NO326157B1 - Dehalogen-forbindelse, antibakterielt middel omfattende denne, samt dens anvendelse - Google Patents
Dehalogen-forbindelse, antibakterielt middel omfattende denne, samt dens anvendelse Download PDFInfo
- Publication number
- NO326157B1 NO326157B1 NO20032255A NO20032255A NO326157B1 NO 326157 B1 NO326157 B1 NO 326157B1 NO 20032255 A NO20032255 A NO 20032255A NO 20032255 A NO20032255 A NO 20032255A NO 326157 B1 NO326157 B1 NO 326157B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- cyclopropyl
- compound
- fluoro
- salts
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 216
- 239000003242 anti bacterial agent Substances 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 claims description 75
- 150000004677 hydrates Chemical class 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- VQBWOBXQHLLMQP-RPVQJOFSSA-N 1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-7-[(3r)-3-[1-(methylamino)cyclopropyl]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound CNC1([C@H]2CN(CC2)C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2)C)CC1 VQBWOBXQHLLMQP-RPVQJOFSSA-N 0.000 claims description 4
- ZLICIITZJTYKAQ-DIOULYMOSA-N 7-[(3r)-3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-[(1r,2s)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2C[C@@H](CC2)C2(N)CC2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2[C@@H]1C[C@@H]1F ZLICIITZJTYKAQ-DIOULYMOSA-N 0.000 claims description 4
- CHJBKIBZQUTECQ-ISTRZQFTSA-N 7-[(3r)-3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C(N2C[C@@H](CC2)C2(N)CC2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2[C@@H]1C[C@@H]1F CHJBKIBZQUTECQ-ISTRZQFTSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ZULBINOBBBKAFW-ISTRZQFTSA-N 1-[(1r,2s)-2-fluorocyclopropyl]-8-methoxy-7-[(3r)-3-[1-(methylamino)cyclopropyl]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound CNC1([C@H]2CN(CC2)C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2)OC)CC1 ZULBINOBBBKAFW-ISTRZQFTSA-N 0.000 claims description 3
- BOLMDIXLULGTBD-UHFFFAOYSA-N 3,4-dihydro-2h-oxazine Chemical group C1CC=CON1 BOLMDIXLULGTBD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 231
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 177
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 156
- 238000006243 chemical reaction Methods 0.000 description 138
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 130
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 100
- 238000001816 cooling Methods 0.000 description 98
- 239000000203 mixture Substances 0.000 description 84
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 78
- 239000012044 organic layer Substances 0.000 description 78
- 238000005160 1H NMR spectroscopy Methods 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 68
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 238000001914 filtration Methods 0.000 description 64
- 239000013078 crystal Substances 0.000 description 55
- 238000003756 stirring Methods 0.000 description 54
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 53
- 239000000706 filtrate Substances 0.000 description 52
- 238000005406 washing Methods 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- -1 quinolone compound Chemical class 0.000 description 49
- 238000000605 extraction Methods 0.000 description 45
- 125000001424 substituent group Chemical group 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 39
- 101150041968 CDC13 gene Proteins 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- 239000007864 aqueous solution Substances 0.000 description 32
- 238000000921 elemental analysis Methods 0.000 description 29
- 239000010410 layer Substances 0.000 description 29
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- 239000003814 drug Substances 0.000 description 28
- 238000010992 reflux Methods 0.000 description 28
- 239000000126 substance Substances 0.000 description 27
- 229940079593 drug Drugs 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000000843 powder Substances 0.000 description 24
- 230000000844 anti-bacterial effect Effects 0.000 description 23
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000001035 drying Methods 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 230000002378 acidificating effect Effects 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- 241000894006 Bacteria Species 0.000 description 17
- 235000008504 concentrate Nutrition 0.000 description 16
- 239000012141 concentrate Substances 0.000 description 16
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 125000006239 protecting group Chemical group 0.000 description 15
- 239000006188 syrup Substances 0.000 description 15
- 235000020357 syrup Nutrition 0.000 description 15
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000002274 desiccant Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QJTCVIHNVLALCL-SECBINFHSA-N tert-butyl n-[1-[(3r)-pyrrolidin-3-yl]cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1([C@H]2CNCC2)CC1 QJTCVIHNVLALCL-SECBINFHSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229940072132 quinolone antibacterials Drugs 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 210000002700 urine Anatomy 0.000 description 8
- 241000192125 Firmicutes Species 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
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- 238000001704 evaporation Methods 0.000 description 7
- 230000003389 potentiating effect Effects 0.000 description 7
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 7
- 150000007660 quinolones Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- TUKJTSUSKQOYCD-STHAYSLISA-N (1r,2s)-2-fluorocyclopropan-1-amine Chemical compound N[C@@H]1C[C@@H]1F TUKJTSUSKQOYCD-STHAYSLISA-N 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
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- 239000005909 Kieselgur Substances 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
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- VHUSJZPIQCMYND-SNVBAGLBSA-N tert-butyl n-methyl-n-[1-[(3r)-pyrrolidin-3-yl]cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)C1([C@H]2CNCC2)CC1 VHUSJZPIQCMYND-SNVBAGLBSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- DSHKEUIVMLQFCA-DIOULYMOSA-N 7-[(3r)-3-(1-aminocyclopropyl)pyrrolidin-1-yl]-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound NC1([C@@H]2CCN(C2)C2=C(C3=C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)C=C2F)C)CC1 DSHKEUIVMLQFCA-DIOULYMOSA-N 0.000 description 4
- MMPGHRSKSLDBJA-VHSXEESVSA-N 7-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(F)C=CC(C(C(C(O)=O)=C2)=O)=C1N2[C@@H]1C[C@@H]1F MMPGHRSKSLDBJA-VHSXEESVSA-N 0.000 description 4
- DGIDDCMFSFECOC-WDEREUQCSA-N 7-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C(F)C=CC(C(C(C(O)=O)=C2)=O)=C1N2[C@@H]1C[C@@H]1F DGIDDCMFSFECOC-WDEREUQCSA-N 0.000 description 4
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- 206010028470 Mycoplasma infections Diseases 0.000 description 4
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- 125000003342 alkenyl group Chemical group 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
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 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 4
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- BDLXLRIOJUVBQP-GOEBONIOSA-N tert-butyl n-[1-[(3r)-5-oxo-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1([C@H]2CN(C(C2)=O)[C@@H](C)C=2C=CC=CC=2)CC1 BDLXLRIOJUVBQP-GOEBONIOSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
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- CODODJXRTTVLFW-WCBMZHEXSA-N 5-amino-7-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C(F)C=C(N)C(C(C(C(O)=O)=C2)=O)=C1N2[C@@H]1C[C@@H]1F CODODJXRTTVLFW-WCBMZHEXSA-N 0.000 description 3
- CHPGXTXYGBBJHR-XQAQDONZSA-N 7-[(3r)-3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound NC1([C@H]2CN(CC2)C=2C=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2)CC1 CHPGXTXYGBBJHR-XQAQDONZSA-N 0.000 description 3
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- IYFOFTYDZYPQGD-DKSSEZFCSA-N 7-[(3r)-3-[1-(ethylamino)cyclopropyl]pyrrolidin-1-yl]-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CCNC1([C@H]2CN(CC2)C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2)C)CC1 IYFOFTYDZYPQGD-DKSSEZFCSA-N 0.000 description 3
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000352269 | 2000-11-20 | ||
| JP2001248822 | 2001-08-20 | ||
| PCT/JP2001/010086 WO2002040478A1 (fr) | 2000-11-20 | 2001-11-19 | Composes dihalogenes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20032255D0 NO20032255D0 (no) | 2003-05-19 |
| NO20032255L NO20032255L (no) | 2003-07-21 |
| NO326157B1 true NO326157B1 (no) | 2008-10-13 |
Family
ID=26604261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20032255A NO326157B1 (no) | 2000-11-20 | 2003-05-19 | Dehalogen-forbindelse, antibakterielt middel omfattende denne, samt dens anvendelse |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20040063754A1 (es) |
| EP (1) | EP1336611B1 (es) |
| JP (3) | JP3711108B2 (es) |
| KR (1) | KR100777149B1 (es) |
| CN (1) | CN1269817C (es) |
| AR (1) | AR035599A1 (es) |
| AT (1) | ATE372338T1 (es) |
| AU (1) | AU2405002A (es) |
| BR (1) | BR0115326A (es) |
| CA (1) | CA2429440C (es) |
| DE (1) | DE60130359T2 (es) |
| ES (1) | ES2292642T3 (es) |
| HK (1) | HK1056729A1 (es) |
| IL (2) | IL155976A0 (es) |
| MX (1) | MXPA03004437A (es) |
| MY (1) | MY136916A (es) |
| NO (1) | NO326157B1 (es) |
| PT (1) | PT1336611E (es) |
| TW (1) | TWI315308B (es) |
| WO (1) | WO2002040478A1 (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2429440C (en) | 2000-11-20 | 2009-12-29 | Daiichi Pharmaceutical Co., Ltd. | Dehalogeno-compounds |
| JP4675234B2 (ja) * | 2003-06-06 | 2011-04-20 | 第一三共株式会社 | 光学活性なキノロンカルボン酸誘導体の製造中間体およびその製造法 |
| WO2004113321A1 (ja) * | 2003-06-19 | 2004-12-29 | Daiichi Pharmaceutical Co., Ltd. | 選択的なアミノ置換基導入法 |
| JP4629973B2 (ja) * | 2003-09-22 | 2011-02-09 | 第一三共株式会社 | 光学活性シクロプロピルアミン誘導体およびその製造方法 |
| WO2005030752A1 (ja) * | 2003-09-29 | 2005-04-07 | Daiichi Pharmaceutical Co., Ltd. | ８−シアノキノロンカルボン酸誘導体 |
| ES2537976T3 (es) | 2003-12-12 | 2015-06-16 | Daiichi Sankyo Company, Limited | Compuestos intermedios para la producción de derivados de ciclopropilamina ópticamente activos y procedimiento para la producción de los compuestos intermedios |
| RU2007104026A (ru) * | 2004-07-02 | 2008-08-10 | Дайити Фармасьютикал Ко., Лтд. (JP) | Содержащая хинолон лекарственная композиция |
| TW200744598A (en) * | 2005-09-28 | 2007-12-16 | Daiichi Seiyaku Co | Process for the production of freeze-dried preparations containing quinolones |
| CN100441580C (zh) * | 2006-07-14 | 2008-12-10 | 中山大学 | 喹啉二酮衍生物及其在制备抗菌药物中的应用 |
| KR101502453B1 (ko) * | 2006-08-11 | 2015-03-24 | 노던 안티바이오틱스 리미티드 | 폴리믹신 유도체들 및 이들의 용도 |
| JP5174365B2 (ja) * | 2007-03-23 | 2013-04-03 | 第一三共株式会社 | キノロン含有凍結乾燥製剤の製造方法 |
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| EP0207420B1 (en) * | 1985-06-26 | 1992-05-06 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives |
| DE69531305T2 (de) * | 1994-10-20 | 2004-05-13 | Wakunaga Seiyaku K.K. | Pyridoncarboxylat- derivate oder salze davon und antibakterielle zusammensetzungen die diese als aktiven bestandteil enthalten |
| CA2212007C (en) * | 1995-02-02 | 2004-09-14 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives substitued by a bicyclic amino group |
| EP0992501B1 (en) * | 1995-09-22 | 2002-08-28 | Wakunaga Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives as antibacterial agents |
| CN1119343C (zh) | 1995-11-22 | 2003-08-27 | 第一制药株式会社 | 取代的氨基环烷基吡咯烷衍生物 |
| US6121285A (en) * | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
| US6391889B2 (en) * | 1996-07-12 | 2002-05-21 | Daiichi Pharmaceutical Co., Ltd. | Cis-substituted aminocyclopropane derivatives |
| JPH1081682A (ja) | 1996-07-12 | 1998-03-31 | Dai Ichi Seiyaku Co Ltd | シス置換アミノシクロプロパン誘導体 |
| TW519542B (en) * | 1996-09-27 | 2003-02-01 | Daiichi Seiyaku Co | Bicyclic amine derivative |
| IL132982A0 (en) * | 1997-05-21 | 2001-03-19 | Daiichi Seiyaku Co | Cis-disubstituted aminocycloalkyl-pyrrolidine derivatives |
| MY119816A (en) | 1997-05-30 | 2005-07-29 | Daiichi Seiyaku Co | Substituted cyclobutylamine derivatives |
| KR20010014209A (ko) * | 1997-06-24 | 2001-02-26 | 스즈키 다다시 | 시스-치환된 플루오로메틸피롤리딘 유도체 |
| HUP0100051A3 (en) * | 1997-09-15 | 2002-08-28 | Procter & Gamble | Antimicrobial quinolones, their compositions and uses |
| JP2000023709A (ja) * | 1998-07-16 | 2000-01-25 | Shimano Inc | 長 靴 |
| DE19834202A1 (de) | 1998-07-29 | 2000-02-10 | Coherent Luebeck Gmbh | Rauscharmer frequenzvervielfachter Laser mit Strahlseparator |
| ATE297912T1 (de) | 1998-11-24 | 2005-07-15 | Daiichi Seiyaku Co | Cycloalkylsubstituierte aminomethylpyrrolidin- derivate |
| CA2429440C (en) | 2000-11-20 | 2009-12-29 | Daiichi Pharmaceutical Co., Ltd. | Dehalogeno-compounds |
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- 2001-11-19 PT PT01996540T patent/PT1336611E/pt unknown
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