVCZHMANIKWGLT-UHFFFAOYSA-N 0.000 claims description 2
• NMFWYSNVLVTFHM-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(C2CCN(CC=3C=CC=CC=3)CC2)C2=O)=C2CC1 NMFWYSNVLVTFHM-UHFFFAOYSA-N 0.000 claims description 2
• COKSBKLBYZEIAK-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(CN2CC3=C(C(N(C4CCN(CC=5C=CC=CC=5)CC4)N3)=O)CC2)=C1 COKSBKLBYZEIAK-UHFFFAOYSA-N 0.000 claims description 2
• NQTFOHGPHACNIH-UHFFFAOYSA-N 2-(1-phenylethyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound N1C=2CN(CC=3C=NC=CC=3)CCC=2C(=O)N1C(C)C1=CC=CC=C1 NQTFOHGPHACNIH-UHFFFAOYSA-N 0.000 claims description 2
• FLTMNZQDFLXCLI-UHFFFAOYSA-N 2-(2-benzyl-3-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl)-n-methylacetamide Chemical compound C1N(CC(=O)NC)CCC(C2=O)=C1NN2CC1=CC=CC=C1 FLTMNZQDFLXCLI-UHFFFAOYSA-N 0.000 claims description 2
• GMPHFUNHTGLWLB-UHFFFAOYSA-N 2-(2-fluoro-4-methylsulfonylphenyl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(C=2C(=CC(=CC=2)S(C)(=O)=O)F)C2=O)=C2CC1 GMPHFUNHTGLWLB-UHFFFAOYSA-N 0.000 claims description 2
• KRCPDJLMALLDNE-UHFFFAOYSA-N 2-(2-methoxyethyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(CCOC)NC=2CN1CC1=CC=CN=C1 KRCPDJLMALLDNE-UHFFFAOYSA-N 0.000 claims description 2
• CORSDXIQXLUJNY-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-6-(pyridin-2-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1CC2)=O)NC=1CN2CC1=CC=CC=N1 CORSDXIQXLUJNY-UHFFFAOYSA-N 0.000 claims description 2
• IZGGRIQXARYORT-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1CC2)=O)NC=1CN2CC1=CC=CN=C1 IZGGRIQXARYORT-UHFFFAOYSA-N 0.000 claims description 2
• KMBHUBYAENPCRU-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1CC2)=O)NC=1CN2CC1=CC=CC(C(F)(F)F)=C1 KMBHUBYAENPCRU-UHFFFAOYSA-N 0.000 claims description 2
• MFYMJQPWMKYMHF-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(CN2CC3=C(C(N(CCN4CCOCC4)N3)=O)CC2)=C1 MFYMJQPWMKYMHF-UHFFFAOYSA-N 0.000 claims description 2
• MKRSLCOCHLJMCP-UHFFFAOYSA-N 2-(3-methoxyphenyl)-6-(1-phenylethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CCN(CC=3N2)C(C)C=2C=CC=CC=2)=O)=C1 MKRSLCOCHLJMCP-UHFFFAOYSA-N 0.000 claims description 2
• LNPVHEDDQJQZOO-UHFFFAOYSA-N 2-(3-methoxyphenyl)-6-[(2-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CCN(CC=4C(=CC=CC=4)OC)CC=3N2)=O)=C1 LNPVHEDDQJQZOO-UHFFFAOYSA-N 0.000 claims description 2
• JIXVKEKCFRBLNB-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 JIXVKEKCFRBLNB-UHFFFAOYSA-N 0.000 claims description 2
• LPWPONPWEWKKIG-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(C=2C=CC(Cl)=CC=2)C2=O)=C2CC1 LPWPONPWEWKKIG-UHFFFAOYSA-N 0.000 claims description 2
• IJMSEUZVPUIVCO-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(pyridin-2-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2N=CC=CC=2)C2)=C2N1 IJMSEUZVPUIVCO-UHFFFAOYSA-N 0.000 claims description 2
• XBTPTSLULYFGBV-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=NC=CC=2)C2)=C2N1 XBTPTSLULYFGBV-UHFFFAOYSA-N 0.000 claims description 2
• NOBYTVHFKBSJNT-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 NOBYTVHFKBSJNT-UHFFFAOYSA-N 0.000 claims description 2
• PRRGIIYNKCYRFA-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[(4-methylsulfonylphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(NN(C=2C=CC(Cl)=CC=2)C2=O)=C2CC1 PRRGIIYNKCYRFA-UHFFFAOYSA-N 0.000 claims description 2
• FUINMUKVMGTPBS-UHFFFAOYSA-N 2-(4-methoxyphenyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(CCN(CC=2C=NC=CC=2)C2)=C2N1 FUINMUKVMGTPBS-UHFFFAOYSA-N 0.000 claims description 2
• IOLFIMTYRFAKDQ-UHFFFAOYSA-N 2-(7-chloroquinolin-4-yl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(C=2C3=CC=C(Cl)C=C3N=CC=2)C2=O)=C2CC1 IOLFIMTYRFAKDQ-UHFFFAOYSA-N 0.000 claims description 2
• KYDYPXMCQMHKAB-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(CC=2N=C3C=CC=CN3C=2)C2=O)=C2CC1 KYDYPXMCQMHKAB-UHFFFAOYSA-N 0.000 claims description 2
• STDCAOJSYGMDLF-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-6-(4-phenylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(CC=3N=C4C=CC=CN4C=3)C(=O)C=2CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 STDCAOJSYGMDLF-UHFFFAOYSA-N 0.000 claims description 2
• HKAGVFGNBIZIRP-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4N=C5C=CC=CN5C=4)N3)=O)CC2)=C1 HKAGVFGNBIZIRP-UHFFFAOYSA-N 0.000 claims description 2
• RYOIADQIOPOORM-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=NC=CC=2)C2)=C2N1 RYOIADQIOPOORM-UHFFFAOYSA-N 0.000 claims description 2
• KUOIWOBYKKKFIB-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 KUOIWOBYKKKFIB-UHFFFAOYSA-N 0.000 claims description 2
• KTOKHUFMULXOFS-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[(6-chloropyridin-3-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=NC(Cl)=CC=2)C2)=C2N1 KTOKHUFMULXOFS-UHFFFAOYSA-N 0.000 claims description 2
• DKEFMFMCUOVDHE-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=C(C=CC=2)C(F)(F)F)C2)=C2N1 DKEFMFMCUOVDHE-UHFFFAOYSA-N 0.000 claims description 2
• HOKRJJOKSYHKMT-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1OCCN1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 HOKRJJOKSYHKMT-UHFFFAOYSA-N 0.000 claims description 2
• AKZCHNGFMGAGCJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(CCN(C)C)NC=2CN1S(=O)(=O)C1=CC=C(C)C=C1 AKZCHNGFMGAGCJ-UHFFFAOYSA-N 0.000 claims description 2
• BDMVKYCKECTDIN-UHFFFAOYSA-N 2-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-6-methylsulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(N2C(C=3CCN(CC=3N2)S(C)(=O)=O)=O)N=C1 BDMVKYCKECTDIN-UHFFFAOYSA-N 0.000 claims description 2
• VEQHWEUDVUEBLO-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methyl]-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound CN(C)C1=CC=CC=C1CN1C(=O)C(CCN(C2)S(=O)(=O)C=3C=CC(C)=CC=3)=C2N1 VEQHWEUDVUEBLO-UHFFFAOYSA-N 0.000 claims description 2
• YLUVRZAURDXDJR-UHFFFAOYSA-N 2-benzhydryl-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CN=C1 YLUVRZAURDXDJR-UHFFFAOYSA-N 0.000 claims description 2
• HHHKFTOWZDMTFS-UHFFFAOYSA-N 2-benzyl-6-(3-chlorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 HHHKFTOWZDMTFS-UHFFFAOYSA-N 0.000 claims description 2
• UTVHZEPXLBLCGT-UHFFFAOYSA-N 2-benzyl-6-(3-fluorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 UTVHZEPXLBLCGT-UHFFFAOYSA-N 0.000 claims description 2
• QYQLPRRJCSWQTR-UHFFFAOYSA-N 2-benzyl-6-(3-methoxyphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 QYQLPRRJCSWQTR-UHFFFAOYSA-N 0.000 claims description 2
• AISWSLGKTPVRKF-UHFFFAOYSA-N 2-benzyl-6-(4-chlorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 AISWSLGKTPVRKF-UHFFFAOYSA-N 0.000 claims description 2
• IMCUFDDOLALXDR-UHFFFAOYSA-N 2-benzyl-6-(4-fluorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 IMCUFDDOLALXDR-UHFFFAOYSA-N 0.000 claims description 2
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