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 |
| EP2166010A1 (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 |
| EP2165707A1 (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 |
| EP2911667B1 (en) | 2012-10-24 | 2017-02-22 | Glucox Biotech AB | Triazine derivatives for the treatment of conditions associated with nicotinamide adenine dinucleotide phosphate oxidase |
| 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 |
| SG11201910172VA (en) | 2017-05-04 | 2019-11-28 | Glenmark Pharmaceuticals Sa | Substituted bicyclic heterocyclic compounds as nadph oxidase inhibitors |
| 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 |
| WO2020106704A2 (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 |
| AU6320998A (en) * | 1997-02-21 | 1998-09-09 | 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 |
| EP1396493A4 (en) | 2001-04-26 | 2005-08-03 | Ajinomoto Kk | HETEROCYCLIC COMPOUNDS |
| EP1291017A3 (en) | 2001-09-10 | 2003-07-02 | Warner-Lambert Company | Use of statins to inhibit formation of osteoclasts |
| WO2003091256A1 (en) * | 2002-04-23 | 2003-11-06 | Shionogi & Co., Ltd. | PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME |
| WO2004005267A2 (en) | 2002-07-03 | 2004-01-15 | Janssen Pharmaceutica, N.V. | Heteroaryl compounds useful in treating inflammatory disorders |
| NZ542059A (en) | 2003-02-28 | 2009-11-27 | Florey Howard Inst | Therapeutic compositions comprising an aryl sulphonate such as suramin, for the treatment of a pathological condition or event of the systemic vasculature resulting form the producation of reactive oxygen species. |
| 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 |
| DK1737459T3 (da) * | 2004-03-19 | 2009-10-26 | Warner Lambert Co | Imidazopyridin og imidazopyrimidinderivater som antibakterielle midler |
| CA2582674A1 (en) | 2004-10-04 | 2006-04-20 | Myriad Genetics, Inc. | Compounds for alzheimer's disease |
| 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 |
| US20090099179A1 (en) * | 2006-04-04 | 2009-04-16 | Myriad Genetics, Incorporated | Compounds for diseases and disorders |
| 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 |
| PE20091093A1 (es) | 2007-12-03 | 2009-08-25 | Takeda Pharmaceutical | Compuesto heterociclico que contiene nitrogeno y su uso |
| 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 |
| EP2166010A1 (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 |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| WO2011085293A1 (en) | 2010-01-08 | 2011-07-14 | Beth Israel Deaconess Medical Center | Methods and compositions for the treatment of migraine headaches |
| EP2361912A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP2361911A1 (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
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- 2009-09-22 BR BRPI0919331A patent/BRPI0919331A2/pt not_active IP Right Cessation
- 2009-09-22 EP EP09815761.3A patent/EP2342203B1/en active Active
- 2009-09-22 CN CN200980133736.3A patent/CN102137862B/zh not_active Expired - Fee Related
- 2009-09-22 US US13/120,438 patent/US8455486B2/en not_active Expired - Fee Related
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- 2009-09-22 JP JP2011527465A patent/JP5750372B2/ja not_active Expired - Fee Related
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2013
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