FR2625200A1 - 7-(1-Azetidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and their application as medicaments - Google Patents
7-(1-Azetidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and their application as medicaments Download PDFInfo
- Publication number
- FR2625200A1 FR2625200A1 FR8718289A FR8718289A FR2625200A1 FR 2625200 A1 FR2625200 A1 FR 2625200A1 FR 8718289 A FR8718289 A FR 8718289A FR 8718289 A FR8718289 A FR 8718289A FR 2625200 A1 FR2625200 A1 FR 2625200A1
- Authority
- FR
- France
- Prior art keywords
- radical
- formula
- sep
- hydrogen atom
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title claims description 3
- 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 title 1
- -1 alkenyl radical Chemical class 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 150000003254 radicals Chemical class 0.000 claims abstract description 8
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims abstract description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- SUJKVJSPRDGSJX-UHFFFAOYSA-N 6,8-difluoro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=C(F)C=C2C(=O)C(C(=O)O)=CNC2=C1F SUJKVJSPRDGSJX-UHFFFAOYSA-N 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 244000005700 microbiome Species 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000004611 spectroscopical analysis Methods 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- 241000607142 Salmonella Species 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960001732 pipemidic acid Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical group C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102100039814 E3 ubiquitin-protein ligase RNF170 Human genes 0.000 description 2
- 241000588914 Enterobacter Species 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- 241000588724 Escherichia coli Species 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
- 101000667666 Homo sapiens E3 ubiquitin-protein ligase RNF170 Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000191940 Staphylococcus Species 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
- 230000000845 anti-microbial effect Effects 0.000 description 2
- UQUPQEUNHVVNKW-UHFFFAOYSA-N azetidin-1-ium-3-ol;chloride Chemical compound Cl.OC1CNC1 UQUPQEUNHVVNKW-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 230000000694 effects Effects 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
- 238000000338 in vitro Methods 0.000 description 2
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- 241000588919 Citrobacter freundii Species 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 241000588748 Klebsiella Species 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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- XGFIDSVLLXRAJZ-UHFFFAOYSA-N OC1=CC=C(O)C(=O)C1 Chemical compound OC1=CC=C(O)C(=O)C1 XGFIDSVLLXRAJZ-UHFFFAOYSA-N 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 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
- 230000001684 chronic effect Effects 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940092559 enterobacter aerogenes Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FGICMAMEHORFNK-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 FGICMAMEHORFNK-UHFFFAOYSA-N 0.000 description 1
- 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 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
- NEULISDAWPDSFJ-UHFFFAOYSA-N ethyl 3-oxo-2H-quinoline-2-carboxylate Chemical compound C1=CC=CC2=CC(=O)C(C(=O)OCC)N=C21 NEULISDAWPDSFJ-UHFFFAOYSA-N 0.000 description 1
- LKIBSJCOAXOWJY-UHFFFAOYSA-N ethyl 4-oxo-3h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)C=NC2=C1 LKIBSJCOAXOWJY-UHFFFAOYSA-N 0.000 description 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 description 1
- OTTDACPMYLDVTL-UHFFFAOYSA-N ethyl quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OCC)=CN=C21 OTTDACPMYLDVTL-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000011707 mineral Substances 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
- 239000004540 pour-on Substances 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 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)
Priority Applications (19)
| 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 |
| FR888809816A FR2634483B2 (fr) | 1987-12-29 | 1988-07-20 | Derives des acides 7-(1-azetidinyl)-1,4-dihydro-4-oxoquinoleine-3-carboxyliques, leur preparation et leur application en tant que medicaments |
| US07/290,315 US4927926A (en) | 1987-12-29 | 1988-12-27 | Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids, their preparation and application as medicines |
| DE8888403352T DE3876969T2 (de) | 1987-12-29 | 1988-12-28 | 7-(1-azetidinyl)-1,4-dihydro-4-oxochinolin-3-carbonsaeure-derivate, ihre herstellung und ihre verwendung als arzneimittel. |
| SU884613206A SU1731055A3 (ru) | 1987-12-29 | 1988-12-28 | Способ получени азетидиновых производных 1,4-дигидро-4-оксохинолин-3-карбоновых кислот |
| NO885797A NO176605C (no) | 1987-12-29 | 1988-12-28 | Analogifremgangsmåte til fremstilling av terapeutisk aktive 7-(1-azetidinyl)-1,4-dihydro-4-okso-3-kinolinkarboksylsyrederivater |
| JP63335712A JPH0813811B2 (ja) | 1987-12-29 | 1988-12-28 | ７―（１―アセチジニル）―１、４―ジヒドロ―４―オキソキノリン―３―カルボン酸の誘導体、その製造法、およびその医薬としての用途 |
| YU237088A YU47124B (sh) | 1987-12-29 | 1988-12-28 | Postupak za dobijanje novih derivata 7-(1-azetidinil)-1,4-dihidro-4-oksokinolein-3-karboks ilnih kiselina |
| DK726188A DK726188A (da) | 1987-12-29 | 1988-12-28 | Quinolinderivater |
| 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 |
| EP88403352A EP0324298B1 (fr) | 1987-12-29 | 1988-12-28 | Dérivés des acides 7-(1-azétidinyl)-1,4-dihydro-4-oxoquinoléine-3-carboxyliques, leur préparation et leur application en tant que médicaments |
| ES8900318A ES2010114A6 (es) | 1987-12-29 | 1988-12-28 | Procedimiento de preparacion de derivados de los acidos 1,4-dihidro-4-oxoquinolein-3-carboxilicos. |
| PT89352A PT89352B (pt) | 1987-12-29 | 1988-12-28 | Processo para a preparacao de derivados dos acidos 7-(1-azetidinil)-1,4-dihidro-4-oxoquinoleina-3-carboxilicos e de composicoes farmaceuticas que os contem |
| AT88403352T ATE83774T1 (de) | 1987-12-29 | 1988-12-28 | 7-(1-azetidinyl)-1,4-dihydro-4-oxochinolin-3carbons|ure-derivate, ihre herstellung und ihre verwendung als arzneimittel. |
| ZA889705A ZA889705B (en) | 1987-12-29 | 1988-12-29 | Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinoline-carboxylic acids,their preparation and application as medicines |
| HU886648A HU206206B (en) | 1987-12-29 | 1988-12-29 | Process for producing 7-/1-azetidinyl/-1,4-dihydro-4-oxo-3-quinoline- carboxylic acid derivatives and pharmaceutical compositions comprising same as active ingredient |
| AU27578/88A AU617735B2 (en) | 1987-12-29 | 1988-12-29 | Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3- guinolinecarboxylic acids, their preparation and application as medicines |
| KR1019880017747A KR920004136B1 (ko) | 1987-12-29 | 1988-12-29 | 7-(1-아제티디닐)-1,4-디히드로-4-옥소-3-퀴놀린카르복실산의 유도체 및 그의 제조방법 |
| GR920403018T GR3006664T3 (enrdf_load_stackoverflow) | 1987-12-29 | 1992-12-24 |
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2625200A1 true FR2625200A1 (en) | 1989-06-30 |
| FR2625200B1 FR2625200B1 (enrdf_load_stackoverflow) | 1991-04-12 |
Family
ID=9358387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8718289A Granted 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 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005026146A1 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Azetidinyl quinolones as antibacterial agents |
Families Citing this family (2)
| 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0106489A2 (en) * | 1982-09-09 | 1984-04-25 | Warner-Lambert Company | Antibacterial agents |
| EP0047005B1 (en) * | 1980-09-02 | 1984-11-14 | Daiichi Seiyaku Co., Ltd. | Benzoxazine derivatives |
| 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 |
| EP0241206A2 (en) * | 1986-03-31 | 1987-10-14 | Sankyo Company Limited | Quinoline-3-carboxylic acid derivatives, their preparation and use |
-
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
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047005B1 (en) * | 1980-09-02 | 1984-11-14 | Daiichi Seiyaku Co., Ltd. | Benzoxazine derivatives |
| EP0106489A2 (en) * | 1982-09-09 | 1984-04-25 | Warner-Lambert Company | 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 |
| EP0241206A2 (en) * | 1986-03-31 | 1987-10-14 | Sankyo Company Limited | Quinoline-3-carboxylic acid derivatives, their preparation and use |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 32, no. 12, décembre 1984, page 4907; I.HAYAKAWA et al.: "Synthesis and antibacterial activities of substituted 7-Oxo-2,3-dihydro-7H-pyrido[1,2,3-deÜ[1,4Übenzoxazine-6-carboxylic acids" * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005026146A1 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Azetidinyl quinolones as antibacterial agents |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2625200B1 (enrdf_load_stackoverflow) | 1991-04-12 |
| ZA889705B (en) | 1989-10-25 |
| SU1731055A3 (ru) | 1992-04-30 |
| DD283385A5 (de) | 1990-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ER | Errata listed in the french official journal (bopi) |
Free format text: 26/89 |
|
| ST | Notification of lapse |