NO314546B1 - N1-(halogencyklopropyl)-substituert pyridonkarboksylsyrederivat og antibakterielt preparat omfattende en slik forbindelse - Google Patents
N1-(halogencyklopropyl)-substituert pyridonkarboksylsyrederivat og antibakterielt preparat omfattende en slik forbindelse Download PDFInfo
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- NO314546B1 NO314546B1 NO19973530A NO973530A NO314546B1 NO 314546 B1 NO314546 B1 NO 314546B1 NO 19973530 A NO19973530 A NO 19973530A NO 973530 A NO973530 A NO 973530A NO 314546 B1 NO314546 B1 NO 314546B1
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- YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical class OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 title claims description 123
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- -1 pivaloyloxymethyl group Chemical group 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical group C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 3
- 229940124350 antibacterial drug Drugs 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 80
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 60
- 239000002904 solvent Substances 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
- 238000001704 evaporation Methods 0.000 description 41
- 230000008020 evaporation Effects 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 150000007660 quinolones Chemical class 0.000 description 18
- 238000001816 cooling Methods 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 101150041968 CDC13 gene Proteins 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 229940083608 sodium hydroxide Drugs 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 206010028470 Mycoplasma infections Diseases 0.000 description 4
- 206010040047 Sepsis Diseases 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 206010041925 Staphylococcal infections Diseases 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 4
- 229940072132 quinolone antibacterials Drugs 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- TUKJTSUSKQOYCD-STHAYSLISA-N (1r,2s)-2-fluorocyclopropan-1-amine Chemical compound N[C@@H]1C[C@@H]1F TUKJTSUSKQOYCD-STHAYSLISA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
- FFOYMNCZNJJCSO-UHFFFAOYSA-N 4-(carboxymethyl)-3,5,6-trifluorophthalic acid Chemical compound OC(=O)CC1=C(F)C(F)=C(C(O)=O)C(C(O)=O)=C1F FFOYMNCZNJJCSO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 241000192125 Firmicutes Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 206010039438 Salmonella Infections Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 3
- 201000003146 cystitis Diseases 0.000 description 3
- YKDASBAWJFXNAV-UHFFFAOYSA-N dimethyl 3,4,5,6-tetrafluorobenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=C(F)C(F)=C(F)C(F)=C1C(=O)OC YKDASBAWJFXNAV-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- DKKIUDLHMPRWBE-UHFFFAOYSA-N ethyl cyclobutene-1-carboxylate Chemical compound CCOC(=O)C1=CCC1 DKKIUDLHMPRWBE-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
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- 239000012266 salt solution Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DAJNRXACPDNINW-UHFFFAOYSA-N tert-butyl 3-azabicyclo[3.2.0]heptane-5-carboxylate Chemical compound C1NCC2(C(=O)OC(C)(C)C)C1CC2 DAJNRXACPDNINW-UHFFFAOYSA-N 0.000 description 3
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- CISXRFRLKWCFJS-UHFFFAOYSA-N 2,4,5-trifluoro-3-methylbenzoic acid Chemical compound CC1=C(F)C(F)=CC(C(O)=O)=C1F CISXRFRLKWCFJS-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- DCUNANCIRAGDAM-UHFFFAOYSA-N 3-o-benzyl 5-o-tert-butyl 3-azabicyclo[3.2.0]heptane-3,5-dicarboxylate Chemical compound C1C2(C(=O)OC(C)(C)C)CCC2CN1C(=O)OCC1=CC=CC=C1 DCUNANCIRAGDAM-UHFFFAOYSA-N 0.000 description 2
- ZJCJWSOPDXZRMJ-UHFFFAOYSA-N 3-phenylmethoxycarbonyl-3-azabicyclo[3.2.0]heptane-5-carboxylic acid Chemical compound C1C2(C(=O)O)CCC2CN1C(=O)OCC1=CC=CC=C1 ZJCJWSOPDXZRMJ-UHFFFAOYSA-N 0.000 description 2
- MYCPRDKWFULFIU-CRCLSJGQSA-N 6,7,8-trifluoro-1-[(1r,2s)-2-fluorocyclopropyl]-5-hydroxy-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C(O)=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F MYCPRDKWFULFIU-CRCLSJGQSA-N 0.000 description 2
- 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
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- 238000006969 Curtius rearrangement reaction Methods 0.000 description 2
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- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- GLMQXANHMIEJPB-UHFFFAOYSA-N dimethyl 4-(1,3-diethoxy-2-methyl-1,3-dioxopropan-2-yl)-3,5,6-trifluorobenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C(C)(C(=O)OCC)C1=C(F)C(F)=C(C(=O)OC)C(C(=O)OC)=C1F GLMQXANHMIEJPB-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
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- 201000010063 epididymitis Diseases 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- JEUGNDSKQMUJIM-UHFFFAOYSA-N ethyl 3-oxo-3-(2,4,5-trifluoro-3-methyl-6-nitrophenyl)propanoate Chemical compound CCOC(=O)CC(=O)C1=C(F)C(C)=C(F)C(F)=C1[N+]([O-])=O JEUGNDSKQMUJIM-UHFFFAOYSA-N 0.000 description 1
- QQETUOAIVBXRCO-DTWKUNHWSA-N ethyl 6,7-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(C)C(F)=C(F)C([N+]([O-])=O)=C2C(=O)C(C(=O)OCC)=CN1[C@@H]1C[C@@H]1F QQETUOAIVBXRCO-DTWKUNHWSA-N 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- 210000003527 eukaryotic cell Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- IZZJFOLOOYFYFG-VKHMYHEASA-N fluorocyclopropane Chemical group F[C@H]1[CH]C1 IZZJFOLOOYFYFG-VKHMYHEASA-N 0.000 description 1
- 125000006419 fluorocyclopropyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 208000020426 gonococcal urethritis Diseases 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 208000002557 hidradenitis Diseases 0.000 description 1
- 208000008025 hordeolum Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025226 lymphangitis Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000005188 oxoalkyl group Chemical group 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 201000005115 pasteurellosis Diseases 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 201000006509 pleuropneumonia Diseases 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- OQCUGPQOZNYIMV-UHFFFAOYSA-N pyrrolidin-3-ylmethanamine Chemical compound NCC1CCNC1 OQCUGPQOZNYIMV-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003248 quinolines Chemical group 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Stereophonic System (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Earth Drilling (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1561495 | 1995-02-02 | ||
JP1947895 | 1995-02-07 | ||
JP1948195 | 1995-02-07 | ||
PCT/JP1996/000208 WO1996023782A1 (fr) | 1995-02-02 | 1996-02-01 | Composes heterocycliques |
Publications (3)
Publication Number | Publication Date |
---|---|
NO973530D0 NO973530D0 (no) | 1997-07-31 |
NO973530L NO973530L (no) | 1997-10-02 |
NO314546B1 true NO314546B1 (no) | 2003-04-07 |
Family
ID=27281082
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19973530A NO314546B1 (no) | 1995-02-02 | 1997-07-31 | N1-(halogencyklopropyl)-substituert pyridonkarboksylsyrederivat og antibakterielt preparat omfattende en slik forbindelse |
Country Status (13)
Country | Link |
---|---|
US (1) | US5849757A (ko) |
EP (2) | EP1304329B1 (ko) |
KR (1) | KR100389773B1 (ko) |
AT (2) | ATE411309T1 (ko) |
CA (1) | CA2212007C (ko) |
DE (2) | DE69627985T2 (ko) |
DK (1) | DK0807630T3 (ko) |
ES (2) | ES2315432T3 (ko) |
FI (1) | FI973207A (ko) |
NO (1) | NO314546B1 (ko) |
PT (1) | PT807630E (ko) |
TW (1) | TW487701B (ko) |
WO (1) | WO1996023782A1 (ko) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6121285A (en) | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
NZ322202A (en) * | 1995-11-22 | 2000-05-26 | Daiichi Pharmaceutical Company | Aminocycloalkylpyrrolidine derivatives and salts thereof with antibacterial activity |
TW519542B (en) * | 1996-09-27 | 2003-02-01 | Daiichi Seiyaku Co | Bicyclic amine derivative |
ZA984527B (en) * | 1997-05-30 | 1998-12-03 | Daiichi Seiyaku Co | Substituted cyclobutylamine derivative |
SK286420B6 (sk) | 1997-09-15 | 2008-09-05 | The Procter & Gamble Company | Zlúčenina so štruktúrou chinolónu, farmaceutický prostriedok s jej obsahom a jej použitie |
GB9822440D0 (en) * | 1998-10-14 | 1998-12-09 | Smithkline Beecham Plc | Medicaments |
AU3191700A (en) * | 1999-03-17 | 2000-10-04 | Daiichi Pharmaceutical Co., Ltd. | Process for producing 5-amino-8- alkylquinolo necarboxylic acid derivatives and intermediates in the production thereof |
BR0111248A (pt) * | 2000-03-31 | 2003-07-08 | Daiichi Seiyaku Co | Derivados de ácido quinolonacarboxìlico |
KR100777149B1 (ko) * | 2000-11-20 | 2007-11-19 | 다이이찌 세이야꾸 가부시기가이샤 | 데할로게노 화합물 |
GB0112834D0 (en) * | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
KR101041277B1 (ko) * | 2002-05-17 | 2011-06-14 | 다이이찌 세이야꾸 가부시기가이샤 | 퀴놀론카르복실산 유도체의 제조방법 |
US6875784B2 (en) * | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
US7915418B2 (en) * | 2003-06-06 | 2011-03-29 | Daiichi Pharmaceutical Co., Ltd. | Intermediates and process for the production of optically active quinolonecarboxylic acid derivatives |
JP4616770B2 (ja) * | 2003-06-19 | 2011-01-19 | 第一三共株式会社 | 選択的なアミノ置換基導入法 |
EP1669354B1 (en) * | 2003-09-29 | 2013-03-20 | Daiichi Sankyo Company, Limited | 8-cyanoquinolonecarboxylic acid derivative |
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 |
CA2647454A1 (en) | 2006-03-28 | 2007-10-04 | The Procter & Gamble Company | A coupling process for preparing quinolone intermediates |
BRPI0709772B8 (pt) | 2006-03-28 | 2021-05-25 | The Protecter & Gamble Company | sais de malato e polimorfos do ácido (3s,5s)-7-[3-amino-5-metil-piperidinil]-1-ciclopropil-1,4-diidro-8-metóxi-4-oxo-3-quinolinocarboxílico |
JP5197606B2 (ja) * | 2007-01-05 | 2013-05-15 | 第一三共株式会社 | フューズ置換型アミノピロリジン誘導体 |
US8278313B2 (en) | 2008-03-11 | 2012-10-02 | Abbott Laboratories | Macrocyclic spiro pyrimidine derivatives |
US8436005B2 (en) | 2008-04-03 | 2013-05-07 | Abbott Laboratories | Macrocyclic pyrimidine derivatives |
US10300155B2 (en) | 2015-12-31 | 2019-05-28 | Washington University | Alpha-synuclein ligands |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5772981A (en) * | 1980-10-22 | 1982-05-07 | Dainippon Pharmaceut Co Ltd | 1,8-naphthyridine derivative and its salt |
CS274601B2 (en) * | 1983-07-27 | 1991-09-15 | Dainippon Pharmaceutical Co | Method of 1,8-naphthyridine derivative production |
JPS60260577A (ja) * | 1984-06-06 | 1985-12-23 | Dainippon Pharmaceut Co Ltd | 1,8−ナフチリジン誘導体 |
ATE75740T1 (de) * | 1985-06-26 | 1992-05-15 | Daiichi Seiyaku Co | Pyridoncarbonsaeurederivate. |
JPH0676400B2 (ja) * | 1987-08-25 | 1994-09-28 | 大日本製薬株式会社 | 新規ピリドンカルボン酸誘導体、そのエステルおよびその塩 |
MY105136A (en) * | 1988-04-27 | 1994-08-30 | Daiichi Seiyaku Co | Optically active pyridonecarboxylic acid derivatives. |
JP2844079B2 (ja) * | 1988-05-23 | 1999-01-06 | 塩野義製薬株式会社 | ピリドンカルボン酸系抗菌剤 |
RU2049777C1 (ru) * | 1989-08-16 | 1995-12-10 | Пфайзер Инк. | Азабицикло-хинолон-карбоновые кислоты или их фармацевтически приемлемые кислотно-аддитивные соли и промежуточные продукты для их получения |
KR100232937B1 (ko) * | 1991-05-28 | 1999-12-01 | 스즈키 다다시 | 피리돈카복실산 유도체 및 이를 함유하는 항균제 |
KR960011370B1 (ko) * | 1991-12-31 | 1996-08-22 | 재단법인 한국화학연구소 | 스피로알킬아민 유도체와 그의 제조방법 |
EP0550016A1 (en) * | 1991-12-31 | 1993-07-07 | Korea Research Institute Of Chemical Technology | Novel quinolone carboxylic acid derivatives and processes for preparing same |
JP2848538B2 (ja) * | 1994-02-04 | 1999-01-20 | 大日本製薬株式会社 | 2環性アミノ基で置換されたピリドンカルボン酸誘導体、そのエステルおよびその塩ならびにこれらの中間体たる2環性アミン |
NZ322202A (en) * | 1995-11-22 | 2000-05-26 | Daiichi Pharmaceutical Company | Aminocycloalkylpyrrolidine derivatives and salts thereof with antibacterial activity |
-
1996
- 1996-02-01 DK DK96901518T patent/DK0807630T3/da active
- 1996-02-01 DE DE69627985T patent/DE69627985T2/de not_active Expired - Fee Related
- 1996-02-01 ES ES03000883T patent/ES2315432T3/es not_active Expired - Lifetime
- 1996-02-01 EP EP03000883A patent/EP1304329B1/en not_active Expired - Lifetime
- 1996-02-01 PT PT96901518T patent/PT807630E/pt unknown
- 1996-02-01 TW TW85101378A patent/TW487701B/zh active
- 1996-02-01 WO PCT/JP1996/000208 patent/WO1996023782A1/ja active IP Right Grant
- 1996-02-01 DE DE69637717T patent/DE69637717D1/de not_active Expired - Lifetime
- 1996-02-01 US US08/875,678 patent/US5849757A/en not_active Expired - Fee Related
- 1996-02-01 ES ES96901518T patent/ES2198474T3/es not_active Expired - Lifetime
- 1996-02-01 AT AT03000883T patent/ATE411309T1/de not_active IP Right Cessation
- 1996-02-01 EP EP96901518A patent/EP0807630B1/en not_active Expired - Lifetime
- 1996-02-01 KR KR1019970705257A patent/KR100389773B1/ko not_active IP Right Cessation
- 1996-02-01 CA CA002212007A patent/CA2212007C/en not_active Expired - Fee Related
- 1996-02-01 AT AT96901518T patent/ATE239720T1/de not_active IP Right Cessation
-
1997
- 1997-07-31 NO NO19973530A patent/NO314546B1/no not_active IP Right Cessation
- 1997-08-01 FI FI973207A patent/FI973207A/fi unknown
Also Published As
Publication number | Publication date |
---|---|
ATE239720T1 (de) | 2003-05-15 |
EP0807630B1 (en) | 2003-05-07 |
WO1996023782A1 (fr) | 1996-08-08 |
EP1304329A3 (en) | 2004-09-15 |
KR19980701860A (ko) | 1998-06-25 |
DE69627985D1 (de) | 2003-06-12 |
EP1304329A2 (en) | 2003-04-23 |
FI973207A0 (fi) | 1997-08-01 |
NO973530L (no) | 1997-10-02 |
US5849757A (en) | 1998-12-15 |
NO973530D0 (no) | 1997-07-31 |
FI973207A (fi) | 1997-10-01 |
ES2315432T3 (es) | 2009-04-01 |
EP0807630A4 (en) | 1998-05-13 |
ES2198474T3 (es) | 2004-02-01 |
TW487701B (en) | 2002-05-21 |
KR100389773B1 (ko) | 2003-10-23 |
EP0807630A1 (en) | 1997-11-19 |
CA2212007A1 (en) | 1996-08-08 |
ATE411309T1 (de) | 2008-10-15 |
CA2212007C (en) | 2004-09-14 |
PT807630E (pt) | 2003-08-29 |
EP1304329B1 (en) | 2008-10-15 |
DE69637717D1 (de) | 2008-11-27 |
DE69627985T2 (de) | 2004-02-19 |
DK0807630T3 (da) | 2003-09-01 |
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