JP2002505660A - 抗ウィルス剤としての8―ヒドロキシ―7―置換キノリン - Google Patents
抗ウィルス剤としての8―ヒドロキシ―7―置換キノリンInfo
- Publication number
- JP2002505660A JP2002505660A JP51368598A JP51368598A JP2002505660A JP 2002505660 A JP2002505660 A JP 2002505660A JP 51368598 A JP51368598 A JP 51368598A JP 51368598 A JP51368598 A JP 51368598A JP 2002505660 A JP2002505660 A JP 2002505660A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- quinolinecarboxamide
- methyl
- phenyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 8-Hydroxy-7-substituted quinolines Chemical class 0.000 title claims abstract description 260
- 239000003443 antiviral agent Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 315
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims description 171
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 97
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 66
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 229940124530 sulfonamide Drugs 0.000 claims description 27
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000005493 quinolyl group Chemical group 0.000 claims description 22
- JYIAZVFJRYLCBH-UHFFFAOYSA-N 8-hydroxyquinoline-7-carboxylic acid Chemical compound C1=CC=NC2=C(O)C(C(=O)O)=CC=C21 JYIAZVFJRYLCBH-UHFFFAOYSA-N 0.000 claims description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 150000003456 sulfonamides Chemical class 0.000 claims description 15
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000003368 amide group Chemical group 0.000 claims description 14
- 229960003540 oxyquinoline Drugs 0.000 claims description 14
- 125000002619 bicyclic group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 241001024304 Mino Species 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- XOEVYEKLAVYKSD-UHFFFAOYSA-N n-(4-cyanophenyl)-8-hydroxyquinoline-7-carboxamide;hydrochloride Chemical compound Cl.C1=CC2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(C#N)C=C1 XOEVYEKLAVYKSD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
- IVFXGRIJGMFUSY-UHFFFAOYSA-N 8-hydroxy-n-[4-(hydroxymethyl)phenyl]quinoline-7-carboxamide Chemical compound C1=CC(CO)=CC=C1NC(=O)C1=CC=C(C=CC=N2)C2=C1O IVFXGRIJGMFUSY-UHFFFAOYSA-N 0.000 claims description 5
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- FEGGGWACWGSYMM-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-8-hydroxyquinoline-7-carboxamide;hydrochloride Chemical compound Cl.C1=C2OCOC2=CC(NC(=O)C2=C(C3=NC=CC=C3C=C2)O)=C1 FEGGGWACWGSYMM-UHFFFAOYSA-N 0.000 claims description 5
- ZDCWDELLUOWEAS-UHFFFAOYSA-N n-(2-chloro-5-methoxyphenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound COC1=CC=C(Cl)C(NC(=O)C=2C(=C3N=CC=CC3=CC=2)O)=C1 ZDCWDELLUOWEAS-UHFFFAOYSA-N 0.000 claims description 5
- ZDBYKMHJPHLDBL-UHFFFAOYSA-N n-(5-fluoro-2-methylphenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound CC1=CC=C(F)C=C1NC(=O)C1=CC=C(C=CC=N2)C2=C1O ZDBYKMHJPHLDBL-UHFFFAOYSA-N 0.000 claims description 5
- ACLPOFUIYHXBHE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 ACLPOFUIYHXBHE-UHFFFAOYSA-N 0.000 claims description 5
- ZMKFCERNISHYGL-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCCC1=CC=CC(Cl)=C1 ZMKFCERNISHYGL-UHFFFAOYSA-N 0.000 claims description 5
- INYJGWAMAOSZQJ-UHFFFAOYSA-N oxamide;hydrochloride Chemical compound Cl.NC(=O)C(N)=O INYJGWAMAOSZQJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- VXKAJLYQMIDNHT-UHFFFAOYSA-N 5-bromo-n-(4-chlorophenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=C(Br)C2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(Cl)C=C1 VXKAJLYQMIDNHT-UHFFFAOYSA-N 0.000 claims description 4
- NLIQHCOIXRGPCT-UHFFFAOYSA-N 5-chloro-n-(4-chlorophenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=C(Cl)C2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(Cl)C=C1 NLIQHCOIXRGPCT-UHFFFAOYSA-N 0.000 claims description 4
- WSYKRWFJRQDJGS-UHFFFAOYSA-N 8-hydroxy-n-(2-methylcyclohexyl)quinoline-7-carboxamide Chemical compound CC1CCCCC1NC(=O)C1=CC=C(C=CC=N2)C2=C1O WSYKRWFJRQDJGS-UHFFFAOYSA-N 0.000 claims description 4
- GHPQSRDOJYBFMK-UHFFFAOYSA-N 8-hydroxy-n-(2-phenylphenyl)quinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NC1=CC=CC=C1C1=CC=CC=C1 GHPQSRDOJYBFMK-UHFFFAOYSA-N 0.000 claims description 4
- UWKNMECJZXRIGW-UHFFFAOYSA-N 8-hydroxy-n-(3-methylsulfanylphenyl)quinoline-7-carboxamide;hydrochloride Chemical compound Cl.CSC1=CC=CC(NC(=O)C=2C(=C3N=CC=CC3=CC=2)O)=C1 UWKNMECJZXRIGW-UHFFFAOYSA-N 0.000 claims description 4
- LPORMKDGEJJLPD-UHFFFAOYSA-N 8-hydroxy-n-(4-methoxy-2-nitrophenyl)quinoline-7-carboxamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1NC(=O)C1=CC=C(C=CC=N2)C2=C1O LPORMKDGEJJLPD-UHFFFAOYSA-N 0.000 claims description 4
- XQRPKNHUWJZYLQ-UHFFFAOYSA-N 8-hydroxy-n-(8-hydroxyquinolin-2-yl)quinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)NC3=CC=C4C=CC=C(C4=N3)O)=CC=C21 XQRPKNHUWJZYLQ-UHFFFAOYSA-N 0.000 claims description 4
- DNTJUJVAHOZBJZ-UHFFFAOYSA-N 8-hydroxy-n-(naphthalen-1-ylmethyl)quinoline-7-carboxamide Chemical compound C1=CC=C2C(CNC(=O)C3=C(C4=NC=CC=C4C=C3)O)=CC=CC2=C1 DNTJUJVAHOZBJZ-UHFFFAOYSA-N 0.000 claims description 4
- LLDFOWMAYRPOKQ-CQSZACIVSA-N 8-hydroxy-n-[(1r)-1-naphthalen-1-ylethyl]quinoline-7-carboxamide Chemical compound C1=CC=C2C([C@H](NC(=O)C=3C(=C4N=CC=CC4=CC=3)O)C)=CC=CC2=C1 LLDFOWMAYRPOKQ-CQSZACIVSA-N 0.000 claims description 4
- FKRLHKWPGMFQCU-UHFFFAOYSA-N 8-hydroxy-n-[2-methoxy-5-(trifluoromethyl)phenyl]quinoline-7-carboxamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)C1=CC=C(C=CC=N2)C2=C1O FKRLHKWPGMFQCU-UHFFFAOYSA-N 0.000 claims description 4
- LXYCYEUSSFRKCW-UHFFFAOYSA-N 8-hydroxy-n-naphthalen-1-ylquinoline-7-carboxamide Chemical compound C1=CC=C2C(NC(=O)C3=C(C4=NC=CC=C4C=C3)O)=CC=CC2=C1 LXYCYEUSSFRKCW-UHFFFAOYSA-N 0.000 claims description 4
- XKAFDOFWMNXRJC-UHFFFAOYSA-N 8-hydroxy-n-naphthalen-2-ylquinoline-7-carboxamide;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(NC(=O)C3=C(C4=NC=CC=C4C=C3)O)=CC=C21 XKAFDOFWMNXRJC-UHFFFAOYSA-N 0.000 claims description 4
- SWCFSRFPPJXMFS-UHFFFAOYSA-N 8-hydroxy-n-nonylquinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)NCCCCCCCCC)=CC=C21 SWCFSRFPPJXMFS-UHFFFAOYSA-N 0.000 claims description 4
- CIHUQUVAMMKMBY-UHFFFAOYSA-N 8-hydroxy-n-octan-2-ylquinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)NC(C)CCCCCC)=CC=C21 CIHUQUVAMMKMBY-UHFFFAOYSA-N 0.000 claims description 4
- AUJIBWJKZQGQMS-UHFFFAOYSA-N 8-hydroxy-n-octan-3-ylquinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)NC(CC)CCCCC)=CC=C21 AUJIBWJKZQGQMS-UHFFFAOYSA-N 0.000 claims description 4
- MZXOZKKPYALUOV-UHFFFAOYSA-N 8-hydroxy-n-undecylquinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)NCCCCCCCCCCC)=CC=C21 MZXOZKKPYALUOV-UHFFFAOYSA-N 0.000 claims description 4
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 claims description 4
- XGSUJDBHRISNFQ-UHFFFAOYSA-N Cl.OC=1C(=CC=C2C=CC=NC12)C(=O)NC1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound Cl.OC=1C(=CC=C2C=CC=NC12)C(=O)NC1=CC=C(C=C1)C1=CC=CC=C1 XGSUJDBHRISNFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006309 butyl amino group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- KQJWYHRNINCSCL-UHFFFAOYSA-N n-(2,2-diphenylethyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 KQJWYHRNINCSCL-UHFFFAOYSA-N 0.000 claims description 4
- RXLRNENHWCYOOG-UHFFFAOYSA-N n-(2-chloro-4-cyanophenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(C#N)C=C1Cl RXLRNENHWCYOOG-UHFFFAOYSA-N 0.000 claims description 4
- LDKAFORBDHMJPW-UHFFFAOYSA-N n-(2-fluoro-4-iodophenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(I)C=C1F LDKAFORBDHMJPW-UHFFFAOYSA-N 0.000 claims description 4
- APSDLYAXYAETDH-UHFFFAOYSA-N n-(3,3-diphenylpropyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 APSDLYAXYAETDH-UHFFFAOYSA-N 0.000 claims description 4
- GNGSIJXDHQJLTA-UHFFFAOYSA-N n-(4-bromo-2-fluorophenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(Br)C=C1F GNGSIJXDHQJLTA-UHFFFAOYSA-N 0.000 claims description 4
- FWBHHLIGXMDJJG-UHFFFAOYSA-N n-(4-bromophenyl)-8-hydroxyquinoline-7-carboxamide;hydrochloride Chemical compound Cl.C1=CC2=CC=CN=C2C(O)=C1C(=O)NC1=CC=C(Br)C=C1 FWBHHLIGXMDJJG-UHFFFAOYSA-N 0.000 claims description 4
- GXHDYVWMKRLCSK-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-8-hydroxyquinoline-7-carboxamide Chemical compound CC1=CC(F)=CC=C1NC(=O)C1=CC=C(C=CC=N2)C2=C1O GXHDYVWMKRLCSK-UHFFFAOYSA-N 0.000 claims description 4
- DGRKFDWGEOHIRM-UHFFFAOYSA-N n-(4-tert-butylcyclohexyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1CC(C(C)(C)C)CCC1NC(=O)C1=CC=C(C=CC=N2)C2=C1O DGRKFDWGEOHIRM-UHFFFAOYSA-N 0.000 claims description 4
- FQANKYGGELTSCY-LLVKDONJSA-N n-[(1r)-1-(4-bromophenyl)ethyl]-8-hydroxyquinoline-7-carboxamide Chemical compound C1([C@H](NC(=O)C=2C(=C3N=CC=CC3=CC=2)O)C)=CC=C(Br)C=C1 FQANKYGGELTSCY-LLVKDONJSA-N 0.000 claims description 4
- JJPJVLBGFMYOAM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-[2-(furan-2-yl)ethenyl]-8-hydroxyquinoline-7-carboxamide Chemical compound N1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=CC2=CC=C1C=CC1=CC=CO1 JJPJVLBGFMYOAM-UHFFFAOYSA-N 0.000 claims description 4
- AIOACISTHSPLSS-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethyl]-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCCC1=CC=C(Br)C=C1 AIOACISTHSPLSS-UHFFFAOYSA-N 0.000 claims description 4
- FVMKEXOAMJROHI-UHFFFAOYSA-N n-benzhydryl-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 FVMKEXOAMJROHI-UHFFFAOYSA-N 0.000 claims description 4
- HGXLAOALXKMHOQ-UHFFFAOYSA-N n-heptyl-8-hydroxy-2-[2-(4-methoxyphenyl)ethenyl]quinoline-7-carboxamide Chemical compound N=1C2=C(O)C(C(=O)NCCCCCCC)=CC=C2C=CC=1C=CC1=CC=C(OC)C=C1 HGXLAOALXKMHOQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 3
- YTSUPDQZEYRLNX-UHFFFAOYSA-N 5-bromo-n-[5-(4-chlorophenyl)-4-oxo-1,3-thiazol-2-yl]-8-hydroxyquinoline-7-carboxamide Chemical compound C1=C(Br)C2=CC=CN=C2C(O)=C1C(=O)NC(S1)=NC(=O)C1C1=CC=C(Cl)C=C1 YTSUPDQZEYRLNX-UHFFFAOYSA-N 0.000 claims description 3
- CCBBJNQJWATFRI-UHFFFAOYSA-N 8-hydroxy-n-(1-phenylethyl)quinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)NC(C)C1=CC=CC=C1 CCBBJNQJWATFRI-UHFFFAOYSA-N 0.000 claims description 3
- GKZWYDGGJOZYKN-UHFFFAOYSA-N 8-hydroxy-n-(1h-indazol-5-yl)quinoline-7-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(C3=NC=CC=C3C=C2)O)=C1 GKZWYDGGJOZYKN-UHFFFAOYSA-N 0.000 claims description 3
- UELRYROGMPMRGD-UHFFFAOYSA-N 8-hydroxy-n-(2-hydroxy-2-phenylethyl)-2-(2-phenylethenyl)quinoline-7-carboxamide Chemical compound C=1C=CC=CC=1C(O)CNC(=O)C(C(=C1N=2)O)=CC=C1C=CC=2C=CC1=CC=CC=C1 UELRYROGMPMRGD-UHFFFAOYSA-N 0.000 claims description 3
- VTKZWGRVZFBWMU-UHFFFAOYSA-N 8-hydroxy-n-(2-methylsulfanylphenyl)quinoline-7-carboxamide Chemical compound CSC1=CC=CC=C1NC(=O)C1=CC=C(C=CC=N2)C2=C1O VTKZWGRVZFBWMU-UHFFFAOYSA-N 0.000 claims description 3
- MXSDJHYLMNXISD-UHFFFAOYSA-N 8-hydroxy-n-(2-phenylpropyl)quinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)NCC(C)C1=CC=CC=C1 MXSDJHYLMNXISD-UHFFFAOYSA-N 0.000 claims description 3
- JFMWLHULYAMKAC-UHFFFAOYSA-N 8-hydroxy-n-(2-phenylsulfanylethyl)quinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCCSC1=CC=CC=C1 JFMWLHULYAMKAC-UHFFFAOYSA-N 0.000 claims description 3
- VAFSUXREGDAQFU-UHFFFAOYSA-N 8-hydroxy-n-(3-methylcyclohexyl)quinoline-7-carboxamide Chemical compound C1C(C)CCCC1NC(=O)C1=CC=C(C=CC=N2)C2=C1O VAFSUXREGDAQFU-UHFFFAOYSA-N 0.000 claims description 3
- JLEGTEANBXXCLJ-UHFFFAOYSA-N 8-hydroxy-n-(3-phenylmethoxyphenyl)quinoline-7-carboxamide;hydrochloride Chemical compound Cl.C1=CC2=CC=CN=C2C(O)=C1C(=O)NC(C=1)=CC=CC=1OCC1=CC=CC=C1 JLEGTEANBXXCLJ-UHFFFAOYSA-N 0.000 claims description 3
- LMFWDICMGFVCDW-UHFFFAOYSA-N 8-hydroxy-n-(3-phenylpropyl)quinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)NCCCC1=CC=CC=C1 LMFWDICMGFVCDW-UHFFFAOYSA-N 0.000 claims description 3
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- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
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- RFUWRXIYTQGFGA-QRPNPIFTSA-N tert-butyl (2s)-2-amino-4-methylpentanoate;hydron;chloride Chemical compound Cl.CC(C)C[C@H](N)C(=O)OC(C)(C)C RFUWRXIYTQGFGA-QRPNPIFTSA-N 0.000 description 1
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- ZSDRVMRBDJTUQS-UHFFFAOYSA-N tert-butyl 2-(1,3-benzodioxol-4-yl)-2-[[5-[(8-hydroxyquinoline-7-carbonyl)amino]-1,3,4-thiadiazol-2-yl]amino]acetate Chemical compound N=1N=C(NC(=O)C=2C(=C3N=CC=CC3=CC=2)O)SC=1NC(C(=O)OC(C)(C)C)C1=CC=CC2=C1OCO2 ZSDRVMRBDJTUQS-UHFFFAOYSA-N 0.000 description 1
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical group C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2587096P | 1996-09-10 | 1996-09-10 | |
| US60/025,870 | 1996-09-10 | ||
| US5072097P | 1997-06-25 | 1997-06-25 | |
| US60/050,720 | 1997-06-25 | ||
| PCT/US1997/015310 WO1998011073A1 (en) | 1996-09-10 | 1997-09-05 | 8-hydroxy-7-substituted quinolines as anti-viral agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002505660A true JP2002505660A (ja) | 2002-02-19 |
| JP2002505660A5 JP2002505660A5 (https=) | 2005-05-12 |
Family
ID=26700264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51368598A Withdrawn JP2002505660A (ja) | 1996-09-10 | 1997-09-05 | 抗ウィルス剤としての8―ヒドロキシ―7―置換キノリン |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US6310211B1 (https=) |
| EP (1) | EP0927164A1 (https=) |
| JP (1) | JP2002505660A (https=) |
| AU (1) | AU4172197A (https=) |
| CA (1) | CA2262786A1 (https=) |
| WO (1) | WO1998011073A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001518890A (ja) * | 1997-04-08 | 2001-10-16 | サーントゥル ナシオナル ドゥ ラ ルシェルシュ シャーンティフィク (セ エン エール エス) | Hivインテグラーゼの阻害剤としてのキノリン誘導体 |
| WO2005075475A1 (ja) * | 2004-02-04 | 2005-08-18 | Shionogi & Co., Ltd. | Hivインテグラーゼ阻害活性を有するナフチリジン誘導体 |
| JP2006504681A (ja) * | 2002-08-29 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 炎症性、アレルギー性及び増殖性疾患の治療において糖質コルチコイドミメティックスとして使用するための3−(スルホンアミドエチル)−インドール誘導体 |
| JP2006505571A (ja) * | 2002-10-15 | 2006-02-16 | リゲル ファーマシューテイカルズ、インコーポレイテッド | 置換されたインドール及びhcv阻害剤としてのその使用 |
| EP2045242A1 (en) | 2002-08-13 | 2009-04-08 | Shionogi&Co., Ltd. | Heterocyclic compounds having inhibitory activity against HIV integrase |
| JP2013515755A (ja) * | 2009-12-29 | 2013-05-09 | ポリケム・エスエイ | 新規な第3級8−ヒドロキシキノリン−7−カルボキサミド誘導体およびその使用 |
| JP2013515756A (ja) * | 2009-12-29 | 2013-05-09 | ポリケム・エスエイ | 抗真菌剤として使用するための第2級8−ヒドロキシキノリン−7−カルボキサミド誘導体 |
| JP2013515757A (ja) * | 2009-12-29 | 2013-05-09 | ポリケム・エスエイ | 新規な第2級8−ヒドロキシキノリン−7−カルボキサミド誘導体 |
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| JP2002539130A (ja) | 1999-03-09 | 2002-11-19 | ファルマシア・アンド・アップジョン・カンパニー | 抗ウイルス剤としての4−オキソ−4,7−ジヒドロ−チエノ[2,3−b]ピリジン−5−カルボキサミド |
| TW500724B (en) | 1999-10-05 | 2002-09-01 | Pharmacia & Amp Upjohn Company | Oxazinoquinolones useful for the treatment of viral infections |
| CA2399991A1 (en) | 2000-03-21 | 2001-09-27 | Pharmacia & Upjohn Company | 4-hydroxy-1,8-naphthyridine-3-carboxamides as antiviral agents |
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| US6730682B2 (en) * | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
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| US6559145B2 (en) | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| WO2002017969A2 (en) * | 2000-08-30 | 2002-03-07 | Chemocentryx, Inc. | Reagents and methods for the diagnosis of cmv dissemination |
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1999
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2001
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001518890A (ja) * | 1997-04-08 | 2001-10-16 | サーントゥル ナシオナル ドゥ ラ ルシェルシュ シャーンティフィク (セ エン エール エス) | Hivインテグラーゼの阻害剤としてのキノリン誘導体 |
| EP2045242A1 (en) | 2002-08-13 | 2009-04-08 | Shionogi&Co., Ltd. | Heterocyclic compounds having inhibitory activity against HIV integrase |
| JP2006504681A (ja) * | 2002-08-29 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 炎症性、アレルギー性及び増殖性疾患の治療において糖質コルチコイドミメティックスとして使用するための3−(スルホンアミドエチル)−インドール誘導体 |
| JP2006505571A (ja) * | 2002-10-15 | 2006-02-16 | リゲル ファーマシューテイカルズ、インコーポレイテッド | 置換されたインドール及びhcv阻害剤としてのその使用 |
| WO2005075475A1 (ja) * | 2004-02-04 | 2005-08-18 | Shionogi & Co., Ltd. | Hivインテグラーゼ阻害活性を有するナフチリジン誘導体 |
| US7919623B2 (en) | 2004-02-04 | 2011-04-05 | Shionogi & Co., Ltd. | Naphthyridine derivatives having inhibitory activity against HIV integrase |
| JP2013515755A (ja) * | 2009-12-29 | 2013-05-09 | ポリケム・エスエイ | 新規な第3級8−ヒドロキシキノリン−7−カルボキサミド誘導体およびその使用 |
| JP2013515756A (ja) * | 2009-12-29 | 2013-05-09 | ポリケム・エスエイ | 抗真菌剤として使用するための第2級8−ヒドロキシキノリン−7−カルボキサミド誘導体 |
| JP2013515757A (ja) * | 2009-12-29 | 2013-05-09 | ポリケム・エスエイ | 新規な第2級8−ヒドロキシキノリン−7−カルボキサミド誘導体 |
| JP2014528412A (ja) * | 2011-09-30 | 2014-10-27 | キネタ・インコーポレイテツド | 抗ウイルス化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6310211B1 (en) | 2001-10-30 |
| US6252080B1 (en) | 2001-06-26 |
| US6211376B1 (en) | 2001-04-03 |
| WO1998011073A1 (en) | 1998-03-19 |
| EP0927164A1 (en) | 1999-07-07 |
| US6500842B1 (en) | 2002-12-31 |
| AU4172197A (en) | 1998-04-02 |
| CA2262786A1 (en) | 1998-03-19 |
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