JP2012502980A5 - - Google Patents
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- JP2012502980A5 JP2012502980A5 JP2011527465A JP2011527465A JP2012502980A5 JP 2012502980 A5 JP2012502980 A5 JP 2012502980A5 JP 2011527465 A JP2011527465 A JP 2011527465A JP 2011527465 A JP2011527465 A JP 2011527465A JP 2012502980 A5 JP2012502980 A5 JP 2012502980A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- pyridine
- dione
- optionally substituted
- methyl
- 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
- 230000033115 angiogenesis Effects 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- -1 substituted Chemical class 0.000 claims description 13
- 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 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- OUZMVFUWRAVKJL-UHFFFAOYSA-N 2-benzyl-4-[(3-methoxyphenyl)methyl]-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CC2=C3C(=O)N(CC=4C=CC=CC=4)NC3=CC(=O)N2CC=2N=CC=CC=2)=C1 OUZMVFUWRAVKJL-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 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
- 150000005229 pyrazolopyridines Chemical class 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 1
- PUJAVHPFFVDTNW-UHFFFAOYSA-N 2,4,5-trimethyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C(=O)C=C2NN(C)C(=O)C2=C1C PUJAVHPFFVDTNW-UHFFFAOYSA-N 0.000 claims 1
- DUNOKHOOSPBBFW-UHFFFAOYSA-N 2,4-dimethyl-5-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CCN1CCOCC1 DUNOKHOOSPBBFW-UHFFFAOYSA-N 0.000 claims 1
- YBUKFWRURFMXJW-UHFFFAOYSA-N 2,4-dimethyl-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CCC1=CC=CC=N1 YBUKFWRURFMXJW-UHFFFAOYSA-N 0.000 claims 1
- POESYHVFWKJJEZ-UHFFFAOYSA-N 2,4-dimethyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CC1=CC=CC=N1 POESYHVFWKJJEZ-UHFFFAOYSA-N 0.000 claims 1
- RQTCIHJTYXSNAH-UHFFFAOYSA-N 2,5-bis(2-methoxyethyl)-4-(3-phenoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=12C(=O)N(CCOC)NC2=CC(=O)N(CCOC)C=1CCCOC1=CC=CC=C1 RQTCIHJTYXSNAH-UHFFFAOYSA-N 0.000 claims 1
- ZOZJSDXEAOGPMN-UHFFFAOYSA-N 2-(2-methoxyethyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC(=O)N1CCOCC1 ZOZJSDXEAOGPMN-UHFFFAOYSA-N 0.000 claims 1
- DRHBZTXPFCZTGM-UHFFFAOYSA-N 2-(2-methoxyethyl)-4-methyl-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CCC1=CC=CC=N1 DRHBZTXPFCZTGM-UHFFFAOYSA-N 0.000 claims 1
- FKAKWDOGKQHZKQ-UHFFFAOYSA-N 2-(2-methoxyethyl)-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC=N1 FKAKWDOGKQHZKQ-UHFFFAOYSA-N 0.000 claims 1
- JPTWATAXPDEFIN-UHFFFAOYSA-N 2-(2-methoxyethyl)-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC=C1CN1CCOCC1 JPTWATAXPDEFIN-UHFFFAOYSA-N 0.000 claims 1
- YNAOIPBSQNZXBG-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-4-(3-phenoxypropyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1C2=CC(=O)N(CC=3N=CC=CC=3)C(CCCOC=3C=CC=CC=3)=C2C(=O)N1CCN1CCOCC1 YNAOIPBSQNZXBG-UHFFFAOYSA-N 0.000 claims 1
- IGMRUJFDRGIJNT-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C(=CC=C(Cl)C=3)Cl)C(=O)C2=C(C)N1CC(=O)N1CCOCC1 IGMRUJFDRGIJNT-UHFFFAOYSA-N 0.000 claims 1
- MSRMAMINSJYYAL-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-4-methyl-5-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C(=CC=C(Cl)C=3)Cl)C(=O)C2=C(C)N1CCN1CCOCC1 MSRMAMINSJYYAL-UHFFFAOYSA-N 0.000 claims 1
- NESLPNXRZCXEDV-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C(=CC=C(Cl)C=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=N1 NESLPNXRZCXEDV-UHFFFAOYSA-N 0.000 claims 1
- SRSFGXSICOTGNN-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C(=CC=C(Cl)C=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 SRSFGXSICOTGNN-UHFFFAOYSA-N 0.000 claims 1
- SWUVFWLVXYGLTC-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-5-(2-methoxyethyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(CCOC)C(C)=C(C2=O)C=1NN2CC1=CC(Cl)=CC=C1Cl SWUVFWLVXYGLTC-UHFFFAOYSA-N 0.000 claims 1
- OIVBQOLEYJUBFJ-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=N1 OIVBQOLEYJUBFJ-UHFFFAOYSA-N 0.000 claims 1
- RPRFNGSNDQIYRQ-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 RPRFNGSNDQIYRQ-UHFFFAOYSA-N 0.000 claims 1
- GYZYSAGRZKIZMW-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C=CC(Cl)=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=N1 GYZYSAGRZKIZMW-UHFFFAOYSA-N 0.000 claims 1
- DKGSXHQOYLMYAX-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CCOC=3C=CC(Cl)=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=N1 DKGSXHQOYLMYAX-UHFFFAOYSA-N 0.000 claims 1
- DJKCKEORYZBAFA-UHFFFAOYSA-N 2-benzyl-4-(3-chlorophenyl)-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CC=2C=CC=CC=2)C(=O)C=2C1=CC(=O)N(CCOC)C=2C1=CC=CC(Cl)=C1 DJKCKEORYZBAFA-UHFFFAOYSA-N 0.000 claims 1
- ZXJKQNLCANIJDO-UHFFFAOYSA-N 2-benzyl-4-butyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C=CC=CC=3)C(=O)C2=C(CCCC)N1CC1=CC=CC=N1 ZXJKQNLCANIJDO-UHFFFAOYSA-N 0.000 claims 1
- PYVNRQQEFLVCIB-UHFFFAOYSA-N 2-benzyl-4-butyl-5-[(3,5-dimethoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C=CC=CC=3)C(=O)C2=C(CCCC)N1CC1=CC(OC)=CC(OC)=C1 PYVNRQQEFLVCIB-UHFFFAOYSA-N 0.000 claims 1
- GWDCECQGWTWLNM-UHFFFAOYSA-N 2-benzyl-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=N1 GWDCECQGWTWLNM-UHFFFAOYSA-N 0.000 claims 1
- YWDKRTNQEGZPNJ-UHFFFAOYSA-N 2-benzyl-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CC=3C=CC=CC=3)C(=O)C2=C(C)N1C1=CC=CC(OC(F)(F)F)=C1 YWDKRTNQEGZPNJ-UHFFFAOYSA-N 0.000 claims 1
- FCQYKVGSPZHGIS-UHFFFAOYSA-N 2-benzyl-5-(2-methoxyethyl)-4-[(3-methoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CC=2C=CC=CC=2)C(=O)C=2C1=CC(=O)N(CCOC)C=2CC1=CC=CC(OC)=C1 FCQYKVGSPZHGIS-UHFFFAOYSA-N 0.000 claims 1
- UQFLQCVYJWHATB-UHFFFAOYSA-N 2-cyclohexyl-4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C3CCCCC3)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 UQFLQCVYJWHATB-UHFFFAOYSA-N 0.000 claims 1
- CIBZFHVFWWSWSA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(2-methoxyethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC=N1 CIBZFHVFWWSWSA-UHFFFAOYSA-N 0.000 claims 1
- JBQGZHNQAXPDMO-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-5-(2-methoxyethyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C)C(=O)C=2C1=CC(=O)N(CCOC)C=2C1=CC=C(Cl)C(Cl)=C1 JBQGZHNQAXPDMO-UHFFFAOYSA-N 0.000 claims 1
- AIWGTKUMEQJPNL-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-5-(2-methoxyethyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C)C(=O)C=2C1=CC(=O)N(CCOC)C=2C1=CC(Cl)=CC(Cl)=C1 AIWGTKUMEQJPNL-UHFFFAOYSA-N 0.000 claims 1
- VBPFYPKEWPVKJC-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC(C2=C3C(=O)N(CCN4CCOCC4)NC3=CC(=O)N2CC=2N=CC=CC=2)=C1 VBPFYPKEWPVKJC-UHFFFAOYSA-N 0.000 claims 1
- XRENEWWCQFFACG-UHFFFAOYSA-N 4-(3-chlorophenyl)-5-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC(C2=C3C(=O)N(CCC=4C=CC=CC=4)NC3=CC(=O)N2CCN2CCOCC2)=C1 XRENEWWCQFFACG-UHFFFAOYSA-N 0.000 claims 1
- GVSZDQZSTGXUPB-UHFFFAOYSA-N 4-(3-chlorophenyl)-5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CCN2CCOCC2)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2C1=CC=CC(Cl)=C1 GVSZDQZSTGXUPB-UHFFFAOYSA-N 0.000 claims 1
- UDXSFPJSASARFP-UHFFFAOYSA-N 4-(3-chlorophenyl)-5-[(4-chlorophenyl)methyl]-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C=C(NN(CCN2CCOCC2)C2=O)C2=C1C1=CC=CC(Cl)=C1 UDXSFPJSASARFP-UHFFFAOYSA-N 0.000 claims 1
- PJMZQAMXNBLGCM-UHFFFAOYSA-N 4-(4-chlorophenyl)-2,5-bis(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=12C(=O)N(CCOC)NC2=CC(=O)N(CCOC)C=1C1=CC=C(Cl)C=C1 PJMZQAMXNBLGCM-UHFFFAOYSA-N 0.000 claims 1
- ZLIGEFJQLFGMSA-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1C1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC=N1 ZLIGEFJQLFGMSA-UHFFFAOYSA-N 0.000 claims 1
- CORJTERQSHBEDP-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-[(3-methoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1C1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC(OC)=C1 CORJTERQSHBEDP-UHFFFAOYSA-N 0.000 claims 1
- OSWVDOAVYDUPKD-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1C1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC=C1CN1CCOCC1 OSWVDOAVYDUPKD-UHFFFAOYSA-N 0.000 claims 1
- ROYPNZBCCDBRQW-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=12C(=O)N(CCOC)NC2=CC(=O)N(C)C=1C1=CC=C(Cl)C=C1 ROYPNZBCCDBRQW-UHFFFAOYSA-N 0.000 claims 1
- KWFWZWBCFDJVAV-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-morpholin-4-ylethyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C1=C2C(=O)N(CCN3CCOCC3)NC2=CC(=O)N1CCC1=CC=CC=N1 KWFWZWBCFDJVAV-UHFFFAOYSA-N 0.000 claims 1
- LIIWIGDNQXWMAK-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C1=C2C(=O)N(CCN3CCOCC3)NC2=CC(=O)N1CC1=CC=CC=N1 LIIWIGDNQXWMAK-UHFFFAOYSA-N 0.000 claims 1
- BWGHUOANXXLSGP-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[2-(dimethylamino)ethyl]-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1C1=C2C(=O)N(CCN(C)C)NC2=CC(=O)N1CC1=CC=CC=N1 BWGHUOANXXLSGP-UHFFFAOYSA-N 0.000 claims 1
- WFTRDWSJEQMCOH-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CCN2CCOCC2)C(=O)C=2C1=CC(=O)N(CCOC)C=2C1=CC=C(Cl)C=C1 WFTRDWSJEQMCOH-UHFFFAOYSA-N 0.000 claims 1
- AGDUCJQYJICGEM-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(2-methoxyethyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C)C(=O)C=2C1=CC(=O)N(CCOC)C=2C1=CC=C(Cl)C=C1 AGDUCJQYJICGEM-UHFFFAOYSA-N 0.000 claims 1
- MJYGRDRUXPRNTI-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C1=C2C(=O)N(CCC=3C=CC=CC=3)NC2=CC(=O)N1CCN1CCOCC1 MJYGRDRUXPRNTI-UHFFFAOYSA-N 0.000 claims 1
- APCUVNXVBKJAAE-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CCN2CCOCC2)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2C1=CC=C(Cl)C=C1 APCUVNXVBKJAAE-UHFFFAOYSA-N 0.000 claims 1
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| EP2002835A1 (en) | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2000176A1 (en) | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole derivatives as NADPH Oxidase inhibitors |
| EP2166008A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2165707A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166010A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| CN104918616A (zh) | 2012-10-24 | 2015-09-16 | 格卢科克斯生物科技有限公司 | 用于治疗与烟酰胺腺嘌呤二核苷酸磷酸氧化酶相关的病况的三嗪衍生物 |
| US20140212891A1 (en) | 2013-01-29 | 2014-07-31 | Amina El Jamali | Compositions and Methods Using NOX5 |
| JP2018505226A (ja) | 2015-02-16 | 2018-02-22 | グルコックス・バイオテック・アーベー | Ｎ２−（３，４−ジメチルフェニル）−６−（（４−（ｐ−トリル）ピペラジン−１−イル）メチル）−１，３，５−トリアジン−２，４−ジアミン |
| EP3551034A1 (en) | 2016-12-07 | 2019-10-16 | Progenity, Inc. | Gastrointestinal tract detection methods, devices and systems |
| BR112019023109A2 (pt) | 2017-05-04 | 2020-05-26 | Glenmark Pharmaceuticals S.A. | Composto, composição farmacêutica e método para tratar uma doença, distúrbio, síndrome ou afecção mediada por nadph oxidase em um indivíduo |
| EP3479843A1 (en) | 2017-11-01 | 2019-05-08 | GenKyoTex Suisse SA | Use of nox inhibitors for treatment of cancer |
| US12227565B2 (en) | 2018-06-20 | 2025-02-18 | Biora Therapeutics, Inc. | Method of formulating a pharmaceutical composition comprising administering an immune modulator to the small intestine |
| WO2020106757A1 (en) | 2018-11-19 | 2020-05-28 | Progenity, Inc. | Ingestible device for delivery of therapeutic agent to the gastrointestinal tract |
| CN121197633A (zh) | 2019-12-13 | 2025-12-26 | 比特比德科有限责任公司 | 用于将治疗剂递送至胃肠道的可摄取装置 |
| US11896719B2 (en) | 2022-01-24 | 2024-02-13 | Calliditas Therapeutics Ab | Pharmaceutical compositions |
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| US3391407A (en) * | 1966-08-15 | 1968-07-09 | William A. Waters | Helmet |
| US3931407A (en) | 1973-03-01 | 1976-01-06 | American Hoechst Corporation | Method of treatment with and compositions containing condensed pyrroles bearing an N-phenyl substituent |
| DE3728278A1 (de) | 1986-12-17 | 1988-06-23 | Bayer Ag | Herbizide und fungizide mittel auf basis von substituierten pyrazolin-5-on derivaten |
| DE19518082A1 (de) * | 1995-05-17 | 1996-11-21 | Merck Patent Gmbh | 4(-Arylaminomethylen)-2,4-dihydropyrazol-3-one |
| US5763496A (en) | 1995-11-27 | 1998-06-09 | The Research Foundation Of State University Of New York | Prevention of atherosclerosis using NADPH oxidase inhibitors |
| TW432073B (en) | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
| WO1998037068A1 (en) * | 1997-02-21 | 1998-08-27 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| IL144468A0 (en) | 2000-07-27 | 2002-05-23 | Pfizer Prod Inc | Use of growth hormone secretagogues for improvement of functional health status |
| JP4196678B2 (ja) | 2001-04-26 | 2008-12-17 | 味の素株式会社 | 複素環化合物 |
| EP1291017A3 (en) | 2001-09-10 | 2003-07-02 | Warner-Lambert Company | Use of statins to inhibit formation of osteoclasts |
| KR20040097375A (ko) * | 2002-04-23 | 2004-11-17 | 시오노기 앤드 컴파니, 리미티드 | 피라졸로[1, 5-에이]피리미딘 유도체 및 이를 함유한엔에이디(피)에이취 산화효소 저해제 |
| CA2517416A1 (en) | 2003-02-28 | 2004-09-10 | Howard Florey Institute Of Experimental Physiology And Medicine | Therapeutic compositions |
| EP1616576A4 (en) | 2003-04-08 | 2010-02-10 | Mitsubishi Tanabe Pharma Corp | SPECIFIC NAD (P) H OXIDASE HEMMER |
| WO2005080378A1 (ja) | 2004-02-24 | 2005-09-01 | Mitsubishi Pharma Corporation | 縮合ピリダジン誘導体 |
| US7563788B2 (en) * | 2004-03-19 | 2009-07-21 | Pfizer Inc. | Substituted Imidazo[1,2-a]pyridines as Antibacterial Agents |
| KR20070060156A (ko) | 2004-10-04 | 2007-06-12 | 미리어드 제네틱스, 인크. | 알츠하이머병 치료용 화합물 |
| FR2882654B1 (fr) | 2005-03-01 | 2007-04-27 | Servier Lab | Utilisation de derives de la diosmetine pour le traitement et la prevention des pathologies thrombotiques |
| US7759337B2 (en) | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
| US20070014739A1 (en) | 2005-07-14 | 2007-01-18 | Eldridge Gary R | Compositions and methods for controlling biofilms and bacterial infections |
| DE102005048897A1 (de) | 2005-10-12 | 2007-04-19 | Sanofi-Aventis Deutschland Gmbh | Diacylindazol-derivate als Inhibitoren von Lipasen und Phospholipasen |
| JP2009532501A (ja) * | 2006-04-04 | 2009-09-10 | ミリアド ジェネティクス， インコーポレイテッド | 疾患および障害のための化合物 |
| EP2002835A1 (en) | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2000176A1 (en) * | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole derivatives as NADPH Oxidase inhibitors |
| WO2009072643A1 (en) | 2007-12-03 | 2009-06-11 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound and use thereof |
| US20090163452A1 (en) | 2007-12-20 | 2009-06-25 | Schwartz Janice B | Compositions and methods for lowering serum cholesterol |
| FR2929276B1 (fr) | 2008-04-01 | 2010-04-23 | Servier Lab | Nouveaux derives de diosmetine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP2165707A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166008A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166010A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| CA2823974A1 (en) | 2010-01-08 | 2011-07-14 | Beth Israel Deaconess Medical Center | Methods and compositions for the treatment of migraine headaches |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP2361912A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| CN102014373B (zh) | 2010-11-22 | 2015-04-01 | 中兴通讯股份有限公司 | 一种激活配置的方法及装置 |
| EP2591782A1 (en) | 2011-11-11 | 2013-05-15 | Johann Wolfgang Goethe-Universität | Nadph oxidase 4 inhibitors and use thereof |
-
2008
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- 2009-09-22 KR KR1020117006133A patent/KR101716511B1/ko not_active Expired - Fee Related
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