CA2789406A1 - Pyrazolo piperidine derivatives as nadph oxidase inhibitors - Google Patents

Info

Publication number

CA2789406A1

CA2789406A1 CA2789406A CA2789406A CA2789406A1 CA 2789406 A1 CA2789406 A1 CA 2789406A1 CA 2789406 A CA2789406 A CA 2789406A CA 2789406 A CA2789406 A CA 2789406A CA 2789406 A1 CA2789406 A1 CA 2789406A1

Authority

CA

Canada

Prior art keywords

pyridin

pyrazolo

hexahydro

optionally substituted

methyl

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 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 39
• 108010002998 NADPH Oxidases Proteins 0.000 title claims abstract description 39
• 102000004722 NADPH Oxidases Human genes 0.000 title claims abstract description 39
• 239000003112 inhibitor Substances 0.000 title description 3
• 238000011282 treatment Methods 0.000 claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 102100021217 Dual oxidase 2 Human genes 0.000 claims abstract description 12
• 101000968308 Homo sapiens Dual oxidase 1 Proteins 0.000 claims abstract description 11
• 101000968305 Homo sapiens Dual oxidase 2 Proteins 0.000 claims abstract description 11
• -1 6-chloropyridin-3-yl Chemical group 0.000 claims description 129
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 119
• 150000001875 compounds Chemical class 0.000 claims description 103
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 89
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 70
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 64
• 201000010099 disease Diseases 0.000 claims description 61
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 60
• 208000035475 disorder Diseases 0.000 claims description 58
• 238000000034 method Methods 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 57
• 206010028980 Neoplasm Diseases 0.000 claims description 54
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 50
• 230000033115 angiogenesis Effects 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
• 125000003107 substituted aryl group Chemical group 0.000 claims description 36
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 27
• 208000023504 respiratory system disease Diseases 0.000 claims description 23
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 20
• 208000027866 inflammatory disease Diseases 0.000 claims description 17
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• 230000001419 dependent effect Effects 0.000 claims description 15
• 208000020084 Bone disease Diseases 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 13
• 210000005095 gastrointestinal system Anatomy 0.000 claims description 13
• 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
• 208000010668 atopic eczema Diseases 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 208000019423 liver disease Diseases 0.000 claims description 12
• 230000036407 pain Effects 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 12
• 208000032456 Hemorrhagic Shock Diseases 0.000 claims description 11
• 206010040070 Septic Shock Diseases 0.000 claims description 11
• 206010049771 Shock haemorrhagic Diseases 0.000 claims description 11
• 230000000172 allergic effect Effects 0.000 claims description 11
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
• 210000003027 ear inner Anatomy 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 230000002008 hemorrhagic effect Effects 0.000 claims description 11
• 206010002199 Anaphylactic shock Diseases 0.000 claims description 10
• 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 10
• 208000003455 anaphylaxis Diseases 0.000 claims description 10
• 208000030159 metabolic disease Diseases 0.000 claims description 10
• 230000002314 neuroinflammatory effect Effects 0.000 claims description 10
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 238000001959 radiotherapy Methods 0.000 claims description 5
• PKZMKBGLUCUHJV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[(3-chloro-4-fluorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1CN1CC(C(=O)N(C=2C=C3OCOC3=CC=2)N2)=C2CC1 PKZMKBGLUCUHJV-UHFFFAOYSA-N 0.000 claims description 4
• MSLXXVXVASCLGG-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[(4-chlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(C=2C=C3OCOC3=CC=2)N2)=C2CC1 MSLXXVXVASCLGG-UHFFFAOYSA-N 0.000 claims description 4
• TZNRCUWFPYPPMY-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(C=2C=C3OCOC3=CC=2)N2)=C2CC1 TZNRCUWFPYPPMY-UHFFFAOYSA-N 0.000 claims description 4
• RYZISLNAQUCHEB-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[(4-methylsulfonylphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(C(=O)N(C=2C=C3OCOC3=CC=2)N2)=C2CC1 RYZISLNAQUCHEB-UHFFFAOYSA-N 0.000 claims description 4
• UAMOIDZFJAUOJA-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(CN2CC=3C(=O)N(C=4C=C5OCOC5=CC=4)NC=3CC2)=C1 UAMOIDZFJAUOJA-UHFFFAOYSA-N 0.000 claims description 4
• NLIIFVXJSJMVAM-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound FC1=CC=CC=C1N1C(=O)C(CN(CC=2C=NC=CC=2)CC2)=C2N1 NLIIFVXJSJMVAM-UHFFFAOYSA-N 0.000 claims description 4
• KFOSIZPIWHVOKY-UHFFFAOYSA-N 2-(2-hydroxyethyl)-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CCO)N2)=C2CC1 KFOSIZPIWHVOKY-UHFFFAOYSA-N 0.000 claims description 4
• NSZAEAYIHSNZLK-UHFFFAOYSA-N 2-(2-methoxyethyl)-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(CCOC)NC=2CCN1CC1=CC=C(OC)C=C1 NSZAEAYIHSNZLK-UHFFFAOYSA-N 0.000 claims description 4
• FAZQTVRCISFNSB-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-5-(pyridin-2-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=CC=N1 FAZQTVRCISFNSB-UHFFFAOYSA-N 0.000 claims description 4
• ZGUZDIDQNIPNSF-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=CN=C1 ZGUZDIDQNIPNSF-UHFFFAOYSA-N 0.000 claims description 4
• ZISOBPVMGZLFBU-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-(pyridin-2-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4N=CC=CC=4)CCC=3N2)=O)=C1 ZISOBPVMGZLFBU-UHFFFAOYSA-N 0.000 claims description 4
• DYLYFEADADAEKQ-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-[(4-phenylmethoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C=CC(OCC=5C=CC=CC=5)=CC=4)CCC=3N2)=O)=C1 DYLYFEADADAEKQ-UHFFFAOYSA-N 0.000 claims description 4
• UEACRNOYALDGCN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CN(CC=2C=NC=CC=2)CC2)=C2N1 UEACRNOYALDGCN-UHFFFAOYSA-N 0.000 claims description 4
• AOEPYPXMYVFQGI-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(CN2C(C=3CN(CC=4C=NC=CC=4)CCC=3N2)=O)=C1 AOEPYPXMYVFQGI-UHFFFAOYSA-N 0.000 claims description 4
• HYPRWZQSFIMVOE-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CC=2C=C(OC)C=CC=2)N2)=C2CC1 HYPRWZQSFIMVOE-UHFFFAOYSA-N 0.000 claims description 4
• HZUUJMNCGZMIMV-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-5-[(4-methoxyphenyl)methyl]-1,3a,4,6,7,7a-hexahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC2C(=O)N(CCOC=3C=CC(Cl)=CC=3)NC2CC1 HZUUJMNCGZMIMV-UHFFFAOYSA-N 0.000 claims description 4
• HYCGNGLYTNISJG-UHFFFAOYSA-N 2-benzyl-5-(pyridin-2-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CC=N1 HYCGNGLYTNISJG-UHFFFAOYSA-N 0.000 claims description 4
• PZMBBXPKGHCAJG-UHFFFAOYSA-N 2-benzyl-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CN=C1 PZMBBXPKGHCAJG-UHFFFAOYSA-N 0.000 claims description 4
• BMRMPINGYPPQEA-UHFFFAOYSA-N 2-benzyl-5-[(2,4-dichlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 BMRMPINGYPPQEA-UHFFFAOYSA-N 0.000 claims description 4
• XDYTVJRRXCISHF-UHFFFAOYSA-N 2-benzyl-5-[(3,4-dichlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 XDYTVJRRXCISHF-UHFFFAOYSA-N 0.000 claims description 4
• UDUWUZWRUZZOBQ-UHFFFAOYSA-N 2-benzyl-5-[(3,5-dichlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC(Cl)=CC(CN2CC=3C(=O)N(CC=4C=CC=CC=4)NC=3CC2)=C1 UDUWUZWRUZZOBQ-UHFFFAOYSA-N 0.000 claims description 4
• DVHJCTHTLRUBPC-UHFFFAOYSA-N 2-benzyl-5-[(3,5-dimethoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC(OC)=CC(CN2CC=3C(=O)N(CC=4C=CC=CC=4)NC=3CC2)=C1 DVHJCTHTLRUBPC-UHFFFAOYSA-N 0.000 claims description 4
• TXTPFFPIHIHGGZ-UHFFFAOYSA-N 2-benzyl-5-[(6-chloropyridin-3-yl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=NC(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 TXTPFFPIHIHGGZ-UHFFFAOYSA-N 0.000 claims description 4
• JXPHMWUWWPQRIJ-UHFFFAOYSA-N 2-phenyl-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(C=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CN=C1 JXPHMWUWWPQRIJ-UHFFFAOYSA-N 0.000 claims description 4
• WPDSDEXJLCZUDR-UHFFFAOYSA-N 2-phenyl-5-propyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(CCC)CCC=2NN1C1=CC=CC=C1 WPDSDEXJLCZUDR-UHFFFAOYSA-N 0.000 claims description 4
• JMQKBJPRXWKQPV-UHFFFAOYSA-N 3-[5-[(4-chlorophenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(C=2C=C(C=CC=2)C#N)N2)=C2CC1 JMQKBJPRXWKQPV-UHFFFAOYSA-N 0.000 claims description 4
• CSHZQYUUJUNVQV-UHFFFAOYSA-N 3-fluoro-4-[[2-(2-methyl-1,3-benzothiazol-6-yl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=C(C#N)C=C1F CSHZQYUUJUNVQV-UHFFFAOYSA-N 0.000 claims description 4
• XABOZUZUESTPPY-UHFFFAOYSA-N 3a-benzyl-5-[(4-chlorophenyl)methyl]-2-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-3-one Chemical compound C1C2(CC=3C=CC=CC=3)C(=O)N(C)N=C2CCN1CC1=CC=C(Cl)C=C1 XABOZUZUESTPPY-UHFFFAOYSA-N 0.000 claims description 4
• HSWCBWVBJFLVMT-UHFFFAOYSA-N 4-[(2-benzyl-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methyl]benzonitrile Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=C(C#N)C=C1 HSWCBWVBJFLVMT-UHFFFAOYSA-N 0.000 claims description 4
• ZCOWWFDUPKYTFH-UHFFFAOYSA-N 4-[[2-(1,3-benzodioxol-5-yl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1CC=2NN(C=3C=C4OCOC4=CC=3)C(=O)C=2CN1CC1=CC=C(C#N)C=C1 ZCOWWFDUPKYTFH-UHFFFAOYSA-N 0.000 claims description 4
• NZMCPKDOUPMLRX-UHFFFAOYSA-N 4-[[2-(2-fluorophenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound FC1=CC=CC=C1N1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 NZMCPKDOUPMLRX-UHFFFAOYSA-N 0.000 claims description 4
• BNQSWOGSBZOBLN-UHFFFAOYSA-N 4-[[2-(2-hydroxyethyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1C=2C(=O)N(CCO)NC=2CCN1CC1=CC=C(C#N)C=C1 BNQSWOGSBZOBLN-UHFFFAOYSA-N 0.000 claims description 4
• DHDRIPLNGBVTEP-UHFFFAOYSA-N 4-[[2-(2-methyl-1,3-benzothiazol-6-yl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=C(C#N)C=C1 DHDRIPLNGBVTEP-UHFFFAOYSA-N 0.000 claims description 4
• KBIQWEDKTDFZEM-UHFFFAOYSA-N 4-[[2-(3-methoxyphenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C=CC(=CC=4)C#N)CCC=3N2)=O)=C1 KBIQWEDKTDFZEM-UHFFFAOYSA-N 0.000 claims description 4
• FJIHSDZFHIEHSX-UHFFFAOYSA-N 4-[[2-(4-chlorophenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 FJIHSDZFHIEHSX-UHFFFAOYSA-N 0.000 claims description 4
• WQZAKMZSGPBIPB-UHFFFAOYSA-N 4-[[2-(4-methoxyphenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 WQZAKMZSGPBIPB-UHFFFAOYSA-N 0.000 claims description 4
• BQGAGLRRHJUASH-UHFFFAOYSA-N 4-[[2-[(2-methoxyphenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound COC1=CC=CC=C1CN1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 BQGAGLRRHJUASH-UHFFFAOYSA-N 0.000 claims description 4
• QKXSHACDEDMFNR-UHFFFAOYSA-N 4-[[2-[(3-methoxyphenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound COC1=CC=CC(CN2C(C=3CN(CC=4C=CC(=CC=4)C#N)CCC=3N2)=O)=C1 QKXSHACDEDMFNR-UHFFFAOYSA-N 0.000 claims description 4
• UEFJJIWOSRKCBI-UHFFFAOYSA-N 5-(3-methylbutyl)-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(CCC(C)C)CCC=2NN1C1=CC=CC=C1 UEFJJIWOSRKCBI-UHFFFAOYSA-N 0.000 claims description 4
• KOIRZCHDSGZXNA-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-2-(3-methoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C=C(Cl)C=CC=4)CCC=3N2)=O)=C1 KOIRZCHDSGZXNA-UHFFFAOYSA-N 0.000 claims description 4
• HEAUNENNFPCHJV-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(1-methylpiperidin-4-yl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CN(C)CCC1N1C(=O)C(CN(CC=2C=CC(Cl)=CC=2)CC2)=C2N1 HEAUNENNFPCHJV-UHFFFAOYSA-N 0.000 claims description 4
• NNPSYURULNVWIA-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(2-hydroxyethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(CCO)NC=2CCN1CC1=CC=C(Cl)C=C1 NNPSYURULNVWIA-UHFFFAOYSA-N 0.000 claims description 4
• JWSWYKVDHIQLAP-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(2-methyl-1,3-benzothiazol-6-yl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=C(Cl)C=C1 JWSWYKVDHIQLAP-UHFFFAOYSA-N 0.000 claims description 4
• VVDRVIGOBFJPMU-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(2-morpholin-4-ylethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(CCN2CCOCC2)N2)=C2CC1 VVDRVIGOBFJPMU-UHFFFAOYSA-N 0.000 claims description 4
• RADAISFGUZBEMD-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(3-methoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C=CC(Cl)=CC=4)CCC=3N2)=O)=C1 RADAISFGUZBEMD-UHFFFAOYSA-N 0.000 claims description 4
• FBQNLYWYSIYSBL-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-[(2-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC=C1CN1C(=O)C(CN(CC=2C=CC(Cl)=CC=2)CC2)=C2N1 FBQNLYWYSIYSBL-UHFFFAOYSA-N 0.000 claims description 4
• BVZBJRSSDNRJKI-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-(1-methylpiperidin-4-yl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(C2CCN(C)CC2)N2)=C2CC1 BVZBJRSSDNRJKI-UHFFFAOYSA-N 0.000 claims description 4
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