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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- IWGMJRBACXRCNW-FUHWJXTLSA-N tert-butyl n-ethyl-n-[1-[(3r)-5-oxo-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)N(CC)C1([C@@H]2CC(=O)N([C@@H](C)C=3C=CC=CC=3)C2)CC1 IWGMJRBACXRCNW-FUHWJXTLSA-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 And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 |
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| Application Number | Title | Priority Date | Filing Date |
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| NO20032255A NO326157B1 (no) | 2000-11-20 | 2003-05-19 | Dehalogen-forbindelse, antibakterielt middel omfattende denne, samt dens anvendelse |
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| Country | Link |
|---|---|
| US (2) | US20040063754A1 (ja) |
| EP (1) | EP1336611B1 (ja) |
| JP (3) | JP3711108B2 (ja) |
| KR (1) | KR100777149B1 (ja) |
| CN (1) | CN1269817C (ja) |
| AR (1) | AR035599A1 (ja) |
| AT (1) | ATE372338T1 (ja) |
| AU (1) | AU2405002A (ja) |
| BR (1) | BR0115326A (ja) |
| CA (1) | CA2429440C (ja) |
| DE (1) | DE60130359T2 (ja) |
| ES (1) | ES2292642T3 (ja) |
| HK (1) | HK1056729A1 (ja) |
| IL (2) | IL155976A0 (ja) |
| MX (1) | MXPA03004437A (ja) |
| MY (1) | MY136916A (ja) |
| NO (1) | NO326157B1 (ja) |
| PT (1) | PT1336611E (ja) |
| TW (1) | TWI315308B (ja) |
| WO (1) | WO2002040478A1 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60130359T2 (de) | 2000-11-20 | 2008-06-26 | Daiichi Sankyo Co., Ltd. | Deshalogenverbindungen |
| EP1632482A4 (en) * | 2003-06-06 | 2009-10-28 | Daiichi Seiyaku Co | INTERMEDIATES AND PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE QUINOLONECARBOXYLIC ACID DERIVATIVES |
| 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 |
| EP1693364B1 (en) * | 2003-12-12 | 2015-05-20 | Daiichi Sankyo Company, Limited | Intermediates for the production of optically active cyclopropylamine derivatives and process for the production of the intermediates |
| MX2007000336A (es) * | 2004-07-02 | 2007-03-28 | Daiichi Seiyaku Co | Composicion medicinal que contiene quinolona. |
| JPWO2007037330A1 (ja) | 2005-09-28 | 2009-04-09 | 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 |
| 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 |
| EP2057185B1 (en) * | 2006-08-11 | 2016-05-11 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| 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 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE75740T1 (de) * | 1985-06-26 | 1992-05-15 | Daiichi Seiyaku Co | Pyridoncarbonsaeurederivate. |
| 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 |
| ATE239720T1 (de) * | 1995-02-02 | 2003-05-15 | Daiichi Seiyaku Co | Heterozyklische verbindungen |
| PT992501E (pt) | 1995-09-22 | 2003-01-31 | Wakunaga Pharma Co Ltd | Derivados de acido piridonacarboxilico como agentes antibacterianos |
| US6121285A (en) * | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
| CA2238765A1 (en) | 1995-11-22 | 1997-05-29 | Satoru Miyauchi | Substituted aminocycloalkylpyrrolidine derivatives |
| KR100488284B1 (ko) | 1996-07-12 | 2005-05-11 | 다이이찌 세이야꾸 가부시기가이샤 | 시스-치환된 아미노사이클로프로판 유도체 및 이를 함유하는 항균약 |
| 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 |
| EP0995744B1 (en) * | 1997-06-24 | 2003-02-12 | Daiichi Pharmaceutical Co., Ltd. | Cis-substituted fluoromethylpyrrolidine derivatives |
| 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 |
| EP1134219B1 (en) | 1998-11-24 | 2005-06-15 | Daiichi Pharmaceutical Co., Ltd. | Cycloalkyl-substituted aminomethylpyrrolidine derivatives |
| DE60130359T2 (de) | 2000-11-20 | 2008-06-26 | Daiichi Sankyo Co., Ltd. | Deshalogenverbindungen |
-
2001
- 2001-11-19 DE DE60130359T patent/DE60130359T2/de not_active Expired - Lifetime
- 2001-11-19 ES ES01996540T patent/ES2292642T3/es not_active Expired - Lifetime
- 2001-11-19 JP JP2002543488A patent/JP3711108B2/ja not_active Expired - Fee Related
- 2001-11-19 AT AT01996540T patent/ATE372338T1/de active
- 2001-11-19 IL IL15597601A patent/IL155976A0/xx unknown
- 2001-11-19 WO PCT/JP2001/010086 patent/WO2002040478A1/ja active IP Right Grant
- 2001-11-19 AR ARP010105401A patent/AR035599A1/es active IP Right Grant
- 2001-11-19 BR BR0115326-9A patent/BR0115326A/pt active Search and Examination
- 2001-11-19 US US10/432,043 patent/US20040063754A1/en not_active Abandoned
- 2001-11-19 PT PT01996540T patent/PT1336611E/pt unknown
- 2001-11-19 KR KR1020037006835A patent/KR100777149B1/ko not_active IP Right Cessation
- 2001-11-19 MX MXPA03004437A patent/MXPA03004437A/es active IP Right Grant
- 2001-11-19 EP EP01996540A patent/EP1336611B1/en not_active Expired - Lifetime
- 2001-11-19 AU AU2405002A patent/AU2405002A/xx not_active Withdrawn
- 2001-11-19 CN CNB018220746A patent/CN1269817C/zh not_active Expired - Fee Related
- 2001-11-19 CA CA002429440A patent/CA2429440C/en not_active Expired - Fee Related
- 2001-11-20 MY MYPI20015301A patent/MY136916A/en unknown
- 2001-11-20 TW TW090128688A patent/TWI315308B/zh not_active IP Right Cessation
-
2003
- 2003-05-19 NO NO20032255A patent/NO326157B1/no not_active IP Right Cessation
- 2003-05-19 IL IL155976A patent/IL155976A/en not_active IP Right Cessation
- 2003-12-15 HK HK03109128A patent/HK1056729A1/xx not_active IP Right Cessation
-
2004
- 2004-05-26 JP JP2004156517A patent/JP2004269544A/ja active Pending
- 2004-12-28 JP JP2004379455A patent/JP3760172B2/ja not_active Expired - Fee Related
-
2006
- 2006-12-26 US US11/644,901 patent/US7902226B2/en not_active Expired - Fee Related
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