JP2012502980A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- HVJPHHLBRBHJEJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[(3-methoxyphenyl)methyl]-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(CCN4CCOCC4)N3)=O)=C2C=2C=CC(Cl)=CC=2)=O)=C1 HVJPHHLBRBHJEJ-UHFFFAOYSA-N 0.000 claims 1
- PBXXLIYKNZZAQX-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[(4-chlorophenyl)methyl]-2-(2-methoxyethyl)-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=C(Cl)C=C1 PBXXLIYKNZZAQX-UHFFFAOYSA-N 0.000 claims 1
- NNSKJPHOLMCMKY-UHFFFAOYSA-N 4-(4-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=C(Cl)C=C1 NNSKJPHOLMCMKY-UHFFFAOYSA-N 0.000 claims 1
- SVIUNYOULJGPQL-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[(4-methoxyphenyl)methyl]-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=C(NN(CCN2CCOCC2)C2=O)C2=C1C1=CC=C(Cl)C=C1 SVIUNYOULJGPQL-UHFFFAOYSA-N 0.000 claims 1
- RDLGXRPESIUATF-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methyl-2-(1-methylpiperidin-4-yl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCC1N1C(=O)C2=C(C=3C=CC(Cl)=CC=3)N(C)C(=O)C=C2N1 RDLGXRPESIUATF-UHFFFAOYSA-N 0.000 claims 1
- OVUSAYDQNMMGQW-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methyl-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(C)C=2C1=CC=C(Cl)C=C1 OVUSAYDQNMMGQW-UHFFFAOYSA-N 0.000 claims 1
- BQSFZKCTHVPDGN-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-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=2COC1=CC=C(Cl)C=C1 BQSFZKCTHVPDGN-UHFFFAOYSA-N 0.000 claims 1
- WDEVIMIOHCAKMP-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-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=2COC1=CC=C(Cl)C=C1 WDEVIMIOHCAKMP-UHFFFAOYSA-N 0.000 claims 1
- YSPFILHKAANWAT-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-5-[(3-methoxyphenyl)methyl]-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(CCN4CCOCC4)N3)=O)=C2COC=2C=CC(Cl)=CC=2)=O)=C1 YSPFILHKAANWAT-UHFFFAOYSA-N 0.000 claims 1
- MYWNPOSQWIBFBG-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-(2-methoxyethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(F)C=CC=1OCC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC=N1 MYWNPOSQWIBFBG-UHFFFAOYSA-N 0.000 claims 1
- QXDWRQQGYPMLHN-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-(2-methoxyethyl)-5-[(3-methoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(F)C=CC=1OCC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC=CC(OC)=C1 QXDWRQQGYPMLHN-UHFFFAOYSA-N 0.000 claims 1
- WXUNRHGGPNNOED-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(F)=CC=C1OCC1=C2C(=O)N(CCN3CCOCC3)NC2=CC(=O)N1CCC1=CC=CC=N1 WXUNRHGGPNNOED-UHFFFAOYSA-N 0.000 claims 1
- BHIJBNMXZGAWNV-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-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=2COC1=CC=C(F)C=C1 BHIJBNMXZGAWNV-UHFFFAOYSA-N 0.000 claims 1
- RALZUZJWCPZSDE-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-5-[(4-methoxyphenyl)methyl]-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=C(NN(CCN2CCOCC2)C2=O)C2=C1COC1=CC=C(F)C=C1 RALZUZJWCPZSDE-UHFFFAOYSA-N 0.000 claims 1
- YXCJVHIMJFZHRX-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-5-methyl-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(C)C=2COC1=CC=C(F)C=C1 YXCJVHIMJFZHRX-UHFFFAOYSA-N 0.000 claims 1
- HMZLMRLQFJOPSA-UHFFFAOYSA-N 4-butyl-2-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(CCCC)N1CC1=CC=CC=N1 HMZLMRLQFJOPSA-UHFFFAOYSA-N 0.000 claims 1
- OPLWNUKRRKIZRG-UHFFFAOYSA-N 4-butyl-5-[(4-chlorophenyl)methyl]-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(CCCC)N1CC1=CC=C(Cl)C=C1 OPLWNUKRRKIZRG-UHFFFAOYSA-N 0.000 claims 1
- FRANYBFLIHSLKR-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)-5-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CC(C)C)NC2=CC(=O)N1CCN1CCOCC1 FRANYBFLIHSLKR-UHFFFAOYSA-N 0.000 claims 1
- PVRJYEUZWAJLDC-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CC(C)C)NC2=CC(=O)N1CC1=CC=CN=C1 PVRJYEUZWAJLDC-UHFFFAOYSA-N 0.000 claims 1
- XMRUVYQDUHQGKP-UHFFFAOYSA-N 4-methyl-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CCN3CCOCC3)C(=O)C2=C(C)N1CC1=CC=CC=N1 XMRUVYQDUHQGKP-UHFFFAOYSA-N 0.000 claims 1
- IDMMWOMTIJWNPH-UHFFFAOYSA-N 4-methyl-2-(2-phenylethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CCC=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=N1 IDMMWOMTIJWNPH-UHFFFAOYSA-N 0.000 claims 1
- CRRGPFCYBLKMNB-UHFFFAOYSA-N 4-methyl-5-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CCC=3C=CC=CC=3)C(=O)C2=C(C)N1CCN1CCOCC1 CRRGPFCYBLKMNB-UHFFFAOYSA-N 0.000 claims 1
- FYWGRZWXGYEYGS-UHFFFAOYSA-N 4-methyl-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-2-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CCC=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=C1CN1CCOCC1 FYWGRZWXGYEYGS-UHFFFAOYSA-N 0.000 claims 1
- DVOWUOFDQUOXLU-UHFFFAOYSA-N 5-(2,3-dihydro-1h-inden-1-yl)-4-methyl-2-(2-methylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CC2=CC=CC=C2C1N1C(=O)C=C2NN(CC(C)C)C(=O)C2=C1C DVOWUOFDQUOXLU-UHFFFAOYSA-N 0.000 claims 1
- SNAOSTSCZMZTEO-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-4-(3-phenoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CCN2CCOCC2)C(=O)C=2C1=CC(=O)N(CCOC)C=2CCCOC1=CC=CC=C1 SNAOSTSCZMZTEO-UHFFFAOYSA-N 0.000 claims 1
- LLNNIOXPNJVOQM-UHFFFAOYSA-N 5-(2-methoxyethyl)-4-methyl-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(CCOC)C(C)=C(C2=O)C=1NN2CCN1CCOCC1 LLNNIOXPNJVOQM-UHFFFAOYSA-N 0.000 claims 1
- RYXBDCGRGBJKOR-UHFFFAOYSA-N 5-(2-methoxyethyl)-4-methyl-2-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(CCOC)C(C)=C(C2=O)C=1NN2CCC1=CC=CC=C1 RYXBDCGRGBJKOR-UHFFFAOYSA-N 0.000 claims 1
- PWKWDEGUUVWRFL-UHFFFAOYSA-N 5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CCN2CCOCC2)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2COCC1=CC=CC=C1 PWKWDEGUUVWRFL-UHFFFAOYSA-N 0.000 claims 1
- YBENYAPDCYJZSY-UHFFFAOYSA-N 5-(3-ethoxypropyl)-4-[(4-fluorophenoxy)methyl]-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=2COC1=CC=C(F)C=C1 YBENYAPDCYJZSY-UHFFFAOYSA-N 0.000 claims 1
- IODRHPFWTINVAF-UHFFFAOYSA-N 5-(furan-2-ylmethyl)-2,4-dimethyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CC1=CC=CO1 IODRHPFWTINVAF-UHFFFAOYSA-N 0.000 claims 1
- QTRCAJKPZVUDJJ-UHFFFAOYSA-N 5-[(1-acetylpiperidin-4-yl)methyl]-4-(4-chlorophenyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C(=O)C)CCC1CN1C(=O)C=C(NN(C)C2=O)C2=C1C1=CC=C(Cl)C=C1 QTRCAJKPZVUDJJ-UHFFFAOYSA-N 0.000 claims 1
- CFKYKSYBWSBIKU-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-4-methyl-2-(2-methylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CC(C)C)NC2=CC(=O)N1CC1=CC=C(Cl)C=C1Cl CFKYKSYBWSBIKU-UHFFFAOYSA-N 0.000 claims 1
- XXPBQQLRAVJRHZ-UHFFFAOYSA-N 5-[(2,5-dichlorophenyl)methyl]-4-methyl-2-(2-methylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CC(C)C)NC2=CC(=O)N1CC1=CC(Cl)=CC=C1Cl XXPBQQLRAVJRHZ-UHFFFAOYSA-N 0.000 claims 1
- JXIIYSYKRQKMID-UHFFFAOYSA-N 5-[(3,5-dimethoxyphenyl)methyl]-2-(2-methoxyethyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=C2C(=O)N(CCOC)NC2=CC(=O)N1CC1=CC(OC)=CC(OC)=C1 JXIIYSYKRQKMID-UHFFFAOYSA-N 0.000 claims 1
- JFXQSQODYRESON-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-2-(2-morpholin-4-ylethyl)-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(CCN4CCOCC4)N3)=O)=C2COCC=2C=CC=CC=2)=O)=C1 JFXQSQODYRESON-UHFFFAOYSA-N 0.000 claims 1
- ZCCYBMQNKIJUSI-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-4-methyl-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(CCN4CCOCC4)N3)=O)=C2C)=O)=C1 ZCCYBMQNKIJUSI-UHFFFAOYSA-N 0.000 claims 1
- XSXWUAWRIBEXPC-UHFFFAOYSA-N 5-[(4-benzylmorpholin-2-yl)methyl]-4-(4-chlorophenyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1C1=C2C(=O)N(C)NC2=CC(=O)N1CC(OCC1)CN1CC1=CC=CC=C1 XSXWUAWRIBEXPC-UHFFFAOYSA-N 0.000 claims 1
- OGWXPINUWDIXBE-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2,4-dimethyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(C)N1CC1=CC=C(Cl)C=C1 OGWXPINUWDIXBE-UHFFFAOYSA-N 0.000 claims 1
- QNYGNYFQYRQFGW-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-4-[(4-fluorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(F)=CC=C1OCC1=C2C(=O)N(CCN3CCOCC3)NC2=CC(=O)N1CC1=CC=C(Cl)C=C1 QNYGNYFQYRQFGW-UHFFFAOYSA-N 0.000 claims 1
- DWZHPUPEFPAOOX-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-4-methyl-2-(2-morpholin-4-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(CCN3CCOCC3)C(=O)C2=C(C)N1CC1=CC=C(Cl)C=C1 DWZHPUPEFPAOOX-UHFFFAOYSA-N 0.000 claims 1
- OWWUCBMJGKOXKV-UHFFFAOYSA-N 5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-[(2-chloro-4-fluorophenyl)methyl]-4-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)N1CC(=O)N(CC1)CCN1CC1=CC=CC=C1 OWWUCBMJGKOXKV-UHFFFAOYSA-N 0.000 claims 1
- ZTOLHQMQNFQCLH-UHFFFAOYSA-N 5-benzyl-4-methyl-2-(1-methylpiperidin-4-yl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C)CCC1N1C(=O)C2=C(C)N(CC=3C=CC=CC=3)C(=O)C=C2N1 ZTOLHQMQNFQCLH-UHFFFAOYSA-N 0.000 claims 1
- NZFCNHOQYNASNZ-UHFFFAOYSA-N 5-methyl-2-(2-morpholin-4-ylethyl)-4-(3-phenoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CCN2CCOCC2)C(=O)C=2C1=CC(=O)N(C)C=2CCCOC1=CC=CC=C1 NZFCNHOQYNASNZ-UHFFFAOYSA-N 0.000 claims 1
- 229930024421 Adenine Natural products 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- 206010002199 Anaphylactic shock Diseases 0.000 claims 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 1
- 102000004316 Oxidoreductases Human genes 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 229960000643 adenine Drugs 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- ZUYSZDNMBOFKSH-UHFFFAOYSA-N n-[3-(2-benzyl-4-methyl-3,6-dioxo-1h-pyrazolo[4,3-c]pyridin-5-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(C=C3C(C(N(CC=4C=CC=CC=4)N3)=O)=C2C)=O)=C1 ZUYSZDNMBOFKSH-UHFFFAOYSA-N 0.000 claims 1
- MRALYMXSTMMJPG-UHFFFAOYSA-N n-[3-[[2-[(2-chloro-4-fluorophenyl)methyl]-4-methyl-3,6-dioxo-1h-pyrazolo[4,3-c]pyridin-5-yl]methyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CN2C(C=C3C(C(N(CC=4C(=CC(F)=CC=4)Cl)N3)=O)=C2C)=O)=C1 MRALYMXSTMMJPG-UHFFFAOYSA-N 0.000 claims 1
- RFPKDSNACKLRFY-UHFFFAOYSA-N n-[3-[[4-methyl-3,6-dioxo-2-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridin-5-yl]methyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CN2C(C=C3C(C(N(CCC=4C=CC=CC=4)N3)=O)=C2C)=O)=C1 RFPKDSNACKLRFY-UHFFFAOYSA-N 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 208000016192 Demyelinating disease Diseases 0.000 description 7
- 206010012305 Demyelination Diseases 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 210000004204 blood vessel Anatomy 0.000 description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 description 5
- 206010006451 bronchitis Diseases 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010019280 Heart failures Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 3
- 206010029113 Neovascularisation Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 206010048554 Endothelial dysfunction Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 201000002980 Hyperparathyroidism Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 description 2
- 208000016604 Lyme disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010047115 Vasculitis Diseases 0.000 description 2
- 208000009956 adenocarcinoma Diseases 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- 238000002399 angioplasty Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 210000001736 capillary Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000003210 demyelinating effect Effects 0.000 description 2
- 208000010643 digestive system disease Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 230000008694 endothelial dysfunction Effects 0.000 description 2
- 230000003511 endothelial effect Effects 0.000 description 2
- 208000018685 gastrointestinal system disease Diseases 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 description 2
- 239000003642 reactive oxygen metabolite Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 210000000264 venule Anatomy 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- UZUYKYNVSJTWEH-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC(CC(Cl)=O)=C1 UZUYKYNVSJTWEH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002329 Aneurysm Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 201000003076 Angiosarcoma Diseases 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010053555 Arthritis bacterial Diseases 0.000 description 1
- 206010003256 Arthritis gonococcal Diseases 0.000 description 1
- 206010003267 Arthritis reactive Diseases 0.000 description 1
- 208000036487 Arthropathies Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010006448 Bronchiolitis Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 206010007749 Cataract diabetic Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 description 1
- 208000005243 Chondrosarcoma Diseases 0.000 description 1
- 201000009047 Chordoma Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010011903 Deafness traumatic Diseases 0.000 description 1
- 206010051055 Deep vein thrombosis Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
- 208000002251 Dissecting Aneurysm Diseases 0.000 description 1
- 201000009084 Dysgammaglobulinemia Diseases 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000006168 Ewing Sarcoma Diseases 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 206010016207 Familial Mediterranean fever Diseases 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 206010018634 Gouty Arthritis Diseases 0.000 description 1
- 208000001258 Hemangiosarcoma Diseases 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 208000031220 Hemophilia Diseases 0.000 description 1
- 208000009292 Hemophilia A Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000004454 Hyperalgesia Diseases 0.000 description 1
- 208000035154 Hyperesthesia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 0.000 description 1
- 206010020877 Hypertrophic osteoarthropathy Diseases 0.000 description 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 1
- 208000004575 Infectious Arthritis Diseases 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 208000032382 Ischaemic stroke Diseases 0.000 description 1
- 208000012659 Joint disease Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 208000018142 Leiomyosarcoma Diseases 0.000 description 1
- 208000034800 Leukoencephalopathies Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 208000027530 Meniere disease Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 208000001145 Metabolic Syndrome Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000004221 Multiple Trauma Diseases 0.000 description 1
- 102000006386 Myelin Proteins Human genes 0.000 description 1
- 108010083674 Myelin Proteins Proteins 0.000 description 1
- 208000003926 Myelitis Diseases 0.000 description 1
- 206010028570 Myelopathy Diseases 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000002946 Noise-Induced Hearing Loss Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 201000000023 Osteosclerosis Diseases 0.000 description 1
- 206010033109 Ototoxicity Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 208000006735 Periostitis Diseases 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- 206010065159 Polychondritis Diseases 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- 208000007048 Polymyalgia Rheumatica Diseases 0.000 description 1
- 206010036346 Posterior capsule opacification Diseases 0.000 description 1
- 206010036626 Presbyacusis Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 102000029797 Prion Human genes 0.000 description 1
- 108091000054 Prion Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000018359 Systemic autoimmune disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000002240 Tennis Elbow Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- 206010044541 Traumatic shock Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 206010047097 Vascular purpura Diseases 0.000 description 1
- 206010072810 Vascular wall hypertrophy Diseases 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 208000008383 Wilms tumor Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000002491 angiogenic effect Effects 0.000 description 1
- 230000001772 anti-angiogenic effect Effects 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 206010002895 aortic dissection Diseases 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000027746 artery morphogenesis Effects 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 208000003295 carpal tunnel syndrome Diseases 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 208000006990 cholangiocarcinoma Diseases 0.000 description 1
- 208000002849 chondrocalcinosis Diseases 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 210000001268 chyle Anatomy 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000002445 cystadenocarcinoma Diseases 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000007025 diabetic cataract Diseases 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
- 201000002664 drug-induced hearing loss Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 210000003566 hemangioblast Anatomy 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000021267 infertility disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 208000020658 intracerebral hemorrhage Diseases 0.000 description 1
- 201000007450 intrahepatic cholangiocarcinoma Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 208000023569 ischemic bowel disease Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 206010024627 liposarcoma Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 230000035168 lymphangiogenesis Effects 0.000 description 1
- 208000012804 lymphangiosarcoma Diseases 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 208000037819 metastatic cancer Diseases 0.000 description 1
- 230000006510 metastatic growth Effects 0.000 description 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 201000011201 multicentric reticulohistiocytosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- 230000023105 myelination Effects 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 208000001611 myxosarcoma Diseases 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000014399 negative regulation of angiogenesis Effects 0.000 description 1
- 208000025189 neoplasm of testis Diseases 0.000 description 1
- 201000008026 nephroblastoma Diseases 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 208000004235 neutropenia Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 208000020629 overactive bladder Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 208000004019 papillary adenocarcinoma Diseases 0.000 description 1
- 201000010198 papillary carcinoma Diseases 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 210000003460 periosteum Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 208000009169 relapsing polychondritis Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 201000008407 sebaceous adenocarcinoma Diseases 0.000 description 1
- 201000007321 sebaceous carcinoma Diseases 0.000 description 1
- 201000001223 septic arthritis Diseases 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 208000007056 sickle cell anemia Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000003839 sprouting angiogenesis Effects 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000007863 steatosis Effects 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 201000010965 sweat gland carcinoma Diseases 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000001720 vestibular Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20080164849 EP2166009A1 (en) | 2008-09-23 | 2008-09-23 | Pyrazolo pyridine derivatives as nadph oxidase inhibitors |
| EP08164849.5 | 2008-09-23 | ||
| PCT/IB2009/054155 WO2010035220A1 (en) | 2008-09-23 | 2009-09-22 | Pyrazolo pyridine derivatives as nadph oxidase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012502980A JP2012502980A (ja) | 2012-02-02 |
| JP2012502980A5 true JP2012502980A5 (https=) | 2012-11-08 |
| JP5750372B2 JP5750372B2 (ja) | 2015-07-22 |
Family
ID=40299403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011527465A Expired - Fee Related JP5750372B2 (ja) | 2008-09-23 | 2009-09-22 | Ｎａｄｐｈオキシダーゼインヒビターとしてのピラゾロピリジン誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8455486B2 (https=) |
| EP (2) | EP2166009A1 (https=) |
| JP (1) | JP5750372B2 (https=) |
| KR (1) | KR101716511B1 (https=) |
| CN (1) | CN102137862B (https=) |
| AU (1) | AU2009298007B2 (https=) |
| BR (1) | BRPI0919331A2 (https=) |
| CA (1) | CA2737538C (https=) |
| ES (1) | ES2561210T3 (https=) |
| IL (1) | IL211891B (https=) |
| RU (1) | RU2548022C2 (https=) |
| WO (1) | WO2010035220A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| US10173988B2 (en) | 2015-02-16 | 2019-01-08 | Glucox Biotech Ab | N2-(3,4-dimethylphenyl)-6-((4-(p-tolyl)piperazin-1-yl)methyl)-1,3,5-triazine-2,4-diamine |
| US10610104B2 (en) | 2016-12-07 | 2020-04-07 | Progenity, Inc. | Gastrointestinal tract detection methods, devices and systems |
| EP3619209A1 (en) | 2017-05-04 | 2020-03-11 | Glenmark Pharmaceuticals S.A. | 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 |
| US20220249814A1 (en) | 2018-11-19 | 2022-08-11 | Progenity, Inc. | Methods and devices for treating a disease with biotherapeutics |
| 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 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7902179B2 (en) | 2001-04-26 | 2011-03-08 | Ajinomoto Co., Inc. | Heterocyclic compounds |
| EP1291017A3 (en) | 2001-09-10 | 2003-07-02 | Warner-Lambert Company | Use of statins to inhibit formation of osteoclasts |
| EP1505068A4 (en) * | 2002-04-23 | 2008-03-19 | Shionogi & Co | PYRAZOLO (1,5-a) PYRIMIDINE DERIVATIVE AND INHIBITOR OF NAD (P) H OXIDASE CONTAINING SAID DERIVATIVE |
| JP2006520326A (ja) | 2003-02-28 | 2006-09-07 | ハワード フローリー インスティチュート オブ エクスペリメンタル フィジオロジー アンド メディシン | 治療薬 |
| JPWO2004089412A1 (ja) | 2003-04-08 | 2006-07-06 | 三菱ウェルファーマ株式会社 | 特異的ｎａｄ（ｐ）ｈオキシダーゼ抑制剤 |
| TW200533356A (en) | 2004-02-24 | 2005-10-16 | Mitsubishi Pharma Corp | Fused pyridazine derivatives |
| EP1737459B1 (en) * | 2004-03-19 | 2009-08-05 | Warner-Lambert Company LLC | Imidazopyridine and imidazopyrimidine derivatives as antibacterial agents |
| AU2005294404A1 (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 |
| CA2648652A1 (en) * | 2006-04-04 | 2007-10-11 | Myriad Genetics, Inc. | 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 |
| TW200930713A (en) | 2007-12-03 | 2009-07-16 | Takeda Pharmaceutical | 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 |
| 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 |
| 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 |
| 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
- 2008-09-23 EP EP20080164849 patent/EP2166009A1/en not_active Withdrawn
-
2009
- 2009-09-22 KR KR1020117006133A patent/KR101716511B1/ko not_active Expired - Fee Related
- 2009-09-22 CA CA2737538A patent/CA2737538C/en not_active Expired - Fee Related
- 2009-09-22 EP EP09815761.3A patent/EP2342203B1/en active Active
- 2009-09-22 ES ES09815761.3T patent/ES2561210T3/es active Active
- 2009-09-22 RU RU2011116232/04A patent/RU2548022C2/ru active
- 2009-09-22 JP JP2011527465A patent/JP5750372B2/ja not_active Expired - Fee Related
- 2009-09-22 US US13/120,438 patent/US8455486B2/en not_active Expired - Fee Related
- 2009-09-22 BR BRPI0919331A patent/BRPI0919331A2/pt not_active IP Right Cessation
- 2009-09-22 AU AU2009298007A patent/AU2009298007B2/en not_active Ceased
- 2009-09-22 CN CN200980133736.3A patent/CN102137862B/zh not_active Expired - Fee Related
- 2009-09-22 WO PCT/IB2009/054155 patent/WO2010035220A1/en not_active Ceased
-
2011
- 2011-03-23 IL IL211891A patent/IL211891B/en active IP Right Grant
-
2013
- 2013-01-31 US US13/755,617 patent/US9006238B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012502980A5 (https=) | ||
| JP2012502979A5 (https=) | ||
| JP2012502981A5 (https=) | ||
| JP2012502978A5 (https=) | ||
| JP6964096B2 (ja) | ３−オキソ−２，６−ジフェニル−２，３−ジヒドロピリダジン−４−カルボキサミド類 | |
| RU2538041C2 (ru) | Пиразолопиридиновые производные как ингибиторы надфн-оксидазы | |
| RU2640862C2 (ru) | Гетероциклические соединения, эффективные для ингибирования киназы | |
| RU2532161C2 (ru) | Пиразолопиридиновые производные как ингибиторы надфн-оксидазы | |
| JP5750372B2 (ja) | Ｎａｄｐｈオキシダーゼインヒビターとしてのピラゾロピリジン誘導体 | |
| JP5207983B2 (ja) | 肥満および他のｃｎｓ障害を治療するためのピラゾール類 | |
| JP5707406B2 (ja) | Ｎａｄｐｈオキシダーゼインヒビターとしてのピラゾリンジオン誘導体 | |
| AU2008214372A1 (en) | Therapeutic agents | |
| JP2011528372A (ja) | α７ニコチン性アセチルコリンレセプターインヒビター | |
| JP2002520324A (ja) | 新規な血管形成インヒビター | |
| JP2011504499A (ja) | トリプターゼ阻害剤として使用するためのスピロピペリジン | |
| JP2013519724A (ja) | Ｎａｄｐｈオキシダーゼ阻害剤としてのピラゾロピペリジン誘導体 | |
| JP2012502978A (ja) | Ｎａｄｐｈオキシダーゼインヒビターとしてのピラゾロピリジン誘導体 | |
| CN101490077A (zh) | 用作免疫调节剂的胆汁酸酰胺的磺酰基氨基羰基衍生物 | |
| CN102209540A (zh) | 使用α7-选择性配体的治疗方法 | |
| TWI471329B (zh) | 噻唑基及唑基－異喹啉酮及其使用方法 | |
| JP6970691B2 (ja) | Ｔｒｐｖ４拮抗薬 | |
| JPWO2019131582A1 (ja) | 含窒素６員環化合物 | |
| JP2010523627A (ja) | Ｇｐｂａｒ１アゴニストとしてのピリダジン誘導体、ピリジン誘導体およびピラン誘導体 | |
| JP2021515787A (ja) | アミノ−ベンゾイソチアゾール及びアミノ−ベンゾイソチアジアゾールのアミド化合物 | |
| JP6416125B2 (ja) | ｍＧｌｕＲ３の正のアロステリックモジュレーター |