JP5363457B2 - オキサゾリジノン抗生物質誘導体 - Google Patents

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Publication number

JP5363457B2

JP5363457B2 JP2010502625A JP2010502625A JP5363457B2 JP 5363457 B2 JP5363457 B2 JP 5363457B2 JP 2010502625 A JP2010502625 A JP 2010502625A JP 2010502625 A JP2010502625 A JP 2010502625A JP 5363457 B2 JP5363457 B2 JP 5363457B2

Authority

JP

Japan

Prior art keywords

methoxy

oxo

oxazolidine

benzo

naphthyridin

Prior art date

2007-04-11

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.)

Expired - Fee Related

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• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 21
• 230000003115 biocidal effect Effects 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 587
• -1 two of U Inorganic materials 0.000 claims abstract description 245
• 150000003839 salts Chemical class 0.000 claims abstract description 167
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 158
• 239000001257 hydrogen Substances 0.000 claims abstract description 157
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 72
• 150000002367 halogens Chemical group 0.000 claims abstract description 72
• 229910052720 vanadium Inorganic materials 0.000 claims abstract description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 52
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 45
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 34
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 124
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 104
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 64
• 229910052770 Uranium Inorganic materials 0.000 claims description 37
• 229910052721 tungsten Inorganic materials 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 229910052796 boron Inorganic materials 0.000 claims description 26
• 125000002252 acyl group Chemical group 0.000 claims description 22
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
• 229940080818 propionamide Drugs 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• 229910052727 yttrium Inorganic materials 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
• 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 description 6
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
• 208000035143 Bacterial infection Diseases 0.000 claims description 6
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
• 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 description 5
• 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 description 5
• XTWUKYVBIQGZOO-HXUWFJFHSA-N (5r)-5-[[2-aminoethyl-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]methyl]-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(CCN)CCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 XTWUKYVBIQGZOO-HXUWFJFHSA-N 0.000 claims description 5
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 5
• MGVYVVXBAYKKTK-IUYQLWOBSA-N (e)-2-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-methoxy-1,5-naphthyridin-4-yl)prop-2-enamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)C\C(=C/C3=CC=NC4=CC=C(N=C43)OC)C(N)=O)=CC=C21 MGVYVVXBAYKKTK-IUYQLWOBSA-N 0.000 claims description 5
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 5
• KRFFCEDENCPOKM-XOFWJLNASA-N (e)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-fluoroquinolin-4-yl)prop-2-enamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)/C=C/C3=CC=NC4=CC=C(C=C43)F)=CC=C21 KRFFCEDENCPOKM-XOFWJLNASA-N 0.000 claims description 5
• ZVLIWGKIXNXARG-ROSSNEFBSA-N (e)-n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-n-ethyl-3-(6-methoxy-1,5-naphthyridin-4-yl)prop-2-enamide Chemical compound C1=C(OC)N=C2C(/C=C/C(=O)N(C[C@H]3OC(=O)N(C3)C=3C=C4OCCOC4=CC=3)CC)=CC=NC2=C1 ZVLIWGKIXNXARG-ROSSNEFBSA-N 0.000 claims description 5
• 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 description 5
• 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 description 5
• PXJNTWREQMXNKP-ACGJQVIASA-N (e)-n-[[(5r)-3-(4-ethylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-methoxy-1,5-naphthyridin-4-yl)-n-methylprop-2-enamide Chemical compound C1=CC(CC)=CC=C1N1C(=O)O[C@H](CN(C)C(=O)\C=C\C=2C3=NC(OC)=CC=C3N=CC=2)C1 PXJNTWREQMXNKP-ACGJQVIASA-N 0.000 claims description 5
• MJOVFSNDLWWYLF-LJQANCHMSA-N 2-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-n-[2-(6-methoxyquinolin-4-yl)ethyl]acetamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CC(=O)NCCC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 MJOVFSNDLWWYLF-LJQANCHMSA-N 0.000 claims description 5
• LJZZPLQFFIZTQI-OAHLLOKOSA-N 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)acetamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNCC(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 LJZZPLQFFIZTQI-OAHLLOKOSA-N 0.000 claims description 5
• DHKWWHPQKXUMFA-GOSISDBHSA-N 3-(3-methoxyquinolin-5-yl)-n-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNC(=O)CCC3=CC=CC4=NC=C(C=C43)OC)=CC=C21 DHKWWHPQKXUMFA-GOSISDBHSA-N 0.000 claims description 5
• SETBUNMXWRAZJU-CQSZACIVSA-N n-(6-methoxy-1,5-naphthyridin-4-yl)-2-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methylamino]acetamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCC(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 SETBUNMXWRAZJU-CQSZACIVSA-N 0.000 claims description 5
• KLHYZPFGWWOAQP-BEFAXECRSA-N n-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]-n-methyl-2-[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]acetamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CC(=O)N(C)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 KLHYZPFGWWOAQP-BEFAXECRSA-N 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• GWTDVJQSOFKOCO-CDVVCGDMSA-N (e)-3-(3-methoxyquinoxalin-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(N=C43)OC)=CC=C21 GWTDVJQSOFKOCO-CDVVCGDMSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• PVDLURUKQFAXPY-JQFNYASXSA-N (z)-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)prop-2-enamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)/C=C(O)/C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 PVDLURUKQFAXPY-JQFNYASXSA-N 0.000 claims description 4
• PSEUSGJOYHPQRH-OAHLLOKOSA-N 6-[(5r)-5-[3-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methylamino]propyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCNCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 PSEUSGJOYHPQRH-OAHLLOKOSA-N 0.000 claims description 4
• BCBZGCPUTBXNMO-QGZVFWFLSA-N 6-[(5r)-5-[[3-(6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 BCBZGCPUTBXNMO-QGZVFWFLSA-N 0.000 claims description 4
• NEMXTGMHUAJMPG-HSZRJFAPSA-N ethyl 4-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]butanoate Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(CCCC=3C4=NC(OC)=CC=C4N=CC=3)CCCC(=O)OCC)=CC=C21 NEMXTGMHUAJMPG-HSZRJFAPSA-N 0.000 claims description 4
• SZLXTADWZXRIHC-MRXNPFEDSA-N n-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]-2-[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]acetamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CC(=O)NCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 SZLXTADWZXRIHC-MRXNPFEDSA-N 0.000 claims description 4
• BTCHHOYRNHCKAO-QGZVFWFLSA-N n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(6-methoxy-1,5-naphthyridin-4-yl)propanamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNC(=O)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 BTCHHOYRNHCKAO-QGZVFWFLSA-N 0.000 claims description 4
• PMXMPKWIYBBOTF-NNJIEVJOSA-N 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)CC(O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 PMXMPKWIYBBOTF-NNJIEVJOSA-N 0.000 claims description 4
• BQESENDXBATYJT-HXUWFJFHSA-N n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-n-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]acetamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(CCCC3=CC=NC4=CC=C(N=C43)OC)C(C)=O)=CC=C21 BQESENDXBATYJT-HXUWFJFHSA-N 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
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• SYKBFSOGRVYFJF-LJQANCHMSA-N (5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[[4-(6-methoxy-1,5-naphthyridin-4-yl)butylamino]methyl]-1,3-oxazolidin-2-one Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CNCCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 SYKBFSOGRVYFJF-LJQANCHMSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• YFSFRWYNKKXQNX-QKYXPGDISA-N (e)-n-[[(5r)-3-(3-bromo-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(Br)=C1 YFSFRWYNKKXQNX-QKYXPGDISA-N 0.000 claims description 3
• 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 description 3
• KVPMVABPONGYPD-CHHNCHTKSA-N (e)-n-[[(5r)-3-(4-bromo-3-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(Br)C(C)=C1 KVPMVABPONGYPD-CHHNCHTKSA-N 0.000 claims description 3
• YREJNZWICOEDQQ-CQSZACIVSA-N 2-[(6-methoxy-1,5-naphthyridin-4-yl)oxy]-n-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNC(=O)COC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 YREJNZWICOEDQQ-CQSZACIVSA-N 0.000 claims description 3
• BAXABXIZQPAJEF-UHFFFAOYSA-N 2-methoxyquinoxaline Chemical compound C1=CC=CC2=NC(OC)=CN=C21 BAXABXIZQPAJEF-UHFFFAOYSA-N 0.000 claims description 3
• KBONJIXEEPYPEJ-HXUWFJFHSA-N 3-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]propanoic acid Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(CCC(O)=O)CCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 KBONJIXEEPYPEJ-HXUWFJFHSA-N 0.000 claims description 3
• HFRUZJVUVPIYRG-LJQANCHMSA-N 4-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]amino]-4-oxobutanoic acid Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CN(CCCC3=CC=NC4=CC=C(N=C43)OC)C(=O)CCC(O)=O)=CC=C21 HFRUZJVUVPIYRG-LJQANCHMSA-N 0.000 claims description 3
• DURLQIXKWILACH-QGZVFWFLSA-N 6-[(5r)-5-[3-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methyl-(2-hydroxyethyl)amino]propyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCN(CCO)CC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 DURLQIXKWILACH-QGZVFWFLSA-N 0.000 claims description 3
• DWUNTRDOLJYHMJ-GOSISDBHSA-N 6-[(5r)-5-[3-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methyl-(3-hydroxypropyl)amino]propyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCN(CCCO)CC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 DWUNTRDOLJYHMJ-GOSISDBHSA-N 0.000 claims description 3
• UEPPRFICKSLIBZ-GOSISDBHSA-N 6-[(5r)-5-[3-[3-aminopropyl-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methyl]amino]propyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCN(CCCN)CC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 UEPPRFICKSLIBZ-GOSISDBHSA-N 0.000 claims description 3
• QYSXECGRJJQKKS-QZTJIDSGSA-N 6-[(5r)-5-[3-[[(2r)-2,3-dihydroxypropyl]-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methyl]amino]propyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCN(CC3=C(F)C=NC4=CC=C(N=C43)OC)C[C@@H](O)CO)=CC=C21 QYSXECGRJJQKKS-QZTJIDSGSA-N 0.000 claims description 3
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• DJIGCDKKJZESAV-OAHLLOKOSA-N 6-[(5r)-5-[[2-[(6-methoxy-1,5-naphthyridin-4-yl)amino]ethylamino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCNC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 DJIGCDKKJZESAV-OAHLLOKOSA-N 0.000 claims description 3
• PTYDABZTWXFOTF-OAHLLOKOSA-N 6-[(5r)-5-[[3-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CNCCCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 PTYDABZTWXFOTF-OAHLLOKOSA-N 0.000 claims description 3
• DZUOBFUXVYZSNR-OAHLLOKOSA-N 6-[(5r)-5-[[3-(6-methoxy-1,5-naphthyridin-4-yl)propylamino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(N3C[C@H](OC3=O)CNCCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 DZUOBFUXVYZSNR-OAHLLOKOSA-N 0.000 claims description 3
• IVTZVMWPPUDXJU-QZTJIDSGSA-N 6-[(5r)-5-[[[(2r)-2,3-dihydroxypropyl]-[3-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=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 IVTZVMWPPUDXJU-QZTJIDSGSA-N 0.000 claims description 3
• PBGLLILIVPGVKN-WOJBJXKFSA-N 6-[(5r)-5-[[[(2r)-2,3-dihydroxypropyl]-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N3C[C@H](OC3=O)CN(C[C@@H](O)CO)CCCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 PBGLLILIVPGVKN-WOJBJXKFSA-N 0.000 claims description 3
• YDQOQSNRURZSJF-FHJLPGHOSA-N 6-[(5s)-5-[(1s,2r)-3-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)methylamino]-1,2-dihydroxypropyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=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 YDQOQSNRURZSJF-FHJLPGHOSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• AWBBGPLBHLJCOE-LJQANCHMSA-N n-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]-n-[[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CN(CCCC=3C4=NC(OC)=CC=C4N=CC=3)C(=O)CC)=CC=C21 AWBBGPLBHLJCOE-LJQANCHMSA-N 0.000 claims description 3
• XBNDNNFQZYAFFM-HXUWFJFHSA-N n-[[(5r)-3-(3-fluoro-4-methylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-(3-methoxyquinolin-5-yl)-n-methylpropanamide Chemical compound C([C@H](OC1=O)CN(C)C(=O)CCC2=CC=CC3=NC=C(C=C32)OC)N1C1=CC=C(C)C(F)=C1 XBNDNNFQZYAFFM-HXUWFJFHSA-N 0.000 claims description 3
• LQHHRDYHPPKWGT-JOCHJYFZSA-N tert-butyl 2-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]acetate Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(CCCC3=CC=NC4=CC=C(N=C43)OC)CC(=O)OC(C)(C)C)=CC=C21 LQHHRDYHPPKWGT-JOCHJYFZSA-N 0.000 claims description 3
• 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 description 2
• 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 description 2
• UCJDBMJONBOTHG-LJQANCHMSA-N 2-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl-[3-(6-methoxy-1,5-naphthyridin-4-yl)propyl]amino]acetic acid Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CN(CCCC3=CC=NC4=CC=C(N=C43)OC)CC(O)=O)=CC=C21 UCJDBMJONBOTHG-LJQANCHMSA-N 0.000 claims description 2
• UMHWYYBQRVPEPF-UHFFFAOYSA-N n'-(6-methoxy-1,5-naphthyridin-4-yl)ethane-1,2-diamine Chemical compound N1=CC=C(NCCN)C2=NC(OC)=CC=C21 UMHWYYBQRVPEPF-UHFFFAOYSA-N 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 13
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• PKNLWLCURZNADF-UHFFFAOYSA-N hex-5-enoyl chloride Chemical compound ClC(=O)CCCC=C PKNLWLCURZNADF-UHFFFAOYSA-N 0.000 description 1
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• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 244000052637 human pathogen Species 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 239000011147 inorganic material Substances 0.000 description 1
• 150000004694 iodide salts Chemical class 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 206010023332 keratitis Diseases 0.000 description 1
• 239000010985 leather Substances 0.000 description 1
• 229940115932 legionella pneumophila Drugs 0.000 description 1
• 239000011968 lewis acid catalyst Substances 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 229940041033 macrolides Drugs 0.000 description 1
• 201000004792 malaria Diseases 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 208000004396 mastitis Diseases 0.000 description 1
• BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 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
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• IGXUNVGAYDXRGF-SNVBAGLBSA-N methyl (3r)-3-hydroxy-3-(6-methoxy-1,5-naphthyridin-4-yl)propanoate Chemical compound C1=C(OC)N=C2C([C@H](O)CC(=O)OC)=CC=NC2=C1 IGXUNVGAYDXRGF-SNVBAGLBSA-N 0.000 description 1
• UDBRBWPTRNJDLB-ATVHPVEESA-N methyl (z)-3-(6-methoxy-1,5-naphthyridin-4-yl)-2-(phenylmethoxycarbonylamino)prop-2-enoate Chemical compound C=1C=NC2=CC=C(OC)N=C2C=1/C=C(C(=O)OC)\NC(=O)OCC1=CC=CC=C1 UDBRBWPTRNJDLB-ATVHPVEESA-N 0.000 description 1
• XVMBQETUXDVSKL-UHFFFAOYSA-N methyl 2-(benzhydrylamino)-3-hydroxy-3-(6-methoxy-1,5-naphthyridin-4-yl)propanoate Chemical compound C=1C=NC2=CC=C(OC)N=C2C=1C(O)C(C(=O)OC)NC(C=1C=CC=CC=1)C1=CC=CC=C1 XVMBQETUXDVSKL-UHFFFAOYSA-N 0.000 description 1
• PQTOLHHWLUCKSB-UHFFFAOYSA-N methyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1C(=NCC(=O)OC)C1=CC=CC=C1 PQTOLHHWLUCKSB-UHFFFAOYSA-N 0.000 description 1
• VKNVMFBFFVVJAJ-UHFFFAOYSA-N methyl 2-amino-3-(6-methoxy-1,5-naphthyridin-4-yl)propanoate Chemical compound C1=C(OC)N=C2C(CC(N)C(=O)OC)=CC=NC2=C1 VKNVMFBFFVVJAJ-UHFFFAOYSA-N 0.000 description 1
• GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical compound COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
• RRJQUCMNBUYNKP-GOSISDBHSA-N methyl 2-methoxy-8-[[3-[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]propylamino]methyl]quinoline-5-carboxylate Chemical compound C12=NC(OC)=CC=C2C(C(=O)OC)=CC=C1CNCCC[C@H]1OC(=O)N(C=2C=C3NC(=O)CSC3=CC=2)C1 RRJQUCMNBUYNKP-GOSISDBHSA-N 0.000 description 1
• FOIDXARKVHHTOH-GOSISDBHSA-N methyl 2-methoxy-8-[[3-[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzoxazin-6-yl)-1,3-oxazolidin-5-yl]propylamino]methyl]quinoline-5-carboxylate Chemical compound C12=NC(OC)=CC=C2C(C(=O)OC)=CC=C1CNCCC[C@H]1OC(=O)N(C=2C=C3NC(=O)COC3=CC=2)C1 FOIDXARKVHHTOH-GOSISDBHSA-N 0.000 description 1
• RRJQUCMNBUYNKP-SFHVURJKSA-N methyl 2-methoxy-8-[[3-[(5s)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]propylamino]methyl]quinoline-5-carboxylate Chemical compound C12=NC(OC)=CC=C2C(C(=O)OC)=CC=C1CNCCC[C@@H]1OC(=O)N(C=2C=C3NC(=O)CSC3=CC=2)C1 RRJQUCMNBUYNKP-SFHVURJKSA-N 0.000 description 1
• FOIDXARKVHHTOH-SFHVURJKSA-N methyl 2-methoxy-8-[[3-[(5s)-2-oxo-3-(3-oxo-4h-1,4-benzoxazin-6-yl)-1,3-oxazolidin-5-yl]propylamino]methyl]quinoline-5-carboxylate Chemical compound C12=NC(OC)=CC=C2C(C(=O)OC)=CC=C1CNCCC[C@@H]1OC(=O)N(C=2C=C3NC(=O)COC3=CC=2)C1 FOIDXARKVHHTOH-SFHVURJKSA-N 0.000 description 1
• RRJQUCMNBUYNKP-UHFFFAOYSA-N methyl 2-methoxy-8-[[3-[2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]propylamino]methyl]quinoline-5-carboxylate Chemical compound C12=NC(OC)=CC=C2C(C(=O)OC)=CC=C1CNCCCC1OC(=O)N(C=2C=C3NC(=O)CSC3=CC=2)C1 RRJQUCMNBUYNKP-UHFFFAOYSA-N 0.000 description 1
• FOIDXARKVHHTOH-UHFFFAOYSA-N methyl 2-methoxy-8-[[3-[2-oxo-3-(3-oxo-4h-1,4-benzoxazin-6-yl)-1,3-oxazolidin-5-yl]propylamino]methyl]quinoline-5-carboxylate Chemical compound C12=NC(OC)=CC=C2C(C(=O)OC)=CC=C1CNCCCC1OC(=O)N(C=2C=C3NC(=O)COC3=CC=2)C1 FOIDXARKVHHTOH-UHFFFAOYSA-N 0.000 description 1
• AHFNIEBYCNMECW-UHFFFAOYSA-N methyl 3-(6-methoxy-1,5-naphthyridin-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=C(OC)N=C2C(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=NC2=C1 AHFNIEBYCNMECW-UHFFFAOYSA-N 0.000 description 1
• CFBHIYLQVAREQY-HXUWFJFHSA-N methyl 3-[(6-methoxy-1,5-naphthyridin-4-yl)methyl-[3-[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]propyl]amino]propanoate Chemical compound C1=C(OC)N=C2C(CN(CCC[C@H]3OC(=O)N(C3)C=3C=C4NC(=O)CSC4=CC=3)CCC(=O)OC)=CC=NC2=C1 CFBHIYLQVAREQY-HXUWFJFHSA-N 0.000 description 1
• CFBHIYLQVAREQY-FQEVSTJZSA-N methyl 3-[(6-methoxy-1,5-naphthyridin-4-yl)methyl-[3-[(5s)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]propyl]amino]propanoate Chemical compound C1=C(OC)N=C2C(CN(CCC[C@@H]3OC(=O)N(C3)C=3C=C4NC(=O)CSC4=CC=3)CCC(=O)OC)=CC=NC2=C1 CFBHIYLQVAREQY-FQEVSTJZSA-N 0.000 description 1
• CFBHIYLQVAREQY-UHFFFAOYSA-N methyl 3-[(6-methoxy-1,5-naphthyridin-4-yl)methyl-[3-[2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]propyl]amino]propanoate Chemical compound C1=C(OC)N=C2C(CN(CCCC3OC(=O)N(C3)C=3C=C4NC(=O)CSC4=CC=3)CCC(=O)OC)=CC=NC2=C1 CFBHIYLQVAREQY-UHFFFAOYSA-N 0.000 description 1
• SKNUMHSZBRXXQW-OAQYLSRUSA-N methyl 3-[2-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]ethyl-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]amino]propanoate Chemical compound C1=C(OC)N=C2C(CCN(CC[C@H]3OC(=O)N(C3)C=3C=C4OCCOC4=CC=3)CCC(=O)OC)=CC=NC2=C1 SKNUMHSZBRXXQW-OAQYLSRUSA-N 0.000 description 1
• SKNUMHSZBRXXQW-NRFANRHFSA-N methyl 3-[2-[(5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]ethyl-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]amino]propanoate Chemical compound C1=C(OC)N=C2C(CCN(CC[C@@H]3OC(=O)N(C3)C=3C=C4OCCOC4=CC=3)CCC(=O)OC)=CC=NC2=C1 SKNUMHSZBRXXQW-NRFANRHFSA-N 0.000 description 1
• SKNUMHSZBRXXQW-UHFFFAOYSA-N methyl 3-[2-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]ethyl-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]amino]propanoate Chemical compound C1=C(OC)N=C2C(CCN(CCC3OC(=O)N(C3)C=3C=C4OCCOC4=CC=3)CCC(=O)OC)=CC=NC2=C1 SKNUMHSZBRXXQW-UHFFFAOYSA-N 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
• XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
• ZJIWLTLIOYQKCT-UHFFFAOYSA-N n-(6-methoxy-1,5-naphthyridin-4-yl)-4-(oxiran-2-yl)butanamide Chemical compound C12=NC(OC)=CC=C2N=CC=C1NC(=O)CCCC1CO1 ZJIWLTLIOYQKCT-UHFFFAOYSA-N 0.000 description 1
• YFZIGAFDZIIDFJ-OAHLLOKOSA-N n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(5r)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]butanamide Chemical compound S1CC(=O)NC2=CC(N3C[C@H](OC3=O)CCCC(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 YFZIGAFDZIIDFJ-OAHLLOKOSA-N 0.000 description 1
• YFZIGAFDZIIDFJ-HNNXBMFYSA-N n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(5s)-2-oxo-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-5-yl]butanamide Chemical compound S1CC(=O)NC2=CC(N3C[C@@H](OC3=O)CCCC(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 YFZIGAFDZIIDFJ-HNNXBMFYSA-N 0.000 description 1
• UJEREMOYANLCSS-UHFFFAOYSA-N n-(6-methoxy-1,5-naphthyridin-4-yl)hex-5-enamide Chemical compound N1=CC=C(NC(=O)CCCC=C)C2=NC(OC)=CC=C21 UJEREMOYANLCSS-UHFFFAOYSA-N 0.000 description 1
• MAUNARRYUKTYDC-TZIWHRDSSA-N n-[(3r)-1-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]acetamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CC[C@@H](CCC3=CC=NC4=CC=C(N=C43)OC)NC(C)=O)=CC=C21 MAUNARRYUKTYDC-TZIWHRDSSA-N 0.000 description 1
• BSMPWPREMUAWOE-UYAOXDASSA-N n-[(3r)-1-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]methanesulfonamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CC[C@@H](CCC3=CC=NC4=CC=C(N=C43)OC)NS(C)(=O)=O)=CC=C21 BSMPWPREMUAWOE-UYAOXDASSA-N 0.000 description 1
• MAUNARRYUKTYDC-CTNGQTDRSA-N n-[(3r)-1-[(5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]acetamide Chemical compound O1CCOC2=CC(N3C[C@@H](OC3=O)CC[C@@H](CCC3=CC=NC4=CC=C(N=C43)OC)NC(C)=O)=CC=C21 MAUNARRYUKTYDC-CTNGQTDRSA-N 0.000 description 1
• BSMPWPREMUAWOE-QUCCMNQESA-N n-[(3r)-1-[(5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]methanesulfonamide Chemical compound O1CCOC2=CC(N3C[C@@H](OC3=O)CC[C@@H](CCC3=CC=NC4=CC=C(N=C43)OC)NS(C)(=O)=O)=CC=C21 BSMPWPREMUAWOE-QUCCMNQESA-N 0.000 description 1
• MAUNARRYUKTYDC-PZJWPPBQSA-N n-[(3s)-1-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]acetamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CC[C@H](CCC3=CC=NC4=CC=C(N=C43)OC)NC(C)=O)=CC=C21 MAUNARRYUKTYDC-PZJWPPBQSA-N 0.000 description 1
• BSMPWPREMUAWOE-AZUAARDMSA-N n-[(3s)-1-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]methanesulfonamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CC[C@H](CCC3=CC=NC4=CC=C(N=C43)OC)NS(C)(=O)=O)=CC=C21 BSMPWPREMUAWOE-AZUAARDMSA-N 0.000 description 1
• MAUNARRYUKTYDC-FPOVZHCZSA-N n-[(3s)-1-[(5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]acetamide Chemical compound O1CCOC2=CC(N3C[C@@H](OC3=O)CC[C@H](CCC3=CC=NC4=CC=C(N=C43)OC)NC(C)=O)=CC=C21 MAUNARRYUKTYDC-FPOVZHCZSA-N 0.000 description 1
• BSMPWPREMUAWOE-ICSRJNTNSA-N n-[(3s)-1-[(5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]methanesulfonamide Chemical compound O1CCOC2=CC(N3C[C@@H](OC3=O)CC[C@H](CCC3=CC=NC4=CC=C(N=C43)OC)NS(C)(=O)=O)=CC=C21 BSMPWPREMUAWOE-ICSRJNTNSA-N 0.000 description 1
• MAUNARRYUKTYDC-UHFFFAOYSA-N n-[1-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]acetamide Chemical compound O1CCOC2=CC(N3CC(OC3=O)CCC(CCC3=CC=NC4=CC=C(N=C43)OC)NC(C)=O)=CC=C21 MAUNARRYUKTYDC-UHFFFAOYSA-N 0.000 description 1
• BSMPWPREMUAWOE-UHFFFAOYSA-N n-[1-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]-5-(6-methoxy-1,5-naphthyridin-4-yl)pentan-3-yl]methanesulfonamide Chemical compound O1CCOC2=CC(N3CC(OC3=O)CCC(CCC3=CC=NC4=CC=C(N=C43)OC)NS(C)(=O)=O)=CC=C21 BSMPWPREMUAWOE-UHFFFAOYSA-N 0.000 description 1
• XXCZNYJXMBWPSH-QGZVFWFLSA-N n-[2-[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]ethyl]-2-(3-methoxyquinoxalin-5-yl)acetamide Chemical compound O1CCOC2=CC(N3C[C@H](OC3=O)CCNC(=O)CC3=CC=CC4=NC=C(N=C43)OC)=CC=C21 XXCZNYJXMBWPSH-QGZVFWFLSA-N 0.000 description 1
• XXCZNYJXMBWPSH-KRWDZBQOSA-N n-[2-[(5s)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]ethyl]-2-(3-methoxyquinoxalin-5-yl)acetamide Chemical compound O1CCOC2=CC(N3C[C@@H](OC3=O)CCNC(=O)CC3=CC=CC4=NC=C(N=C43)OC)=CC=C21 XXCZNYJXMBWPSH-KRWDZBQOSA-N 0.000 description 1
• ATPOPUGPCPAEGE-LLVKDONJSA-N n-[[(5r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound O=C1O[C@H](CNC(=O)C=C)CN1C1=CC=C(OCCO2)C2=C1 ATPOPUGPCPAEGE-LLVKDONJSA-N 0.000 description 1
• TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
• 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 238000005580 one pot reaction Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• 239000012285 osmium tetroxide Substances 0.000 description 1
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
• BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
• 239000003973 paint Substances 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• 150000002940 palladium Chemical class 0.000 description 1
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