SK9072000A3 - 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents - Google Patents
4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents Download PDFInfo
- Publication number
- SK9072000A3 SK9072000A3 SK907-2000A SK9072000A SK9072000A3 SK 9072000 A3 SK9072000 A3 SK 9072000A3 SK 9072000 A SK9072000 A SK 9072000A SK 9072000 A3 SK9072000 A3 SK 9072000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- hydroxy
- chlorobenzyl
- quinolinecarboxamide
- fluoro
- amino
- Prior art date
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- CVAWACBLSANHSQ-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=CN=C21 CVAWACBLSANHSQ-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000003443 antiviral agent Substances 0.000 title description 5
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 213
- 241000282414 Homo sapiens Species 0.000 claims abstract description 5
- 241000701022 Cytomegalovirus Species 0.000 claims description 273
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 262
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 161
- -1 het Chemical group 0.000 claims description 156
- 125000000217 alkyl group Chemical group 0.000 claims description 127
- 238000000034 method Methods 0.000 claims description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 60
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 56
- 239000000460 chlorine Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 47
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 47
- VMPDJKLCDOCUMM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxypropyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(CCCO)=CC=C2NC=C1C(=O)NCC1=CC=C(Cl)C=C1 VMPDJKLCDOCUMM-UHFFFAOYSA-N 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 239000011734 sodium Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- LOXYWCTUWMUGPT-UHFFFAOYSA-N 7-amino-n-[(4-chlorophenyl)methyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(N)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 LOXYWCTUWMUGPT-UHFFFAOYSA-N 0.000 claims description 17
- VHHFNJHPTPNPAB-UPHRSURJSA-N n-[(4-chlorophenyl)methyl]-6-[(z)-3-hydroxyprop-1-enyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(\C=C/CO)=CC=C2NC=C1C(=O)NCC1=CC=C(Cl)C=C1 VHHFNJHPTPNPAB-UPHRSURJSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- MTNUANJKLNRYLU-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-iodo-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(F)C=C(I)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 MTNUANJKLNRYLU-UHFFFAOYSA-N 0.000 claims description 15
- FAZJLPDPYHBDBS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-hydroxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(O)=CC(F)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 FAZJLPDPYHBDBS-UHFFFAOYSA-N 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 12
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- KRGAUGKCBXLSAJ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-7-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(C(F)(F)F)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 KRGAUGKCBXLSAJ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 241001529453 unidentified herpesvirus Species 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- IKNNGWLTIGPUIP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(OC)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 IKNNGWLTIGPUIP-UHFFFAOYSA-N 0.000 claims description 9
- LWFZOUPESAMEFY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-(3-hydroxypropyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(CCCO)=CC(F)=C2NC=C1C(=O)NCC1=CC=C(Cl)C=C1 LWFZOUPESAMEFY-UHFFFAOYSA-N 0.000 claims description 9
- BYKVZEXISUORNC-UHFFFAOYSA-N 3-[3-[(4-chlorophenyl)methylcarbamoyl]-8-fluoro-4-oxo-1h-quinolin-6-yl]prop-2-ynyl formate Chemical compound C1=NC2=C(F)C=C(C#CCOC=O)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 BYKVZEXISUORNC-UHFFFAOYSA-N 0.000 claims description 8
- GOJACPPDOHWDFE-UHFFFAOYSA-N 6-amino-n-[(4-chlorophenyl)methyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(N)=CC=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 GOJACPPDOHWDFE-UHFFFAOYSA-N 0.000 claims description 8
- DEVWEFBXXYMHIL-UHFFFAOYSA-N CCCOP(O)=O Chemical compound CCCOP(O)=O DEVWEFBXXYMHIL-UHFFFAOYSA-N 0.000 claims description 8
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 8
- JSUVTMOOWMPMCA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-6-thiophen-2-yl-1h-quinoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C1=CNC2=CC=C(C=3SC=CC=3)C=C2C1=O JSUVTMOOWMPMCA-UHFFFAOYSA-N 0.000 claims description 8
- LHCASPYXLIAHLU-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(C#CCO)=CC=C2NC=C1C(=O)NCC1=CC=C(Cl)C=C1 LHCASPYXLIAHLU-UHFFFAOYSA-N 0.000 claims description 8
- YRPHWITUXRMKSN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-fluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC=C(F)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 YRPHWITUXRMKSN-UHFFFAOYSA-N 0.000 claims description 8
- CFIAXZRQVGMVTG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-(3-hydroxypropyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(CCCO)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 CFIAXZRQVGMVTG-UHFFFAOYSA-N 0.000 claims description 8
- GPKUWVZXVACSID-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-4-oxo-6-thiophen-2-yl-1h-quinoline-3-carboxamide Chemical compound FC1=CC(C=2SC=CC=2)=CC(C2=O)=C1NC=C2C(=O)NCC1=CC=C(Cl)C=C1 GPKUWVZXVACSID-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- KYTBOTIQMLVHRY-UHFFFAOYSA-N 6-tert-butyl-n-[(4-chlorophenyl)methyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C(C)(C)C)=CC=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 KYTBOTIQMLVHRY-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- KUSOWIJDRCKDTM-UHFFFAOYSA-N [(2-methylpropan-2-yl)oxycarbonylamino] hexanoate Chemical compound CCCCCC(=O)ONC(=O)OC(C)(C)C KUSOWIJDRCKDTM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- WYGBVHZXHIFMAH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-5,7-bis(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 WYGBVHZXHIFMAH-UHFFFAOYSA-N 0.000 claims description 7
- VHHFNJHPTPNPAB-OWOJBTEDSA-N n-[(4-chlorophenyl)methyl]-6-[(e)-3-hydroxyprop-1-enyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(/C=C/CO)=CC=C2NC=C1C(=O)NCC1=CC=C(Cl)C=C1 VHHFNJHPTPNPAB-OWOJBTEDSA-N 0.000 claims description 7
- QEIVUQDPYGTBBQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-fluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(F)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 QEIVUQDPYGTBBQ-UHFFFAOYSA-N 0.000 claims description 7
- JXDKLSIEXCTXTG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(2-hydroxyethoxy)-6-(3-hydroxypropyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(CCCO)=CC(OCCO)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 JXDKLSIEXCTXTG-UHFFFAOYSA-N 0.000 claims description 7
- BKMMZMGCCUYPSL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-(4-hydroxybutyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound O=C1C2=CC(CCCCO)=CC(F)=C2NC=C1C(=O)NCC1=CC=C(Cl)C=C1 BKMMZMGCCUYPSL-UHFFFAOYSA-N 0.000 claims description 7
- FUEMBCYJAWLFGT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-methoxy-6-(3-methoxyprop-1-ynyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C#CCOC)=CC(OC)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 FUEMBCYJAWLFGT-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- GBGCQZQJCOQSLB-UHFFFAOYSA-N 2,6-diaminohexanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCCCCC(N)C(O)=O GBGCQZQJCOQSLB-UHFFFAOYSA-N 0.000 claims description 6
- YUOWJJJFSOZYJN-UHFFFAOYSA-N 3-[3-[(4-chlorophenyl)methylcarbamoyl]-8-fluoro-4-oxo-1h-quinolin-6-yl]propyl 2-bromoacetate Chemical compound C1=NC2=C(F)C=C(CCCOC(=O)CBr)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 YUOWJJJFSOZYJN-UHFFFAOYSA-N 0.000 claims description 6
- CKWCLJCUKOULCE-UHFFFAOYSA-N 6-chloro-n-[(4-chlorophenyl)methyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC=C(Cl)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 CKWCLJCUKOULCE-UHFFFAOYSA-N 0.000 claims description 6
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 229910052744 lithium Chemical group 0.000 claims description 6
- IRKIMPUKNZIHQR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C1=CNC2=CC=CC=C2C1=O IRKIMPUKNZIHQR-UHFFFAOYSA-N 0.000 claims description 6
- DPFXLCQANYWHBG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-6-phenyl-1h-quinoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=NC2=CC=C1C1=CC=CC=C1 DPFXLCQANYWHBG-UHFFFAOYSA-N 0.000 claims description 6
- KWVQMBPLOPKYMO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6,8-difluoro-7-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(F)C(OC)=C(F)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 KWVQMBPLOPKYMO-UHFFFAOYSA-N 0.000 claims description 6
- WURWQYBUULEEOM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-8-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C(OC)=CC(C#CCO)=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 WURWQYBUULEEOM-UHFFFAOYSA-N 0.000 claims description 6
- GYMIEQSOBSALAC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxypropyl)-8-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C(OC)=CC(CCCO)=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 GYMIEQSOBSALAC-UHFFFAOYSA-N 0.000 claims description 6
- ZHRMWDJSSOFUNV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=NC2=CC=C1CN1CCOCC1 ZHRMWDJSSOFUNV-UHFFFAOYSA-N 0.000 claims description 6
- PUJOTKBPZPNSDZ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-iodo-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC=C(I)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 PUJOTKBPZPNSDZ-UHFFFAOYSA-N 0.000 claims description 6
- UMKACZLOVBKTMC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-iodo-8-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C(OC)=CC(I)=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 UMKACZLOVBKTMC-UHFFFAOYSA-N 0.000 claims description 6
- SBEIHTFBACYMND-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-methoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(OC)=CC=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 SBEIHTFBACYMND-UHFFFAOYSA-N 0.000 claims description 6
- HRKBEYSWSVPUJY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C)=CC=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 HRKBEYSWSVPUJY-UHFFFAOYSA-N 0.000 claims description 6
- YOISIFZYDCTXRP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-(4-hydroxybutyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(CCCCO)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 YOISIFZYDCTXRP-UHFFFAOYSA-N 0.000 claims description 6
- ZUZVLSCMJSYXFG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound FC1=CC=CC(C2=O)=C1NC=C2C(=O)NCC1=CC=C(Cl)C=C1 ZUZVLSCMJSYXFG-UHFFFAOYSA-N 0.000 claims description 6
- OZMXASYDKNEGDB-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C)=CC(F)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 OZMXASYDKNEGDB-UHFFFAOYSA-N 0.000 claims description 6
- HJAFKBYNHUCWON-UHFFFAOYSA-N 8-chloro-n-[(4-chlorophenyl)methyl]-4-oxo-5-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(Cl)C=CC(C(F)(F)F)=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 HJAFKBYNHUCWON-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- KGADANBTHXAVTA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6,7-difluoro-8-(2-methoxyethoxy)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C(OCCOC)=C(F)C(F)=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 KGADANBTHXAVTA-UHFFFAOYSA-N 0.000 claims description 5
- DPLKASWWBYFFLV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6,7-dimethoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC1=C2C=C(OC)C(OC)=CC2=NC=C1C(=O)NCC1=CC=C(Cl)C=C1 DPLKASWWBYFFLV-UHFFFAOYSA-N 0.000 claims description 5
- CNRCSOAIOXVYQO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6,8-dimethoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(OC)=CC(OC)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 CNRCSOAIOXVYQO-UHFFFAOYSA-N 0.000 claims description 5
- PMZHQTGAFFJROV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxybutyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(CCC(O)C)=CC=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 PMZHQTGAFFJROV-UHFFFAOYSA-N 0.000 claims description 5
- HHGGIMHFAUFZNT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-8-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C#CCO)=CC(C(F)(F)F)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 HHGGIMHFAUFZNT-UHFFFAOYSA-N 0.000 claims description 5
- VITOHQCMXVQCMS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(4-hydroxy-2-methylbutan-2-yl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C(C)(CCO)C)=CC=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 VITOHQCMXVQCMS-UHFFFAOYSA-N 0.000 claims description 5
- BJIFLZONIXEFCQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(cyanomethyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC=C(CC#N)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 BJIFLZONIXEFCQ-UHFFFAOYSA-N 0.000 claims description 5
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- WRHXUGRUTJJRQQ-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=C(C)C=C2C(=O)C(C(=O)OCC)=CNC2=C1 WRHXUGRUTJJRQQ-UHFFFAOYSA-N 0.000 description 1
- DBJCDCSZGDONQQ-UHFFFAOYSA-N ethyl 6-nitro-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C(C(=O)OCC)=CNC2=C1 DBJCDCSZGDONQQ-UHFFFAOYSA-N 0.000 description 1
- XJTQOCCGSVWPFH-UHFFFAOYSA-N ethyl 6-tert-butyl-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC(C(C)(C)C)=CC2=C(O)C(C(=O)OCC)=CN=C21 XJTQOCCGSVWPFH-UHFFFAOYSA-N 0.000 description 1
- FAEKTUDLKDVPSY-UHFFFAOYSA-N ethyl 7,8-dichloro-4-oxo-1h-quinoline-3-carboxylate Chemical compound ClC1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1Cl FAEKTUDLKDVPSY-UHFFFAOYSA-N 0.000 description 1
- BIFIWEDEMMZFND-UHFFFAOYSA-N ethyl 7,8-difluoro-4-oxo-1h-quinoline-3-carboxylate Chemical compound FC1=C(F)C=CC2=C(O)C(C(=O)OCC)=CN=C21 BIFIWEDEMMZFND-UHFFFAOYSA-N 0.000 description 1
- LDZCUWZFXKDMHH-UHFFFAOYSA-N ethyl 7-fluoro-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=C(F)C=CC2=C(O)C(C(=O)OCC)=CN=C21 LDZCUWZFXKDMHH-UHFFFAOYSA-N 0.000 description 1
- GWLDDWJZROMBRD-UHFFFAOYSA-N ethyl 7-methoxy-4-oxo-1h-quinoline-3-carboxylate Chemical compound COC1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 GWLDDWJZROMBRD-UHFFFAOYSA-N 0.000 description 1
- OZOMNKPYBWQMAH-UHFFFAOYSA-N ethyl 7-methyl-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=C(C)C=CC2=C(O)C(C(=O)OCC)=CN=C21 OZOMNKPYBWQMAH-UHFFFAOYSA-N 0.000 description 1
- CVTZGJPEFPRNNB-UHFFFAOYSA-N ethyl 8-chloro-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1Cl CVTZGJPEFPRNNB-UHFFFAOYSA-N 0.000 description 1
- ZMWABMUGLUDDDA-UHFFFAOYSA-N ethyl 8-chloro-6-methylquinoline-2-carboxylate Chemical compound C1=C(C)C=C(Cl)C2=NC(C(=O)OCC)=CC=C21 ZMWABMUGLUDDDA-UHFFFAOYSA-N 0.000 description 1
- IOXBKBFKCYONPW-UHFFFAOYSA-N ethyl 8-cyano-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1C#N IOXBKBFKCYONPW-UHFFFAOYSA-N 0.000 description 1
- RTKRHLHDOWHMCV-UHFFFAOYSA-N ethyl 8-fluoro-4-hydroxy-6-iodo-2-oxo-1h-quinoline-3-carboxylate Chemical compound IC1=CC(F)=C2NC(=O)C(C(=O)OCC)=C(O)C2=C1 RTKRHLHDOWHMCV-UHFFFAOYSA-N 0.000 description 1
- UVMOUEVDDPOSCH-UHFFFAOYSA-N ethyl 8-fluoro-6-(2-methylphenyl)-4-oxo-1h-quinoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=CN=C2C(F)=CC=1C1=CC=CC=C1C UVMOUEVDDPOSCH-UHFFFAOYSA-N 0.000 description 1
- KEWAAPTWQARHSY-UHFFFAOYSA-N ethyl 8-fluoro-6-methyl-4-oxo-1h-quinoline-3-carboxylate Chemical compound FC1=CC(C)=CC2=C(O)C(C(=O)OCC)=CN=C21 KEWAAPTWQARHSY-UHFFFAOYSA-N 0.000 description 1
- DJGXPLQGGHSMGV-UHFFFAOYSA-N ethyl 8-hydroxy-4-oxo-1h-quinoline-3-carboxylate Chemical compound OC1=CC=CC2=C(O)C(C(=O)OCC)=CN=C21 DJGXPLQGGHSMGV-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 208000024697 human cytomegalovirus infection Diseases 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- JJUSTAVGGFEOJN-UHFFFAOYSA-N morpholin-4-yl acetate Chemical compound CC(=O)ON1CCOCC1 JJUSTAVGGFEOJN-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- WIHJIUAIGYVISH-UHFFFAOYSA-N n'-(4-chlorophenyl)-6,7,8-trifluoro-4-oxo-1h-quinoline-3-carbohydrazide Chemical compound C1=NC2=C(F)C(F)=C(F)C=C2C(O)=C1C(=O)NNC1=CC=C(Cl)C=C1 WIHJIUAIGYVISH-UHFFFAOYSA-N 0.000 description 1
- SJQSMTIYFUQWRA-UHFFFAOYSA-N n'-(4-chlorophenyl)-8-fluoro-6-methyl-4-oxo-1h-quinoline-3-carbohydrazide Chemical compound OC=1C2=CC(C)=CC(F)=C2N=CC=1C(=O)NNC1=CC=C(Cl)C=C1 SJQSMTIYFUQWRA-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- JHVRNAZUOXAAGO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-6-[(2-phenylpyrazol-3-yl)sulfamoyl]-1h-quinoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=NC2=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1 JHVRNAZUOXAAGO-UHFFFAOYSA-N 0.000 description 1
- DKMWSMZSSYHEDF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6,8-difluoro-7-methoxy-4-oxo-1-(2-trimethylsilylethoxymethyl)quinoline-3-carboxamide Chemical compound FC=1C(OC)=C(F)C=C(C2=O)C=1N(COCC[Si](C)(C)C)C=C2C(=O)NCC1=CC=C(Cl)C=C1 DKMWSMZSSYHEDF-UHFFFAOYSA-N 0.000 description 1
- HRVOTGKLXMUGBS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(2-cyanoethyl)-8-fluoro-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(F)C=C(CCC#N)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 HRVOTGKLXMUGBS-UHFFFAOYSA-N 0.000 description 1
- HBAGITGVYBITFV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-fluoro-7,8-dimethoxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(OC)C(OC)=C(F)C=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 HBAGITGVYBITFV-UHFFFAOYSA-N 0.000 description 1
- FVZBGGRZEZAHLX-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-(3-hydroxyprop-1-ynyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(C#CCO)=CC=C2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 FVZBGGRZEZAHLX-UHFFFAOYSA-N 0.000 description 1
- SOSCRSSNTXGJHI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-[(4-chlorophenyl)sulfonylamino]-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1C=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=NC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 SOSCRSSNTXGJHI-UHFFFAOYSA-N 0.000 description 1
- FAOFKDXAGOKCRV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-(3-methylsulfanylpropyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(CCCSC)=CC(F)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 FAOFKDXAGOKCRV-UHFFFAOYSA-N 0.000 description 1
- IZLWCPWSLPTDOF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-fluoro-6-(5-hydroxypent-1-ynyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(C#CCCCO)=CC(F)=C2N=CC=1C(=O)NCC1=CC=C(Cl)C=C1 IZLWCPWSLPTDOF-UHFFFAOYSA-N 0.000 description 1
- KUKSUQKELVOKBH-UHFFFAOYSA-N n-[bis[(2-methylpropan-2-yl)oxy]phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(OC(C)(C)C)OC(C)(C)C KUKSUQKELVOKBH-UHFFFAOYSA-N 0.000 description 1
- ANORDWOIBSUYBN-UHFFFAOYSA-N n-chloro-1-phenylmethanamine Chemical compound ClNCC1=CC=CC=C1 ANORDWOIBSUYBN-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N n-hendecanoic acid Natural products CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- IXUZGCXZCUXGAN-UHFFFAOYSA-N n-methyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C(=O)NC)=CNC2=C1 IXUZGCXZCUXGAN-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical class [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000005331 phenylglycines Chemical class 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000005731 phosphitylation reaction Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- PRAHMDIEZMWIRW-UHFFFAOYSA-N propyl dihydrogen phosphite Chemical compound CCCOP(O)O PRAHMDIEZMWIRW-UHFFFAOYSA-N 0.000 description 1
- LMKOGFPNETZZTE-UHFFFAOYSA-N pyrido[2,3-f]quinoxaline Chemical class C1=CN=C2C3=NC=CC=C3C=CC2=N1 LMKOGFPNETZZTE-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical group NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical class C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
- 229960002211 sulfapyridine Drugs 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000002462 tachykinin receptor antagonist Substances 0.000 description 1
- GOYFLHNOYTZKNH-UHFFFAOYSA-N tert-butyl dihydrogen phosphite Chemical class CC(C)(C)OP(O)O GOYFLHNOYTZKNH-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon 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
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- Chemical & Material Sciences (AREA)
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- Plural Heterocyclic Compounds (AREA)
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- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
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PCT/US1998/025192 WO1999032450A1 (en) | 1997-12-22 | 1998-12-01 | 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents |
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SK907-2000A SK9072000A3 (en) | 1997-12-22 | 1998-12-01 | 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents |
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Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6248739B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | Quinolinecarboxamides as antiviral agents |
US6248736B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | 4-oxo-1,4-dihydro-3-quinolinecarboxamides as antiviral agents |
BR0010308A (pt) * | 1999-05-06 | 2002-01-08 | Neurogen Corp | Composto, composição farmacêutica, uso de um composto, e, métodos para o tratamento de uma doença ou distúrbio associados com o agonismo patogênico, agonismo inverso ou antagonismo do receptor de gabaa, para localizar receptores de gabaa em uma amostra de tecido, para inibir a ligação de um composto de benzodiazepina a um receptor de gabaa e para alterar a atividade da transdução de sinal dos receptores de gabaa, e, composição farmacêutica embalada |
BR0109391A (pt) | 2000-03-21 | 2003-06-03 | Upjohn Co | 4-hidroxicinolina-3-carboxiamidas como agentes antivirais |
DE60100999T2 (de) | 2000-03-21 | 2004-09-02 | Pharmacia & Upjohn Co., Kalamazoo | 4-oxo-1,4-dihydro-3-cinnolinecarbonsäure-amide als antivirusmittel |
JP2003529601A (ja) * | 2000-03-21 | 2003-10-07 | 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−1,4−ジヒドロ[1,8]ナフチリジン−3−カルボキサミド |
WO2001070742A1 (en) * | 2000-03-21 | 2001-09-27 | Pharmacia & Upjohn Company | 4-hydroxy-1,8-naphthyridine-3-carboxamides as antiviral agents |
PE20011349A1 (es) * | 2000-06-16 | 2002-01-19 | Upjohn Co | 1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales |
US6525049B2 (en) | 2000-07-05 | 2003-02-25 | Pharmacia & Upjohn Company | Pyrroloquinolones as antiviral agents |
US6559145B2 (en) * | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
US6562822B2 (en) | 2000-07-12 | 2003-05-13 | Pharmacia & Upjohn Company | Heterocyle carboxamides as antiviral agents |
US6730682B2 (en) * | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
ES2274913T3 (es) | 2000-10-12 | 2007-06-01 | MERCK & CO., INC. | Aza y poliaza-naftalenil carboxamidas utiles como inhibidores de vih integrada. |
US6919351B2 (en) | 2000-10-12 | 2005-07-19 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl-carboxamides useful as HIV integrase inhibitors |
AU1152702A (en) | 2000-10-12 | 2002-04-22 | Merck & Co Inc | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
CA2433467A1 (en) | 2001-03-01 | 2002-09-12 | Joseph W. Strohbach | Substituted quinolinecarboxamides as antiviral agents |
AR036256A1 (es) | 2001-08-17 | 2004-08-25 | Merck & Co Inc | Sal sodica de un inhibidor de integrasa del vih, procesos para su preparacion, composiciones farmaceuticas que lo contienen y su uso para la manufactura de un medicamento |
WO2003020728A1 (en) | 2001-08-30 | 2003-03-13 | Pharmacia & Upjohn Company | 4-THIOXO-4,7-DIHYDRO-THIENO[2,3-b]PYRIDINE-5-CARBOTHIOAMIDES AS ANTIVIRAL AGENTS |
US7064139B2 (en) * | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
AU2002350244A1 (en) * | 2001-12-20 | 2003-07-09 | Pharmacia And Upjohn Company | Pyridoquinoxaline antivirals |
AR038117A1 (es) | 2002-01-14 | 2004-12-29 | Upjohn Co | Agentes antivirales derivados de la 4- oxo-4,7 -dihidrofuro [2,3-b]piridin-5-carboxamida |
AR038294A1 (es) | 2002-01-14 | 2005-01-12 | Upjohn Co | Oxotieno(3,2-b)piridincarboxamidas como agentes antivirales |
AR038118A1 (es) | 2002-01-14 | 2004-12-29 | Upjohn Co | Compuestos derivados de la bencinamida del acido 7-oxo-4,7-dihidrotien[2,3-b[piridin-6-carboxilico 3-sustituido que son utiles como antivirales |
US7323460B2 (en) | 2002-03-15 | 2008-01-29 | Merck & Co., Inc. | N-(substituted benzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamides useful as HIV integrase inhibitors |
WO2004014377A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 4-hydroxyquinoline derivatives as matrix metalloproteinase inhibitors |
US7358249B2 (en) | 2002-08-13 | 2008-04-15 | Shionogi & Co., Ltd. | Heterocyclic compounds having inhibitory activity against HIV integrase |
TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
CN100471842C (zh) | 2003-07-24 | 2009-03-25 | 安斯泰来制药有限公司 | 喹诺酮衍生物或其盐 |
GB0322726D0 (en) * | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
GB0322722D0 (en) * | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
GB0324551D0 (en) * | 2003-10-21 | 2003-11-26 | Karobio Ab | Novel compounds |
EA010369B1 (ru) * | 2004-02-04 | 2008-08-29 | Пфайзер Продактс Инк. | Замещенные хинолиновые соединения |
CN100457737C (zh) * | 2005-04-05 | 2009-02-04 | 中国人民解放军军事医学科学院毒物药物研究所 | 喹啉酰胺衍生物、其制备方法和用途 |
DK2465580T3 (en) | 2005-04-28 | 2014-03-10 | Viiv Healthcare Co | POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVES WITH HIV INTEGRASE INHIBITIVE ACTIVITY |
EP1919871A4 (en) * | 2005-08-02 | 2010-08-18 | Glaxosmithkline Llc | PROCESS FOR SYNTHESIS OF CHINOLINE DERIVATIVES |
JP5789611B2 (ja) * | 2009-10-23 | 2015-10-07 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | 嚢胞性線維症膜コンダクタンス制御因子のモジュレーターを調製するためのプロセス |
CN102267984B (zh) * | 2010-06-04 | 2014-07-30 | 中国人民解放军军事医学科学院毒物药物研究所 | 4-羟基喹啉-3-酰胺衍生物及其制备方法和用途 |
WO2013019682A1 (en) * | 2011-07-29 | 2013-02-07 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
BR112014029016A8 (pt) * | 2012-05-23 | 2018-01-09 | European Molecular Biology Laboratory | derivados de ácido 7-oxo-tiazolopiridina carbônico e seu uso no tratamento, melhora ou prevenção de uma doença viral |
KR20150070348A (ko) | 2012-10-16 | 2015-06-24 | 얀센 파마슈티카 엔.브이. | RoRγt의 헤테로아릴 결합 퀴놀리닐 조절제 |
SG11201502935VA (en) | 2012-10-16 | 2015-09-29 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of ror-gamma-t |
BR112015008308A2 (pt) | 2012-10-16 | 2017-12-05 | Janssen Pharmaceutica Nv | moduladores de quinolinila ligados por metileno do ror-gama-t |
WO2014120815A1 (en) * | 2013-01-31 | 2014-08-07 | Vertex Pharmaceuticals Incorporated | Quinoline and quinazoline amides as modulators of sodium channels |
CN103224466A (zh) * | 2013-04-15 | 2013-07-31 | 北京大学 | 具有β-分泌酶抑制功能的化合物及其制备方法与应用 |
US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
JP6423423B2 (ja) | 2013-10-15 | 2018-11-14 | ヤンセン ファーマシューティカ エヌ.ベー. | Rorγtのアルキル結合キノリニルモジュレーター |
US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
KR20160068956A (ko) | 2013-10-15 | 2016-06-15 | 얀센 파마슈티카 엔.브이. | RORyT의 퀴놀리닐 조절제 |
US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
WO2016077240A2 (en) | 2014-11-10 | 2016-05-19 | Forge Life Science, Llc | Anti-hcmv compositions and methods |
CN105330602B (zh) * | 2015-12-07 | 2018-02-09 | 江南大学 | 一种癸氧喹酯类似物及其应用 |
US9932310B2 (en) | 2016-02-08 | 2018-04-03 | City Of Hope | DNA2 inhibitors for cancer treatment |
KR20200099548A (ko) * | 2017-12-15 | 2020-08-24 | 바이엘 애니멀 헬스 게엠베하 | 구충제 4-아미노-퀴놀린-3-카르복스아미드 유도체를 제조하는 방법 |
US11072610B2 (en) | 2018-09-12 | 2021-07-27 | Novartis Ag | Antiviral pyridopyrazinedione compounds |
MX2021005314A (es) | 2018-11-09 | 2021-08-24 | Vivace Therapeutics Inc | Compuestos biciclicos. |
EP3956033A4 (en) | 2019-04-16 | 2023-01-11 | Vivace Therapeutics, Inc. | BICYCLIC LINKS |
TW202126649A (zh) | 2019-09-26 | 2021-07-16 | 瑞士商諾華公司 | 抗病毒吡唑并吡啶酮化合物 |
CN111763706B (zh) * | 2020-07-14 | 2023-08-18 | 武汉科技大学 | 一种应用天然免疫激活剂抗病毒的方法 |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE279887C (xx) * | ||||
DE1908548A1 (de) * | 1968-02-29 | 1970-11-05 | Warner Lambert Co | Chinolinderivate |
US3496184A (en) * | 1969-03-18 | 1970-02-17 | Ciba Geigy Corp | Cyclopropylmethoxy-3-quinoline carboxylic acids and esters |
US3864329A (en) * | 1970-12-29 | 1975-02-04 | Sumitomo Chemical Co | Penicillins substituted with heterocyclic groups |
US3951955A (en) * | 1970-12-29 | 1976-04-20 | Sumitomo Chemical Company, Limited | Penicillins substituted with heterocyclic groups |
CA1034124A (en) * | 1973-05-11 | 1978-07-04 | Ciba-Geigy Ag | Process for the manufacture of new quinolines |
FR2482596A1 (fr) * | 1980-05-19 | 1981-11-20 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur procede de preparation et leur application comme medicament |
FR2509728A1 (fr) * | 1981-07-17 | 1983-01-21 | Roussel Uclaf | Nouveaux derives de la quinoleine, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
DE3615767A1 (de) * | 1986-05-10 | 1987-11-12 | Bayer Ag | Verfahren zur herstellung von 4-hydroxy-chinolin-3-carbonsaeuren |
DE3875820T2 (de) * | 1987-01-20 | 1993-03-18 | Dainippon Pharmaceutical Co | Aromatische heterozyklische karbonsaeureamidabkoemmlinge, verfahren zur herstellung und arzneimittel, die diese enthalten. |
GB8816519D0 (en) * | 1987-07-23 | 1988-08-17 | Ici Plc | Antibiotic compounds |
US4777252A (en) * | 1987-08-13 | 1988-10-11 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
US4786644A (en) * | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
DE3808118A1 (de) * | 1988-03-11 | 1989-09-21 | Bayer Ag | Verfahren zur herstellung von 1-cyclopropyl-chinoloncarbonsaeuren und deren derivaten |
US5491139A (en) * | 1988-10-24 | 1996-02-13 | The Procter & Gamble Company | Antimicrobial quinolonyl lactams |
JPH02152966A (ja) * | 1988-12-05 | 1990-06-12 | Otsuka Pharmaceut Co Ltd | 4−ヒドロキシカルボスチリル誘導体 |
JP2832535B2 (ja) * | 1989-04-04 | 1998-12-09 | 富山化学工業株式会社 | キノロンカルボン酸またはその塩の可溶化法 |
US4959363A (en) * | 1989-06-23 | 1990-09-25 | Sterling Drug Inc. | Quinolonecarboxamide compounds, their preparation and use as antivirals. |
CA2024282A1 (en) * | 1989-09-21 | 1991-03-22 | Peter H. Ermann | Heterocyclic hydrazide derivatives of monocyclic beta-lactam antibiotics |
US5378694A (en) * | 1990-09-07 | 1995-01-03 | Schering Corporation | Acyl and alkoxy substituted quinolines |
US5175151A (en) * | 1990-09-07 | 1992-12-29 | Schering Corporation | Antiviral compounds and antihypertensive compounds |
WO1994006280A1 (en) * | 1992-09-11 | 1994-03-31 | The Regents Of The University Of California | Inhibitors of metazoan parasite proteases |
ZW4194A1 (en) * | 1993-03-29 | 1994-12-21 | Zeneca Ltd | Heterocyclic compounds |
DK122693D0 (da) * | 1993-10-29 | 1993-10-29 | Hempels Skibsfarve Fab J C | Marin struktur |
JP3754467B2 (ja) * | 1994-09-30 | 2006-03-15 | 富山化学工業株式会社 | 新規なナフチリドンまたはキノロン化合物もしくはそれらの塩、それらからなる抗ウイルス剤 |
AU704911B2 (en) * | 1994-11-24 | 1999-05-06 | Basilea Pharmaceutica Ag | Novel benzyl pyrimidines |
GB9507318D0 (en) * | 1995-04-07 | 1995-05-31 | Zeneca Ltd | Alpha substituted pyridazino quinoline compounds |
BR9604823A (pt) * | 1995-04-08 | 1999-01-05 | Basf Ag | Processo para controlar funggs nocivos e pragas fúngicas mistura sinérgica adequada para controlar pragas fúngicas e uso de compostos |
JPH08301849A (ja) * | 1995-05-01 | 1996-11-19 | Takeda Chem Ind Ltd | ヘテロ環化合物およびその製造法 |
EP0841929B1 (en) * | 1995-08-02 | 2003-05-07 | Darwin Discovery Limited | Quinolones and their therapeutic use |
US5886186A (en) * | 1995-10-25 | 1999-03-23 | Versicor, Inc. | Synthesis of substituted N-heteroaromatic compounds and methods of use thereof |
PL330814A1 (en) * | 1996-06-20 | 1999-06-07 | Regents Board Of | Compounds for and methods of delivering pharmaceutical preparations and their application |
DE19638486A1 (de) * | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
DE19642290A1 (de) * | 1996-10-14 | 1998-04-16 | Hoechst Marion Roussel De Gmbh | Verwendung von nicht-peptidischen Bradykinin-Antagonisten zur Herstellung von Arzneimitteln zur Behandlung von Prävention der Alzheimer'schen Krankheit |
-
1998
- 1998-12-01 CA CA002309882A patent/CA2309882A1/en not_active Abandoned
- 1998-12-01 AU AU16063/99A patent/AU755707B2/en not_active Ceased
- 1998-12-01 ES ES98960479T patent/ES2248923T3/es not_active Expired - Lifetime
- 1998-12-01 KR KR1020007006877A patent/KR20010033405A/ko not_active Application Discontinuation
- 1998-12-01 JP JP2000525387A patent/JP2001526265A/ja active Pending
- 1998-12-01 NZ NZ505362A patent/NZ505362A/xx unknown
- 1998-12-01 WO PCT/US1998/025192 patent/WO1999032450A1/en not_active Application Discontinuation
- 1998-12-01 AT AT98960479T patent/ATE303993T1/de not_active IP Right Cessation
- 1998-12-01 RU RU2000119803/04A patent/RU2220960C2/ru not_active IP Right Cessation
- 1998-12-01 DE DE69831506T patent/DE69831506T2/de not_active Expired - Fee Related
- 1998-12-01 EP EP98960479A patent/EP1042295B1/en not_active Expired - Lifetime
- 1998-12-01 HU HU0101999A patent/HUP0101999A3/hu unknown
- 1998-12-01 PL PL98341364A patent/PL341364A1/xx unknown
- 1998-12-01 US US09/203,259 patent/US6093732A/en not_active Expired - Fee Related
- 1998-12-01 BR BR9814323-9A patent/BR9814323A/pt not_active Application Discontinuation
- 1998-12-01 SK SK907-2000A patent/SK9072000A3/sk unknown
- 1998-12-01 CN CN98811915A patent/CN1128790C/zh not_active Expired - Fee Related
- 1998-12-21 ID IDP981657A patent/ID21526A/id unknown
-
2000
- 2000-06-21 NO NO20003233A patent/NO317421B1/no unknown
-
2001
- 2001-06-18 HK HK01104170A patent/HK1033463A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
AU1606399A (en) | 1999-07-12 |
CN1128790C (zh) | 2003-11-26 |
KR20010033405A (ko) | 2001-04-25 |
EP1042295A1 (en) | 2000-10-11 |
HUP0101999A3 (en) | 2003-06-30 |
BR9814323A (pt) | 2004-06-29 |
EP1042295B1 (en) | 2005-09-07 |
US6093732A (en) | 2000-07-25 |
DE69831506T2 (de) | 2006-06-29 |
HK1033463A1 (en) | 2001-08-31 |
ES2248923T3 (es) | 2006-03-16 |
AU755707B2 (en) | 2002-12-19 |
PL341364A1 (en) | 2001-04-09 |
WO1999032450A1 (en) | 1999-07-01 |
CN1281439A (zh) | 2001-01-24 |
NO20003233D0 (no) | 2000-06-21 |
HUP0101999A2 (hu) | 2001-11-28 |
ATE303993T1 (de) | 2005-09-15 |
NO317421B1 (no) | 2004-10-25 |
NO20003233L (no) | 2000-08-22 |
CA2309882A1 (en) | 1999-07-01 |
JP2001526265A (ja) | 2001-12-18 |
ID21526A (id) | 1999-06-24 |
NZ505362A (en) | 2004-12-24 |
DE69831506D1 (en) | 2005-10-13 |
RU2220960C2 (ru) | 2004-01-10 |
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