JP2012502979A5

JP2012502979A5 -

Download PDF

Info

Publication number: JP2012502979A5
Authority: JP; Japan
Prior art keywords: methyl; pyrazolo; pyridine; dione; optionally substituted
Prior art date: 2009-09-22
Legal status : Granted

Application number

JP2011527464A

Other languages

English (en)

Japanese (ja)

Other versions

JP2012502979A (ja

JP5700836B2 (ja

Filing date

2009-09-22

Publication date

2012-11-08

2008-09-23 Priority claimed from EP20080164853 external-priority patent/EP2165707A1/en

2009-09-22 Application filed filed Critical

2012-02-02 Publication of JP2012502979A publication Critical patent/JP2012502979A/ja

2012-11-08 Publication of JP2012502979A5 publication Critical patent/JP2012502979A5/ja

2015-04-15 Application granted granted Critical

2015-04-15 Publication of JP5700836B2 publication Critical patent/JP5700836B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-09-22 Anticipated expiration legal-status Critical

Links

-1 substituted Chemical class 0.000 claims description 99
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 37
201000010099 disease Diseases 0.000 claims description 37
125000001072 heteroaryl group Chemical group 0.000 claims description 37
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
230000033115 angiogenesis Effects 0.000 claims description 22
208000035475 disorder Diseases 0.000 claims description 22
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
206010028980 Neoplasm Diseases 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 14
125000003107 substituted aryl group Chemical group 0.000 claims description 14
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
201000011510 cancer Diseases 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
208000018522 Gastrointestinal disease Diseases 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 10
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 9
108010002998 NADPH Oxidases Proteins 0.000 claims description 9
102000004722 NADPH Oxidases Human genes 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
208000024172 Cardiovascular disease Diseases 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
208000017169 kidney disease Diseases 0.000 claims description 6
208000015122 neurodegenerative disease Diseases 0.000 claims description 6
230000002314 neuroinflammatory effect Effects 0.000 claims description 6
150000005229 pyrazolopyridines Chemical class 0.000 claims description 6
208000017520 skin disease Diseases 0.000 claims description 6
125000000547 substituted alkyl group Chemical group 0.000 claims description 6
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 5
208000020084 Bone disease Diseases 0.000 claims description 5
208000032456 Hemorrhagic Shock Diseases 0.000 claims description 5
208000002193 Pain Diseases 0.000 claims description 5
206010040070 Septic Shock Diseases 0.000 claims description 5
206010049771 Shock haemorrhagic Diseases 0.000 claims description 5
208000010668 atopic eczema Diseases 0.000 claims description 5
210000003027 ear inner Anatomy 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
230000002008 hemorrhagic effect Effects 0.000 claims description 5
208000019423 liver disease Diseases 0.000 claims description 5
208000030159 metabolic disease Diseases 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
230000001850 reproductive effect Effects 0.000 claims description 5
230000009885 systemic effect Effects 0.000 claims description 5
230000000472 traumatic effect Effects 0.000 claims description 5
206010002199 Anaphylactic shock Diseases 0.000 claims description 4
208000036110 Neuroinflammatory disease Diseases 0.000 claims description 4
230000000172 allergic effect Effects 0.000 claims description 4
208000003455 anaphylaxis Diseases 0.000 claims description 4
208000010643 digestive system disease Diseases 0.000 claims description 4
208000018685 gastrointestinal system disease Diseases 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
208000023504 respiratory system disease Diseases 0.000 claims description 4
125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 7
ICZVBOAABXHPSZ-UHFFFAOYSA-N piperidine-2,5-dione Chemical compound O=C1CCC(=O)NC1 ICZVBOAABXHPSZ-UHFFFAOYSA-N 0.000 claims 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims 2
150000001412 amines Chemical class 0.000 claims 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
PCVFZSJLTSQWCC-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=C(Cl)C=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2COC1=CC=C(F)C=C1 PCVFZSJLTSQWCC-UHFFFAOYSA-N 0.000 claims 1
HODXRQUEUJSFJO-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=C(Cl)C=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COC1=CC=C(F)C=C1 HODXRQUEUJSFJO-UHFFFAOYSA-N 0.000 claims 1
SREMKOWATWBMSA-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-5-(2-methoxyethyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC(F)=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2CN1CCCC1 SREMKOWATWBMSA-UHFFFAOYSA-N 0.000 claims 1
KDLREDKHWFPVCT-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-5-(2-pyridin-2-ylethyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC(F)=CC=C1N1C(=O)C2=C(CN3CCCC3)N(CCC=3N=CC=CC=3)C(=O)C=C2N1 KDLREDKHWFPVCT-UHFFFAOYSA-N 0.000 claims 1
QQNVDLUTNHLRQA-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-5-(3-ethoxypropyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC(F)=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2CN1CCCC1 QQNVDLUTNHLRQA-UHFFFAOYSA-N 0.000 claims 1
ZFJLYGWZJQPISO-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-5-(furan-2-ylmethyl)-4-(methoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(COC)N1CC1=CC=CO1 ZFJLYGWZJQPISO-UHFFFAOYSA-N 0.000 claims 1
BVRWBOSTUNIQEL-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-5-[(3,5-dimethoxyphenyl)methyl]-4-(methoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(COC)N1CC1=CC(OC)=CC(OC)=C1 BVRWBOSTUNIQEL-UHFFFAOYSA-N 0.000 claims 1
GYJAUAOTJLWYSV-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(1,3-thiazol-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC=3SC=CN=3)C(=O)C=C2N1 GYJAUAOTJLWYSV-UHFFFAOYSA-N 0.000 claims 1
KUVJYRJKTAQCEJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CCC=3N=CC=CC=3)C(=O)C=C2N1 KUVJYRJKTAQCEJ-UHFFFAOYSA-N 0.000 claims 1
LESNLOUGJWKDBG-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(piperidin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC3CNCCC3)C(=O)C=C2N1 LESNLOUGJWKDBG-UHFFFAOYSA-N 0.000 claims 1
WCORCCGDUGHUSA-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(piperidin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC3CCNCC3)C(=O)C=C2N1 WCORCCGDUGHUSA-UHFFFAOYSA-N 0.000 claims 1
TULJLCAZHLOETP-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC=3N=CC=NC=3)C(=O)C=C2N1 TULJLCAZHLOETP-UHFFFAOYSA-N 0.000 claims 1
UIOLSVGUKXXHFJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC=3N=CC=CC=3)C(=O)C=C2N1 UIOLSVGUKXXHFJ-UHFFFAOYSA-N 0.000 claims 1
IJAYIBLRYLHOAY-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC=3C=NC=CC=3)C(=O)C=C2N1 IJAYIBLRYLHOAY-UHFFFAOYSA-N 0.000 claims 1
PTAIFFKKIRTBAK-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(phenylmethoxymethyl)-5-(pyridin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC=3C=CN=CC=3)C(=O)C=C2N1 PTAIFFKKIRTBAK-UHFFFAOYSA-N 0.000 claims 1
BPGHSDLVMHHPOM-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(2-chlorophenyl)methoxymethyl]-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2COCC1=CC=CC=C1Cl BPGHSDLVMHHPOM-UHFFFAOYSA-N 0.000 claims 1
VEJYRLZGHNZLBY-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(2-chlorophenyl)methoxymethyl]-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1COCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CN=CC=N1 VEJYRLZGHNZLBY-UHFFFAOYSA-N 0.000 claims 1
AKFDZSFXUZDRNA-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(2-chlorophenyl)methoxymethyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1COCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=CN=C1 AKFDZSFXUZDRNA-UHFFFAOYSA-N 0.000 claims 1
REOJKUXEPLDYGO-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(2-chlorophenyl)methoxymethyl]-5-(pyridin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1COCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=NC=C1 REOJKUXEPLDYGO-UHFFFAOYSA-N 0.000 claims 1
SNHQTGDXVCIDJK-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(2-chlorophenyl)methoxymethyl]-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C=CC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COCC=2C(=CC=CC=2)Cl)=O)=N1 SNHQTGDXVCIDJK-UHFFFAOYSA-N 0.000 claims 1
BJHKLPQKEIDLSQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-chlorophenyl)methoxymethyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COCC1=CC=CC(Cl)=C1 BJHKLPQKEIDLSQ-UHFFFAOYSA-N 0.000 claims 1
ANMHNDLZEVWJRO-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxy-n-methylanilino)methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(N(C)CC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2C=NC=CC=2)=C1 ANMHNDLZEVWJRO-UHFFFAOYSA-N 0.000 claims 1
QFAYHOWWOSNWDF-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxy-n-methylanilino)methyl]-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(N(C)CC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC2=NN(C)C=C2)=C1 QFAYHOWWOSNWDF-UHFFFAOYSA-N 0.000 claims 1
NAXGJRRBDMXISQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenoxy)methyl]-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2N=CC=NC=2)=C1 NAXGJRRBDMXISQ-UHFFFAOYSA-N 0.000 claims 1
CDWOXZNFZCGYHN-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenoxy)methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2C=NC=CC=2)=C1 CDWOXZNFZCGYHN-UHFFFAOYSA-N 0.000 claims 1
ZUNPVZJUTGGJQB-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenoxy)methyl]-5-(pyridin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2C=CN=CC=2)=C1 ZUNPVZJUTGGJQB-UHFFFAOYSA-N 0.000 claims 1
GMJJKBZTFSBPKF-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenoxy)methyl]-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC2=NN(C)C=C2)=C1 GMJJKBZTFSBPKF-UHFFFAOYSA-N 0.000 claims 1
RLGVSNQFZXNMKQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenoxy)methyl]-5-[(4-methylmorpholin-2-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC2OCCN(C)C2)=C1 RLGVSNQFZXNMKQ-UHFFFAOYSA-N 0.000 claims 1
LICSECSKDFEXOI-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenoxy)methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2C)=C1 LICSECSKDFEXOI-UHFFFAOYSA-N 0.000 claims 1
BITUOKHKOCDHHR-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenyl)methoxymethyl]-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(COCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2N=CC=NC=2)=C1 BITUOKHKOCDHHR-UHFFFAOYSA-N 0.000 claims 1
CGQXEXIALWHOES-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenyl)methoxymethyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(COCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2C=NC=CC=2)=C1 CGQXEXIALWHOES-UHFFFAOYSA-N 0.000 claims 1
CKNAILSHTZETKU-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenyl)methoxymethyl]-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(COCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC2=NN(C)C=C2)=C1 CKNAILSHTZETKU-UHFFFAOYSA-N 0.000 claims 1
SWXBCEZBBMYBNO-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(3-methoxyphenyl)methoxymethyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(COCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2C)=C1 SWXBCEZBBMYBNO-UHFFFAOYSA-N 0.000 claims 1
RDBKPMHHYJSHAM-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-chlorophenyl)methoxymethyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COCC1=CC=C(Cl)C=C1 RDBKPMHHYJSHAM-UHFFFAOYSA-N 0.000 claims 1
ROKAONXTQJMORF-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2COC1=CC=C(F)C=C1 ROKAONXTQJMORF-UHFFFAOYSA-N 0.000 claims 1
IDVNQBAHDISGIR-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(F)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CCC1=CC=CC=N1 IDVNQBAHDISGIR-UHFFFAOYSA-N 0.000 claims 1
FXWAGVNZOBSMPL-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(F)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=CC=N1 FXWAGVNZOBSMPL-UHFFFAOYSA-N 0.000 claims 1
WCDAFXNVEAGWJZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(F)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=CN=C1 WCDAFXNVEAGWJZ-UHFFFAOYSA-N 0.000 claims 1
PDSFYGCLMNGRIS-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(pyridin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(F)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=NC=C1 PDSFYGCLMNGRIS-UHFFFAOYSA-N 0.000 claims 1
WQFUFEZXJXKPNC-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound S1C(C)=NC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COC=2C=CC(F)=CC=2)=O)=C1 WQFUFEZXJXKPNC-UHFFFAOYSA-N 0.000 claims 1
PNTLNACPURAKKI-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O1C(C)=NC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COC=2C=CC(F)=CC=2)=O)=N1 PNTLNACPURAKKI-UHFFFAOYSA-N 0.000 claims 1
NKBUBPMUSCKSEJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COC1=CC=C(F)C=C1 NKBUBPMUSCKSEJ-UHFFFAOYSA-N 0.000 claims 1
AFPPOVXVWBEHFT-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(4-methoxyphenyl)methoxymethyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(OC)=CC=C1COCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1C AFPPOVXVWBEHFT-UHFFFAOYSA-N 0.000 claims 1
NTNUCNNNZOVXED-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[(n-methylanilino)methyl]-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1N(C)CC(=C1C(=O)N(C=2C(=CC=CC=2)Cl)NC1=CC1=O)N1CCC1=CC=CC=N1 NTNUCNNNZOVXED-UHFFFAOYSA-N 0.000 claims 1
KMLFRTNOVIRGQT-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[2-(4-chlorophenyl)ethoxymethyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COCCC1=CC=C(Cl)C=C1 KMLFRTNOVIRGQT-UHFFFAOYSA-N 0.000 claims 1
DCDVCXUBBULIGH-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[3-(2,3-dihydroindol-1-yl)propyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(C)C(CCCN2C3=CC=CC=C3CC2)=C(C2=O)C=1NN2C1=CC=CC=C1Cl DCDVCXUBBULIGH-UHFFFAOYSA-N 0.000 claims 1
QIQLQSVMPCAADM-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(2-chlorophenyl)methyl-methylamino]methyl]-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2CN(C)CC1=CC=CC=C1Cl QIQLQSVMPCAADM-UHFFFAOYSA-N 0.000 claims 1
QVIFOVHTIOYBQQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(2-chlorophenyl)methyl-methylamino]methyl]-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1N=CC=NC=1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=C1Cl QVIFOVHTIOYBQQ-UHFFFAOYSA-N 0.000 claims 1
DFGDWHBOJRLOME-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(2-chlorophenyl)methyl-methylamino]methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CN=CC=1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=C1Cl DFGDWHBOJRLOME-UHFFFAOYSA-N 0.000 claims 1
DYPIVXZMGAJAFC-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(2-chlorophenyl)methyl-methylamino]methyl]-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=C1Cl DYPIVXZMGAJAFC-UHFFFAOYSA-N 0.000 claims 1
PDEFXGWGZRZFRY-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2CN(C)CC1=CC=CC(F)=C1 PDEFXGWGZRZFRY-UHFFFAOYSA-N 0.000 claims 1
FMSGBSWCDJBFTR-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CN=CC=1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 FMSGBSWCDJBFTR-UHFFFAOYSA-N 0.000 claims 1
DZWIEAUZAUJQAJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 DZWIEAUZAUJQAJ-UHFFFAOYSA-N 0.000 claims 1
ORKLPVMNGBILDW-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(3-methoxyphenyl)methyl-methylamino]methyl]-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN(C)CC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2N=CC=NC=2)=C1 ORKLPVMNGBILDW-UHFFFAOYSA-N 0.000 claims 1
DSCTWGGFYBWPAS-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(3-methoxyphenyl)methyl-methylamino]methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN(C)CC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2CC=2C=NC=CC=2)=C1 DSCTWGGFYBWPAS-UHFFFAOYSA-N 0.000 claims 1
ILMZWVBYWSINAU-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[(3-methoxyphenyl)methyl-methylamino]methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN(C)CC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2C)=C1 ILMZWVBYWSINAU-UHFFFAOYSA-N 0.000 claims 1
BKEWRSNQQOBGSN-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[3-(dimethylamino)phenoxy]methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN(C)C1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2C)=C1 BKEWRSNQQOBGSN-UHFFFAOYSA-N 0.000 claims 1
VUBAHUREQXFOEZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[3-(dimethylamino)phenyl]methoxymethyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN(C)C1=CC=CC(COCC2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2C)=C1 VUBAHUREQXFOEZ-UHFFFAOYSA-N 0.000 claims 1
KXNRZKHEZQYIQR-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[4-(2-chlorophenyl)piperazin-1-yl]methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2CN(CC1)CCN1C1=CC=CC=C1Cl KXNRZKHEZQYIQR-UHFFFAOYSA-N 0.000 claims 1
HVNHAXIVZGRLDD-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2CN(CC1)CCN1C1=CC=CC(Cl)=C1 HVNHAXIVZGRLDD-UHFFFAOYSA-N 0.000 claims 1
PHGJTVIQXZDFDQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(N2CCN(CC3=C4C(=O)N(C=5C(=CC=CC=5)Cl)NC4=CC(=O)N3C)CC2)=C1 PHGJTVIQXZDFDQ-UHFFFAOYSA-N 0.000 claims 1
QBRVWOAHPRQRRK-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[methyl(pyridin-2-ylmethyl)amino]methyl]-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1N=CC=NC=1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=N1 QBRVWOAHPRQRRK-UHFFFAOYSA-N 0.000 claims 1
AFFCSEJJKWBHBQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-[[methyl(pyridin-2-ylmethyl)amino]methyl]-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CN=CC=1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=N1 AFFCSEJJKWBHBQ-UHFFFAOYSA-N 0.000 claims 1
CVAKRDJTLMCEKA-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(2-methoxyethyl)-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2COCC1=CC=CC=C1 CVAKRDJTLMCEKA-UHFFFAOYSA-N 0.000 claims 1
OJSLKNKQJDZNTC-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(2-methoxyethyl)-4-[(3-methoxy-n-methylanilino)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2CN(C)C1=CC=CC(OC)=C1 OJSLKNKQJDZNTC-UHFFFAOYSA-N 0.000 claims 1
ZPGBSPXOVFRTRW-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(2-methoxyethyl)-4-[(3-methoxyphenoxy)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2COC1=CC=CC(OC)=C1 ZPGBSPXOVFRTRW-UHFFFAOYSA-N 0.000 claims 1
NQBZUEAMVDOXGP-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(2-methoxyethyl)-4-[(3-methoxyphenyl)methoxymethyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCOC)C=2COCC1=CC=CC(OC)=C1 NQBZUEAMVDOXGP-UHFFFAOYSA-N 0.000 claims 1
FISLGKGNZPOVLW-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2COCC1=CC=CC=C1 FISLGKGNZPOVLW-UHFFFAOYSA-N 0.000 claims 1
ZQEBNAAEUDNPBJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-[(4-fluorophenoxy)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2COC1=CC=C(F)C=C1 ZQEBNAAEUDNPBJ-UHFFFAOYSA-N 0.000 claims 1
YRDSLVOTHYKTLM-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-[(n-methylanilino)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2CN(C)C1=CC=CC=C1 YRDSLVOTHYKTLM-UHFFFAOYSA-N 0.000 claims 1
VDAIGDCFQUNZLD-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(pyrazin-2-ylmethyl)-4-(pyridin-3-ylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=NC=CC=3)N(CC=3N=CC=NC=3)C(=O)C=C2N1 VDAIGDCFQUNZLD-UHFFFAOYSA-N 0.000 claims 1
BVBLBWXFGVCILK-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C=CC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COCC=2C=CC=CC=2)=O)=N1 BVBLBWXFGVCILK-UHFFFAOYSA-N 0.000 claims 1
SRQKMUHXDLERQV-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-(pyridin-3-ylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C=CC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COCC=2C=NC=CC=2)=O)=N1 SRQKMUHXDLERQV-UHFFFAOYSA-N 0.000 claims 1
ZLPDECVEZVMLBD-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(2-methyl-1,3-thiazol-4-yl)methyl]-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound S1C(C)=NC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COCC=2C=CC=CC=2)=O)=C1 ZLPDECVEZVMLBD-UHFFFAOYSA-N 0.000 claims 1
SXHVBXXHRBCRAA-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CCC1=NOC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COCC=2C=CC=CC=2)=O)=N1 SXHVBXXHRBCRAA-UHFFFAOYSA-N 0.000 claims 1
PSPLMPHSWFGDGM-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O1C(C)=NC(CN2C(C=C3C(C(N(C=4C(=CC=CC=4)Cl)N3)=O)=C2COCC=2C=CC=CC=2)=O)=N1 PSPLMPHSWFGDGM-UHFFFAOYSA-N 0.000 claims 1
SKGQWRZFUKPQFQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[3-(diethylamino)propyl]-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCN(CC)CC)C=2COCC1=CC=CC=C1 SKGQWRZFUKPQFQ-UHFFFAOYSA-N 0.000 claims 1
HZZOZOZRNPBYCU-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-(3-phenoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2CCCOC1=CC=CC=C1 HZZOZOZRNPBYCU-UHFFFAOYSA-N 0.000 claims 1
WDKHEFAIQXURCH-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-(naphthalen-1-yloxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C(=O)N(C)C(COC=2C3=CC=CC=C3C=CC=2)=C(C2=O)C=1NN2C1=CC=CC=C1Cl WDKHEFAIQXURCH-UHFFFAOYSA-N 0.000 claims 1
VOSDIQDPMXJBIK-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COCC1=CC=CC=C1 VOSDIQDPMXJBIK-UHFFFAOYSA-N 0.000 claims 1
PUXUSIBPJWOVDC-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-[(2,2,2-trifluoro-1-phenylethoxy)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COC(C(F)(F)F)C1=CC=CC=C1 PUXUSIBPJWOVDC-UHFFFAOYSA-N 0.000 claims 1
RTZQBTBBGCVPGW-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-[(4-phenylpiperidin-1-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2CN(CC1)CCC1C1=CC=CC=C1 RTZQBTBBGCVPGW-UHFFFAOYSA-N 0.000 claims 1
IDSCLPNNBKCIOE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2CN(CC1)CCN1C1=CC=CC=N1 IDSCLPNNBKCIOE-UHFFFAOYSA-N 0.000 claims 1
PPPFANCKKAKHLZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-[3-(n-methylanilino)propyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1N(C)CCCC(=C1C2=O)N(C)C(=O)C=C1NN2C1=CC=CC=C1Cl PPPFANCKKAKHLZ-UHFFFAOYSA-N 0.000 claims 1
UIYIGSVLWPQFFG-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-[[methyl(pyridin-2-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=N1 UIYIGSVLWPQFFG-UHFFFAOYSA-N 0.000 claims 1
MWRWDZFQIZJDDV-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 MWRWDZFQIZJDDV-UHFFFAOYSA-N 0.000 claims 1
CFLABQRWEQVNSH-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-(phenylmethoxymethyl)-5-(pyrazin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC=3N=CC=NC=3)C(=O)C=C2N1 CFLABQRWEQVNSH-UHFFFAOYSA-N 0.000 claims 1
JUILUCRSSOJWLQ-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-[(3-methoxyphenyl)methoxymethyl]-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(COCC2=C3C(=O)N(C=4C(=CC=CC=4)OC)NC3=CC(=O)N2CC2=NN(C)C=C2)=C1 JUILUCRSSOJWLQ-UHFFFAOYSA-N 0.000 claims 1
HBPBGFBHFJGNIU-UHFFFAOYSA-N 2-(2-methoxyphenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC=C1N1C(=O)C2=C(COCC=3C=CC=CC=3)N(CC3=NN(C)C=C3)C(=O)C=C2N1 HBPBGFBHFJGNIU-UHFFFAOYSA-N 0.000 claims 1
CTRFVZMHMDQEMA-UHFFFAOYSA-N 2-(2-methoxyphenyl)-5-methyl-4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC=C1N1C(=O)C2=C(CN3CCN(CC3)C=3N=CC=CC=3)N(C)C(=O)C=C2N1 CTRFVZMHMDQEMA-UHFFFAOYSA-N 0.000 claims 1
ZVKSOONMTMLIPC-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(methoxymethyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=C(Cl)C=CC=3)C(=O)C2=C(COC)N1CCC1=CC=CC=N1 ZVKSOONMTMLIPC-UHFFFAOYSA-N 0.000 claims 1
VRAPLEXZKCZADX-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(methoxymethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=C(Cl)C=CC=3)C(=O)C2=C(COC)N1CC1=CC=CC=N1 VRAPLEXZKCZADX-UHFFFAOYSA-N 0.000 claims 1
KOQVPUQGNZNVME-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(methoxymethyl)-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=C(Cl)C=CC=3)C(=O)C2=C(COC)N1CC1=CC=CC=C1CN1CCOCC1 KOQVPUQGNZNVME-UHFFFAOYSA-N 0.000 claims 1
KWAQPBQCMRVQLT-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=C(Cl)C=CC=2)C(=O)C=2C1=CC(=O)N(CCOC)C=2CN(C)CC1=CC=CC(F)=C1 KWAQPBQCMRVQLT-UHFFFAOYSA-N 0.000 claims 1
NTVLCCJRJMDHEF-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=NC=1CCN1C(=O)C=C2NN(C=3C=C(Cl)C=CC=3)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 NTVLCCJRJMDHEF-UHFFFAOYSA-N 0.000 claims 1
VZPUQKHSETYHGT-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(2-methoxyethyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=C(Cl)C=CC=2)C(=O)C=2C1=CC(=O)N(CCOC)C=2CN1CCCC1 VZPUQKHSETYHGT-UHFFFAOYSA-N 0.000 claims 1
LSTCCSADZCKTOW-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(2-pyridin-2-ylethyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC(N2C(C3=C(CN4CCCC4)N(CCC=4N=CC=CC=4)C(=O)C=C3N2)=O)=C1 LSTCCSADZCKTOW-UHFFFAOYSA-N 0.000 claims 1
SOQVZQMSVFEHKR-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(3-ethoxypropyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=C(Cl)C=CC=2)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2CN1CCCC1 SOQVZQMSVFEHKR-UHFFFAOYSA-N 0.000 claims 1
NZSLOYWWORETJT-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(3-ethoxypropyl)-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=C(Cl)C=CC=2)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2CN(C)CC1=CC=CC(F)=C1 NZSLOYWWORETJT-UHFFFAOYSA-N 0.000 claims 1
RUOPOUSFNSMWOA-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[(4-chlorophenyl)methyl]-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C(=O)C=C2NN(C=3C=C(Cl)C=CC=3)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 RUOPOUSFNSMWOA-UHFFFAOYSA-N 0.000 claims 1
JCWBXLVQULSORV-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=C(Cl)C=CC=2)C(=O)C=2C1=CC(=O)N(C)C=2CN1CCCC1 JCWBXLVQULSORV-UHFFFAOYSA-N 0.000 claims 1
UQRJSBFHCUVKJF-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)-5-(pyridin-3-ylmethyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CCCN1CC1=C2C(=O)N(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)NC2=CC(=O)N1CC1=CC=CN=C1 UQRJSBFHCUVKJF-UHFFFAOYSA-N 0.000 claims 1
XCDKLNXYPSAOGE-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-3,6-dioxo-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridin-5-yl]-n,n-dimethylacetamide Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CC(=O)N(C)C)C=2COCC1=CC=CC=C1 XCDKLNXYPSAOGE-UHFFFAOYSA-N 0.000 claims 1
RLNJZSSWIFGNEM-UHFFFAOYSA-N 2-benzyl-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-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=2CN(C)CC1=CC=CC(F)=C1 RLNJZSSWIFGNEM-UHFFFAOYSA-N 0.000 claims 1
JBZJTJCEAKLNKW-UHFFFAOYSA-N 2-benzyl-5-(2-methoxyethyl)-4-(pyrrolidin-1-ylmethyl)-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=2CN1CCCC1 JBZJTJCEAKLNKW-UHFFFAOYSA-N 0.000 claims 1
OZNVPYWERKTDRI-UHFFFAOYSA-N 2-benzyl-5-(3-ethoxypropyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(CC=2C=CC=CC=2)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2CN1CCCC1 OZNVPYWERKTDRI-UHFFFAOYSA-N 0.000 claims 1
HHGNXLAMHHSSMK-UHFFFAOYSA-N 2-benzyl-5-(3-ethoxypropyl)-4-[[(3-fluorophenyl)methyl-methylamino]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(CCCOCC)C=2CN(C)CC1=CC=CC(F)=C1 HHGNXLAMHHSSMK-UHFFFAOYSA-N 0.000 claims 1
SSJUJFPVDJGMLR-UHFFFAOYSA-N 2-benzyl-5-[(3,5-dimethoxyphenyl)methyl]-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC(OC)=CC(CN2C(C=C3C(C(N(CC=4C=CC=CC=4)N3)=O)=C2CN2CCCC2)=O)=C1 SSJUJFPVDJGMLR-UHFFFAOYSA-N 0.000 claims 1
MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims 1
YFYXARILUNMSAZ-UHFFFAOYSA-N 2-methyl-4-(3-phenoxypropyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1OCCCC1=C2C(=O)N(C)NC2=CC(=O)N1CCC1=CC=CC=N1 YFYXARILUNMSAZ-UHFFFAOYSA-N 0.000 claims 1
XYVBABQLSHGAOD-UHFFFAOYSA-N 2-methyl-4-(3-phenoxypropyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1OCCCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=CC=N1 XYVBABQLSHGAOD-UHFFFAOYSA-N 0.000 claims 1
PIYZQSNNZLYBJO-UHFFFAOYSA-N 2-methyl-4-(phenoxymethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1OCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=CC=N1 PIYZQSNNZLYBJO-UHFFFAOYSA-N 0.000 claims 1
HGWGCIAGIYDOJB-UHFFFAOYSA-N 2-methyl-4-(phenylmethoxymethyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1COCC1=C2C(=O)N(C)NC2=CC(=O)N1CCC1=CC=CC=N1 HGWGCIAGIYDOJB-UHFFFAOYSA-N 0.000 claims 1
PAPUYEIGEIJCSD-UHFFFAOYSA-N 2-methyl-4-(phenylmethoxymethyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1COCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=CC=N1 PAPUYEIGEIJCSD-UHFFFAOYSA-N 0.000 claims 1
FWBNUZREMDSUTP-UHFFFAOYSA-N 2-methyl-4-(phenylmethoxymethyl)-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1COCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=CN=C1 FWBNUZREMDSUTP-UHFFFAOYSA-N 0.000 claims 1
UCSZBDACPVZVSG-UHFFFAOYSA-N 4-(4-benzylmorpholin-2-yl)-2-(2-chlorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2C(OCC1)CN1CC1=CC=CC=C1 UCSZBDACPVZVSG-UHFFFAOYSA-N 0.000 claims 1
MGJDCGKHNMUARC-UHFFFAOYSA-N 4-(benzhydryloxymethyl)-2-(2-chlorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COC(C=1C=CC=CC=1)C1=CC=CC=C1 MGJDCGKHNMUARC-UHFFFAOYSA-N 0.000 claims 1
FGDVLAFTRHNMJH-UHFFFAOYSA-N 4-(methoxymethyl)-2-methyl-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(COC)N1CCC1=CC=CC=N1 FGDVLAFTRHNMJH-UHFFFAOYSA-N 0.000 claims 1
CCXDPHWQGWYYDP-UHFFFAOYSA-N 4-[(3-chlorophenoxy)methyl]-2-(2-chlorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COC1=CC=CC(Cl)=C1 CCXDPHWQGWYYDP-UHFFFAOYSA-N 0.000 claims 1
OBGXQDDSGBYMHS-UHFFFAOYSA-N 4-[(3-methoxyphenoxy)methyl]-2-(2-methoxyphenyl)-5-[(1-methylpyrazol-3-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(OCC2=C3C(=O)N(C=4C(=CC=CC=4)OC)NC3=CC(=O)N2CC2=NN(C)C=C2)=C1 OBGXQDDSGBYMHS-UHFFFAOYSA-N 0.000 claims 1
DUQMDVKXRMCKLU-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-2-(2-chlorophenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=CC=N1 DUQMDVKXRMCKLU-UHFFFAOYSA-N 0.000 claims 1
ZGHQPQMCIWSNHE-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-2-(2-chlorophenyl)-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=CN=C1 ZGHQPQMCIWSNHE-UHFFFAOYSA-N 0.000 claims 1
IHJYJLKIBIZRRV-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-2-(2-chlorophenyl)-5-(pyridin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1OCC1=C2C(=O)N(C=3C(=CC=CC=3)Cl)NC2=CC(=O)N1CC1=CC=NC=C1 IHJYJLKIBIZRRV-UHFFFAOYSA-N 0.000 claims 1
IYBCGBWBZNZORE-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-2-(2-chlorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC=CC=2)Cl)C(=O)C=2C1=CC(=O)N(C)C=2COC1=CC=C(Cl)C=C1 IYBCGBWBZNZORE-UHFFFAOYSA-N 0.000 claims 1
JOWGSSFRCUSROF-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-2-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1OCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=CC=N1 JOWGSSFRCUSROF-UHFFFAOYSA-N 0.000 claims 1
AEPIPEQFKKPVBH-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-5-(3-ethoxypropyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2COC1=CC=C(Cl)C=C1 AEPIPEQFKKPVBH-UHFFFAOYSA-N 0.000 claims 1
LSHCPWCVVGRBMF-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]-5-[(3-methoxyphenyl)methyl]-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(C)N3)=O)=C2COC=2C=CC(Cl)=CC=2)=O)=C1 LSHCPWCVVGRBMF-UHFFFAOYSA-N 0.000 claims 1
HUAWDZUTZBHTTN-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-methyl-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(F)C=CC=1OCC1=C2C(=O)N(C)NC2=CC(=O)N1CCC1=CC=CC=N1 HUAWDZUTZBHTTN-UHFFFAOYSA-N 0.000 claims 1
VSDKYMVLLSYSOZ-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-methyl-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(C)NC2=CC(=O)N1CC1=CC=CC=N1 VSDKYMVLLSYSOZ-UHFFFAOYSA-N 0.000 claims 1
VHTFEPFRGBZZST-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-methyl-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(F)C=CC=1OCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=CN=C1 VHTFEPFRGBZZST-UHFFFAOYSA-N 0.000 claims 1
GTUYFROUGNQRJB-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(F)C=CC=1OCC1=C2C(=O)N(C)NC2=CC(=O)N1CC(N=1)=CC=CC=1N1CCOCC1 GTUYFROUGNQRJB-UHFFFAOYSA-N 0.000 claims 1
ALKCJLBKHJSZID-UHFFFAOYSA-N 4-[[(3-fluorophenyl)methyl-methylamino]methyl]-2-(4-phenylmethoxyphenyl)-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CN=CC=1CN1C(=O)C=C2NN(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 ALKCJLBKHJSZID-UHFFFAOYSA-N 0.000 claims 1
KZFGWGKWQXABEX-UHFFFAOYSA-N 4-[[benzyl(methyl)amino]methyl]-2-(2-chloro-4-fluorophenyl)-5-(3-methoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C(=CC(F)=CC=2)Cl)C(=O)C=2C1=CC(=O)N(CCCOC)C=2CN(C)CC1=CC=CC=C1 KZFGWGKWQXABEX-UHFFFAOYSA-N 0.000 claims 1
QFTQBMVIQXRZFM-UHFFFAOYSA-N 4-[[benzyl(methyl)amino]methyl]-2-(2-chlorophenyl)-5-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CC=C1 QFTQBMVIQXRZFM-UHFFFAOYSA-N 0.000 claims 1
YTWKQQOMKHGYIA-UHFFFAOYSA-N 4-butyl-2-(2-chloro-4-fluorophenyl)-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(CCCC)N(CCOC)C(=O)C=C2NN1C1=CC=C(F)C=C1Cl YTWKQQOMKHGYIA-UHFFFAOYSA-N 0.000 claims 1
MWQUVRBQYDLVAM-UHFFFAOYSA-N 4-butyl-2-(2-chloro-4-fluorophenyl)-5-(2-pyridin-2-ylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(CCCC)N1CCC1=CC=CC=N1 MWQUVRBQYDLVAM-UHFFFAOYSA-N 0.000 claims 1
PERJEFPIGLGUMG-UHFFFAOYSA-N 4-butyl-2-(2-chloro-4-fluorophenyl)-5-(furan-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(CCCC)N1CC1=CC=CO1 PERJEFPIGLGUMG-UHFFFAOYSA-N 0.000 claims 1
PPUXVKVMOBSSQR-UHFFFAOYSA-N 4-butyl-2-(2-chloro-4-fluorophenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(CCCC)N1CC1=CC=CC=N1 PPUXVKVMOBSSQR-UHFFFAOYSA-N 0.000 claims 1
CWTGFEKCWCVQRV-UHFFFAOYSA-N 4-butyl-2-(2-chloro-4-fluorophenyl)-5-[(3,5-dimethoxyphenyl)methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(CCCC)N1CC1=CC(OC)=CC(OC)=C1 CWTGFEKCWCVQRV-UHFFFAOYSA-N 0.000 claims 1
FONZIFPDKGIOAZ-UHFFFAOYSA-N 4-butyl-2-(2-chloro-4-fluorophenyl)-5-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC(F)=CC=3)Cl)C(=O)C2=C(CCCC)N1CC1=CC=CC=C1CN1CCOCC1 FONZIFPDKGIOAZ-UHFFFAOYSA-N 0.000 claims 1
LCEMDVWFYIFMPZ-UHFFFAOYSA-N 4-butyl-2-(4-phenylmethoxyphenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C(=O)C2=C(CCCC)N1CC1=CC=CC=N1 LCEMDVWFYIFMPZ-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
RBDDJJJVYAXBQA-UHFFFAOYSA-N 4-butyl-5-(2-methoxyethyl)-2-(4-phenylmethoxyphenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(CCCC)N(CCOC)C(=O)C=C2NN1C(C=C1)=CC=C1OCC1=CC=CC=C1 RBDDJJJVYAXBQA-UHFFFAOYSA-N 0.000 claims 1
RREZZIRYQGXVMQ-UHFFFAOYSA-N 4-butyl-5-[(4-chlorophenyl)methyl]-2-(4-phenylmethoxyphenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C(=O)C2=C(CCCC)N1CC1=CC=C(Cl)C=C1 RREZZIRYQGXVMQ-UHFFFAOYSA-N 0.000 claims 1
UXYWUVGBGONHDH-UHFFFAOYSA-N 4-butyl-5-methyl-2-(4-phenylmethoxyphenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(CCCC)N(C)C(=O)C=C2NN1C(C=C1)=CC=C1OCC1=CC=CC=C1 UXYWUVGBGONHDH-UHFFFAOYSA-N 0.000 claims 1
WDROKLHXOUGJDY-UHFFFAOYSA-N 5-(3-ethoxypropyl)-2-methyl-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C)C(=O)C=2C1=CC(=O)N(CCCOCC)C=2COCC1=CC=CC=C1 WDROKLHXOUGJDY-UHFFFAOYSA-N 0.000 claims 1
JKHNJTABOXBJBO-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methyl]-2-methyl-4-(3-phenoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC=C1CN1C(=O)C=C(NN(C)C2=O)C2=C1CCCOC1=CC=CC=C1 JKHNJTABOXBJBO-UHFFFAOYSA-N 0.000 claims 1
BMWXONLKKJDSPF-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-2-methyl-4-(3-phenoxypropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(C)N3)=O)=C2CCCOC=2C=CC=CC=2)=O)=C1 BMWXONLKKJDSPF-UHFFFAOYSA-N 0.000 claims 1
DTVBYIPILBIHBT-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-2-methyl-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound COC1=CC=CC(CN2C(C=C3C(C(N(C)N3)=O)=C2COCC=2C=CC=CC=2)=O)=C1 DTVBYIPILBIHBT-UHFFFAOYSA-N 0.000 claims 1
OIIYLEJKTZSSOQ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(4-phenylmethoxyphenyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C=C(NN(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C2=O)C2=C1CN1CCCC1 OIIYLEJKTZSSOQ-UHFFFAOYSA-N 0.000 claims 1
SMWCPQGJYIQMDJ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-methyl-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CCCN1CC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=C(Cl)C=C1 SMWCPQGJYIQMDJ-UHFFFAOYSA-N 0.000 claims 1
BHIWYPBBOGHYDI-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-4-(methoxymethyl)-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C)C(=O)C2=C(COC)N1CC1=CC=C(Cl)C=C1 BHIWYPBBOGHYDI-UHFFFAOYSA-N 0.000 claims 1
MXTWXMNKVIXAQX-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-4-[(4-fluorophenoxy)methyl]-2-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(F)C=CC=1OCC1=C2C(=O)N(C)NC2=CC(=O)N1CC1=CC=C(Cl)C=C1 MXTWXMNKVIXAQX-UHFFFAOYSA-N 0.000 claims 1
HAWFSRXAJURQMV-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-4-[[(3-fluorophenyl)methyl-methylamino]methyl]-2-(4-phenylmethoxyphenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C(=O)C=C2NN(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 HAWFSRXAJURQMV-UHFFFAOYSA-N 0.000 claims 1
DNCYXIAUMQXGAF-UHFFFAOYSA-N 5-benzyl-2-(2-chlorophenyl)-4-(morpholin-4-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(CN3CCOCC3)N(CC=3C=CC=CC=3)C(=O)C=C2N1 DNCYXIAUMQXGAF-UHFFFAOYSA-N 0.000 claims 1
FXCQZNNIRIQPDV-UHFFFAOYSA-N 5-methyl-2-(4-phenylmethoxyphenyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound N1N(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(=O)C=2C1=CC(=O)N(C)C=2CN1CCCC1 FXCQZNNIRIQPDV-UHFFFAOYSA-N 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
150000001263 acyl chlorides Chemical class 0.000 claims 1
125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
230000003796 beauty Effects 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
SORCQEKUVWTRFV-UHFFFAOYSA-N n-[3-[[2-(2-chlorophenyl)-4-[(4-fluorophenoxy)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(C=4C(=CC=CC=4)Cl)N3)=O)=C2COC=2C=CC(F)=CC=2)=O)=C1 SORCQEKUVWTRFV-UHFFFAOYSA-N 0.000 claims 1
JIRGRLZZVCCPAI-UHFFFAOYSA-N n-[3-[[2-methyl-3,6-dioxo-4-(phenylmethoxymethyl)-1h-pyrazolo[4,3-c]pyridin-5-yl]methyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CN2C(C=C3C(C(N(C)N3)=O)=C2COCC=2C=CC=CC=2)=O)=C1 JIRGRLZZVCCPAI-UHFFFAOYSA-N 0.000 claims 1
SDRBNAKOJXNMDZ-UHFFFAOYSA-N n-[3-[[3,6-dioxo-2-(4-phenylmethoxyphenyl)-4-(pyrrolidin-1-ylmethyl)-1h-pyrazolo[4,3-c]pyridin-5-yl]methyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CN2C(C=C3C(C(N(C=4C=CC(OCC=5C=CC=CC=5)=CC=4)N3)=O)=C2CN2CCCC2)=O)=C1 SDRBNAKOJXNMDZ-UHFFFAOYSA-N 0.000 claims 1
OGEDJRXHHJLZTM-UHFFFAOYSA-N n-[3-[[4-[(4-chlorophenoxy)methyl]-2-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(C)N3)=O)=C2COC=2C=CC(Cl)=CC=2)=O)=C1 OGEDJRXHHJLZTM-UHFFFAOYSA-N 0.000 claims 1
IIZLKLPQZZYVTR-UHFFFAOYSA-N n-[3-[[4-[[(3-fluorophenyl)methyl-methylamino]methyl]-3,6-dioxo-2-(4-phenylmethoxyphenyl)-1h-pyrazolo[4,3-c]pyridin-5-yl]methyl]phenyl]acetamide Chemical compound C=1C=CC(NC(C)=O)=CC=1CN1C(=O)C=C2NN(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C(=O)C2=C1CN(C)CC1=CC=CC(F)=C1 IIZLKLPQZZYVTR-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
239000010452 phosphate Substances 0.000 claims 1
235000015047 pilsener Nutrition 0.000 claims 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 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
0 *C(C(N(*=I)C(*)=C12)=O)=C1N(*)N(*)C2=O Chemical compound *C(C(N(*=I)C(*)=C12)=O)=C1N(*)N(*)C2=O 0.000 description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
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
210000004204 blood vessel Anatomy 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
125000004193 piperazinyl group Chemical group 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
230000002401 inhibitory effect Effects 0.000 description 4
210000000056 organ Anatomy 0.000 description 4
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
102100021217 Dual oxidase 2 Human genes 0.000 description 3
206010019280 Heart failures Diseases 0.000 description 3
101000968308 Homo sapiens Dual oxidase 1 Proteins 0.000 description 3
101000968305 Homo sapiens Dual oxidase 2 Proteins 0.000 description 3
208000022559 Inflammatory bowel disease Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
201000006417 multiple sclerosis Diseases 0.000 description 3
238000000746 purification Methods 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
208000011580 syndromic disease Diseases 0.000 description 3
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 2
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
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
206010048554 Endothelial dysfunction Diseases 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
210000001736 capillary Anatomy 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000003210 demyelinating effect Effects 0.000 description 2
125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 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
230000012010 growth Effects 0.000 description 2
210000002216 heart Anatomy 0.000 description 2
125000005842 heteroatom Chemical group 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
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 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
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
125000003386 piperidinyl group Chemical group 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
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
125000000719 pyrrolidinyl group Chemical group 0.000 description 2
239000003642 reactive oxygen metabolite 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
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
AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical group C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
PNGGWQMSHKIEAF-UHFFFAOYSA-N 2-(4-fluorophenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(F)C=C1 PNGGWQMSHKIEAF-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 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
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
125000005217 alkenylheteroaryl group Chemical group 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
125000004103 aminoalkyl group Chemical group 0.000 description 1
125000005097 aminocarbonylalkyl group Chemical group 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
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
208000003295 carpal tunnel syndrome Diseases 0.000 description 1
239000000969 carrier Substances 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
239000013078 crystal Substances 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
208000037765 diseases and disorders Diseases 0.000 description 1
201000002664 drug-induced hearing loss Diseases 0.000 description 1
239000003480 eluent Substances 0.000 description 1
206010014599 encephalitis Diseases 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
235000019439 ethyl acetate Nutrition 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
238000003818 flash chromatography Methods 0.000 description 1
125000004175 fluorobenzyl group Chemical group 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000002541 furyl group Chemical group 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
125000004404 heteroalkyl group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
208000020346 hyperlipoproteinemia Diseases 0.000 description 1
125000002883 imidazolyl group Chemical group 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
125000001041 indolyl group Chemical group 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
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
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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940095102 methyl benzoate Drugs 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
239000000203 mixture Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
ACOHAEBNFWGQCL-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)acetamide Chemical compound CC(=O)NCC1=CC=CC=N1 ACOHAEBNFWGQCL-UHFFFAOYSA-N 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
125000001624 naphthyl group Chemical group 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
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
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
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
125000001715 oxadiazolyl group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 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
125000001147 pentyl group Chemical group C(CCCC)* 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
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
150000003053 piperidines Chemical class 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
230000002265 prevention Effects 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
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
230000005855 radiation Effects 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
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
201000010965 sweat gland carcinoma Diseases 0.000 description 1
201000004595 synovitis Diseases 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
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 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
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

JP2011527464A 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 Expired - Fee Related JP5700836B2 (ja)