NO871727L - Fremgangsmaate for fremstilling av nye kinolinderivater. - Google Patents
Fremgangsmaate for fremstilling av nye kinolinderivater.Info
- Publication number
- NO871727L NO871727L NO871727A NO871727A NO871727L NO 871727 L NO871727 L NO 871727L NO 871727 A NO871727 A NO 871727A NO 871727 A NO871727 A NO 871727A NO 871727 L NO871727 L NO 871727L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- group
- hydrogen atom
- lower alkyl
- cyclopropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 10
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 122
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 25
- 125000003277 amino group Chemical group 0.000 claims description 21
- 125000006239 protecting group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
- 239000000203 mixture Substances 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- -1 acetic Chemical class 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000001914 filtration Methods 0.000 description 18
- 239000007858 starting material Substances 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 15
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 13
- 235000011054 acetic acid Nutrition 0.000 description 13
- 208000015181 infectious disease Diseases 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000000844 anti-bacterial effect Effects 0.000 description 11
- CQPUZLMNORVQPG-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C=2C(N)=C(F)C(F)=C(F)C=2N1C1CC1 CQPUZLMNORVQPG-UHFFFAOYSA-N 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- RFZHFIFSQNIHAI-UHFFFAOYSA-N 1-cyclopropyl-5,6,7,8-tetrafluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 RFZHFIFSQNIHAI-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- IIFSGGRTVWXXBK-UHFFFAOYSA-N 5-amino-7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CCN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F IIFSGGRTVWXXBK-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- UVPAOMFBMNZWTA-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(C)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F UVPAOMFBMNZWTA-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- AGSWPKBTSCTGIV-NWDGAFQWSA-N 5-amino-1-cyclopropyl-7-[(3r,4r)-3-ethyl-4-(ethylaminomethyl)pyrrolidin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@H](CC)[C@H](CNCC)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F AGSWPKBTSCTGIV-NWDGAFQWSA-N 0.000 description 4
- NUEBFYJEZHOXRC-GMSGAONNSA-N 5-amino-7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](N)[C@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F NUEBFYJEZHOXRC-GMSGAONNSA-N 0.000 description 4
- GMTQODAJNSSRQH-UHFFFAOYSA-N 7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F GMTQODAJNSSRQH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- ODNFQSJPMHJALQ-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-[3-(fluoromethyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(CF)NCC3)=C(F)C(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 ODNFQSJPMHJALQ-UHFFFAOYSA-N 0.000 description 3
- WGOWOSXVPSBDEY-UHFFFAOYSA-N 3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCNC1 WGOWOSXVPSBDEY-UHFFFAOYSA-N 0.000 description 3
- FPTGKCPCYVCMJD-UHFFFAOYSA-N 5-amino-7-(3-amino-3-ethylpyrrolidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CC)(N)CCN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F FPTGKCPCYVCMJD-UHFFFAOYSA-N 0.000 description 3
- ZOKDYXCIFLCJLB-OIBJUYFYSA-N 7-[(3s,4s)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](N)[C@@H](C)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F ZOKDYXCIFLCJLB-OIBJUYFYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KCXHMWDUZQIXQO-UHFFFAOYSA-N C(C)(=O)N1C(CN(CC1)C1=C(C(=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C1F)F)F)F)C Chemical compound C(C)(=O)N1C(CN(CC1)C1=C(C(=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C1F)F)F)F)C KCXHMWDUZQIXQO-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 125000002496 methyl group Chemical group [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
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000003797 solvolysis reaction Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SLTMFXXAJKCIPQ-RFZPGFLSSA-N (3s,4r)-4-methylpyrrolidin-3-amine Chemical compound C[C@@H]1CNC[C@H]1N SLTMFXXAJKCIPQ-RFZPGFLSSA-N 0.000 description 2
- IJMWPCSFRUDKFB-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCNCC3)=C(F)C(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 IJMWPCSFRUDKFB-UHFFFAOYSA-N 0.000 description 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 2
- CDUICXTVURICQY-UHFFFAOYSA-N 5-amino-7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1C(C)(N)CCN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F CDUICXTVURICQY-UHFFFAOYSA-N 0.000 description 2
- MQVPVBQTYNVHFA-DTWKUNHWSA-N 5-amino-7-[(3r,4r)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](CN)[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F MQVPVBQTYNVHFA-DTWKUNHWSA-N 0.000 description 2
- VEBMVQVIWUIMIB-OULXEKPRSA-N 5-amino-7-[(3r,4r)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1[C@@H](CN)[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F VEBMVQVIWUIMIB-OULXEKPRSA-N 0.000 description 2
- KNQFZXDCIPRPFH-NXEZZACHSA-N 5-amino-7-[(3r,4s)-3-(aminomethyl)-4-ethylpyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](CN)[C@H](CC)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F KNQFZXDCIPRPFH-NXEZZACHSA-N 0.000 description 2
- MQVPVBQTYNVHFA-RKDXNWHRSA-N 5-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](CN)[C@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F MQVPVBQTYNVHFA-RKDXNWHRSA-N 0.000 description 2
- ZOKDYXCIFLCJLB-GMSGAONNSA-N 7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](N)[C@H](C)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F ZOKDYXCIFLCJLB-GMSGAONNSA-N 0.000 description 2
- FKXGBQWZQYPTQI-OIBJUYFYSA-N 7-[(3s,4s)-3-amino-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@H](CF)[C@H](N)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F FKXGBQWZQYPTQI-OIBJUYFYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- QIPQASLPWJVQMH-DTORHVGOSA-N Orbifloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F QIPQASLPWJVQMH-DTORHVGOSA-N 0.000 description 2
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005101 aryl methoxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HREKGMYVJBVEOU-UHFFFAOYSA-N ethyl 1-cyclopropyl-5-(ethoxycarbonylamino)-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C1=C(C(=O)OCC)C(=O)C=2C(NC(=O)OCC)=C(F)C(F)=C(F)C=2N1C1CC1 HREKGMYVJBVEOU-UHFFFAOYSA-N 0.000 description 1
- DWRDNFXSCILLLP-UHFFFAOYSA-N ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=C(F)C(NCC=3C=CC=CC=3)=C2C(=O)C(C(=O)OCC)=CN1C1CC1 DWRDNFXSCILLLP-UHFFFAOYSA-N 0.000 description 1
- BOFBKJLYZUFZMV-UHFFFAOYSA-N ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=C(F)C(N)=C2C(=O)C(C(=O)OCC)=CN1C1CC1 BOFBKJLYZUFZMV-UHFFFAOYSA-N 0.000 description 1
- DMIMOPIWTDBMFD-UHFFFAOYSA-N ethyl 7-(3-acetamido-3-methylpyrrolidin-1-yl)-1-cyclopropyl-5-(ethoxycarbonylamino)-6,8-difluoro-4-oxoquinoline-3-carboxylate Chemical compound FC=1C=2N(C3CC3)C=C(C(=O)OCC)C(=O)C=2C(NC(=O)OCC)=C(F)C=1N1CCC(C)(NC(C)=O)C1 DMIMOPIWTDBMFD-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- FHUVQAZMVCLIIW-UHFFFAOYSA-N n-(3-methylpyrrolidin-3-yl)acetamide Chemical compound CC(=O)NC1(C)CCNC1 FHUVQAZMVCLIIW-UHFFFAOYSA-N 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940055076 parasympathomimetics choline ester Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 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
- 230000036325 urinary excretion Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9754386 | 1986-04-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO871727D0 NO871727D0 (no) | 1987-04-24 |
| NO871727L true NO871727L (no) | 1987-10-26 |
Family
ID=14195155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO871727A NO871727L (no) | 1986-04-25 | 1987-04-24 | Fremgangsmaate for fremstilling av nye kinolinderivater. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4886810A (ru) |
| EP (1) | EP0242789A3 (ru) |
| JP (1) | JP2572591B2 (ru) |
| KR (1) | KR870010005A (ru) |
| CN (1) | CN87103138A (ru) |
| AU (1) | AU7190987A (ru) |
| DD (1) | DD263290A5 (ru) |
| DK (1) | DK208787A (ru) |
| FI (1) | FI871788A (ru) |
| HU (1) | HU198198B (ru) |
| IL (1) | IL82246A0 (ru) |
| NO (1) | NO871727L (ru) |
| PH (1) | PH23326A (ru) |
| PT (1) | PT84749B (ru) |
| SU (3) | SU1582986A3 (ru) |
| YU (4) | YU73987A (ru) |
| ZA (1) | ZA872874B (ru) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4822801A (en) * | 1984-07-20 | 1989-04-18 | Warner-Lambert Company | 4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial agents |
| ATE75740T1 (de) * | 1985-06-26 | 1992-05-15 | Daiichi Seiyaku Co | Pyridoncarbonsaeurederivate. |
| AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
| DE3711193A1 (de) * | 1987-04-02 | 1988-10-13 | Bayer Ag | 5-substituierte chinolon- und naphthyridoncarbonsaeure-derivate |
| US5591744A (en) * | 1987-04-16 | 1997-01-07 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| IL88003A (en) * | 1987-10-16 | 1992-11-15 | Dainippon Pharmaceutical Co | Quinoline derivatives,their preparation and pharmaceutical compositions containing them |
| NO885426L (no) * | 1987-12-11 | 1989-06-12 | Dainippon Pharmaceutical Co | Kinolinderivater, samt fremgangsmaate ved fremstilling derav. |
| US4920120A (en) * | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
| US5585491A (en) * | 1988-01-25 | 1996-12-17 | Otsuka Pharmaceutical Co., Ltd. | Antibacterial agents |
| DE3814517A1 (de) * | 1988-02-05 | 1989-08-17 | Bayer Ag | Chinolon- und naphthyridoncarbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| US5173484A (en) * | 1988-02-05 | 1992-12-22 | Bayer Aktiengesellschaft | Quinolone- and naphthyridone carboxylic acid derivatives, process for their production, antibacterial compositions and feed additives containing them |
| AU609974B2 (en) * | 1988-05-18 | 1991-05-09 | Warner-Lambert Company | Improved process for the preparation of 5-amino-7- (substituted amino)-quinoline-3-carboxylic acids |
| JPH0674261B2 (ja) * | 1988-06-21 | 1994-09-21 | 塩野義製薬株式会社 | キノロンカルボン酸誘導体 |
| US5057523A (en) * | 1988-09-22 | 1991-10-15 | Abbott Laboratories | Dipeptide quinolone derivatives |
| CA1332605C (en) * | 1988-10-03 | 1994-10-18 | Yasuhiro Nishitani | Pyridonecarboxylic acids |
| US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
| CA2058424A1 (en) * | 1989-07-21 | 1991-01-22 | Akihiro Shibata | Quinoline carboxylic acid derivatives |
| ES2019551A6 (es) * | 1990-04-11 | 1991-06-16 | Ercros Sa | Procedimiento para la obtencion de derivados del acido 6-fluor-1, 4-dihidro-4-oxo-7-piperacinil-3-quinlincarboxilico. |
| ES2147721T3 (es) | 1990-04-18 | 2000-10-01 | Procter & Gamble Pharma | Quinolonil lactamas antimicrobianas. |
| DE4019023A1 (de) * | 1990-06-14 | 1991-12-19 | Bayer Ag | Verfahren zur herstellung von chinolincarbonsaeuren |
| US5221676A (en) * | 1992-02-06 | 1993-06-22 | Warner-Lambert Company | 7-substituted quinolones and naphthyridones as antibacterial agents |
| EP0677522A4 (en) * | 1992-12-28 | 1995-12-27 | Yoshitomi Pharmaceutical | 8-METHOXYQUINOLONECARBOXYLIC ACID DERIVATIVE. |
| CA2152828A1 (en) * | 1993-03-16 | 1994-07-07 | Shin-Ichi Uesato | 8-methoxy-quinolonecarboxylic acid derivatives |
| TW252107B (ru) * | 1993-08-27 | 1995-07-21 | Hokuriku Pharmacetical Co Ltd | |
| AU8003594A (en) * | 1993-10-28 | 1995-05-22 | Kaken Pharmaceutical Co., Ltd. | Quinolinecarboxylic acid derivative and salt thereof |
| NZ290722A (en) * | 1994-08-02 | 1999-03-29 | Procter & Gamble | A process for making derivatives of quinolonyl lactam (qla's); intermediates |
| JPH10504815A (ja) * | 1994-08-02 | 1998-05-12 | ザ、プロクター、エンド、ギャンブル、カンパニー | 抗微生物化合物の製造方法 |
| WO1996022988A1 (fr) * | 1995-01-24 | 1996-08-01 | Hokuriku Seiyaku Co., Ltd. | Derives de l'acide quiloleine carboxylique |
| MY132897A (en) * | 1997-06-24 | 2007-10-31 | Daiichi Seiyaku Co | Cis- substituted fluoromethylpyrrolidine derivative |
| JP4639149B2 (ja) * | 2003-09-10 | 2011-02-23 | 杏林製薬株式会社 | ７−（４−置換−３−シクロプロピルアミノメチル−１−ピロリジニル）キノロンカルボン酸誘導体 |
| GB0505969D0 (en) | 2005-03-23 | 2005-04-27 | Novartis Ag | Organic compounds |
| US7563805B2 (en) * | 2005-05-19 | 2009-07-21 | Daiichi Pharmaceutical Co., Ltd. | Tri-, tetra-substituted-3-aminopyrrolidine derivative |
| JP5063032B2 (ja) * | 2005-05-19 | 2012-10-31 | 第一三共株式会社 | トリ−、テトラ−置換−３−アミノピロリジン誘導体 |
| JP5197606B2 (ja) | 2007-01-05 | 2013-05-15 | 第一三共株式会社 | フューズ置換型アミノピロリジン誘導体 |
| WO2008143343A1 (ja) * | 2007-05-24 | 2008-11-27 | Kyorin Pharmaceutical Co., Ltd. | １４位置換基に複素芳香環カルボン酸構造を有するムチリン誘導体 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4665079A (en) * | 1984-02-17 | 1987-05-12 | Warner-Lambert Company | Antibacterial agents |
| DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
| ZA852369B (en) * | 1984-04-26 | 1985-12-24 | Abbott Lab | Quinoline antibacterial compounds |
| IE58742B1 (en) * | 1984-07-20 | 1993-11-05 | Warner Lambert Co | Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de] [1,4]benzoxauine-6-carboxylic acids; sibstituted-5-amino-6-6fluoro-4-oxo.1,4-dihydroquinoline-3 carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1.8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds |
| US4771054A (en) * | 1985-01-23 | 1988-09-13 | Warner-Lambert Company | Antibacterial agents |
| US4657913A (en) * | 1985-04-18 | 1987-04-14 | Warner-Lambert Company | Trifluoro- quinoline -3- carboxylic acids and their use as anti-bacterial agents |
| AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
| US4668680A (en) * | 1985-12-12 | 1987-05-26 | Warner-Lambert Company | 5-amino-6,8-difluoroquinolones as antibacterial agents |
| US4977154A (en) * | 1985-12-12 | 1990-12-11 | Warner-Lambert Company | 5-amino and 5-hydroxy-6-fluoroquinolones as antibacterial agents |
| US4771055A (en) * | 1986-07-28 | 1988-09-13 | Warner-Lambert Company | 7-[[3-(aminomethyl)-3-alkyl]-1-pyrrolidinyl]-quinoline-carboxylic acids |
-
1987
- 1987-04-15 EP EP19870105602 patent/EP0242789A3/en not_active Withdrawn
- 1987-04-17 IL IL82246A patent/IL82246A0/xx unknown
- 1987-04-22 DD DD87302040A patent/DD263290A5/de not_active IP Right Cessation
- 1987-04-23 AU AU71909/87A patent/AU7190987A/en not_active Abandoned
- 1987-04-23 PT PT84749A patent/PT84749B/pt unknown
- 1987-04-23 ZA ZA872874A patent/ZA872874B/xx unknown
- 1987-04-23 FI FI871788A patent/FI871788A/fi not_active Application Discontinuation
- 1987-04-23 YU YU00739/87A patent/YU73987A/xx unknown
- 1987-04-24 NO NO871727A patent/NO871727L/no unknown
- 1987-04-24 JP JP62102586A patent/JP2572591B2/ja not_active Expired - Lifetime
- 1987-04-24 DK DK208787A patent/DK208787A/da not_active Application Discontinuation
- 1987-04-24 PH PH35178A patent/PH23326A/en unknown
- 1987-04-24 HU HU871795A patent/HU198198B/hu not_active IP Right Cessation
- 1987-04-25 KR KR870004013A patent/KR870010005A/ko not_active Application Discontinuation
- 1987-04-25 CN CN198787103138A patent/CN87103138A/zh active Pending
- 1987-04-27 US US07/042,806 patent/US4886810A/en not_active Expired - Fee Related
-
1988
- 1988-02-11 YU YU00276/88A patent/YU27688A/xx unknown
- 1988-02-11 YU YU00277/88A patent/YU27788A/xx unknown
- 1988-02-11 YU YU00274/88A patent/YU27488A/xx unknown
- 1988-03-28 SU SU884355430A patent/SU1582986A3/ru active
- 1988-03-30 SU SU884355417A patent/SU1588281A3/ru active
- 1988-04-18 SU SU884355529A patent/SU1588282A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| YU27688A (en) | 1988-12-31 |
| EP0242789A3 (en) | 1990-09-05 |
| SU1588282A3 (ru) | 1990-08-23 |
| ZA872874B (en) | 1987-10-12 |
| SU1582986A3 (ru) | 1990-07-30 |
| AU7190987A (en) | 1987-10-29 |
| IL82246A0 (en) | 1987-10-30 |
| JP2572591B2 (ja) | 1997-01-16 |
| YU27488A (en) | 1988-10-31 |
| EP0242789A2 (en) | 1987-10-28 |
| PT84749B (en) | 1989-06-07 |
| KR870010005A (ko) | 1987-11-30 |
| DK208787A (da) | 1987-10-26 |
| YU73987A (en) | 1988-08-31 |
| DD263290A5 (de) | 1988-12-28 |
| NO871727D0 (no) | 1987-04-24 |
| US4886810A (en) | 1989-12-12 |
| YU27788A (en) | 1990-04-30 |
| JPS6345261A (ja) | 1988-02-26 |
| PH23326A (en) | 1989-07-14 |
| HU198198B (en) | 1989-08-28 |
| HUT45520A (en) | 1988-07-28 |
| SU1588281A3 (ru) | 1990-08-23 |
| FI871788A0 (fi) | 1987-04-23 |
| PT84749A (en) | 1987-05-01 |
| DK208787D0 (da) | 1987-04-24 |
| FI871788A (fi) | 1987-10-26 |
| CN87103138A (zh) | 1987-11-04 |
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