JP2010523645A5 - - Google Patents
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- Publication number
- JP2010523645A5 JP2010523645A5 JP2010502625A JP2010502625A JP2010523645A5 JP 2010523645 A5 JP2010523645 A5 JP 2010523645A5 JP 2010502625 A JP2010502625 A JP 2010502625A JP 2010502625 A JP2010502625 A JP 2010502625A JP 2010523645 A5 JP2010523645 A5 JP 2010523645A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- oxo
- oxazolidine
- benzo
- naphthyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 95
- 239000001257 hydrogen Substances 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 25
- -1 or U Inorganic materials 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- DIPAJRPMUWRRON-GOEBONIOSA-N (2s)-2-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methylamino]-n-(6-methoxy-1,5-naphthyridin-4-yl)propanamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN[C@@H](C)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 DIPAJRPMUWRRON-GOEBONIOSA-N 0.000 claims 1
- PMXMPKWIYBBOTF-CRAIPNDOSA-N (3r)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-hydroxy-3-(6-methoxy-1,5-naphthyridin-4-yl)propanamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)C[C@@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 PMXMPKWIYBBOTF-CRAIPNDOSA-N 0.000 claims 1
- PMXMPKWIYBBOTF-QAPCUYQASA-N (3s)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-hydroxy-3-(6-methoxy-1,5-naphthyridin-4-yl)propanamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 PMXMPKWIYBBOTF-QAPCUYQASA-N 0.000 claims 1
- DSVMKDHDRHMTKZ-MRXNPFEDSA-N (5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[[3-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNCCCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 DSVMKDHDRHMTKZ-MRXNPFEDSA-N 0.000 claims 1
- MKHCXQBPPZAGJW-GOSISDBHSA-N (5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[[3-(6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 MKHCXQBPPZAGJW-GOSISDBHSA-N 0.000 claims 1
- YIWPNZUUIRGGSC-RBUKOAKNSA-N (5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[[[(2s)-2,3-dihydroxypropyl]-[3-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]methyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(C[C@H](O)CO)CCCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 YIWPNZUUIRGGSC-RBUKOAKNSA-N 0.000 claims 1
- DBCZLHYJNOSPLS-OAQYLSRUSA-N (5r)-3-(3-bromo-4-methylphenyl)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](OC1=O)CN(C)CCCC2=CC=CC3=NC=C(C=C32)OC)N1C1=CC=C(C)C(Br)=C1 DBCZLHYJNOSPLS-OAQYLSRUSA-N 0.000 claims 1
- UOLCWZLXFFPAHE-OAQYLSRUSA-N (5r)-3-(3-fluoro-4-methylphenyl)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](OC1=O)CN(C)CCCC2=CC=CC3=NC=C(C=C32)OC)N1C1=CC=C(C)C(F)=C1 UOLCWZLXFFPAHE-OAQYLSRUSA-N 0.000 claims 1
- VPNOXVABNOZEMV-LJQANCHMSA-N (5r)-3-(4-bromo-3-fluorophenyl)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](OC1=O)CN(C)CCCC2=CC=CC3=NC=C(C=C32)OC)N1C1=CC=C(Br)C(F)=C1 VPNOXVABNOZEMV-LJQANCHMSA-N 0.000 claims 1
- ROCZFIFXFWINBP-OAQYLSRUSA-N (5r)-3-(4-bromo-3-methylphenyl)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](OC1=O)CN(C)CCCC2=CC=CC3=NC=C(C=C32)OC)N1C1=CC=C(Br)C(C)=C1 ROCZFIFXFWINBP-OAQYLSRUSA-N 0.000 claims 1
- CYMAJBWGQOQMSV-HSZRJFAPSA-N (5r)-3-(4-ethylphenyl)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(CC)=CC=C1N1C(=O)O[C@H](CN(C)CCCC=2C3=CC(OC)=CN=C3C=CC=2)C1 CYMAJBWGQOQMSV-HSZRJFAPSA-N 0.000 claims 1
- HLXJOWIFRMBADB-GOSISDBHSA-N (5r)-5-[5-(6-methoxy-1,5-naphthyridin-4-yl)pentyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 HLXJOWIFRMBADB-GOSISDBHSA-N 0.000 claims 1
- XBKICPPTQVVHTD-OAHLLOKOSA-N (5r)-5-[[2-[(6-methoxy-1,5-naphthyridin-4-yl)amino]ethylamino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCNC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 XBKICPPTQVVHTD-OAHLLOKOSA-N 0.000 claims 1
- OZNWFJDGFLNGSA-OAHLLOKOSA-N (5r)-5-[[3-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 OZNWFJDGFLNGSA-OAHLLOKOSA-N 0.000 claims 1
- MOSJORKSDXLMHA-HXUWFJFHSA-N (5r)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CN(C)CCCC3=CC=CC4=NC=C(C=C43)OC)=CC=C21 MOSJORKSDXLMHA-HXUWFJFHSA-N 0.000 claims 1
- IZEIJQYVRBHTEW-XMMPIXPASA-N (5r)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-3-(4-propylphenyl)-1,3-oxazolidin-2-one Chemical compound C1=CC(CCC)=CC=C1N1C(=O)O[C@H](CN(C)CCCC=2C3=CC(OC)=CN=C3C=CC=2)C1 IZEIJQYVRBHTEW-XMMPIXPASA-N 0.000 claims 1
- NJHGAOKHFGKGER-OAQYLSRUSA-N (5r)-5-[[3-(3-methoxyquinolin-5-yl)propyl-methylamino]methyl]-3-[4-methyl-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](OC1=O)CN(C)CCCC2=CC=CC3=NC=C(C=C32)OC)N1C1=CC=C(C)C(C(F)(F)F)=C1 NJHGAOKHFGKGER-OAQYLSRUSA-N 0.000 claims 1
- KVUONFHGBLYIIL-LJQANCHMSA-N (5r)-5-[[3-(3-methoxyquinolin-5-yl)propylamino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCCC3=CC=CC4=NC=C(C=C43)OC)=CC=C21 KVUONFHGBLYIIL-LJQANCHMSA-N 0.000 claims 1
- DWCIZFIRCOXOND-QGZVFWFLSA-N (5r)-5-[[3-(6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 DWCIZFIRCOXOND-QGZVFWFLSA-N 0.000 claims 1
- UHAKDDHBAQMRQX-GOSISDBHSA-N (5r)-5-[[4-(6-methoxy-1,5-naphthyridin-4-yl)butylamino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 UHAKDDHBAQMRQX-GOSISDBHSA-N 0.000 claims 1
- AOGCTJMNMQWMIZ-ZWKOTPCHSA-N (5r)-5-[[[(2s)-2,3-dihydroxypropyl]-[3-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]methyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CN(C[C@H](O)CO)CCCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 AOGCTJMNMQWMIZ-ZWKOTPCHSA-N 0.000 claims 1
- NKDPFNXDVKNXRU-KPDCDPCYSA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[(1r,2s)-1,2-dihydroxy-3-[(6-methoxy-1,5-naphthyridin-4-yl)methylamino]propyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)[C@H](O)[C@@H](O)CNCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 NKDPFNXDVKNXRU-KPDCDPCYSA-N 0.000 claims 1
- BKZZCXMFWQSBQV-NKKJXINNSA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[(1r,2s)-3-[(3-fluoro-6-methoxyquinolin-4-yl)methylamino]-1,2-dihydroxypropyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)[C@H](O)[C@@H](O)CNCC3=C(F)C=NC4=CC=C(C=C43)OC)=CC=C21 BKZZCXMFWQSBQV-NKKJXINNSA-N 0.000 claims 1
- NKDPFNXDVKNXRU-MONBJTKQSA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[(1s,2r)-1,2-dihydroxy-3-[(6-methoxy-1,5-naphthyridin-4-yl)methylamino]propyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)[C@@H](O)[C@H](O)CNCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 NKDPFNXDVKNXRU-MONBJTKQSA-N 0.000 claims 1
- IMIZBKZISUBYCI-SFHVURJKSA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[3-(6-methoxy-1,5-naphthyridin-4-yl)propoxymethyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)COCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 IMIZBKZISUBYCI-SFHVURJKSA-N 0.000 claims 1
- OZIAYCSFXWCECS-IBGZPJMESA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-[2-[(6-methoxy-1,5-naphthyridin-4-yl)amino]ethyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)C(=O)NCCNC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 OZIAYCSFXWCECS-IBGZPJMESA-N 0.000 claims 1
- DNWWVKJGFLZKHO-FQEVSTJZSA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-[3-(6-methoxy-1,5-naphthyridin-4-yl)prop-2-ynyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)C(=O)NCC#CC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 DNWWVKJGFLZKHO-FQEVSTJZSA-N 0.000 claims 1
- SGALWDNEYDSBHD-FQEVSTJZSA-N (5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)C(=O)NCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 SGALWDNEYDSBHD-FQEVSTJZSA-N 0.000 claims 1
- JZTHYMFALZPLMN-IUKKYPGJSA-N (5s)-5-[(1r,2s)-1,2-dihydroxy-3-[(6-methoxy-1,5-naphthyridin-4-yl)methylamino]propyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)[C@H](O)[C@@H](O)CNCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 JZTHYMFALZPLMN-IUKKYPGJSA-N 0.000 claims 1
- SVPAOYYLEUPBKT-IUKKYPGJSA-N (5s)-5-[(1r,2s)-3-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methylamino]-1,2-dihydroxypropyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)[C@H](O)[C@@H](O)CNCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 SVPAOYYLEUPBKT-IUKKYPGJSA-N 0.000 claims 1
- FFGCCIJTINVZDD-AWRGLXIESA-N (5s)-5-[(1r,2s)-3-[(3-fluoro-6-methoxyquinolin-4-yl)methylamino]-1,2-dihydroxypropyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)[C@H](O)[C@@H](O)CNCC3=C(F)C=NC4=CC=C(C=C43)OC)=CC=C21 FFGCCIJTINVZDD-AWRGLXIESA-N 0.000 claims 1
- ANVURTUJYQWNLI-OALUTQOASA-N (5s)-5-[(1s)-1-hydroxy-2-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethylamino]ethyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)[C@@H](O)CNCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 ANVURTUJYQWNLI-OALUTQOASA-N 0.000 claims 1
- SVPAOYYLEUPBKT-STSQHVNTSA-N (5s)-5-[(1s,2r)-3-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methylamino]-1,2-dihydroxypropyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)[C@@H](O)[C@H](O)CNCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 SVPAOYYLEUPBKT-STSQHVNTSA-N 0.000 claims 1
- RVCSMIYBYTYYDQ-MVHVFESUSA-N (e)-3-(2-cyanoquinolin-8-yl)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound C1=C(C#N)N=C2C(/C=C/C(NC[C@H]3OC(=O)N(C3)C=3C=C4OCCOC4=CC=3)=O)=CC=CC2=C1 RVCSMIYBYTYYDQ-MVHVFESUSA-N 0.000 claims 1
- CXJJZCHOMNTJRP-KRZKXXONSA-N (e)-3-(3-methoxyquinolin-5-yl)-n-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNC(=O)/C=C/C3=CC=CC4=NC=C(C=C43)OC)=CC=C21 CXJJZCHOMNTJRP-KRZKXXONSA-N 0.000 claims 1
- BYULRLFIFZWGBV-BAXHPOPBSA-N (e)-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNC(=O)/C=C/C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 BYULRLFIFZWGBV-BAXHPOPBSA-N 0.000 claims 1
- MLSGMYPITSFRKS-DLGAGEGBSA-N (e)-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-methyl-n-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CN(C)C(=O)/C=C/C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 MLSGMYPITSFRKS-DLGAGEGBSA-N 0.000 claims 1
- LGEHWUAYFPFYQB-CDDKBXLESA-N (e)-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-methyl-n-[[(5r)-2-oxo-3-(4-propylphenyl)-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound C1=CC(CCC)=CC=C1N1C(=O)O[C@H](CN(C)C(=O)\C=C\C=2C3=NC(OC)=CC=C3N=CC=2)C1 LGEHWUAYFPFYQB-CDDKBXLESA-N 0.000 claims 1
- OKBHOHVJSBCWHI-QKYXPGDISA-N (e)-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-methyl-n-[[(5r)-3-[4-methyl-3-(trifluoromethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound C([C@H](OC1=O)CN(C)C(=O)/C=C/C2=CC=NC3=CC=C(N=C32)OC)N1C1=CC=C(C)C(C(F)(F)F)=C1 OKBHOHVJSBCWHI-QKYXPGDISA-N 0.000 claims 1
- NNDAGNBYJZGGDS-MTCRFPMVSA-N (e)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(3-methoxyquinolin-5-yl)prop-2-enamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)/C=C/C3=CC=CC4=NC=C(C=C43)OC)=CC=C21 NNDAGNBYJZGGDS-MTCRFPMVSA-N 0.000 claims 1
- YONGWWCMWVFDDN-ZGRWHYIRSA-N (e)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(3-methoxyquinoxalin-5-yl)prop-2-enamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)/C=C/C3=CC=CC4=NC=C(N=C43)OC)=CC=C21 YONGWWCMWVFDDN-ZGRWHYIRSA-N 0.000 claims 1
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- HDIRGKXJINOOBM-QKYXPGDISA-N (e)-n-[[(5r)-3-(3-fluoro-4-methylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-methylprop-2-enamide Chemical compound C([C@H](OC1=O)CN(C)C(=O)/C=C/C2=CC=NC3=CC=C(N=C32)OC)N1C1=CC=C(C)C(F)=C1 HDIRGKXJINOOBM-QKYXPGDISA-N 0.000 claims 1
- XBUZGZHIAQMJGW-BBOMDTFKSA-N (e)-n-[[(5r)-3-(3-fluoro-4-methylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-methoxy-1,5-naphthyridin-4-yl)prop-2-enamide Chemical compound C([C@H](OC1=O)CNC(=O)/C=C/C2=CC=NC3=CC=C(N=C32)OC)N1C1=CC=C(C)C(F)=C1 XBUZGZHIAQMJGW-BBOMDTFKSA-N 0.000 claims 1
- LGZPWAWNKWVXIZ-ILNGBFOMSA-N (e)-n-[[(5r)-3-(4-bromo-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-methylprop-2-enamide Chemical compound C([C@H](OC1=O)CN(C)C(=O)/C=C/C2=CC=NC3=CC=C(N=C32)OC)N1C1=CC=C(Br)C(F)=C1 LGZPWAWNKWVXIZ-ILNGBFOMSA-N 0.000 claims 1
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| RU2492169C2 (ru) | 2007-12-18 | 2013-09-10 | Актелион Фармасьютиклз Лтд | Производные 5-аминоциклилметилоксазолидин-2-она |
| US8349828B2 (en) | 2008-02-20 | 2013-01-08 | Actelion Pharmaceuticals Ltd. | Azatricyclic antibiotic compounds |
| EP2254887B9 (en) | 2008-02-22 | 2013-05-29 | Actelion Pharmaceuticals Ltd. | Oxazolidinone derivatives |
| MX2011000968A (es) * | 2008-08-04 | 2011-03-02 | Actelion Pharmaceuticals Ltd | Derivados de alquilaminometiloxazolidinona triciclicos. |
| AR073774A1 (es) | 2008-10-07 | 2010-12-01 | Actelion Pharmaceuticals Ltd | Compuestos antibioticos oxazolidinona triciclicos |
| EP2346862B1 (en) * | 2008-10-10 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | 2-benzothiophenyl-and 2-naphthyl-0xaz0lidin0nes and their azaisostere analogues as antibacterial agents |
| NZ593891A (en) | 2008-12-12 | 2013-05-31 | Actelion Pharmaceuticals Ltd | 5-amino-2-(1-hydroxy-ethyl)-tetrahydropyran derivatives |
| EP2509997B1 (en) * | 2009-12-07 | 2017-08-30 | i2 Pharmaceuticals, Inc. | Conjugates comprising an antibody surrogate scaffold with improved pharmacokinetic properties |
| EP2377850A1 (en) | 2010-03-30 | 2011-10-19 | Pharmeste S.r.l. | TRPV1 vanilloid receptor antagonists with a bicyclic portion |
| TW201309689A (zh) | 2011-02-07 | 2013-03-01 | Daiichi Sankyo Co Ltd | 含胺基之吡咯啶酮衍生物 |
| EP2742042A1 (en) | 2011-08-11 | 2014-06-18 | Actelion Pharmaceuticals Ltd. | Quinazoline-2,4-dione derivatives |
| MX344529B (es) * | 2011-11-08 | 2016-12-19 | Actelion Pharmaceuticals Ltd | Derivados antibioticos de 2 - oxo -oxazolidin - 3, 5 -diilo. |
| EP2785721A1 (en) | 2011-11-30 | 2014-10-08 | Actelion Pharmaceuticals Ltd. | 3,7-disubstituted octahydro-2h-pyrido[4,3-e][1,3]oxazin-2-one antibiotics |
| WO2014024056A1 (en) | 2012-08-06 | 2014-02-13 | Daiichi Sankyo Company, Limited | Pyrrolidine derivatives with antibacterial properties |
| MX349214B (es) * | 2012-08-17 | 2017-07-18 | Basf Se | Proceso para la fabricacion de benzoxazinonas. |
| HK1221459A1 (zh) * | 2013-04-16 | 2017-06-02 | Idorsia Pharmaceuticals Ltd | 抗菌双芳香族衍生物 |
| AR102256A1 (es) * | 2014-10-15 | 2017-02-15 | Actelion Pharmaceuticals Ltd | Derivados biaromáticos básicos antibacterianos con sustitución de aminoalcoxi |
| EP3414246A1 (en) * | 2016-02-08 | 2018-12-19 | Redx Pharma PLC | Antibacterial compounds |
| GB201602235D0 (en) * | 2016-02-08 | 2016-03-23 | Redx Pharma Plc | Antibacterial compounds |
| US10487093B2 (en) | 2016-02-08 | 2019-11-26 | Redx Pharma Plc | Heterocyclic compounds, in particular 2-oxo-4,4,5,5,6,6,7,7-octahydrobenzoxazole derivatives, and their use as antibacterial compounds |
| GB2550437B (en) | 2016-05-20 | 2021-06-23 | Bugworks Res Inc | Heterocyclic compounds useful as anti-bacterial agents and method for production |
| TW201833120A (zh) | 2017-02-17 | 2018-09-16 | 瑞士商愛杜西亞製藥有限公司 | 芳基噁唑啶酮抗生素化合物 |
| DK3634968T3 (da) * | 2017-06-08 | 2023-05-01 | Bugworks Res Inc | Heterocykliske forbindelser, der kan anvendes som antibakterielle midler, og fremgangsmåde til fremstilling heraf |
| JP7390728B2 (ja) * | 2017-11-29 | 2023-12-04 | バグワークス・リサーチ・インコーポレイテッド | 抗菌複素環式化合物及びそれらの合成 |
| HUE061835T2 (hu) | 2018-03-28 | 2023-08-28 | Bugworks Res Inc | Oxazolidinon antibiotikus vegyületek és eljárás azok elõállítására |
| CN117532894B (zh) * | 2023-12-05 | 2024-06-14 | 东莞美泰电子有限公司 | 一种用于保护零件的pu皮革热压贴皮工艺 |
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| CA2218705A1 (en) | 1995-04-21 | 1996-10-24 | Shinnippon Pharmaceutical Inc. | Fused imidazo¬1,2-a|pyridines |
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| JP4633925B2 (ja) | 1998-05-08 | 2011-02-16 | スミスクライン ビーチャム ピー エル シー | フェニル尿素およびフェニルチオ尿素誘導体 |
| ATE269303T1 (de) | 1999-01-07 | 2004-07-15 | Wyeth Corp | Arylpiperazinyl-cyclohexyl indolderivate zur behandlung von depressionen |
| GB9914486D0 (en) | 1999-06-21 | 1999-08-18 | Smithkline Beecham Plc | Medicaments |
| EE04592B1 (et) | 1999-06-28 | 2006-02-15 | Janssen Pharmaceutica N.V. | Respiratoorse süntsütiaalviiruse replikatsiooni inhibiitorid, nende valmistamismeetod, kasutamine ja vaheühendid, farmatseutiline kompositsioon ja selle valmistamismeetod ning produkt |
| EP1305308B1 (en) | 2000-07-26 | 2006-12-20 | Smithkline Beecham Plc | Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity |
| GB0031086D0 (en) | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0112834D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| AU2003224345A1 (en) * | 2002-04-30 | 2003-11-17 | Orchid Chemicals & Pharmaceuticals | Antibacterial agents |
| TW200406413A (en) | 2002-06-26 | 2004-05-01 | Glaxo Group Ltd | Compounds |
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| CN101817815A (zh) * | 2002-10-10 | 2010-09-01 | 莫弗凯姆联合化学股份公司 | 具有杀菌活性的化合物 |
| DE60324179D1 (de) * | 2002-12-04 | 2008-11-27 | Glaxo Group Ltd | Chinoline und stickstoffhaltige derivatedavon und deren verwendung als antibakterielle mittel |
| AR042486A1 (es) | 2002-12-18 | 2005-06-22 | Glaxo Group Ltd | Compuesto de quinolina y naftiridina halosustituido en la posicion 3, procedimiento para preparar el compuesto, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion . |
| DE10316081A1 (de) | 2003-04-08 | 2004-10-21 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
| EP1484304A1 (en) | 2003-05-28 | 2004-12-08 | Dainippon Ink And Chemicals, Inc. | Process for the preparation of fluorophenylalkylene acid derivatives |
| JP2008502689A (ja) | 2004-06-15 | 2008-01-31 | グラクソ グループ リミテッド | 抗菌剤 |
| FR2872164B1 (fr) * | 2004-06-29 | 2006-11-17 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leur procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2006024741A2 (fr) * | 2004-07-30 | 2006-03-09 | Palumed S.A. | Molecules hybrides qa ou q est une aminoquinoleine et a est un residu antibiotique, leur synthese et leurs utilisations en tant qu'agent antibacterien |
| DE102004041163A1 (de) | 2004-08-25 | 2006-03-02 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
| WO2006032466A2 (en) | 2004-09-24 | 2006-03-30 | Actelion Pharmaceuticals Ltd | New bicyclic antibiotics |
| JP5314244B2 (ja) | 2004-10-27 | 2013-10-16 | 富山化学工業株式会社 | 新規な含窒素複素環化合物およびその塩 |
| GB0426373D0 (en) | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
| EP1854787B1 (en) | 2005-03-03 | 2010-09-01 | Santen Pharmaceutical Co., Ltd. | Novel cyclic compound having quinolylalkylthio group |
| NZ562034A (en) | 2005-03-31 | 2009-10-30 | Janssen Pharmaceutica Nv | Bicyclic pyrazole compounds as antibacterial agents |
| WO2007016610A2 (en) | 2005-08-02 | 2007-02-08 | Glaxo Group Limited | Antibacterial agents |
| JP5107723B2 (ja) | 2005-12-12 | 2012-12-26 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | 新規１６員環４”−ｏ−カルバモイルアザライド誘導体及びその製造方法 |
| CN101374831B (zh) | 2006-01-26 | 2011-04-27 | 埃科特莱茵药品有限公司 | 四氢吡喃抗生素 |
-
2008
- 2008-04-09 CL CL200801003A patent/CL2008001003A1/es unknown
- 2008-04-10 ES ES08737784.2T patent/ES2560870T3/es active Active
- 2008-04-10 TW TW097113095A patent/TWI415614B/zh not_active IP Right Cessation
- 2008-04-10 RU RU2009141310/04A patent/RU2506263C2/ru not_active IP Right Cessation
- 2008-04-10 WO PCT/IB2008/051356 patent/WO2008126024A2/en not_active Ceased
- 2008-04-10 AU AU2008238894A patent/AU2008238894B2/en not_active Ceased
- 2008-04-10 MX MX2009010641A patent/MX2009010641A/es active IP Right Grant
- 2008-04-10 CA CA2679069A patent/CA2679069C/en not_active Expired - Fee Related
- 2008-04-10 BR BRPI0809667-8A2A patent/BRPI0809667A2/pt not_active IP Right Cessation
- 2008-04-10 EP EP08737784.2A patent/EP2146987B1/en not_active Not-in-force
- 2008-04-10 AR ARP080101485A patent/AR066012A1/es unknown
- 2008-04-10 KR KR1020097023303A patent/KR101563752B1/ko not_active Expired - Fee Related
- 2008-04-10 CN CN200880011810.XA patent/CN101657450B/zh not_active Expired - Fee Related
- 2008-04-10 JP JP2010502625A patent/JP5363457B2/ja not_active Expired - Fee Related
- 2008-04-10 US US12/595,711 patent/US8114867B2/en not_active Expired - Fee Related
- 2008-04-10 PL PL08737784T patent/PL2146987T3/pl unknown
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