CA1259315A - Acide 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxo-3-quinoleine-carboxylique - Google Patents

Acide 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxo-3-quinoleine-carboxylique

Info

Publication number: CA1259315A
Authority: CA; Canada
Prior art keywords: oxo; cyclopropyl; dihydro; acid; fluoro
Prior art date: 1984-06-04
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.): Expired

Application number

CA000577424A

Other languages

English (en)

Inventor

Uwe Petersen

Klaus Grohe

Hans-Joachim Zeiler

Karl G. Metzger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1984-06-04

Filing date

1988-09-14

Publication date

1989-09-12

1984-06-04 Priority claimed from DE19843420743 external-priority patent/DE3420743A1/de

1985-05-31 Priority claimed from CA000482912A external-priority patent/CA1248954A/fr

1988-09-14 Application filed by Bayer AG filed Critical Bayer AG

1988-09-14 Priority to CA000577424A priority Critical patent/CA1259315A/fr

1989-09-12 Application granted granted Critical

1989-09-12 Publication of CA1259315A publication Critical patent/CA1259315A/fr

Status Expired legal-status Critical Current

Links

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 title claims abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 59
LKQCRNYORFBFHR-UHFFFAOYSA-N 1-cyclopropyl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 LKQCRNYORFBFHR-UHFFFAOYSA-N 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
239000002253 acid Substances 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
-1 methoxy, amino, dimethylamino Chemical group 0.000 description 26
239000000203 mixture Substances 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
238000000034 method Methods 0.000 description 16
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 15
125000000896 monocarboxylic acid group Chemical group 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
229910052731 fluorine Inorganic materials 0.000 description 11
239000011737 fluorine Substances 0.000 description 11
239000003981 vehicle Substances 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000003826 tablet Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
239000011230 binding agent Substances 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 5
XWCKIXLTBNGIHV-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(F)=C1F XWCKIXLTBNGIHV-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
244000052769 pathogen Species 0.000 description 5
229960005141 piperazine Drugs 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RIMRLBGNCLMSNH-UHFFFAOYSA-N 2-phenylpiperazine Chemical compound C1NCCNC1C1=CC=CC=C1 RIMRLBGNCLMSNH-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
239000006187 pill Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000588914 Enterobacter Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000588769 Proteus <enterobacteria> Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
230000009977 dual effect Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 3
229960001180 norfloxacin Drugs 0.000 description 3
125000005188 oxoalkyl group Chemical group 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
WWYFHDNQGVTJJJ-UHFFFAOYSA-N 2-cyclohexylpiperazine Chemical class C1CCCCC1C1NCCNC1 WWYFHDNQGVTJJJ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000192125 Firmicutes Species 0.000 description 2
241000206672 Gelidium Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000588748 Klebsiella Species 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
235000010419 agar Nutrition 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
235000012216 bentonite Nutrition 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
WNSKAEJGWQCOQH-UHFFFAOYSA-N diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C1=CC(F)=C(F)C(F)=C1F WNSKAEJGWQCOQH-UHFFFAOYSA-N 0.000 description 2
YAHUDNWHZFLCBN-ZRDIBKRKSA-N ethyl (e)-2-benzoyl-3-ethoxyprop-2-enoate Chemical compound CCO\C=C(\C(=O)OCC)C(=O)C1=CC=CC=C1 YAHUDNWHZFLCBN-ZRDIBKRKSA-N 0.000 description 2
239000003925 fat Substances 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000000499 gel Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000006072 paste Substances 0.000 description 2
150000004885 piperazines Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 2
239000001993 wax Substances 0.000 description 2
229940058015 1,3-butylene glycol Drugs 0.000 description 1
WFZMKGKYUACCTB-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-7-(3-phenylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C12=CC(N3CC(NCC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 WFZMKGKYUACCTB-UHFFFAOYSA-N 0.000 description 1
SFKRXQKJTIYUAG-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(F)=C1F SFKRXQKJTIYUAG-UHFFFAOYSA-N 0.000 description 1
IFBLQYWVJXGZPY-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)piperazine Chemical compound C1=C2OCOC2=CC=C1C1CNCCN1 IFBLQYWVJXGZPY-UHFFFAOYSA-N 0.000 description 1
XMTDOVQYBQWJAL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)piperazine Chemical compound C1=C(OC)C(OC)=CC=C1C1NCCNC1 XMTDOVQYBQWJAL-UHFFFAOYSA-N 0.000 description 1
VGANTLKDSNLDDD-UHFFFAOYSA-N 2-(3-nitrophenyl)piperazine Chemical compound [O-][N+](=O)C1=CC=CC(C2NCCNC2)=C1 VGANTLKDSNLDDD-UHFFFAOYSA-N 0.000 description 1
ZXWFFOCOSVMOPB-UHFFFAOYSA-N 2-(4-bromophenyl)piperazine Chemical compound C1=CC(Br)=CC=C1C1NCCNC1 ZXWFFOCOSVMOPB-UHFFFAOYSA-N 0.000 description 1
OTOVNNDSINVUBR-UHFFFAOYSA-N 2-(4-chlorophenyl)piperazine Chemical compound C1=CC(Cl)=CC=C1C1NCCNC1 OTOVNNDSINVUBR-UHFFFAOYSA-N 0.000 description 1
NZAKSEMIIIZYEM-UHFFFAOYSA-N 2-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1C1NCCNC1 NZAKSEMIIIZYEM-UHFFFAOYSA-N 0.000 description 1
INKLSJITWMAFRT-UHFFFAOYSA-N 2-(4-methoxyphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1C1NCCNC1 INKLSJITWMAFRT-UHFFFAOYSA-N 0.000 description 1
FCNXNUWTNOYQME-UHFFFAOYSA-N 2-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1C1NCCNC1 FCNXNUWTNOYQME-UHFFFAOYSA-N 0.000 description 1
WWRUGVIJFUXWFW-UHFFFAOYSA-N 2-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1NCCNC1 WWRUGVIJFUXWFW-UHFFFAOYSA-N 0.000 description 1
MUECOXPJCJWOTK-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)piperazine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1C1CNCCN1 MUECOXPJCJWOTK-UHFFFAOYSA-N 0.000 description 1
QUINYTMXFWCKTN-UHFFFAOYSA-N 2-(4-phenylphenyl)piperazine Chemical compound C1NCCNC1C1=CC=C(C=2C=CC=CC=2)C=C1 QUINYTMXFWCKTN-UHFFFAOYSA-N 0.000 description 1
LOKVZWIGUJYFLY-UHFFFAOYSA-N 2-(furan-2-yl)piperazine Chemical compound C1NCCNC1C1=CC=CO1 LOKVZWIGUJYFLY-UHFFFAOYSA-N 0.000 description 1
125000002934 2-oxopropylidene group Chemical group 0.000 description 1
OCGGVAKKHYAFJW-UHFFFAOYSA-N 2-piperazin-2-ylphenol Chemical compound OC1=CC=CC=C1C1NCCNC1 OCGGVAKKHYAFJW-UHFFFAOYSA-N 0.000 description 1
BFVCDPJJFUPNAQ-UHFFFAOYSA-N 2-thiophen-2-ylpiperazine Chemical compound C1NCCNC1C1=CC=CS1 BFVCDPJJFUPNAQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000577424A 1984-06-04 1988-09-14 Acide 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxo-3-quinoleine-carboxylique Expired CA1259315A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000577424A CA1259315A (fr)	1984-06-04	1988-09-14	Acide 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxo-3-quinoleine-carboxylique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19843420743 DE3420743A1 (de)	1984-06-04	1984-06-04	7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DEP3420798.8		1984-06-04
CA000482912A CA1248954A (fr)	1984-06-04	1985-05-31	Acides 7-(3-aryl-1-piperazinyl)- et 7-(3-cyclohexyl-1 -piperazinyl)-3-quinolone-carboxyliques
CA000577424A CA1259315A (fr)	1984-06-04	1988-09-14	Acide 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxo-3-quinoleine-carboxylique

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000482912A Division CA1248954A (fr)	1984-06-04	1985-05-31	Acides 7-(3-aryl-1-piperazinyl)- et 7-(3-cyclohexyl-1 -piperazinyl)-3-quinolone-carboxyliques

Publications (1)

Publication Number	Publication Date
CA1259315A true CA1259315A (fr)	1989-09-12

Family

ID=25670696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000577424A Expired CA1259315A (fr)	1984-06-04	1988-09-14	Acide 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxo-3-quinoleine-carboxylique

Country Status (1)

Country	Link
CA (1)	CA1259315A (fr)

1988
- 1988-09-14 CA CA000577424A patent/CA1259315A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-09-12	MKEX	Expiry

Publication	Publication Date	Title
KR920005112B1 (ko)	1992-06-26	7-아미노-1-시클로프로필-6,8-디할로게노-1,4-디히드로-4-옥소-3-퀴놀린카르복실산의 제조방법
US4599334A (en)	1986-07-08	7-(3-aryl-1-piperazinyl)- and 7-(3-cyclohexyl-1-piperazinyl)-3-quinolonecarboxylic acid antibacterials
CA1304738C (fr)	1992-07-07	Acide 7-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4- oxoquinoline-3-carboxyliques, procedes pour leur preparation et agents antibacteriens encontenant
KR870001003B1 (ko)	1987-05-18	1-사이클로프로필-6-플루오로-1,4-디하이드로-4-옥소-7-(알킬-1-피레라지닐)퀴놀린-3-카복실산의 제조방법
US5072038A (en)	1991-12-10	2,3,4,5-tetrahalogenobenzene derivatives
JPH05213836A (ja)	1993-08-24	シクロプロピルアミン類
HU203231B (en)	1991-06-28	Process for producing antibacterial 5-amino and 5-hydroxyquinoline derivatives and pharmaceutical compositions comprising same
KR910006635B1 (ko)	1991-08-29	1,7-디아미노-1,4-디하이드로-4-옥소-3-(아자)퀴놀린카복실산의 제조방법
CA1218069A (fr)	1987-02-17	Acides 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7- [4-(oxo-alcoyl)-1-piperazinyl]-quinoline-3- carboxyliques et leurs derives; preparation et agents antibacteriens qui en renfermant
US4588726A (en)	1986-05-13	1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinolinecarboxylic acid antibacterial agents
US5385906A (en)	1995-01-31	Antibacterial quinolone compounds
US4703047A (en)	1987-10-27	1-Cyclopropyl-1,4-dihydro-4-oxo-7-(4-(2-oxo-1,3-dioxol-4-yl-methyl)-1-piperazinyl)-3-quinolinecarboxylic acid antibacterial agents
WO1990006307A2 (fr)	1990-06-14	Composes de quinolone antibacteriens
US5565614A (en)	1996-10-15	2,4,5-trihalogeno-and 2,3,4,5-tetrahalogenobenzene derivatives
US5468861A (en)	1995-11-21	8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and alkyl esters thereof
FI89045B (fi)	1993-04-30	Foerfarande foer framstaellning av kinolinkarboxylsyraderivat
NZ239717A (en)	1992-02-25	Fluorinated alkyl benzoic acids and esters and their preparation