DD283385A5 - Verfahren zur herstellung von derivaten der 7-(1-azetidinyl)-1,4-dihydro-4-oxoquinolein-3-carboxylsaeure - Google Patents
Verfahren zur herstellung von derivaten der 7-(1-azetidinyl)-1,4-dihydro-4-oxoquinolein-3-carboxylsaeure Download PDFInfo
- Publication number
- DD283385A5 DD283385A5 DD88324257A DD32425788A DD283385A5 DD 283385 A5 DD283385 A5 DD 283385A5 DD 88324257 A DD88324257 A DD 88324257A DD 32425788 A DD32425788 A DD 32425788A DD 283385 A5 DD283385 A5 DD 283385A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- dihydro
- azetidinyl
- cyclopropyl
- quinolinecarboxylic acid
- Prior art date
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- -1 1-AZETIDINYL Chemical class 0.000 title claims description 78
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- FWDSBOPYZSSIOZ-UHFFFAOYSA-N 7-(3-acetyloxyazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(OC(=O)C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F FWDSBOPYZSSIOZ-UHFFFAOYSA-N 0.000 claims description 4
- QLHBFUQSCBWFAS-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-(2,4-difluorophenyl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1F QLHBFUQSCBWFAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- UHRNUAOWXYNRRP-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-6,8-difluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(F)=CC=3)C2=C1F UHRNUAOWXYNRRP-UHFFFAOYSA-N 0.000 claims description 3
- YNOXZFMMWKSQMB-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-6-fluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1 YNOXZFMMWKSQMB-UHFFFAOYSA-N 0.000 claims description 3
- URLUPDCRQWXDCW-UHFFFAOYSA-N 7-[3-(aminomethyl)azetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CN)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F URLUPDCRQWXDCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- UUXXDPWABMNWFB-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-6-fluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2CCF UUXXDPWABMNWFB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- JMWWRQAAIBOINE-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F JMWWRQAAIBOINE-UHFFFAOYSA-N 0.000 claims 1
- LBTBHXWVRBEJNU-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-ethyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CC(C)(N)C1 LBTBHXWVRBEJNU-UHFFFAOYSA-N 0.000 claims 1
- PAWLYNZWCMTLIM-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-6,8-difluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CCF)C2=C1F PAWLYNZWCMTLIM-UHFFFAOYSA-N 0.000 claims 1
- ZMZJWNQVCHLZAX-UHFFFAOYSA-N 7-(azetidin-1-yl)-4-oxo-1h-quinoline-3-carboxylic acid Chemical class C=1C=C2C(=O)C(C(=O)O)=CNC2=CC=1N1CCC1 ZMZJWNQVCHLZAX-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- MEPPHXILHQKRGG-UHFFFAOYSA-N ethyl 7-[3-(acetamidomethyl)azetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(N3CC(CNC(C)=O)C3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 MEPPHXILHQKRGG-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 208000015181 infectious disease Diseases 0.000 abstract description 3
- 241000192125 Firmicutes Species 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 105
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 83
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 54
- 238000002844 melting Methods 0.000 description 53
- 230000008018 melting Effects 0.000 description 53
- 238000004611 spectroscopical analysis Methods 0.000 description 51
- 239000000203 mixture Substances 0.000 description 49
- 238000010992 reflux Methods 0.000 description 44
- 238000005481 NMR spectroscopy Methods 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 241000193830 Bacillus <bacterium> Species 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 9
- 244000005700 microbiome Species 0.000 description 9
- 241000607768 Shigella Species 0.000 description 8
- 108091005960 Citrine Proteins 0.000 description 7
- 239000011035 citrine Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241001467018 Typhis Species 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NCMNCUSDKZJEKW-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(O)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F NCMNCUSDKZJEKW-UHFFFAOYSA-N 0.000 description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- 241000588767 Proteus vulgaris Species 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 229940007042 proteus vulgaris Drugs 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XDLPWPNVUPKKSN-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(methylamino)azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NC)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 XDLPWPNVUPKKSN-UHFFFAOYSA-N 0.000 description 3
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 3
- FEMZVDSBIXDODB-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F FEMZVDSBIXDODB-UHFFFAOYSA-N 0.000 description 3
- BVFQNHJTTGCGNK-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F BVFQNHJTTGCGNK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000193755 Bacillus cereus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000588769 Proteus <enterobacteria> Species 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- UQUPQEUNHVVNKW-UHFFFAOYSA-N azetidin-1-ium-3-ol;chloride Chemical compound Cl.OC1CNC1 UQUPQEUNHVVNKW-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NMASXYCNDJMMFR-UHFFFAOYSA-N 1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 NMASXYCNDJMMFR-UHFFFAOYSA-N 0.000 description 2
- KNEXGVPHPGXAGF-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 KNEXGVPHPGXAGF-UHFFFAOYSA-N 0.000 description 2
- QSNYNWOQOIJCFV-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-(methylamino)azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F QSNYNWOQOIJCFV-UHFFFAOYSA-N 0.000 description 2
- KRMVDUVKZGVFBU-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(dimethylamino)azetidin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N(C)C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F KRMVDUVKZGVFBU-UHFFFAOYSA-N 0.000 description 2
- RGNZSFXVBCYEPT-UHFFFAOYSA-N 2,2,2-trifluoro-n-(3-methylazetidin-3-yl)acetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)NC1(C)CNC1 RGNZSFXVBCYEPT-UHFFFAOYSA-N 0.000 description 2
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 2
- UAYYWDWWESZIPA-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 UAYYWDWWESZIPA-UHFFFAOYSA-N 0.000 description 2
- IKZBNCORGKYEDZ-UHFFFAOYSA-N 7-(3-aminoazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F IKZBNCORGKYEDZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 239000012891 Ringer solution Substances 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- HGQULGDOROIPJN-UHFFFAOYSA-N azetidin-1-ium;chloride Chemical compound Cl.C1CNC1 HGQULGDOROIPJN-UHFFFAOYSA-N 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
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- 239000008121 dextrose Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- PGXGEQOSJMUQBW-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(N3CC(O)C3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 PGXGEQOSJMUQBW-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- PWOYTBYNBYNZCO-UHFFFAOYSA-N ethyl quinoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)OCC)=CC=C21 PWOYTBYNBYNZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- DHXXDTCOJUYKOQ-UHFFFAOYSA-N n,n-dimethylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CN(C)C1CNC1 DHXXDTCOJUYKOQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- RLKQFGFEEROESJ-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F RLKQFGFEEROESJ-UHFFFAOYSA-N 0.000 description 1
- LTEMZCCDDFSPQZ-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6,8-difluoro-7-[3-methyl-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1F LTEMZCCDDFSPQZ-UHFFFAOYSA-N 0.000 description 1
- XZLGGGLACMVVTI-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-[3-[[(2,2,2-trifluoroacetyl)amino]methyl]azetidin-1-yl]quinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(CNC(=O)C(F)(F)F)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 XZLGGGLACMVVTI-UHFFFAOYSA-N 0.000 description 1
- SZKDCHHLZYNMLV-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-methyl-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F SZKDCHHLZYNMLV-UHFFFAOYSA-N 0.000 description 1
- XOMWMRGJYMHAON-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-methyl-3-[[(2,2,2-trifluoroacetyl)amino]methyl]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(CNC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F XOMWMRGJYMHAON-UHFFFAOYSA-N 0.000 description 1
- QDJIIIDZZJHSOD-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-methyl-3-[[(2,2,2-trifluoroacetyl)amino]methyl]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(CNC(=O)C(F)(F)F)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 QDJIIIDZZJHSOD-UHFFFAOYSA-N 0.000 description 1
- KCXCROGVXIKNKX-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(dimethylamino)-3-methylazetidin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N(C)C)(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F KCXCROGVXIKNKX-UHFFFAOYSA-N 0.000 description 1
- WDVARCXIMHNTPQ-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(dimethylamino)azetidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N(C)C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 WDVARCXIMHNTPQ-UHFFFAOYSA-N 0.000 description 1
- XCMSBTPBSCLKOX-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(ethylaminomethyl)-3-methylazetidin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNCC)(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F XCMSBTPBSCLKOX-UHFFFAOYSA-N 0.000 description 1
- HVUJMIKTWOKCJD-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(ethylaminomethyl)-3-methylazetidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNCC)(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 HVUJMIKTWOKCJD-UHFFFAOYSA-N 0.000 description 1
- VYGBBZUTGOJPBB-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(ethylaminomethyl)azetidin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNCC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F VYGBBZUTGOJPBB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical class NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- XEUIUSSYDUIFRI-UHFFFAOYSA-N 3-methylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CC1(N)CNC1 XEUIUSSYDUIFRI-UHFFFAOYSA-N 0.000 description 1
- YCAZALSUJDPQPP-UHFFFAOYSA-N 4-oxo-3h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)C=NC2=C1 YCAZALSUJDPQPP-UHFFFAOYSA-N 0.000 description 1
- KRBQJNAQTNYREQ-UHFFFAOYSA-N 6,7,8-trifluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)O)=CN(CCF)C2=C1F KRBQJNAQTNYREQ-UHFFFAOYSA-N 0.000 description 1
- BFCGHXVOVSHPIC-UHFFFAOYSA-N 6,7-dichloro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound ClC1=C(Cl)C=C2C(=O)C(C(=O)O)=CNC2=C1 BFCGHXVOVSHPIC-UHFFFAOYSA-N 0.000 description 1
- ZBGVFPLTIBCTRU-UHFFFAOYSA-N 6,7-difluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)O)=CN(CCF)C2=C1 ZBGVFPLTIBCTRU-UHFFFAOYSA-N 0.000 description 1
- RWCWKPZDWFXAFG-UHFFFAOYSA-N 6,7-difluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 RWCWKPZDWFXAFG-UHFFFAOYSA-N 0.000 description 1
- UXQLQLPOBVXSHN-UHFFFAOYSA-N 7-(azetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 UXQLQLPOBVXSHN-UHFFFAOYSA-N 0.000 description 1
- LYCJYANNJJCKHJ-UHFFFAOYSA-N 7-[3-(acetamidomethyl)azetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNC(=O)C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F LYCJYANNJJCKHJ-UHFFFAOYSA-N 0.000 description 1
- LFUFXWPGZKTTHK-UHFFFAOYSA-N 7-[3-(aminomethyl)-3-methylazetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(CN)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F LFUFXWPGZKTTHK-UHFFFAOYSA-N 0.000 description 1
- RXEMBKIPUSCYPB-UHFFFAOYSA-N 7-[3-(aminomethyl)-3-methylazetidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(CN)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 RXEMBKIPUSCYPB-UHFFFAOYSA-N 0.000 description 1
- GVNYGWLTQUNLFJ-UHFFFAOYSA-N 7-[3-amino-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-1-(2,4-difluorophenyl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1F GVNYGWLTQUNLFJ-UHFFFAOYSA-N 0.000 description 1
- ADGVPYJZEKBEBB-UHFFFAOYSA-N 7-[3-amino-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-6,8-difluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(F)=CC=3)C2=C1F ADGVPYJZEKBEBB-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- UNCFNIZANBZRHN-UHFFFAOYSA-N Cl.FC(C(=O)NN1CCC1)(F)F Chemical compound Cl.FC(C(=O)NN1CCC1)(F)F UNCFNIZANBZRHN-UHFFFAOYSA-N 0.000 description 1
- JBGSWIBJAGBGOP-UHFFFAOYSA-N Dehydronuciferine Natural products C1=CC=C2C3=C(OC)C(OC)=CC(CCN4C)=C3C4=CC2=C1 JBGSWIBJAGBGOP-UHFFFAOYSA-N 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 101001081176 Homo sapiens Hyaluronan mediated motility receptor Proteins 0.000 description 1
- 102100027735 Hyaluronan mediated motility receptor Human genes 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 206010024774 Localised infection Diseases 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- OOSDLMAZIRAMDN-UHFFFAOYSA-N azetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.NC1CNC1 OOSDLMAZIRAMDN-UHFFFAOYSA-N 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940092559 enterobacter aerogenes Drugs 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SIHPPMBRVAOGNG-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,8-difluoro-7-(3-methylsulfonyloxyazetidin-1-yl)-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(N3CC(C3)OS(C)(=O)=O)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 SIHPPMBRVAOGNG-UHFFFAOYSA-N 0.000 description 1
- GCYPBNZGXFMKST-UHFFFAOYSA-N ethyl 7-amino-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(N)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 GCYPBNZGXFMKST-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229940045505 klebsiella pneumoniae Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VNLUDOWOYBHVIO-UHFFFAOYSA-N n-(azetidin-3-ylmethyl)-2,2,2-trifluoroacetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)NCC1CNC1 VNLUDOWOYBHVIO-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- DASZTFGYDXJWBT-UHFFFAOYSA-N quinoline-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(C(=O)O)=CC=C21 DASZTFGYDXJWBT-UHFFFAOYSA-N 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- PLTCLMZAIZEHGD-UHFFFAOYSA-M sodium;quinoline-2-carboxylate Chemical compound [Na+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 PLTCLMZAIZEHGD-UHFFFAOYSA-M 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8718289A FR2625200A1 (en) | 1987-12-29 | 1987-12-29 | 7-(1-Azetidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and their application as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD283385A5 true DD283385A5 (de) | 1990-10-10 |
Family
ID=9358387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88324257A DD283385A5 (de) | 1987-12-29 | 1988-12-28 | Verfahren zur herstellung von derivaten der 7-(1-azetidinyl)-1,4-dihydro-4-oxoquinolein-3-carboxylsaeure |
Country Status (4)
| Country | Link |
|---|---|
| DD (1) | DD283385A5 (enrdf_load_stackoverflow) |
| FR (1) | FR2625200A1 (enrdf_load_stackoverflow) |
| SU (1) | SU1731055A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA889705B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5527910A (en) * | 1992-12-30 | 1996-06-18 | Cheil Foods & Chemicals, Inc. | Pyridone carboxylic acid compounds and their uses for treating infectious diseases caused by bacteria |
| DE69840599D1 (de) * | 1997-09-15 | 2009-04-09 | Procter & Gamble | Antimikrobielle chinolone, ihre zusammensetzungen und ihre verwendungen |
| WO2005026146A1 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Azetidinyl quinolones as antibacterial agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| US4617308A (en) * | 1985-01-25 | 1986-10-14 | Warner-Lambert Company | 7-substituted amino-1-aryl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids and derivatives thereof as antibacterial agents |
| CN1019114B (zh) * | 1986-03-31 | 1992-11-18 | 三共株式会社 | 喹啉-3-羟酸衍生物的制备方法 |
-
1987
- 1987-12-29 FR FR8718289A patent/FR2625200A1/fr active Granted
-
1988
- 1988-12-28 SU SU884613206A patent/SU1731055A3/ru active
- 1988-12-28 DD DD88324257A patent/DD283385A5/de not_active IP Right Cessation
- 1988-12-29 ZA ZA889705A patent/ZA889705B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2625200B1 (enrdf_load_stackoverflow) | 1991-04-12 |
| ZA889705B (en) | 1989-10-25 |
| SU1731055A3 (ru) | 1992-04-30 |
| FR2625200A1 (en) | 1989-06-30 |
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