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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- 201000009151 chronic rhinitis Diseases 0.000 description 1
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- 239000006071 cream Substances 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 206010062952 diffuse panbronchiolitis Diseases 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 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
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010014665 endocarditis Diseases 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 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
- 238000009472 formulation Methods 0.000 description 1
- 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)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Earth Drilling (AREA)
- Stereophonic System (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1561495 | 1995-02-02 | ||
| JP1948195 | 1995-02-07 | ||
| JP1947895 | 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 (de) |
| EP (2) | EP0807630B1 (de) |
| KR (1) | KR100389773B1 (de) |
| AT (2) | ATE239720T1 (de) |
| CA (1) | CA2212007C (de) |
| DE (2) | DE69627985T2 (de) |
| DK (1) | DK0807630T3 (de) |
| ES (2) | ES2198474T3 (de) |
| FI (1) | FI973207A (de) |
| NO (1) | NO314546B1 (de) |
| PT (1) | PT807630E (de) |
| TW (1) | TW487701B (de) |
| WO (1) | WO1996023782A1 (de) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE317393T1 (de) * | 1995-11-22 | 2006-02-15 | Daiichi Seiyaku Co | Substituierte aminocycloalkylpyrrolidinderivate |
| US6121285A (en) * | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
| TW519542B (en) * | 1996-09-27 | 2003-02-01 | Daiichi Seiyaku Co | Bicyclic amine derivative |
| MY119816A (en) * | 1997-05-30 | 2005-07-29 | Daiichi Seiyaku Co | Substituted cyclobutylamine derivatives |
| CN1264837C (zh) | 1997-09-15 | 2006-07-19 | 普罗克特和甘保尔公司 | 喹诺酮抗微生物剂、其组合物和应用 |
| GB9822440D0 (en) * | 1998-10-14 | 1998-12-09 | Smithkline Beecham Plc | Medicaments |
| EP1167344A4 (de) * | 1999-03-17 | 2004-06-16 | Daiichi Seiyaku Co | Verfahren zur herstellung von 5-amino-8-alkylchinoloncarbonsäure-derivate und zwischenprodukte in ihrer herstellung |
| EP1298131A4 (de) * | 2000-03-31 | 2004-09-08 | Daiichi Seiyaku Co | Derivate der chinoloncarbonsäure |
| WO2002040478A1 (fr) * | 2000-11-20 | 2002-05-23 | Daiichi Pharmaceutical Co., Ltd. | Composes dihalogenes |
| GB0112834D0 (en) * | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| WO2003097634A1 (fr) * | 2002-05-17 | 2003-11-27 | Daiichi Pharmaceutical Co., Ltd. | Procede de production d'un derive d'acide carboxylique et quinoloneprocede de production d'un derive d'acide carboxylique et quinolone |
| US6875784B2 (en) | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
| WO2004108680A1 (ja) * | 2003-06-06 | 2004-12-16 | Daiichi Pharmaceutical Co., Ltd. | 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 |
| US7626029B2 (en) * | 2003-06-19 | 2009-12-01 | Daiichi Pharmaceutical Co., Ltd. | Method of selectively introducing amino substituent |
| JP4619952B2 (ja) * | 2003-09-29 | 2011-01-26 | 第一三共株式会社 | ８−シアノキノロンカルボン酸誘導体 |
| HUE025625T2 (en) | 2003-12-12 | 2016-04-28 | Daiichi Sankyo Co Ltd | Intermediates for the preparation of optically active cyclopropylamine derivatives and a process for the preparation of intermediates |
| BRPI0709220A2 (pt) | 2006-03-28 | 2011-07-12 | Procter & Gamble | processo de acoplamento para preparo de intermediários de quinolona |
| 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 |
| EP2097400B1 (de) | 2007-01-05 | 2013-07-03 | Daiichi Sankyo Company, Limited | Anelliertes substituiertes aminopyrrolidinderivat |
| 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 |
| EP0207420B1 (de) * | 1985-06-26 | 1992-05-06 | Daiichi Pharmaceutical Co., Ltd. | Pyridoncarbonsäurederivate |
| 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 |
| IL90062A (en) * | 1988-04-27 | 1994-10-07 | Daiichi Seiyaku Co | History of pyridonecarboxylic acid, their preparation and pharmaceutical preparations containing them |
| 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 |
| WO1991002526A1 (en) * | 1989-08-16 | 1991-03-07 | Pfizer Inc. | Azabicyclo quinolone carboxylic acids |
| US5696132A (en) * | 1991-05-28 | 1997-12-09 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives |
| KR960011370B1 (ko) * | 1991-12-31 | 1996-08-22 | 재단법인 한국화학연구소 | 스피로알킬아민 유도체와 그의 제조방법 |
| EP0550016A1 (de) * | 1991-12-31 | 1993-07-07 | Korea Research Institute Of Chemical Technology | Chinoloncarbonsäure-Derivate und Verfahren zu ihrer Herstellung |
| DE69526595T2 (de) * | 1994-02-04 | 2002-08-22 | Dainippon Pharmaceutical Co | Pyridoncarbonsäurederivate substituiert von bicyclischer aminogruppe, deren ester und salze, und bicyclisches amin als zwischenprodukt davon |
| ATE317393T1 (de) * | 1995-11-22 | 2006-02-15 | Daiichi Seiyaku Co | Substituierte aminocycloalkylpyrrolidinderivate |
-
1996
- 1996-02-01 DE DE69627985T patent/DE69627985T2/de not_active Expired - Fee Related
- 1996-02-01 TW TW85101378A patent/TW487701B/zh active
- 1996-02-01 AT AT96901518T patent/ATE239720T1/de not_active IP Right Cessation
- 1996-02-01 EP EP96901518A patent/EP0807630B1/de not_active Expired - Lifetime
- 1996-02-01 EP EP03000883A patent/EP1304329B1/de not_active Expired - Lifetime
- 1996-02-01 PT PT96901518T patent/PT807630E/pt unknown
- 1996-02-01 WO PCT/JP1996/000208 patent/WO1996023782A1/ja active IP Right Grant
- 1996-02-01 CA CA002212007A patent/CA2212007C/en not_active Expired - Fee Related
- 1996-02-01 ES ES96901518T patent/ES2198474T3/es not_active Expired - Lifetime
- 1996-02-01 DK DK96901518T patent/DK0807630T3/da active
- 1996-02-01 AT AT03000883T patent/ATE411309T1/de not_active IP Right Cessation
- 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 ES03000883T patent/ES2315432T3/es not_active Expired - Lifetime
- 1996-02-01 KR KR1019970705257A patent/KR100389773B1/ko 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 |
|---|---|
| EP0807630A4 (de) | 1998-05-13 |
| ES2315432T3 (es) | 2009-04-01 |
| NO973530D0 (no) | 1997-07-31 |
| CA2212007A1 (en) | 1996-08-08 |
| DK0807630T3 (da) | 2003-09-01 |
| EP0807630A1 (de) | 1997-11-19 |
| FI973207A0 (fi) | 1997-08-01 |
| EP1304329B1 (de) | 2008-10-15 |
| EP0807630B1 (de) | 2003-05-07 |
| CA2212007C (en) | 2004-09-14 |
| KR100389773B1 (ko) | 2003-10-23 |
| EP1304329A3 (de) | 2004-09-15 |
| ES2198474T3 (es) | 2004-02-01 |
| ATE239720T1 (de) | 2003-05-15 |
| DE69627985T2 (de) | 2004-02-19 |
| KR19980701860A (ko) | 1998-06-25 |
| WO1996023782A1 (fr) | 1996-08-08 |
| PT807630E (pt) | 2003-08-29 |
| US5849757A (en) | 1998-12-15 |
| FI973207A (fi) | 1997-10-01 |
| TW487701B (en) | 2002-05-21 |
| DE69627985D1 (de) | 2003-06-12 |
| NO973530L (no) | 1997-10-02 |
| DE69637717D1 (de) | 2008-11-27 |
| ATE411309T1 (de) | 2008-10-15 |
| EP1304329A2 (de) | 2003-04-23 |
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