ES2256331T3 - Derivados de quinolina antimicrobianos y uso de los mismos para tratar infecciones bacterianas. - Google Patents
Derivados de quinolina antimicrobianos y uso de los mismos para tratar infecciones bacterianas.Info
- Publication number
- ES2256331T3 ES2256331T3 ES01994117T ES01994117T ES2256331T3 ES 2256331 T3 ES2256331 T3 ES 2256331T3 ES 01994117 T ES01994117 T ES 01994117T ES 01994117 T ES01994117 T ES 01994117T ES 2256331 T3 ES2256331 T3 ES 2256331T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- alkyl
- compounds
- pharmaceutically acceptable
- haloalkyl
- 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.)
- Expired - Lifetime
Links
- 208000035143 Bacterial infection Diseases 0.000 title description 4
- 208000022362 bacterial infectious disease Diseases 0.000 title description 4
- 230000000845 anti-microbial effect Effects 0.000 title description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 230000000813 microbial effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- 239000007787 solid Substances 0.000 description 37
- 239000000460 chlorine Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 27
- -1 pyridine-substituted phenyloxazolidinone Chemical class 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 15
- 239000003981 vehicle Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 150000007660 quinolones Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000001143 conditioned effect Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- UGBKYDASQNOIHP-SSDOTTSWSA-N (5r)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(Br)C(F)=C1 UGBKYDASQNOIHP-SSDOTTSWSA-N 0.000 description 3
- HXMUHVDMNLEZDX-NSHDSACASA-N (5s)-5-(aminomethyl)-3-(3-fluoro-4-piperazin-1-ylphenyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN)CN1C(C=C1F)=CC=C1N1CCNCC1 HXMUHVDMNLEZDX-NSHDSACASA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 3
- AGDJSLIQSMMJEF-UHFFFAOYSA-N 2-methylpropyl n-(4-bromo-3-fluorophenyl)carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(Br)C(F)=C1 AGDJSLIQSMMJEF-UHFFFAOYSA-N 0.000 description 2
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 2
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- MKANDICJBVWDOV-HNNXBMFYSA-N 7-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)C(F)=C1 MKANDICJBVWDOV-HNNXBMFYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
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- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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- 239000008223 sterile water Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25790400P | 2000-12-21 | 2000-12-21 | |
| US257904P | 2000-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2256331T3 true ES2256331T3 (es) | 2006-07-16 |
Family
ID=22978270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01994117T Expired - Lifetime ES2256331T3 (es) | 2000-12-21 | 2001-11-29 | Derivados de quinolina antimicrobianos y uso de los mismos para tratar infecciones bacterianas. |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6689769B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1349853B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2004518677A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE319710T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2424402A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60117861T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2256331T3 (cg-RX-API-DMAC7.html) |
| PE (1) | PE20030137A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002059116A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| WO2003031441A1 (en) * | 2001-10-04 | 2003-04-17 | Morphochen Aktiengesellschaft Für Kombinatorische Chemie | Multiple action compounds |
| WO2003031443A1 (en) * | 2001-10-04 | 2003-04-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Dual actions antibiotics comprising a oxazoldinone and a quinolone or naphthyridinone moiety |
| US6875784B2 (en) * | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
| ES2312839T3 (es) * | 2002-12-04 | 2009-03-01 | Glaxo Group Limited | Quinolinas y sus derivados nitrogenados y su uso como agentes antibacterianos. |
| JP2006516991A (ja) * | 2003-02-07 | 2006-07-13 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 抗菌剤 |
| WO2004069244A1 (en) * | 2003-02-07 | 2004-08-19 | Warner-Lambert Company Llc | Oxazolidinone derivatives n-substituted by a bicyclic ring, for use as antibacterial agents |
| ATE397930T1 (de) * | 2003-04-30 | 2008-07-15 | Morphochem Ag Komb Chemie | Verwendung von oxazolidinon-chinolin-hybrid- antibiotika zur behandlung von anthrax und anderen infektionen |
| JP2007521283A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | シクロプロピル基で置換されたオキサゾリジノン系抗生物質およびその誘導体 |
| EP1646629B1 (en) | 2003-07-02 | 2010-06-23 | Merck Sharp & Dohme Corp. | Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof |
| DE10340485B4 (de) | 2003-09-03 | 2015-05-13 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Verfahren zur Herstellung von Oxazolidinon-Chinolon Hybriden |
| US7304050B2 (en) * | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| DK1709044T4 (da) * | 2003-12-18 | 2014-01-20 | Morphochem Ag Komb Chemie | Oxazolidinon-quinolon-hybridantibiotika |
| US8158797B2 (en) | 2003-12-18 | 2012-04-17 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| EP1557416A1 (en) * | 2004-01-23 | 2005-07-27 | Morphochem Aktiengesellschaft Für Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| EP1732897A1 (en) * | 2004-03-31 | 2006-12-20 | Bayer Pharmaceuticals Corporation | Quinolone carboxylic acid derivatives for treatment of hyperproliferative conditions |
| US20060105941A1 (en) * | 2004-11-12 | 2006-05-18 | Allergan, Inc. | Mixed antibiotic codrugs |
| US8546423B2 (en) * | 2005-05-18 | 2013-10-01 | Mpex Pharmaceuticals, Inc. | Aerosolized fluoroquinolones and uses thereof |
| US7838532B2 (en) * | 2005-05-18 | 2010-11-23 | Mpex Pharmaceuticals, Inc. | Aerosolized fluoroquinolones and uses thereof |
| AR054608A1 (es) * | 2005-08-08 | 2007-06-27 | Actelion Pharmaceuticals Ltd | Derivados de oxazolidinona enlazados a quinolonas como antibacterianos |
| EP2028936A4 (en) * | 2006-02-13 | 2014-02-26 | Univ Boston | COMPOSITIONS AND METHODS FOR ANTIBIOTIC REINFORCEMENT AND ACTIVE INFLUENCE |
| US20070197548A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V S | Fluoroquinolone compositions |
| US20070196398A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V S | Fluoroquinolone fatty acid salt compositions |
| US20100234348A1 (en) * | 2006-08-04 | 2010-09-16 | Trustees Of Boston University | Compositions and methods for potentiating antibiotic activity |
| US8124623B2 (en) * | 2006-11-10 | 2012-02-28 | Actelion Pharmaceuticals Ltd. | 5-hydroxymethyl-oxazolidin-2-one-derivatives and their uses as antibacterials |
| ES2380388T3 (es) * | 2006-11-10 | 2012-05-11 | Actelion Pharmaceuticals Ltd. | Derivados de 5-hidroximetil-oxazolidin-2-ona |
| CN102014903B (zh) * | 2008-05-09 | 2013-07-10 | 埃科特莱茵药品有限公司 | 用于治疗细菌性肠疾病的5-羟基甲基-*唑烷-2-酮衍生物 |
| KR100980681B1 (ko) * | 2008-09-16 | 2010-09-07 | 한국과학기술연구원 | 디플루오로페닐 유도체를 갖는 신규한 옥사졸리디논 유도체또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 하는 항생제 조성물 |
| JP2012505223A (ja) | 2008-10-07 | 2012-03-01 | エムペックス・ファーマシューティカルズ・インコーポレーテッド | 薬物動態の改善のためのエアゾールフルオロキノロン配合物 |
| US8629139B2 (en) * | 2008-10-07 | 2014-01-14 | Mpex Pharmaceuticals, Inc. | Topical use of Levofloxacin for reducing lung inflammation |
| CN102724983A (zh) | 2009-09-04 | 2012-10-10 | Mpex医药有限公司 | 雾化左氧氟沙星治疗囊性纤维化的用途 |
| CN102040591B (zh) * | 2009-10-15 | 2013-12-11 | 山东轩竹医药科技有限公司 | 7-苯基喹诺酮类化合物 |
| US20120065170A1 (en) | 2010-09-10 | 2012-03-15 | Micurx Pharmaceuticals, Inc. | Antimicrobial Cyclocarbonyl Heterocyclic Compounds For Treatment Of Bacterial Infections |
| WO2014191109A1 (en) | 2013-05-28 | 2014-12-04 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Combination therapy comprising oxazolidinone-quinolones for use in treating bacterial infections |
| CN112089714A (zh) | 2013-05-28 | 2020-12-18 | 莫弗凯姆有限公司 | 用于胃肠外治疗或预防细菌性疾病的噁唑烷酮-喹诺酮杂合物抗菌剂 |
| WO2017017631A2 (en) | 2015-07-28 | 2017-02-02 | Vyome Biosciences Pvt. Ltd. | Antibacterial therapeutics and prophylactics |
| WO2017156519A1 (en) | 2016-03-11 | 2017-09-14 | The Board Of Trustees Of The University Of Illinois | Small-molecules active against gram-negative bacteria |
| CN107286182A (zh) * | 2016-04-12 | 2017-10-24 | 李靖 | 新型噁唑烷酮‑氟喹诺酮衍生物及用途 |
| US10087171B2 (en) | 2016-12-19 | 2018-10-02 | Actelion Pharmaceuticals Ltd | Crystalline forms of cadazolid |
| WO2018237140A1 (en) | 2017-06-23 | 2018-12-27 | The Board Of Trustees Of The University Of Illinois | Topoisomerase inhibitors with antibacterial and antcancer activity |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL137326C (cg-RX-API-DMAC7.html) | 1967-08-26 | |||
| US3669965A (en) | 1969-12-29 | 1972-06-13 | Lilly Co Eli | 1-lower alkyl or alkylene substituted-6,7-methylenedioxy-4(1h)-oxocinnoline-3-carboxylic acids and methods for making and using same |
| US4000155A (en) | 1975-12-11 | 1976-12-28 | Eli Lilly And Company | Herbicidal 2-methyl-4-phenyl-5-pyrazolinones[and isoxazolinones] |
| US4283403A (en) | 1976-06-14 | 1981-08-11 | Eli Lilly And Company | Substituted isoxazolines for control of plant phytopathogens |
| IL51092A0 (en) * | 1976-12-10 | 1977-02-28 | Abic Ltd | Naphthyridine derivatives and their preparation |
| JPS5746986A (en) | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| DE3142854A1 (de) | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US4620007A (en) | 1980-09-03 | 1986-10-28 | Bayer Aktiengesellschaft | 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid |
| JPS5788182A (en) | 1980-11-21 | 1982-06-01 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazinecarboxylic acid derivative |
| JPS5872589A (ja) | 1981-10-28 | 1983-04-30 | Dai Ichi Seiyaku Co Ltd | ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾオキサジン誘導体 |
| DE3248507A1 (de) | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | Mikrobizide mittel auf chinoloncarbonsaeure basis |
| DE3248505A1 (de) | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US4705799A (en) | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| DK170473B1 (da) | 1985-06-20 | 1995-09-11 | Daiichi Seiyaku Co | S(-)-pyridobenzoxazinforbindelser |
| US4921869A (en) | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4801600A (en) | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4977173A (en) | 1987-10-21 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| US4948801A (en) | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| US5254577A (en) | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| US5130316A (en) | 1988-07-29 | 1992-07-14 | Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazlidinyl arylbenzene derivatives useful as antibacterial agents |
| JPH0269478A (ja) * | 1988-09-05 | 1990-03-08 | Sagami Chem Res Center | キノロンカルボン酸誘導体 |
| US5164510A (en) | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| ATE123494T1 (de) * | 1989-03-30 | 1995-06-15 | Wakunaga Seiyaku Kk | Chinolon-derivate und deren salze, verfahren zu deren herstellung und diese enthaltende antibakterielle wirkstoffe. |
| DE69216251T2 (de) | 1991-11-01 | 1997-05-15 | Pharmacia & Upjohn Co., Kalamazoo, Mich. | Substituierte aryl- und heteroaryl-phenyloxazolidinone |
| HUT74099A (en) | 1992-12-08 | 1996-11-28 | Upjohn Co | Tropone-substituted phenyloxazolidinone antibacterial agents and pharmaceutical compositions containing the same |
| DE4425609A1 (de) | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
| DE4425613A1 (de) | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| DE4425612A1 (de) | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| DE19514313A1 (de) | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
| US6124334A (en) * | 1995-02-03 | 2000-09-26 | Pharmacia & Upjohn Company | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials |
| DE19601265A1 (de) * | 1996-01-16 | 1997-07-17 | Bayer Ag | 2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone |
| WO1998007708A1 (en) | 1996-08-21 | 1998-02-26 | Pharmacia & Upjohn Company | Isoxazoline derivatives useful as antimicrobials |
| DK1054874T3 (da) | 1998-02-13 | 2002-12-30 | Upjohn Co | Substituerede aminophenylisoxazolinderivater, der er anvendelige som antimokrobielle midler |
| TW572757B (en) | 1998-08-24 | 2004-01-21 | Bristol Myers Squibb Co | Novel isoxazolinone antibacterial agents |
-
2001
- 2001-11-29 CA CA002424402A patent/CA2424402A1/en not_active Abandoned
- 2001-11-29 ES ES01994117T patent/ES2256331T3/es not_active Expired - Lifetime
- 2001-11-29 JP JP2002559418A patent/JP2004518677A/ja active Pending
- 2001-11-29 AT AT01994117T patent/ATE319710T1/de not_active IP Right Cessation
- 2001-11-29 DE DE60117861T patent/DE60117861T2/de not_active Expired - Fee Related
- 2001-11-29 US US09/996,927 patent/US6689769B2/en not_active Expired - Fee Related
- 2001-11-29 EP EP01994117A patent/EP1349853B1/en not_active Expired - Lifetime
- 2001-11-29 WO PCT/US2001/044731 patent/WO2002059116A2/en not_active Ceased
- 2001-12-20 PE PE2001001284A patent/PE20030137A1/es not_active Application Discontinuation
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2003
- 2003-12-05 US US10/729,816 patent/US6869965B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60117861T2 (de) | 2006-11-02 |
| US6869965B2 (en) | 2005-03-22 |
| US20030013737A1 (en) | 2003-01-16 |
| WO2002059116A3 (en) | 2002-12-05 |
| EP1349853A2 (en) | 2003-10-08 |
| ATE319710T1 (de) | 2006-03-15 |
| PE20030137A1 (es) | 2003-03-08 |
| WO2002059116A2 (en) | 2002-08-01 |
| EP1349853B1 (en) | 2006-03-08 |
| US20040215017A1 (en) | 2004-10-28 |
| DE60117861D1 (de) | 2006-05-04 |
| US6689769B2 (en) | 2004-02-10 |
| CA2424402A1 (en) | 2002-08-01 |
| JP2004518677A (ja) | 2004-06-24 |
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