JP2008534672A - 抗菌剤としての７−フルオロ−１，３−ジヒドロ−インドール−２−オンオキサゾリジノン - Google Patents
抗菌剤としての７−フルオロ−１，３−ジヒドロ−インドール−２−オンオキサゾリジノン Download PDFInfo
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- JP2008534672A JP2008534672A JP2008504870A JP2008504870A JP2008534672A JP 2008534672 A JP2008534672 A JP 2008534672A JP 2008504870 A JP2008504870 A JP 2008504870A JP 2008504870 A JP2008504870 A JP 2008504870A JP 2008534672 A JP2008534672 A JP 2008534672A
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- Prior art keywords
- fluoro
- compound
- dihydro
- indol
- mmol
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- 239000003242 anti bacterial agent Substances 0.000 title abstract description 15
- FFMDRLBKWBUTEW-UHFFFAOYSA-N 7-fluoro-1,3-dihydroindol-2-one;1,3-oxazolidin-2-one Chemical compound O=C1NCCO1.FC1=CC=CC2=C1NC(=O)C2 FFMDRLBKWBUTEW-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 32
- 208000015181 infectious disease Diseases 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 208000035143 Bacterial infection Diseases 0.000 claims description 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 241000186367 Mycobacterium avium Species 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 241000588621 Moraxella Species 0.000 claims description 3
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 3
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 241000606125 Bacteroides Species 0.000 claims description 2
- 241000606161 Chlamydia Species 0.000 claims description 2
- 208000008960 Diabetic foot Diseases 0.000 claims description 2
- 206010014666 Endocarditis bacterial Diseases 0.000 claims description 2
- 208000001860 Eye Infections Diseases 0.000 claims description 2
- 241000192125 Firmicutes Species 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims description 2
- 241000606768 Haemophilus influenzae Species 0.000 claims description 2
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 2
- 206010031252 Osteomyelitis Diseases 0.000 claims description 2
- 208000005141 Otitis Diseases 0.000 claims description 2
- 241000295644 Staphylococcaceae Species 0.000 claims description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 2
- 208000009361 bacterial endocarditis Diseases 0.000 claims description 2
- 208000019258 ear infection Diseases 0.000 claims description 2
- 206010014665 endocarditis Diseases 0.000 claims description 2
- 201000007119 infective endocarditis Diseases 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- RYXZVPPFWXWUKQ-JTQLQIEISA-N methyl n-[[(5s)-3-(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC)CN1C(C=C1F)=CC2=C1N(C)C(=O)C2 RYXZVPPFWXWUKQ-JTQLQIEISA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 241001112695 Clostridiales Species 0.000 claims 1
- 241000194032 Enterococcus faecalis Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 241000191967 Staphylococcus aureus Species 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 208000011323 eye infectious disease Diseases 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
- 238000002360 preparation method Methods 0.000 description 67
- 238000004128 high performance liquid chromatography Methods 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 239000007787 solid Substances 0.000 description 48
- -1 bicyclic oxazolidinone derivatives Chemical class 0.000 description 46
- 239000000203 mixture Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000012267 brine Substances 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- 239000011734 sodium Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 102000010909 Monoamine Oxidase Human genes 0.000 description 15
- 108010062431 Monoamine oxidase Proteins 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- SZKVETRZYWTMOM-UHFFFAOYSA-N 7-fluoro-1-methyl-5-nitro-3h-indol-2-one Chemical compound [O-][N+](=O)C1=CC(F)=C2N(C)C(=O)CC2=C1 SZKVETRZYWTMOM-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- HFKPSXLOLLNFRT-UHFFFAOYSA-N 2-(2,3-difluoro-5-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC([N+]([O-])=O)=CC(F)=C1F HFKPSXLOLLNFRT-UHFFFAOYSA-N 0.000 description 9
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NWIUSWJEIXFMSG-UHFFFAOYSA-N 7-fluoro-1-methyl-3h-indol-2-one Chemical compound C1=CC(F)=C2N(C)C(=O)CC2=C1 NWIUSWJEIXFMSG-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- WMMMBCVEFLMOGE-SECBINFHSA-N (5r)-5-(aminomethyl)-3-(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)-1,3-oxazolidin-2-one Chemical compound C=1C(F)=C2N(C)C(=O)CC2=CC=1N1C[C@@H](CN)OC1=O WMMMBCVEFLMOGE-SECBINFHSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000007911 parenteral administration Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZBBGKXNNTNBRBH-LURJTMIESA-N tert-butyl n-[[(2s)-oxiran-2-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H]1CO1 ZBBGKXNNTNBRBH-LURJTMIESA-N 0.000 description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 4
- ZEHWERXBZDEZAK-UHFFFAOYSA-N 5-amino-7-fluoro-1-methyl-3h-indol-2-one Chemical compound NC1=CC(F)=C2N(C)C(=O)CC2=C1 ZEHWERXBZDEZAK-UHFFFAOYSA-N 0.000 description 4
- XWTUHLYJQKEZSI-UHFFFAOYSA-N 7-fluoro-1-methylindole-2,3-dione Chemical compound C1=CC(F)=C2N(C)C(=O)C(=O)C2=C1 XWTUHLYJQKEZSI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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- QOMGYYDCVLVQOT-UHFFFAOYSA-N 2-fluoro-n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1F QOMGYYDCVLVQOT-UHFFFAOYSA-N 0.000 description 3
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
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- YRQFKVAESZZKDZ-UHFFFAOYSA-N C(N)(OC(C)(C)C)=O.C(=O)(Cl)Cl Chemical compound C(N)(OC(C)(C)C)=O.C(=O)(Cl)Cl YRQFKVAESZZKDZ-UHFFFAOYSA-N 0.000 description 2
- FDAPSKCCSOCDQK-UHFFFAOYSA-N ClC(=O)OC.COC(N)=O Chemical compound ClC(=O)OC.COC(N)=O FDAPSKCCSOCDQK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- KLLLRSBWNKVLPG-BYPYZUCNSA-N methyl n-[[(2s)-oxiran-2-yl]methyl]carbamate Chemical compound COC(=O)NC[C@H]1CO1 KLLLRSBWNKVLPG-BYPYZUCNSA-N 0.000 description 1
- AMTZJEAPUIQPIH-NSHDSACASA-N methyl n-[[(5s)-3-(1-ethyl-7-fluoro-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C=1C(F)=C2N(CC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC)OC1=O AMTZJEAPUIQPIH-NSHDSACASA-N 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YGCLIPSOSCUQIT-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(1-cyclopropyl-7-fluoro-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound C1=2C(F)=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=2CC(=O)N1C1CC1 YGCLIPSOSCUQIT-CQSZACIVSA-N 0.000 description 1
- VBLBMUZMFMXIJD-OAHLLOKOSA-N tert-butyl n-[(2r)-3-[[1-(cyclopropylmethyl)-7-fluoro-2-oxo-3h-indol-5-yl]amino]-2-hydroxypropyl]carbamate Chemical compound C1=2C(F)=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=2CC(=O)N1CC1CC1 VBLBMUZMFMXIJD-OAHLLOKOSA-N 0.000 description 1
- SHRKLXHLIHIWNY-CYBMUJFWSA-N tert-butyl n-[(2r)-3-[[7-fluoro-1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]amino]-2-hydroxypropyl]carbamate Chemical compound FC1=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC2=C1N(CCF)C(=O)C2 SHRKLXHLIHIWNY-CYBMUJFWSA-N 0.000 description 1
- WQSICRVEYPRROJ-LBPRGKRZSA-N tert-butyl n-[[(5s)-3-(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C=1C(F)=C2N(C)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC(C)(C)C)OC1=O WQSICRVEYPRROJ-LBPRGKRZSA-N 0.000 description 1
- LPLUWIGBFLNFPX-AWEZNQCLSA-N tert-butyl n-[[(5s)-3-(7-fluoro-2-oxo-1-propan-2-yl-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C=1C(F)=C2N(C(C)C)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC(C)(C)C)OC1=O LPLUWIGBFLNFPX-AWEZNQCLSA-N 0.000 description 1
- ASWYDKGGNIWGIM-ZDUSSCGKSA-N tert-butyl n-[[(5s)-3-[7-fluoro-1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC(C)(C)C)CN1C(C=C1F)=CC2=C1N(CCF)C(=O)C2 ASWYDKGGNIWGIM-ZDUSSCGKSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66871505P | 2005-04-06 | 2005-04-06 | |
| US68403305P | 2005-05-24 | 2005-05-24 | |
| PCT/IB2006/000954 WO2006106427A1 (en) | 2005-04-06 | 2006-03-27 | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008534672A true JP2008534672A (ja) | 2008-08-28 |
| JP2008534672A5 JP2008534672A5 (https=) | 2009-05-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008504870A Withdrawn JP2008534672A (ja) | 2005-04-06 | 2006-03-27 | 抗菌剤としての７−フルオロ−１，３−ジヒドロ−インドール−２−オンオキサゾリジノン |
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| Country | Link |
|---|---|
| US (1) | US7435751B2 (https=) |
| EP (1) | EP1869030A1 (https=) |
| JP (1) | JP2008534672A (https=) |
| KR (1) | KR20070108938A (https=) |
| AP (1) | AP2007004172A0 (https=) |
| AR (1) | AR053839A1 (https=) |
| AU (1) | AU2006231919A1 (https=) |
| BR (1) | BRPI0610533A2 (https=) |
| CA (1) | CA2603899A1 (https=) |
| CR (1) | CR9417A (https=) |
| DO (1) | DOP2006000080A (https=) |
| GT (1) | GT200600133A (https=) |
| IL (1) | IL186119A0 (https=) |
| MX (1) | MX2007012386A (https=) |
| NL (1) | NL1031525C2 (https=) |
| NO (1) | NO20075505L (https=) |
| PE (1) | PE20061301A1 (https=) |
| TN (1) | TNSN07373A1 (https=) |
| TW (1) | TW200716101A (https=) |
| UY (1) | UY29452A1 (https=) |
| WO (1) | WO2006106427A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1781642A1 (en) * | 2004-08-06 | 2007-05-09 | Pharmacia & Upjohn Company LLC | Oxazolidinones containing oxindoles as antibacterial agents |
| KR100891485B1 (ko) | 2007-10-29 | 2009-04-02 | 주식회사 만도 | 디스크 브레이크의 주차브레이크 장치 |
| US20090124737A1 (en) * | 2007-11-12 | 2009-05-14 | Eastman Chemical Company | Acrylic plastisol viscosity reducers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164510A (en) * | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| JP2865211B2 (ja) | 1988-09-15 | 1999-03-08 | ファルマシア・アンド・アップジョン・カンパニー | ５’―インドリニル―５β―アミドメチルオキサゾリジン―２―オン類、３―（縮合環置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類および３―（窒素原子置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類 |
| DE4425612A1 (de) | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| DE4425613A1 (de) | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| US6015429A (en) * | 1994-09-08 | 2000-01-18 | Gore Enterprise Holdings, Inc. | Procedures for introducing stents and stent-grafts |
| DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| DE19649095A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue Heteroaryl-Oxazolidinone |
| BR9907183A (pt) | 1998-01-23 | 2003-06-10 | Versicor Inc | Colet neas combinatórias de oxazolidinona, composições e processos de preparação |
| DE69912264T2 (de) | 1998-04-14 | 2004-07-22 | Samsung Fine Chemicals Co., Ltd. | Verfahren zur herstellung chiraler (s)-2,3-disubstituierter 1-propylamin-derivate |
| AU1379900A (en) | 1998-11-17 | 2000-06-05 | Bayer Aktiengesellschaft | Novel substituted phenyloxazolidone derivatives |
| HK1040707A1 (zh) | 1998-11-27 | 2002-06-21 | 法玛西雅厄普约翰美国公司 | 具有硫代羰基官能團的噁唑烷酮抗菌劑 |
| JP2003501351A (ja) | 1999-05-27 | 2003-01-14 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌剤としての二環系オキサゾリジノン |
| ES2256318T3 (es) | 2000-10-17 | 2006-07-16 | PHARMACIA & UPJOHN COMPANY LLC | Metodos de produccion de compuestos de oxazolidinona. |
| DE60212959T2 (de) | 2001-04-07 | 2007-02-15 | Astrazeneca Ab | Eine sulfonimid-gruppe enthaltende oxazolidinone als antibiotika |
| AU2002255803B2 (en) | 2001-04-20 | 2008-07-03 | Pharmacia And Upjohn Company | Process to prepare oxazolidinones |
| AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7012088B2 (en) * | 2003-02-24 | 2006-03-14 | Pharmacia & Upjohn Company | Indolone oxazolidinones and derivatives thereof |
| EP1781642A1 (en) * | 2004-08-06 | 2007-05-09 | Pharmacia & Upjohn Company LLC | Oxazolidinones containing oxindoles as antibacterial agents |
-
2006
- 2006-03-26 AU AU2006231919A patent/AU2006231919A1/en not_active Abandoned
- 2006-03-27 JP JP2008504870A patent/JP2008534672A/ja not_active Withdrawn
- 2006-03-27 CA CA002603899A patent/CA2603899A1/en not_active Abandoned
- 2006-03-27 EP EP06727519A patent/EP1869030A1/en not_active Withdrawn
- 2006-03-27 KR KR1020077022657A patent/KR20070108938A/ko not_active Ceased
- 2006-03-27 MX MX2007012386A patent/MX2007012386A/es unknown
- 2006-03-27 BR BRPI0610533-5A patent/BRPI0610533A2/pt not_active Application Discontinuation
- 2006-03-27 WO PCT/IB2006/000954 patent/WO2006106427A1/en not_active Ceased
- 2006-03-27 AP AP2007004172A patent/AP2007004172A0/xx unknown
- 2006-03-30 US US11/393,961 patent/US7435751B2/en not_active Expired - Fee Related
- 2006-04-04 TW TW095112018A patent/TW200716101A/zh unknown
- 2006-04-04 AR ARP060101328A patent/AR053839A1/es unknown
- 2006-04-04 PE PE2006000363A patent/PE20061301A1/es not_active Application Discontinuation
- 2006-04-04 UY UY29452A patent/UY29452A1/es not_active Application Discontinuation
- 2006-04-05 DO DO2006000080A patent/DOP2006000080A/es unknown
- 2006-04-05 GT GT200600133A patent/GT200600133A/es unknown
- 2006-04-05 NL NL1031525A patent/NL1031525C2/nl not_active IP Right Cessation
-
2007
- 2007-09-20 IL IL186119A patent/IL186119A0/en unknown
- 2007-10-05 TN TNP2007000373A patent/TNSN07373A1/fr unknown
- 2007-10-05 CR CR9417A patent/CR9417A/es unknown
- 2007-10-31 NO NO20075505A patent/NO20075505L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CR9417A (es) | 2007-12-04 |
| CA2603899A1 (en) | 2006-10-12 |
| MX2007012386A (es) | 2007-11-07 |
| GT200600133A (es) | 2006-11-29 |
| WO2006106427A8 (en) | 2007-12-06 |
| AR053839A1 (es) | 2007-05-23 |
| KR20070108938A (ko) | 2007-11-13 |
| US7435751B2 (en) | 2008-10-14 |
| NO20075505L (no) | 2007-10-31 |
| US20060229349A1 (en) | 2006-10-12 |
| NL1031525A1 (nl) | 2006-10-09 |
| AP2007004172A0 (en) | 2007-10-31 |
| AU2006231919A1 (en) | 2006-10-12 |
| NL1031525C2 (nl) | 2007-01-30 |
| UY29452A1 (es) | 2006-11-30 |
| EP1869030A1 (en) | 2007-12-26 |
| TNSN07373A1 (fr) | 2009-03-17 |
| DOP2006000080A (es) | 2006-12-15 |
| TW200716101A (en) | 2007-05-01 |
| IL186119A0 (en) | 2008-01-20 |
| BRPI0610533A2 (pt) | 2010-06-29 |
| WO2006106427A1 (en) | 2006-10-12 |
| PE20061301A1 (es) | 2007-02-09 |
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