JP2012502981A5 - - Google Patents
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- JP2012502981A5 JP2012502981A5 JP2011527466A JP2011527466A JP2012502981A5 JP 2012502981 A5 JP2012502981 A5 JP 2012502981A5 JP 2011527466 A JP2011527466 A JP 2011527466A JP 2011527466 A JP2011527466 A JP 2011527466A JP 2012502981 A5 JP2012502981 A5 JP 2012502981A5
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- JP
- Japan
- Prior art keywords
- optionally substituted
- pyrazolo
- methyl
- pyridine
- 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
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 201000010099 disease Diseases 0.000 claims description 29
- -1 substituted Chemical class 0.000 claims description 20
- 230000033115 angiogenesis Effects 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 9
- 102000004722 NADPH Oxidases Human genes 0.000 claims description 7
- 108010002998 NADPH Oxidases Proteins 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 230000002314 neuroinflammatory effect Effects 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 206010049771 Shock haemorrhagic Diseases 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 210000003027 ear inner Anatomy 0.000 claims description 2
- 230000002008 hemorrhagic effect Effects 0.000 claims description 2
- 208000019423 liver disease Diseases 0.000 claims description 2
- 208000030159 metabolic disease Diseases 0.000 claims description 2
- 230000001850 reproductive effect Effects 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 230000000472 traumatic effect Effects 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 22
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 21
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- ICZVBOAABXHPSZ-UHFFFAOYSA-N piperidine-2,5-dione Chemical compound O=C1CCC(=O)NC1 ICZVBOAABXHPSZ-UHFFFAOYSA-N 0.000 claims 3
- GIVSZYOESAXKLC-UHFFFAOYSA-N 2,5-dihydro-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1NC=C2C(=O)NNC2=C1 GIVSZYOESAXKLC-UHFFFAOYSA-N 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000005229 pyrazolopyridines Chemical class 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- KYXAVGBVNXUSPJ-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-5-(3-hydroxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=C(Cl)C=CC=2)C(=O)C=2C1=CC(=O)N(CCCO)C=2C1=CC=CC(Cl)=C1 KYXAVGBVNXUSPJ-UHFFFAOYSA-N 0.000 claims 1
- TYKNOHQECDBFFG-UHFFFAOYSA-N 2,4-dimethyl-5-(3-morpholin-4-yl-3-phenylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CCC(C=1C=CC=CC=1)N1CCOCC1 TYKNOHQECDBFFG-UHFFFAOYSA-N 0.000 claims 1
- REPLAUKRSYGQCF-UHFFFAOYSA-N 2,4-dimethyl-5-[(3-phenoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 REPLAUKRSYGQCF-UHFFFAOYSA-N 0.000 claims 1
- KPQLXWBACSEAIY-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 KPQLXWBACSEAIY-UHFFFAOYSA-N 0.000 claims 1
- UYRDYQVNBZUUFO-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCN1C(=O)CCCN1C(=O)C=C(NN(C=2C(=C(Cl)C=CC=2)Cl)C2=O)C2=C1C UYRDYQVNBZUUFO-UHFFFAOYSA-N 0.000 claims 1
- OQUPPCHOLDULTN-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=C(Cl)C=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 OQUPPCHOLDULTN-UHFFFAOYSA-N 0.000 claims 1
- DTPIZSZOPZWOSD-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=C(Cl)C=3)Cl)C(=O)C2=C(C)N1CC(=O)N1CCOCC1 DTPIZSZOPZWOSD-UHFFFAOYSA-N 0.000 claims 1
- KOAHEOQVOXWCEL-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=C(Cl)C=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 KOAHEOQVOXWCEL-UHFFFAOYSA-N 0.000 claims 1
- JSZBTGWTGLVHSN-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4,5-dimethyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(C)C(=O)C=C2NN1C1=CC=C(F)C=C1Cl JSZBTGWTGLVHSN-UHFFFAOYSA-N 0.000 claims 1
- LMDLSVMPBUPEBS-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4-(methoxymethyl)-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(COC)N1CC1=CC=CC=C1CN1CCOCC1 LMDLSVMPBUPEBS-UHFFFAOYSA-N 0.000 claims 1
- GKROQAQDYJPFCN-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(C)N1CC(=O)N1CCOCC1 GKROQAQDYJPFCN-UHFFFAOYSA-N 0.000 claims 1
- PRNBIEYRADGJCE-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCN1C(=O)CCCN1C(=O)C=C(NN(C=2C(=CC(F)=CC=2)Cl)C2=O)C2=C1C PRNBIEYRADGJCE-UHFFFAOYSA-N 0.000 claims 1
- WUBNGXBUNZLASY-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4-methyl-5-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCN1C1=CC=CC=C1CN1C(=O)C=C(NN(C=2C(=CC(F)=CC=2)Cl)C2=O)C2=C1C WUBNGXBUNZLASY-UHFFFAOYSA-N 0.000 claims 1
- VQUDPYBOGYTBBR-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 VQUDPYBOGYTBBR-UHFFFAOYSA-N 0.000 claims 1
- WRCYEDJLNSBZHE-UHFFFAOYSA-N 2-(2-chlorophenyl)-4,5-dimethyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(C)C(=O)C=C2NN1C1=CC=CC=C1Cl WRCYEDJLNSBZHE-UHFFFAOYSA-N 0.000 claims 1
- KJQWOWLDTVSADY-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(2-fluorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2C1=CC=CC=C1F KJQWOWLDTVSADY-UHFFFAOYSA-N 0.000 claims 1
- RGMDYMOVLWNGGN-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-chlorophenyl)-5-(3-ethoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2C1=CC=C(Cl)C=C1 RGMDYMOVLWNGGN-UHFFFAOYSA-N 0.000 claims 1
- VGEVTZMEMJTPCL-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-chlorophenyl)-5-[3-(dimethylamino)propyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCN(C)C)C=2C1=CC=C(Cl)C=C1 VGEVTZMEMJTPCL-UHFFFAOYSA-N 0.000 claims 1
- ZGQGAMXRPSNGAM-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-chlorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2C1=CC=C(Cl)C=C1 ZGQGAMXRPSNGAM-UHFFFAOYSA-N 0.000 claims 1
- KEKFTFDSCQLTLX-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC(=O)N1CCOCC1 KEKFTFDSCQLTLX-UHFFFAOYSA-N 0.000 claims 1
- YRQQEMIXQLMLOU-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-(2-morpholin-4-yl-2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC(C=1C=CC=CC=1)N1CCOCC1 YRQQEMIXQLMLOU-UHFFFAOYSA-N 0.000 claims 1
- JINBUKAYMLVOMA-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-(3-phenylprop-2-ynyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC#CC1=CC=CC=C1 JINBUKAYMLVOMA-UHFFFAOYSA-N 0.000 claims 1
- XDQVGFASNAANGE-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[(2-morpholin-4-ylphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1N1CCOCC1 XDQVGFASNAANGE-UHFFFAOYSA-N 0.000 claims 1
- CIOUWNFQNIJKBV-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[(3-phenoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 CIOUWNFQNIJKBV-UHFFFAOYSA-N 0.000 claims 1
- YQYNWIFVDAIJMK-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC(N=1)=CC=CC=1N1CCOCC1 YQYNWIFVDAIJMK-UHFFFAOYSA-N 0.000 claims 1
- YYWQXACDBDCTHO-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCN1C(=O)CCCN1C(=O)C=C(NN(C=2C(=CC=CC=2)Cl)C2=O)C2=C1C YYWQXACDBDCTHO-UHFFFAOYSA-N 0.000 claims 1
- RNGLVLSXXYCAHO-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 RNGLVLSXXYCAHO-UHFFFAOYSA-N 0.000 claims 1
- XKUPUTKAVAWLTM-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[[4-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC(C=C1)=CC=C1CN1CCOCC1 XKUPUTKAVAWLTM-UHFFFAOYSA-N 0.000 claims 1
- AFZWIYFEICOZIA-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-[[4-[(4-methylpiperazin-1-yl)methyl]phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1CN1C(=O)C=C(NN(C=2C(=CC=CC=2)Cl)C2=O)C2=C1C AFZWIYFEICOZIA-UHFFFAOYSA-N 0.000 claims 1
- RYGPVTKHNQSBNJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-methyl-1-(pyridin-2-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(CCCOCC)C(C)=C(C(N2C=3C(=CC=CC=3)Cl)=O)C=1N2CC1=CC=CC=N1 RYGPVTKHNQSBNJ-UHFFFAOYSA-N 0.000 claims 1
- PDACJHUCRPPXGF-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(CCCOCC)C(C)=C(C2=O)C=1NN2C1=CC=CC=C1Cl PDACJHUCRPPXGF-UHFFFAOYSA-N 0.000 claims 1
- VQXIMZFSMHXQNT-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(3-hydroxypropyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(CCCO)C(=O)C=C2NN1C1=CC=CC=C1Cl VQXIMZFSMHXQNT-UHFFFAOYSA-N 0.000 claims 1
- KRHOFJSKUFLUIO-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(cyclohexylmethyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC1CCCCC1 KRHOFJSKUFLUIO-UHFFFAOYSA-N 0.000 claims 1
- IPOPWQARYBSNET-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(3-phenoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN(CC=3C=C(OC=4C=CC=CC=4)C=CC=3)C(=O)C=C2N1 IPOPWQARYBSNET-UHFFFAOYSA-N 0.000 claims 1
- GZHXOZDAYYANSW-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[2-(3-methoxyphenyl)ethyl]-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CCN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2C)=O)=C1 GZHXOZDAYYANSW-UHFFFAOYSA-N 0.000 claims 1
- RUKMPYVDWDEZDQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[2-(dimethylamino)ethyl]-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(CCN(C)C)C(C)=C(C2=O)C=1NN2C1=CC=CC=C1Cl RUKMPYVDWDEZDQ-UHFFFAOYSA-N 0.000 claims 1
- ABSJAYONOLGODP-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-(1-phenylmethoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1C(C)OCC1=CC=CC=C1 ABSJAYONOLGODP-UHFFFAOYSA-N 0.000 claims 1
- IDDDKICSEMITDK-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-(3-morpholin-4-ylphenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2C(C=1)=CC=CC=1N1CCOCC1 IDDDKICSEMITDK-UHFFFAOYSA-N 0.000 claims 1
- SJZNHPLAJCICKZ-UHFFFAOYSA-N 2-(2-fluorophenyl)-4,5-dimethyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(C)C(=O)C=C2NN1C1=CC=CC=C1F SJZNHPLAJCICKZ-UHFFFAOYSA-N 0.000 claims 1
- DKVPFWLNGSWTND-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-methyl-5-(3-morpholin-4-yl-3-phenylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)F)C(=O)C2=C(C)N1CCC(C=1C=CC=CC=1)N1CCOCC1 DKVPFWLNGSWTND-UHFFFAOYSA-N 0.000 claims 1
- GFFYZUHBVIAMMS-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-methyl-5-[(3-phenoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)F)C(=O)C2=C(C)N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 GFFYZUHBVIAMMS-UHFFFAOYSA-N 0.000 claims 1
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-
2008
- 2008-09-23 EP EP08164857A patent/EP2166010A1/en not_active Withdrawn
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- 2009-09-22 RS RS20150070A patent/RS53781B1/sr unknown
- 2009-09-22 JP JP2011527466A patent/JP5700837B2/ja active Active
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- 2009-09-22 KR KR1020117006134A patent/KR20110056387A/ko not_active Ceased
- 2009-09-22 EP EP14190340.1A patent/EP2860179B1/en active Active
- 2009-09-22 PL PL14190340T patent/PL2860179T3/pl unknown
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- 2009-09-22 WO PCT/IB2009/054156 patent/WO2010035221A1/en not_active Ceased
- 2009-09-22 EP EP09787271.7A patent/EP2344492B1/en active Active
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- 2009-09-22 CN CN200980136710.4A patent/CN102159573B/zh active Active
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