RU2012129206A - Модуляторы атф-связывающих транспортеров - Google Patents
Модуляторы атф-связывающих транспортеров Download PDFInfo
- Publication number
- RU2012129206A RU2012129206A RU2012129206/04A RU2012129206A RU2012129206A RU 2012129206 A RU2012129206 A RU 2012129206A RU 2012129206/04 A RU2012129206/04 A RU 2012129206/04A RU 2012129206 A RU2012129206 A RU 2012129206A RU 2012129206 A RU2012129206 A RU 2012129206A
- Authority
- RU
- Russia
- Prior art keywords
- oxo
- carboxamide
- quinoline
- phenyl
- trifluoromethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 14
- -1 4-oxo-1H-quinolin-3-yl Chemical group 0.000 claims abstract 6
- YOOWERNBGKWPRR-UHFFFAOYSA-N 4-oxo-n-[3-piperidin-1-yl-5-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=CC=1N1CCCCC1 YOOWERNBGKWPRR-UHFFFAOYSA-N 0.000 claims abstract 2
- SLUFNUYIWXWSKZ-UHFFFAOYSA-N 5-hydroxy-4-oxo-n-[5-(trifluoromethyl)-1h-indol-6-yl]-1h-quinoline-3-carboxamide Chemical compound O=C1C=2C(O)=CC=CC=2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC2=C1C=CN2 SLUFNUYIWXWSKZ-UHFFFAOYSA-N 0.000 claims abstract 2
- IVBLHTWYXJMFEN-UHFFFAOYSA-N 6-fluoro-4-oxo-n-[2-(trifluoromethyl)-1h-indol-6-yl]-1h-quinoline-3-carboxamide Chemical compound C1=C2C=C(C(F)(F)F)NC2=CC(NC(=O)C2=CNC3=CC=C(C=C3C2=O)F)=C1 IVBLHTWYXJMFEN-UHFFFAOYSA-N 0.000 claims abstract 2
- FBAODNWPOUCUBQ-UHFFFAOYSA-N 6-methyl-n-[4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound CC1CCCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=C(C)C=C2C1=O FBAODNWPOUCUBQ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- KGHWICYZUHTNHE-UHFFFAOYSA-N n-(4-tert-butyl-2-fluoro-5-hydroxyphenyl)-6,7-difluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(O)C(C(C)(C)C)=CC(F)=C1NC(=O)C1=CNC2=CC(F)=C(F)C=C2C1=O KGHWICYZUHTNHE-UHFFFAOYSA-N 0.000 claims abstract 2
- LRCDFALFHMSABR-UHFFFAOYSA-N n-(4-tert-butyl-3-fluorophenyl)-5-hydroxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(F)C(C(C)(C)C)=CC=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O LRCDFALFHMSABR-UHFFFAOYSA-N 0.000 claims abstract 2
- FMVVSKCRBODQSQ-UHFFFAOYSA-N n-(4-tert-butyl-3-hydroxyphenyl)-6-fluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(O)C(C(C)(C)C)=CC=C1NC(=O)C1=CNC2=CC=C(F)C=C2C1=O FMVVSKCRBODQSQ-UHFFFAOYSA-N 0.000 claims abstract 2
- ISYOJZXAXRBXAV-UHFFFAOYSA-N n-(5-tert-butyl-1h-indol-6-yl)-5-hydroxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC(O)=C2C(=O)C(C(=O)NC3=CC=4NC=CC=4C=C3C(C)(C)C)=CNC2=C1 ISYOJZXAXRBXAV-UHFFFAOYSA-N 0.000 claims abstract 2
- YPCCEGMMRXRZEX-UHFFFAOYSA-N n-[2-fluoro-5-hydroxy-4-(1-methylcyclohexyl)phenyl]-5-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C=2C(C)=CC=CC=2NC=C1C(=O)NC(C(=C1)F)=CC(O)=C1C1(C)CCCCC1 YPCCEGMMRXRZEX-UHFFFAOYSA-N 0.000 claims abstract 2
- ZWTFUOGLWJNIJL-UHFFFAOYSA-N n-[3-hydroxy-4-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(O)=CC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=C1 ZWTFUOGLWJNIJL-UHFFFAOYSA-N 0.000 claims abstract 2
- QAPFEWKLTGKNFV-UHFFFAOYSA-N n-[4-(1,3-dihydroxy-2-methylpropan-2-yl)phenyl]-5-hydroxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC(C(CO)(CO)C)=CC=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O QAPFEWKLTGKNFV-UHFFFAOYSA-N 0.000 claims abstract 2
- UASMHZLYMOUCEW-UHFFFAOYSA-N n-[4-(3,3-dimethylpyrrolidin-1-yl)-2-(trifluoromethyl)phenyl]-6-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(OC)=CC=C2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1N1CCC(C)(C)C1 UASMHZLYMOUCEW-UHFFFAOYSA-N 0.000 claims abstract 2
- XLRKHLCJFZHBME-UHFFFAOYSA-N n-[4-(3,3-dimethylpyrrolidin-1-yl)-2-(trifluoromethyl)phenyl]-6-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(C)=CC=C2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1N1CCC(C)(C)C1 XLRKHLCJFZHBME-UHFFFAOYSA-N 0.000 claims abstract 2
- FCALAVLHOCNQCP-UHFFFAOYSA-N n-[4-tert-butyl-5-hydroxy-2-(trifluoromethyl)phenyl]-5-hydroxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(F)(F)F)=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O FCALAVLHOCNQCP-UHFFFAOYSA-N 0.000 claims abstract 2
- UITKSAIMNCQWER-UHFFFAOYSA-N n-[5-hydroxy-4-propan-2-yl-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(O)C(C(C)C)=CC(C(F)(F)F)=C1NC(=O)C1=CNC2=CC=CC=C2C1=O UITKSAIMNCQWER-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 26
- 201000010099 disease Diseases 0.000 claims 22
- 238000000034 method Methods 0.000 claims 13
- 201000003883 Cystic fibrosis Diseases 0.000 claims 9
- CVAWACBLSANHSQ-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)N)=CN=C21 CVAWACBLSANHSQ-UHFFFAOYSA-N 0.000 claims 8
- 206010033645 Pancreatitis Diseases 0.000 claims 8
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims 8
- 201000010064 diabetes insipidus Diseases 0.000 claims 8
- 208000011580 syndromic disease Diseases 0.000 claims 8
- 208000025678 Ciliary Motility disease Diseases 0.000 claims 7
- 206010006451 bronchitis Diseases 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 7
- 239000012634 fragment Substances 0.000 claims 7
- 201000009266 primary ciliary dyskinesia Diseases 0.000 claims 7
- 206010006474 Bronchopulmonary aspergillosis allergic Diseases 0.000 claims 5
- 208000006778 allergic bronchopulmonary aspergillosis Diseases 0.000 claims 5
- 230000035772 mutation Effects 0.000 claims 5
- ONIBWKKTOPOVIA-UHFFFAOYSA-M prolinate Chemical compound [O-]C(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-M 0.000 claims 5
- 206010010774 Constipation Diseases 0.000 claims 4
- 206010067265 Heterotaxia Diseases 0.000 claims 4
- 206010058271 Hyperexplexia Diseases 0.000 claims 4
- 208000031733 Situs inversus totalis Diseases 0.000 claims 4
- 238000009825 accumulation Methods 0.000 claims 4
- 239000012472 biological sample Substances 0.000 claims 4
- 230000007812 deficiency Effects 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 230000002132 lysosomal effect Effects 0.000 claims 4
- 102000005962 receptors Human genes 0.000 claims 4
- 108020003175 receptors Proteins 0.000 claims 4
- 230000000306 recurrent effect Effects 0.000 claims 4
- 208000008797 situs inversus Diseases 0.000 claims 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 206010010356 Congenital anomaly Diseases 0.000 claims 3
- 208000007466 Male Infertility Diseases 0.000 claims 3
- 230000002146 bilateral effect Effects 0.000 claims 3
- 208000007451 chronic bronchitis Diseases 0.000 claims 3
- 230000001886 ciliary effect Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 210000001177 vas deferen Anatomy 0.000 claims 3
- 102100034452 Alternative prion protein Human genes 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000009575 Angelman syndrome Diseases 0.000 claims 2
- 206010002961 Aplasia Diseases 0.000 claims 2
- 206010003591 Ataxia Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims 2
- 201000002200 Congenital disorder of glycosylation Diseases 0.000 claims 2
- 206010062264 Congenital hyperthyroidism Diseases 0.000 claims 2
- 208000029323 Congenital myotonia Diseases 0.000 claims 2
- 208000024940 Dent disease Diseases 0.000 claims 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 2
- 206010013883 Dwarfism Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000033981 Hereditary haemochromatosis Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 2
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims 2
- 206010051125 Hypofibrinogenaemia Diseases 0.000 claims 2
- 208000000038 Hypoparathyroidism Diseases 0.000 claims 2
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 208000029725 Metabolic bone disease Diseases 0.000 claims 2
- 208000008955 Mucolipidoses Diseases 0.000 claims 2
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 2
- 208000010316 Myotonia congenita Diseases 0.000 claims 2
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 206010031243 Osteogenesis imperfecta Diseases 0.000 claims 2
- 206010049088 Osteopenia Diseases 0.000 claims 2
- 208000035467 Pancreatic insufficiency Diseases 0.000 claims 2
- 206010033647 Pancreatitis acute Diseases 0.000 claims 2
- 206010033649 Pancreatitis chronic Diseases 0.000 claims 2
- 208000025237 Polyendocrinopathy Diseases 0.000 claims 2
- 108091000054 Prion Proteins 0.000 claims 2
- 208000024777 Prion disease Diseases 0.000 claims 2
- 201000005660 Protein C Deficiency Diseases 0.000 claims 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 2
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims 2
- 208000004622 abetalipoproteinemia Diseases 0.000 claims 2
- 201000003229 acute pancreatitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000007547 defect Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims 2
- 208000030409 hereditary angioedema with C1Inh deficiency Diseases 0.000 claims 2
- 208000013746 hereditary thrombophilia due to congenital protein C deficiency Diseases 0.000 claims 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 2
- 201000008980 hyperinsulinism Diseases 0.000 claims 2
- 208000019715 inherited Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 2
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 2
- 230000002988 nephrogenic effect Effects 0.000 claims 2
- 108010040003 polyglutamine Proteins 0.000 claims 2
- 229920000155 polyglutamine Polymers 0.000 claims 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 2
- 201000009890 sinusitis Diseases 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- WWNOUYOXHFVZKM-GOSISDBHSA-N (2r)-1-[4-[(4-oxo-1h-quinoline-3-carbonyl)amino]-3-(trifluoromethyl)phenyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O WWNOUYOXHFVZKM-GOSISDBHSA-N 0.000 claims 1
- WWNOUYOXHFVZKM-SFHVURJKSA-N (2s)-1-[4-[(4-oxo-1h-quinoline-3-carbonyl)amino]-3-(trifluoromethyl)phenyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O WWNOUYOXHFVZKM-SFHVURJKSA-N 0.000 claims 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims 1
- XLQMVHMHVWNGRI-UHFFFAOYSA-N 4-oxo-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C(=O)NC3=CC=C4C(C)(C)CCN(C4=C3)C)=CNC2=C1 XLQMVHMHVWNGRI-UHFFFAOYSA-N 0.000 claims 1
- XSMLFPTYMLWZDQ-UHFFFAOYSA-N 4-oxo-n-(2-pyridin-2-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC1=CC=CC=C1C1=CC=CC=N1 XSMLFPTYMLWZDQ-UHFFFAOYSA-N 0.000 claims 1
- QACDVKWZQAJPAB-UHFFFAOYSA-N 4-oxo-n-(3-thiophen-2-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=1)=CC=CC=1C1=CC=CS1 QACDVKWZQAJPAB-UHFFFAOYSA-N 0.000 claims 1
- CEQMANXOVRMQIY-UHFFFAOYSA-N 4-oxo-n-(4-piperidin-1-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=C1)=CC=C1N1CCCCC1 CEQMANXOVRMQIY-UHFFFAOYSA-N 0.000 claims 1
- SDNLVYKIJDWLJN-UHFFFAOYSA-N 4-oxo-n-(4-pyridin-3-yloxyphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 SDNLVYKIJDWLJN-UHFFFAOYSA-N 0.000 claims 1
- DRZXOZNJKLXEFD-UHFFFAOYSA-N 4-oxo-n-(4-pyrrolidin-1-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=C1)=CC=C1N1CCCC1 DRZXOZNJKLXEFD-UHFFFAOYSA-N 0.000 claims 1
- LSVAGKBGHSEXFA-UHFFFAOYSA-N 4-oxo-n-[2-piperidin-1-yl-4-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C=1N1CCCCC1 LSVAGKBGHSEXFA-UHFFFAOYSA-N 0.000 claims 1
- YMAHLHYBABPGAI-UHFFFAOYSA-N 4-oxo-n-[3-(trifluoromethyl)-1h-indol-6-yl]-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C(=O)NC=3C=C4NC=C(C4=CC=3)C(F)(F)F)=CNC2=C1 YMAHLHYBABPGAI-UHFFFAOYSA-N 0.000 claims 1
- NYZFGGHGNAQOOG-UHFFFAOYSA-N 4-oxo-n-[3-piperidin-1-yl-4-(trifluoromethoxy)phenyl]-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)OC1=CC=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C=C1N1CCCCC1 NYZFGGHGNAQOOG-UHFFFAOYSA-N 0.000 claims 1
- QTLUYOQSTSPQBL-UHFFFAOYSA-N 4-oxo-n-[3-pyrrolidin-1-yl-5-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=CC=1N1CCCC1 QTLUYOQSTSPQBL-UHFFFAOYSA-N 0.000 claims 1
- BPVXFEJJXZTGAV-UHFFFAOYSA-N 4-oxo-n-[4-(4-propan-2-ylpiperazin-1-yl)-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C1CN(C(C)C)CCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O BPVXFEJJXZTGAV-UHFFFAOYSA-N 0.000 claims 1
- XQUAKZAQXHAOLS-UHFFFAOYSA-N 4-oxo-n-[4-phenyl-5-(trifluoromethyl)thiophen-3-yl]-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)C=1SC=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C=1C1=CC=CC=C1 XQUAKZAQXHAOLS-UHFFFAOYSA-N 0.000 claims 1
- OMEUWOBHKBHJCB-UHFFFAOYSA-N 4-oxo-n-[4-piperidin-1-yl-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C(C(F)(F)F)=CC=1N1CCCCC1 OMEUWOBHKBHJCB-UHFFFAOYSA-N 0.000 claims 1
- OEABRXDGEDBLKT-UHFFFAOYSA-N 4-oxo-n-[4-pyrrolidin-1-yl-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C(C(F)(F)F)=CC=1N1CCCC1 OEABRXDGEDBLKT-UHFFFAOYSA-N 0.000 claims 1
- PGOQRZZAIWNQFM-UHFFFAOYSA-N 4-oxo-n-[5-phenylmethoxy-4-propan-2-yl-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound CC(C)C1=CC(C(F)(F)F)=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C=C1OCC1=CC=CC=C1 PGOQRZZAIWNQFM-UHFFFAOYSA-N 0.000 claims 1
- LVPXUXQVEYGFKK-UHFFFAOYSA-N 5-fluoro-4-oxo-n-[4-propan-2-yl-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC(C(C)C)=CC=C1NC(=O)C1=CNC2=CC=CC(F)=C2C1=O LVPXUXQVEYGFKK-UHFFFAOYSA-N 0.000 claims 1
- BDKUNHJMDVNTIK-UHFFFAOYSA-N 5-hydroxy-4-oxo-n-[2-(trifluoromethyl)-1h-indol-6-yl]-1h-quinoline-3-carboxamide Chemical compound C1=C2C=C(C(F)(F)F)NC2=CC(NC(=O)C2=CNC=3C=CC=C(C=3C2=O)O)=C1 BDKUNHJMDVNTIK-UHFFFAOYSA-N 0.000 claims 1
- SOWGYRWNIPNSAO-UHFFFAOYSA-N 5-hydroxy-4-oxo-n-[4-propan-2-yl-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC(C(C)C)=CC=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O SOWGYRWNIPNSAO-UHFFFAOYSA-N 0.000 claims 1
- FONBNPKVUAKNKL-UHFFFAOYSA-N 5-hydroxy-n-(3-hydroxy-4-propan-2-ylphenyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(O)C(C(C)C)=CC=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O FONBNPKVUAKNKL-UHFFFAOYSA-N 0.000 claims 1
- MTWJUVDDQKFHFQ-UHFFFAOYSA-N 5-hydroxy-n-[2-methyl-5-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound CC1=CC=C(C(F)(F)F)C=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O MTWJUVDDQKFHFQ-UHFFFAOYSA-N 0.000 claims 1
- BJJUWJAYFMUSBJ-UHFFFAOYSA-N 5-hydroxy-n-[3-hydroxy-4-(1-methylcyclohexyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(C3=C(O)C=CC=C3NC=2)=O)C=C(O)C=1C1(C)CCCCC1 BJJUWJAYFMUSBJ-UHFFFAOYSA-N 0.000 claims 1
- MDNWGVAKUYIKAY-UHFFFAOYSA-N 5-hydroxy-n-[3-hydroxy-4-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(O)=CC(NC(=O)C=2C(C3=C(O)C=CC=C3NC=2)=O)=C1 MDNWGVAKUYIKAY-UHFFFAOYSA-N 0.000 claims 1
- FEFSUEDBNGECAA-UHFFFAOYSA-N 5-hydroxy-n-[3-hydroxy-5-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC(O)=CC(NC(=O)C=2C(C3=C(O)C=CC=C3NC=2)=O)=C1 FEFSUEDBNGECAA-UHFFFAOYSA-N 0.000 claims 1
- UMFKSVUQFLAMEO-UHFFFAOYSA-N 5-hydroxy-n-[4-(3-methyloxetan-3-yl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(C3=C(O)C=CC=C3NC=2)=O)C=CC=1C1(C)COC1 UMFKSVUQFLAMEO-UHFFFAOYSA-N 0.000 claims 1
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- YAASXWMMYDAIBQ-HUUCEWRRSA-N n-[4-[(2r,5r)-2,5-dimethylpyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-5-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound C[C@@H]1CC[C@@H](C)N1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC(C)=C2C1=O YAASXWMMYDAIBQ-HUUCEWRRSA-N 0.000 claims 1
- WYFKWXBABNPIJT-ZIAGYGMSSA-N n-[4-[(2r,5r)-2,5-dimethylpyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-6-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(OC)=CC=C2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1N1[C@H](C)CC[C@H]1C WYFKWXBABNPIJT-ZIAGYGMSSA-N 0.000 claims 1
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- QHKZWNRCQXNAQN-LBPRGKRZSA-N n-[4-[(2s)-2-methylpyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-4-oxo-5-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C[C@H]1CCCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC(C(F)(F)F)=C2C1=O QHKZWNRCQXNAQN-LBPRGKRZSA-N 0.000 claims 1
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- MIMBQPYGIHWWQQ-OAHLLOKOSA-N n-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1[C@H](N(C)C)CCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O MIMBQPYGIHWWQQ-OAHLLOKOSA-N 0.000 claims 1
- UFUWPJYQYSEIDK-CYBMUJFWSA-N n-[4-[(3r)-3-fluoropyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-5-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C=2C(C)=CC=CC=2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1N1CC[C@@H](F)C1 UFUWPJYQYSEIDK-CYBMUJFWSA-N 0.000 claims 1
- AGYWSLZEXIEJJG-CYBMUJFWSA-N n-[4-[(3r)-3-hydroxypyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1[C@H](O)CCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O AGYWSLZEXIEJJG-CYBMUJFWSA-N 0.000 claims 1
- MIMBQPYGIHWWQQ-HNNXBMFYSA-N n-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1[C@@H](N(C)C)CCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O MIMBQPYGIHWWQQ-HNNXBMFYSA-N 0.000 claims 1
- UFUWPJYQYSEIDK-ZDUSSCGKSA-N n-[4-[(3s)-3-fluoropyrrolidin-1-yl]-2-(trifluoromethyl)phenyl]-5-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C=2C(C)=CC=CC=2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1N1CC[C@H](F)C1 UFUWPJYQYSEIDK-ZDUSSCGKSA-N 0.000 claims 1
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- HBUMMDLJMOVSIZ-UHFFFAOYSA-N n-[4-[4-(2-hydroxyethyl)piperazin-1-yl]-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1CN(CCO)CCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O HBUMMDLJMOVSIZ-UHFFFAOYSA-N 0.000 claims 1
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- QAKYDVYFCSGZPH-UHFFFAOYSA-N n-[4-cyclohexyl-5-hydroxy-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC1=CC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=C(C(F)(F)F)C=C1C1CCCCC1 QAKYDVYFCSGZPH-UHFFFAOYSA-N 0.000 claims 1
- BXCABMGAGNUVQD-UHFFFAOYSA-N n-[4-cyclohexyl-5-phenylmethoxy-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1C=CC=CC=1COC=1C=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C(C(F)(F)F)=CC=1C1CCCCC1 BXCABMGAGNUVQD-UHFFFAOYSA-N 0.000 claims 1
- FDLDKJFDVMTSBG-UHFFFAOYSA-N n-[4-cyclopentyl-5-hydroxy-2-(3-hydroxyprop-1-ynyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C(C#CCO)=CC=1C1CCCC1 FDLDKJFDVMTSBG-UHFFFAOYSA-N 0.000 claims 1
- MJWZWIGRZUACEM-UHFFFAOYSA-N n-[4-cyclopentyloxy-2-(trifluoromethyl)phenyl]-5-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C=2C(C)=CC=CC=2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1OC1CCCC1 MJWZWIGRZUACEM-UHFFFAOYSA-N 0.000 claims 1
- PITJRHPJBQDSJP-UHFFFAOYSA-N n-[4-morpholin-4-yl-2-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C(C(F)(F)F)=CC=1N1CCOCC1 PITJRHPJBQDSJP-UHFFFAOYSA-N 0.000 claims 1
- SCTJLRYTJIGLIJ-UHFFFAOYSA-N n-[4-tert-butyl-5-hydroxy-2-(trifluoromethyl)phenyl]-6-fluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(F)(F)F)=C1NC(=O)C1=CNC2=CC=C(F)C=C2C1=O SCTJLRYTJIGLIJ-UHFFFAOYSA-N 0.000 claims 1
- ZICGRJUZWHBSAI-UHFFFAOYSA-N n-[6-methoxy-5-(trifluoromethyl)pyridin-2-yl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(OC)=NC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=C1 ZICGRJUZWHBSAI-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 230000020978 protein processing Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 230000000391 smoking effect Effects 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- 210000001215 vagina Anatomy 0.000 claims 1
- ZYAYKJLHFIOMKY-UHFFFAOYSA-N 5-hydroxy-n-[3-methoxy-5-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC(OC)=CC(NC(=O)C=2C(C3=C(O)C=CC=C3NC=2)=O)=C1 ZYAYKJLHFIOMKY-UHFFFAOYSA-N 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- ISSMOIJHKWNSFW-UHFFFAOYSA-N n-[2-fluoro-5-hydroxy-4-(trifluoromethyl)phenyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(O)=CC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=C1F ISSMOIJHKWNSFW-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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Abstract
1. Соединение, выбранное из следующих:6,7-дифтор-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;5-гидрокси-N-[5-гидрокси-4-трет-бутил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;4-оксо-N-[3-(1-пиперидил)-5-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;N-[4-(3,3-диметилпирролидин-1-ил)-2-(трифторметил)фенил]-6-метил-4-оксо-1H-хинолин-3-карбоксамид;6-фтор-N-(3-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;N-(3-фтор-4-трет-бутил-фенил)-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;метил 1-[4-[(4-оксо-1H-хинолин-3-ил)карбониламино]-3-(трифторметил)фенил]пиперидин-2-карбоксилат;5-гидрокси-N-[4-[2-гидрокси-1-(гидроксиметил)-1-метил-этил]фенил]-4-оксо-1H-хинолин-3-карбоксамид;5-гидрокси-4-оксо-N-[5-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;6-фтор-4-оксо-N-[2-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;N-(5-гидрокси-2,4-дитрет-бутил-фенил)-6-метокси-4-оксо-1H-хинолин-3-карбоксамид;N-[5-гидрокси-4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-5-метил-4-оксо-1H-хинолин-3-карбоксамид;N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-7-метил-4-оксо-1H-хинолин-3-карбоксамид;5-гидрокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;N-[2-фтор-5-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;5-гидрокси-N-[3-метокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;6-метил-N-[4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;N-[4-(3,3-диметилпирролидин-1-ил)-2-(трифторметил)фенил]-6-метокси-4-оксо-1H-хинолин-3-карбоксамид;8-циано-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;N-[3-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;N-(2-этил-5-гидр
Claims (20)
1. Соединение, выбранное из следующих:
6,7-дифтор-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[5-гидрокси-4-трет-бутил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-(1-пиперидил)-5-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;
N-[4-(3,3-диметилпирролидин-1-ил)-2-(трифторметил)фенил]-6-метил-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-(3-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-(3-фтор-4-трет-бутил-фенил)-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;
метил 1-[4-[(4-оксо-1H-хинолин-3-ил)карбониламино]-3-(трифторметил)фенил]пиперидин-2-карбоксилат;
5-гидрокси-N-[4-[2-гидрокси-1-(гидроксиметил)-1-метил-этил]фенил]-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-4-оксо-N-[5-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
6-фтор-4-оксо-N-[2-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-6-метокси-4-оксо-1H-хинолин-3-карбоксамид;
N-[5-гидрокси-4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-7-метил-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-[2-фтор-5-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[3-метокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-метил-N-[4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-(3,3-диметилпирролидин-1-ил)-2-(трифторметил)фенил]-6-метокси-4-оксо-1H-хинолин-3-карбоксамид;
8-циано-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-[3-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(2-этил-5-гидрокси-4-трет-бутил-фенил)-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-трет-бутил-5-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
6-фтор-N-[5-гидрокси-4-трет-бутил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-(1-пиперидил)-4-трет-бутил-фенил]-1H-хинолин-3-карбоксамид;
(S)-5-метил-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-[4-циклопентил-5-гидрокси-2-(3-гидроксипроп-1-инил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(3-(диметиламино)пирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
4-оксо-N-[2-(1-пиперидил)-4-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-6-(трифторметил)-1H-хинолин-3-карбоксамид;
N-(4-((2S,5S)-2,5-диметилпирролидин-1-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
8-этокси-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2-метил-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
8-циано-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-5-(трифторметил)-1H-хинолин-3-карбоксамид;
6-фтор-N-[4-(3-метилоксетан-3-ил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-циклогексил-3-гидрокси-фенил)-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-(3-метилоксетан-3-ил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-этокси-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-циано-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
8-этокси-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-(3-фтор-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-(3,3-дифторпирролидин-1-ил)-2-(трифторметил)фенил]-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[4-(3-метилоксетан-3-ил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(2S,3S)-метил 3-метил-1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пирролидин-2-карбоксилат;
(1S,2S,5R)-метил 3-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)-3-азабицикло[3,1,0]гексан-2-карбоксилат;
N-[2-хлор-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-метокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
(R)-N-(4-(3-(диметиламино)пирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
5-гидрокси-4-оксо-N-(3-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-[4-(3,3-диметилпирролидин-1-ил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[2-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
N-[2-метил-4-(трифторметокси)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-((2R,5R)-2,5-диметилпирролидин-1-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
(R)-трет-бутил 1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пирролидин-2-карбоксилат;
(R)-N-(4-(3-фторпирролидин-1-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-5-метиламино-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[4-(1-пиперидил)фенил]-1H-хинолин-3-карбоксамид;
6-диметиламино-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
5-метил-N-[4-(3-метилпирролидин-1-ил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-изопропокси-2-(трифторметил)фенил]-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
7-циано-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-(2-тиенил)фенил]-1H-хинолин-3-карбоксамид;
(2S,4R)-метил 4-трет-бутокси-1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пирролидин-2-карбоксилат;
N-(4-гидрокси-2-нафтил)-4-оксо-1H-хинолин-3-карбоксамид;
5-фтор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-бром-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-4-оксо-N-(3-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-[4-(3-метилпирролидин-1-ил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-(2,2-диметилпропаноиламино)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
7-циано-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-8-(трифторметил)-1H-хинолин-3-карбоксамид;
N-[4-(2,5-диметилпиррол-1-ил)-3-метокси-фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-хлор-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-4-оксо-N-[4-пирролидин-1-ил-2-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;
N-[3-гидрокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-циклогексил-3-гидрокси-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-метил-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
6-фтор-N-[1-(2-метоксиэтил)-5-(трифторметил)индол-6-ил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-1-[4-[(4-оксо-1H-хинолин-3-ил)карбониламино]-3-(трифторметил)фенил]пирролидин-2-карбоновой кислот;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-((2R,5R)-2,5-диметилпирролидин-1-ил)-2-(трифторметил)фенил)-6-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-[5-бензилокси-4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[6-метокси-5-(трифторметил)-2-пиридил]-4-оксо-1H-хинолин-3-карбоксамид;
(R)-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
8-фтор-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-[3-гидрокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(3-гидрокси-4-изопропил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
7-метил-4-оксо-N-[5-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
N-[2-метил-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-(3,3-диметилпирролидин-1-ил)-2-(трифторметил)фенил]-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-пирролидин-1-ил-4-(трифторметокси)фенил]-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-8-(трифторметил)-1H-хинолин-3-карбоксамид;
(S)-5-метил-N-(6-(2-метилпирролидин-1-ил)-2-(трифторметил)пиридин-3-ил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-(4-((1S,4R)-2-азабицикло[2,2,1]гептан-2-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-7-метокси-4-оксо-1H-хинолин-3-карбоксамид;
N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-6-метокси-4-оксо-1H-хинолин-3-карбоксамид;
5-амино-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
(R)-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-5-(трифторметил)-1,4-дигидрохинолин-3-карбоксамид;
5-гидрокси-N-(3-гидрокси-4-изопропил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-(5-гидрокси-2-метил-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6,7-дифтор-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-[2-гидрокси-1-(гидроксиметил)-1-метил-этил]фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(5-этил-1H-индол-6-ил)-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-((2R,5S)-2,5-диметилпирролидин-1-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
4-оксо-N-[3-пирролидин-1-ил-5-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;
N-(3-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-циклопентокси-2-(трифторметил)фенил]-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-(5-фтор-1H-индол-6-ил)-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-(3-гидрокси-4-изопропил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-морфолино-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[3-гидрокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
трет-бутил [[4-[(4-оксо-1H-хинолин-3-ил)карбониламино]-3-(трифторметил)фенил]амино]формиат;
(S)-6-метокси-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
4-оксо-N-(3-трет-бутилфенил)-1H-хинолин-3-карбоксамид;
6-хлор-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
7-ацетил-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
8-этил-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[3-гидрокси-4-(1-метилциклогексил)-фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-7-метил-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-(2,4-дихлор-5-гидрокси-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-(5-гидрокси-2-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-фтор-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
7-фтор-6-метокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-[4-(3,3-диметил-1-пиперидил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(R)-5-метил-N-(4-(3-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
4-оксо-N-[4-(3-пиридилокси)фенил]-1H-хинолин-3-карбоксамид;
N-(2-метил-4-пирролидин-1-ил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
8-этокси-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-7-метокси-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-[4-циклогексил-5-гидрокси-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-4-оксо-N-(3-трет-бутилфенил)-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-8-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-(2-циано-4-пирролидин-1-ил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-хлор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-6-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-8-метил-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(3-фторпирролидин-1-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
6-фтор-N-[4-[2-гидрокси-1-(гидроксиметил)-1-метил-этил]фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-[2-хлор-4-(трифторметокси)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-трет-бутил 1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пирролидин-2-карбоксилат;
N-[2,5-бис(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-метил 2-метил-1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пирролидин-2-карбоксилат;
4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-7-(трифторметокси)-1H-хинолин-3-карбоксамид;
5-гидрокси-N-(3-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(2-(гидроксиметил)пирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-[2-хлор-4-(трифторметил)фенил]-5-гидрокси-4-оксо-1H-хинолин-3-карбоксамид;
N-[2-хлор-4-(трифторметил)фенил]-6-фтор-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-изопропил-2-(трифторметил)фенил]-8-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-8-(трифторметил)-1H-хинолин-3-карбоксамид;
N-[4-(4-изопропилпиперазин-1-ил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-7-метил-4-оксо-1H-хинолин-3-карбоксамид;
8-этокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
(S)-7-метокси-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
5-метил-N-[4-(3-метил-1-пиперидил)-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
8-метил-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-(3-фтор-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6,7-дифтор-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-(4-циклогексил-2-метил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(2-этил-5-гидрокси-4-трет-бутил-фенил)-6-фтор-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-[3-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-циклогексил-3-гидрокси-фенил)-6-фтор-4-оксо-1H-хинолин-3-карбоксамид;
7-гидрокси-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
8-этил-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
N-[5-бензилокси-4-циклогексил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(3-гидроксипирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
5-фтор-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
6-хлор-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[4-пирролидин-1-ил-2-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;
N-(2-этил-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
(S)-этил 1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пиперидин-3-карбоксилат;
5-метил-4-оксо-N-[5-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
8-хлор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-4-оксо-N-(3-трет-бутилфенил)-1H-хинолин-3-карбоксамид;
6-фтор-N-(5-гидрокси-2-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-[3-метокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(R)-N-(4-(4,4-дифтор-2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-5-метил-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-[4-[4-(гидроксиметил)-1-пиперидил]-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-5-(трифторметил)-1,4-дигидрохинолин-3-карбоксамид;
(R)-N-(4-(2-(гидроксиметил)пирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-(2-аминобензотиазол-6-ил)-4-оксо-1H-хинолин-3-карбоксамид;
6,7-дифтор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-[4-(2-гидроксиэтил)пиперазин-1-ил]-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-(4-пирролидин-1-илфенил)-1H-хинолин-3-карбоксамид;
N-(2-метокси-4-пирролидин-1-ил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[2-метил-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
7-циано-N-(2-фтор-5-гидрокси-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-[2-метил-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-гидрокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
8-фтор-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
6-этокси-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
8-этил-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-N-(5-гидрокси-2-метил-4-трет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
(R)-6-фтор-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-(4-((2R,5R)-2,5-диметилпирролидин-1-ил)-2-(трифторметил)фенил)-6-метокси-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
4-оксо-N-[4-(1-пиперидил)-2-(трифторметил)фенил]-1H-хинолин-3-карбоксамид;
8-фтор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-6-метил-4-оксо-1H-хинолин-3-карбоксамид;
N-[4-азетидин-1-ил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид
метил 4-[(4-оксо-1H-хинолин-3-ил)карбониламино]-2-трет-бутил-тиофене-3-карбоксилат;
N-[3-метокси-5-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[2-(2-пиридил)фенил]-1H-хинолин-3-карбоксамид;
5-гидрокси-4-оксо-N-[2-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-7-(трифторметокси)-1H-хинолин-3-карбоксамид;
N-(4-хлор-2-фтор-5-гидрокси-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-[3-(1-пиперидил)-4-(трифторметокси)фенил]-1H-хинолин-3-карбоксамид;
(R)-5-метил-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
(R)-1-[4-[(4-оксо-1H-хинолин-3-ил)карбониламино]-3-(трифторметил)фенил]пирролидин-2-карбоновая кислота;
5-фтор-N-[4-изопропил-2-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
5-гидрокси-N-[3-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(3-гидрокси-4-изопропокси-фенил)-5-метил-4-оксо-1H-хинолин-3-карбоксамид;
6-гидрокси-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид;
6-фтор-4-оксо-N-[5-(трифторметил)-1H-индол-6-ил]-1H-хинолин-3-карбоксамид;
7-метил-4-оксо-N-(5-трет-бутил-1H-индол-6-ил)-1H-хинолин-3-карбоксамид;
(R)-N-(4-(3-гидроксипирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
N-[2-фтор-5-гидрокси-4-(1-метилциклогексил)-фенил]-4-оксо-5-(трифторметил)-1H-хинолин-3-карбоксамид;
4-оксо-N-(3-пирролидин-1-ил-4-трет-бутил-фенил)-1H-хинолин-3-карбоксамид;
4-оксо-N-[4-фенил-5-(трифторметил)-3-тиенил]-1H-хинолин-3-карбоксамид;
7-фтор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-6-метокси-4-оксо-1H-хинолин-3-карбоксамид;
4-оксо-N-(1,4,4-триметил-2,3-дигидрохинолин-7-ил)-1H-хинолин-3-карбоксамид;
6-[(4-оксо-1H-хинолин-3-ил)карбониламино]-1H-индол-4-карбоновая кислота;
N-[3-фтор-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
(S)-N-(4-(2-метилпиперидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
(S)-6-фтор-N-(4-(2-метилпирролидин-1-ил)-2-(трифторметил)фенил)-4-оксо-1,4-дигидрохинолин-3-карбоксамид;
(S)-метил 1-(4-(4-оксо-1,4-дигидрохинолин-3-карбоксамид)-3-(трифторметил)фенил)пиперидин-2-карбоксилат;
8-хлор-N-[3-гидрокси-4-(трифторметил)фенил]-4-оксо-1H-хинолин-3-карбоксамид;
N-(4-метокси-2-нафтил)-4-оксо-1H-хинолин-3-карбоксамид; и
5,8-дифтор-N-(5-гидрокси-2,4-дитрет-бутил-фенил)-4-оксо-1H-хинолин-3-карбоксамид,
или его фармацевтически приемлемая соль.
2. Фармацевтическая композиция, содержащая соединение по п.1 и фармацевтически приемлемый носитель или адъювант.
3. Фармацевтическая композиция по п.2, дополнительно содержащая дополнительное средство, выбранное из муколитического средства, бронходилататора, антибиотика, противоинфекционного средства, противовоспалительного средства, модулятора CFTR или питательного вещества.
4. Фармацевтическая композиция по п.3, где указанное дополнительное средство представляет собой модулятор CFTR, отличный от соединения по п.1.
5. Способ лечения или ослабления тяжести заболевания у пациента, где указанное заболевание выбрано из кистозного фиброза, астмы, индуцированного курением COPD, хронического бронхита, риносинусита, запора, панкреатита, панкреатической недостаточности, мужского бесплодия, вызванного врожденным двусторонним отсутствием семявыводящих протоков (CBAVD), слабой формы легочного заболевания, идиопатического панкреатита, аллергического бронхолегочного аспергиллеза (ABPA), заболевания печени, наследственной эмфиземы, наследственного гемохроматоза, нарушений коагуляции-фибринолиза, таких как дефицит белка C, наследственная ангиоэдема типа 1, нарушений липидного процессинга, таких как семейная гиперхолестеринемия, хиломикронемия типа 1, абеталипопротеинемия, болезней лизосомального накопления, таких как I-клеточное заболевание/псевдо-Hurler, мукополисахаридозов, болезни Сандхофа/Тэя-Сакса, синдрома Криглера-Найяра типа II, полиэндокринопатии/гиперинсулинемии, сахарного диабета, карликовости Ларона, дефицита милеопероксидазы, первичного гипопаратиреоидизма, меланомы, гликаноза CDG типа 1, врожденного гипертиреоидизма, несовершенного остеогенеза, наследственной гипофибриногенемии, дефицита ACT, несахарного диабета (DI), нейрофизеального DI, нефрогенного DI, синдрома Шарко-Мари-Тута, болезни Perlizaeus-Merzbacher, нейродегенеративных заболеваний, таких как болезнь Альцгеймера, болезнь Паркинсона, амиотрофический боковой склероз, прогрессирующий супрануклеарный паралич, болезнь Пика, некоторых полиглутаминовых неврологических расстройств, таких как болезнь Гентингтона, спиноцеребуллярная атаксия типа I, спинальная и бульбарная мышечная атрофия, dentatorubal pallidoluysian и миотоническая дистрофия, а также спонгиформных энцефалопатий, таких как наследственная болезнь Крейцфельдта-Якоба (из-за дефекта процессинга прионового белка), болезнь Фабри, синдром Штросслера-Шейнкера, COPD, болезни сухих глаз, панкреатической недостаточности, остеопороза, остеопении, синдрома Горэма, хлоридных каналопатий, врожденной миотонии (формы Томсона и Бекера), синдрома Барттера типа III, болезни Дента, гиперэкплексии, эпилепсии, гиперэкплексии, болезни лизосомального накопления, синдрома Ангельмана, первичной цилиарной дискинезии (PCD), PCD с situs inversus (также известной как синдром Картагенера), PCD без situs inversus и цилиарной аплазии или болезни Шегрена, включающий стадию введения указанному пациенту эффективного количества соединения по п.1.
6. Способ по п.5, где указанное заболевание представляет собой кистозный фиброз.
7. Способ лечения или ослабления тяжести заболевания у пациента, где указанное заболевание связано с пониженной функцией CFTR из-за мутаций в гене, кодирующем CFTR, или экологических факторов, включающий стадию введения указанному пациенту эффективного количества соединения по п.1.
8. Способ по п.7, где заболевание представляет собой кистозный фиброз, хронический бронхит, рецидивирующий бронхит, острый бронхит, мужское бесплодие, вызванное врожденным двусторонним отсутствием семявыводящих протоков (CBAVD), женское бесплодие, вызванное врожденным отсутствием матки или влагалища (CAUV), идиопатический хронический панкреатит (ICP), идиопатический рецидивирующий панкреатит, идиопатический острый панкреатит, хронический риносинусит, первичный склерозирующий холангит, аллергический бронхолегочный аспергиллез, диабет, болезнь сухих глаз, запор, аллергический бронхолегочный аспергиллез (ABPA), заболевания кости и астму.
9. Способ лечения или ослабления тяжести заболевания у пациента, где указанное заболевание связано с нормальной функцией CFTR, включающий стадию введения указанному пациенту эффективного количества соединения по п.1.
10. Способ по п.9, где заболевание представляет собой хроническое обструктивное легочное заболевание (COPD), хронический бронхит, рецидивирующий бронхит, острый бронхит, риносинусит, запор, хронический панкреатит, рецидивирующий панкреатит и острый панкреатит, панкреатическую недостаточность, мужское бесплодие, вызванное врожденным двусторонним отсутствием семявыводящих протоков (CBAVD), слабую форму легочного заболевания, идиопатический панкреатит, заболевание печени, наследственную эмфизему, желчекаменную болезнь, гастро-эзофагеальный рефлюкс, желудочно-кишечные опухоли, воспалительное заболевание кишечника, запор, диабет, артрит, остеопороз и остеопению.
11. Способ по п.9, где заболевание представляет собой наследственный гемохроматоз, нарушения коагуляции-фибринолиза, такие как дефицит белка C, наследственная ангиоэдема типа 1, нарушения липидного процессинга, такие как семейная гиперхолестеринемия, хиломикронемия типа 1, абеталипопротеинемия, болезни лизосомального накопления, такие как I-клеточное заболевание/псевдо-Hurler, мукополисахаридозы, болезнь Сандхофа/Тэя-Сакса, синдром Криглера-Найяра типа II, полиэндокринопатию/гиперинсулинемию, сахарный диабет, карликовость Ларона, дефицит милеопероксидазы, первичный гипопаратиреоидизм, меланому, гликаноз CDG типа 1, врожденный гипертиреоидизм, несовершенный остеогенез, наследственную гипофибриногенемию, дефицит ACT, несахарный диабет (DI), нейрофизеальный DI, нефрогенный DI, синдром Шарко-Мари-Тута, болезнь Perlizaeus-Merzbacher, нейродегенеративные заболевания, такие как болезнь Альцгеймера, болезнь Паркинсона, амиотрофический боковой склероз, прогрессирующий супрануклеарный паралич, болезнь Пика, некоторые полиглутаминовые неврологические расстройства, такие как болезнь Гентингтона, спиноцеребуллярная атаксия типа I, спинальная и бульбарная мышечная атрофия, dentatorubal pallidoluysian и миотоническая дистрофия, а также спонгиформные энцефалопатии, такие как наследственная болезнь Крейцфельдта-Якоба (из-за дефекта процессинга прионового белка), болезнь Фабри, синдром Штросслера-Шейнкера, синдром Горэма, хлоридные каналопатии, врожденную миотонию (формы Томсона и Бекера), синдром Бартера типа III, болезнь Дента, гиперэкплексию, эпилепсию, гиперэкплексию, болезнь лизосомального накопления, синдром Ангельмана, первичную цилиарную дискинезию (PCD), PCD с situs inversus (также известную как синдром Картагенера), PCD без situs inversus и цилиарную аплазию или болезнь Шегрена.
12. Набор для использования в измерении активности CFTR или его фрагмента в биологическом образце in vitro или in vivo, содержащий:
композицию, содержащую соединение по п.1;
инструкции для:
контактирования композиции с биологическим образцом;
измерения активности указанного CFTR или его фрагмента.
13. Набор по п.12, дополнительно содержащий инструкции для:
контактирования дополнительного соединения с биологическим образцом;
измерения активности указанного CFTR или его фрагмента в присутствии указанного дополнительного соединения и
сравнения активности указанного CFTR или его фрагмента в присутствии указанного дополнительного соединения с активностью указанного CFTR или его фрагмента в присутствии композиции, включающей соединение по п.1.
14. Способ модуляции активности CFTR в биологическом образце, включающий стадию контактирования указанного CFTR с соединением по п.1.
15. Набор по п.13, где стадия сравнения активности указанного CFTR или его фрагмента обеспечивает оценку плотности указанного CFTR или его фрагмента.
16. Способ лечения или ослабления тяжести кистозного фиброза (CF) у пациента, включающий стадию введения указанному пациенту эффективного количества соединения по п.1.
17. Способ по п.16, где у пациента имеется трансмембранный рецептор кистозного фиброза (CFTR) с гомозиготной ∆F508 мутацией.
18. Способ по п.16, где у пациента имеется трансмембранный рецептор кистозного фиброза (CFTR) с гомозиготной G551D мутацией.
19. Способ по п.16, где у пациента имеется трансмембранный рецептор кистозного фиброза (CFTR) с гетерозиготной ∆F508 мутацией.
20. Способ по п.16, где у пациента имеется трансмембранный рецептор кистозного фиброза (CFTR) с гетерозиготной G551D мутацией.
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-
2009
- 2009-12-11 US US12/635,927 patent/US8354427B2/en active Active
-
2010
- 2010-12-10 EP EP10793116A patent/EP2509954A1/en not_active Withdrawn
- 2010-12-10 NZ NZ600707A patent/NZ600707A/en unknown
- 2010-12-10 JP JP2012543310A patent/JP2013513617A/ja active Pending
- 2010-12-10 AU AU2010327993A patent/AU2010327993A1/en not_active Abandoned
- 2010-12-10 CN CN201080056022XA patent/CN102652128A/zh active Pending
- 2010-12-10 RU RU2012129206/04A patent/RU2552353C2/ru active
- 2010-12-10 WO PCT/US2010/059920 patent/WO2011072241A1/en active Application Filing
- 2010-12-10 CA CA2783314A patent/CA2783314A1/en not_active Abandoned
- 2010-12-10 MX MX2012006764A patent/MX2012006764A/es active IP Right Grant
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- 2012-11-30 US US13/690,924 patent/US8614327B2/en active Active
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CA2783314A1 (en) | 2011-06-16 |
WO2011072241A9 (en) | 2012-06-14 |
US20100184739A1 (en) | 2010-07-22 |
AU2010327993A1 (en) | 2012-07-12 |
WO2011072241A1 (en) | 2011-06-16 |
IL220283A0 (en) | 2012-07-31 |
AU2010327993A8 (en) | 2012-07-19 |
CN102652128A (zh) | 2012-08-29 |
NZ600707A (en) | 2014-09-26 |
MX2012006764A (es) | 2012-11-23 |
US8354427B2 (en) | 2013-01-15 |
RU2552353C2 (ru) | 2015-06-10 |
EP2509954A1 (en) | 2012-10-17 |
JP2013513617A (ja) | 2013-04-22 |
US8614327B2 (en) | 2013-12-24 |
US20130165442A1 (en) | 2013-06-27 |
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