SE441597B - Substituerade kinolinkarboxylsyraderivat - Google Patents

Substituerade kinolinkarboxylsyraderivat

Info

Publication number
SE441597B
SE441597B SE7908065A SE7908065A SE441597B SE 441597 B SE441597 B SE 441597B SE 7908065 A SE7908065 A SE 7908065A SE 7908065 A SE7908065 A SE 7908065A SE 441597 B SE441597 B SE 441597B
Authority
SE
Sweden
Prior art keywords
carboxylic acid
fluoro
oxo
piperazinyl
dihydroquinoline
Prior art date
Application number
SE7908065A
Other languages
English (en)
Other versions
SE7908065L (sv
Inventor
T Irikura
S Suzue
A Ito
H Koga
Original Assignee
Kyorin Seiyaku Kk
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.)
Filing date
Publication date
Application filed by Kyorin Seiyaku Kk filed Critical Kyorin Seiyaku Kk
Publication of SE7908065L publication Critical patent/SE7908065L/sv
Publication of SE441597B publication Critical patent/SE441597B/sv

Links

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
    • C07D215/48—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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)

Description

7908065-1 1-viny1-6-fluoro-7-(4-metyl-1-píperazínyl)-4§oxo~1.G-díhydro~ Éínolín-3-karboxylsyra, 1-(2-fluoretyl)-6-fluoro-7-(1-píperazínyl)-4-oxo~l.4~díhydro- kínolín-3~karboxy1syra. 1-(2-fluoretyl)-6-fluoro-7-(4-metyl-1-píperazínyl)-4-oxo~l,ê« -dinydrokinolin-3-karboxylsyra. 1-etyl-6-fluoro-7-[á-(p-amínobensyl)-l-píperazinyl]-4-oxo-1.4- -díhydrokínolin-3-karboxylsyra. 1-etyl-6-f1uoro-7-(1-píperazínyl)-4-oxo-1.4-äíhydrokíno1ín-3- -karboxylsyraetylester, '“ 1-metyl-6-f1uoro-7-(l~píperazíny1)-4~oxo-1.A-díhydrokínolin-3» -karboxylsyrahydrokloríd, 1-propy1-6-f1uoro-7-(1-píperazínyl)-4-oxo-l,4-díhydrokino1ín-3- -karboxylsyrahydrokloríd och 1-allyl-6-fluoro-7-(1-piperazínyl)-4-oxo-1.4-díhydrokíno1in-3- -karboxylsyrahydrokloríd.
Följande exempel avser att illustrera uppfinningen.
Exemgel L En blandning av 0,17 g 1-etyl-1.4-díhydro-6-f1uoro-7-(l-píper- azínyl)-4-oxo-1.8-naftyrídín-3-karboxyleyraetylester. 0.06 g natríumhydroxid och 0.5 ml vatten upphettades under omröring vid 80 - 90°C under 40 minuter. Reaktíonsblandníngen índuns- tades under vakuum och återstoden omkristallíserades ur en blandning av koncentrerad saltsyra och etanol under bildning av 0.08 g 1-etyl-l,4-díhydro-6-fluoro-7-(1-piperazínyl)-ß-oxo~ -1.8-naftyrídin-3-karboxylsyrahydrokloríd. Smp. större än 300°C.
KB: _1 IRymaï cm “z 1720 (COOH). 1628 (CO) HS m/e: 320 (Mà-HCl), 276 (M*-HC1-C02) Exemgel 2 En blandning av 0.96 g (3 mmol) 1-etyl-6-fluoro-7-(l-piper- azínyl)~ê-oxo-1.4-dihydrokínolin-3-karboxylsyra. 0.94 g (6 mmol) jodoetyl. 0.6 q (6 mmol) tríetylamin och 10 ml di- 7908065~a metylformamid upphettades till 70 - 80°C under 2.5 timma: *under omröring. Efter kylning indunstades reaktionsblandningen under vakuum och återstoden löstes i diklormetan. tvättades. torkades med vattenfritt natriumsulfat och lösningsmedlet av~ lägsnades. Återstoden omkristalliserades ur en blandning av CHC13 och bensen och man erhöll 0.75 g (72 %) 1-ety1-6- -f1uoro~7-(4-etyl»l-piperazinyl)-4-oxo~l.4-díhydrokinolin-3-karb oxylsyra. ' Smp. 251 - 253°C, Analys: C H 0 N F 18 22 3 3 1/4H2° C H N 61.44 6.45 11.94 61.49 6.24 11.70 Beräknat: Fllflflet! Exemge1_1 En blandning av 65 mg (0.153 mmol) 1-(2-kloretyl)-6-f1uoro-7- -(4-acetylel-piperazinyl)-4-oxo-1.4-dihydrokinolín-3-karboxyl- 0.10 g Na0H. l ml H O och 1 ml etanol upp- 2 hettades vid 95 - 100°C under 4 timmar under omröring. Efter syraetylester. kylning surgjordes reaktionsblandningen med ättíksyra och ín- dunstades under vakuum. Återstoden omkristalliserades ur eta- nol, varigenom erhölls 48 mg 1-vinyl-6~f1uoro-7-(1-piper~ azinyl)e4-oxo-1.4-dihydrokinolín-3-karboxylsyrahydroklorid.
Smp. ej under 300°C.
KB: _l IR ¶ max cm : Ms m/é: 317 (M*-Hcl). 273 (M*-Hcl-coz) 1720 (COOH). 1625 (CO) Exempel g En blandning av 0,89 g (3.3 mmol) 1~vinyl-6-fluoro-7-kloro-4- -oxo-1.4-díhydrokínolínf3-karboxylsyra. 1.7 g (17 mmol) N-me- tylpiperazín och 2 ml pyridin upphettades vid 135 - 145°C under 12 timmar. Efter kylning indunstades reaktionsblandning~ en under vakuum. surgjordes med ättiksyra och befriades från icke löst material genom filtrering. Filtratet neutraliserades med en vattenlösning av kaustík soda. extraherades med 7908065*'! CHC13. tvättades. torkades med vattenfritt natriumsulfat och lösningsmedlet avlågsnades. Återstoden löstes i HCI och etanol tillsattes. Lösningen kyldes med is och den bildade fällningen filtrerades. tvättades med etanol och torkades för erhållande av ett svagt gulfärgat pulver av 0.05 g l-vinyl-6-f1uoro-7-(4- -metyl-l-piperazinyl)-4-oxo-l,4-díhydrokinolin-3-karboxylsyrahyd rokldrid.
Smp. ej under 300°C.
Ksr _l IR'v max Cm I Ms m/e: 331 (M*-Hcl). 1720 (COOH). 1630 (CO) 287 Exemgel Q En blandning av 0.87 g (3 mmol) 1-(2-fluoretyl)-6-fluoro-7- -kloro-4-oxo-1,4-dihydrokinolín-3-karboxylsyra. l.3 g (15 mmol) piperazin och Q ml piperidin upphettades vid 135 - l45°C under 12 timmar. Efter kylning indunstades reaktionsblandning- en under vakuum och återstoden surgjordes med ättiksyra. o1ös~ ligt material frånfiltrerades och fíltratet neutraliserades med en vattenlösníng av kaustik soda. Fällningen fíltrerades. tvättades. torkades och löstes i utspädd HCl under tillsats av etanol och kyldes med is. Fällningen frânfiltrerades. tvätta- des med etanol och torkades. Efter omkristallisation ur etanol erhölls 0.30 g (27 à) 1-(2-fluoretyl)-6-fluoro-7-(l-piper- azinyl)-4~oxo-1.4-dihydrokinolin-3-karboxylsyrahydrokloríd i form av ett pulver med smältpunkten 292°C (sönderdelníng).
Analysf C H O N F .HCl.H20 16 17 3 3 2 C H -i N Beräknat: 49.05 5.15 10.72 Funnet: 48.91 4,91 10.68 Exemgel Q En blandning av 0.72 g (2,5 mmol) l-(2-fluoretyl)-6-fluoro-7- -kloro-4-oxo-1.4-dihydrokinolin-3-karboxylsyra. 1.25 g (l2.5 mmol) N-metylpiperazin och 2 ml pyridín upphettades till 135 - - l45°C under 10 timmar. Efter kylning indunstades reaktions- 7908Û65~1 blandningen under vakuum. Äterstoden surgjordes med ättíksyra, icke upplöst material frånfiltrerades och filtratet neutra1i~ serades med en vattenlösníng av kaustik soda. Fällníngen filt- rerades, tvättades och torkades. Efter omkrístallisation ur etanol erhölls 0.50 g (57 %) 1-(2-fluoretyl)~6-fluoro-7-(4- ~mety1-l-píperazinyl)-4-oxo-1.4-dihydrokínoline3-karboxylsyra med smältpunkten 256 - 258°C.
Analys: C17H19O3N3F2 C H N Beräknat: 58.11 5.45 11.96 Funnet: 58.13 5.47 11.95 ExemQel_1 En blandning av 2.0 g 1-etyl-l,4-díhydro-6-fluoro-7-[4-(p- -nitrobensyl)~l-píperazínyl]-4-oxokínolin-3-karboxylsyra. 0,40 g av en katalysator av 5 % På/C och 50 ml ísättíka bríngades att absorbera en teoretisk mängd vätgas (296 ml). Efter av- lägsnande av katalysatorn inåunstades fíltratet under vakuum och återstoden omkristallíserades ur konc. HC1-etanol. vari- genom erhölls l,4 g (64 %) l-etyl-7-{4-(p-aminobensyl)-l- -píperazínyl]-1.4-díhydro~6-f1uoro~4-oxokínolin-3-karboxylsyra~ -hydrokloríd.
Smp. 220 - 223°C (sönderdelning).
Analys: C23H2503N4F.2HCl 1/2 H20 C H « N Beräknat: 54.55 5,57 11.06 Funnet: 54.72 5.47 10.98 Exempel Q l-etyl-6-f1uoro-7-(1-píperazinyl)-4-oxo-1,4-dihydrokíno1ín-3- -karboxylsyra-etylester. Smp. 182 - 184°C.
Analys: C18H2203N3F C H N Beräknat: 62.23 6.38 12.10 Funnet: 62.02 6.34 11.97 790806541 Exemgel 2 1-mety1-6-f1uoro-7-(1-píperazínyl)-4-oxo-1.4-äihydrokíno1ín-3- -karboxylsyra-hydrokloríd. Smp- ej under 300°C.
Analys: C H 0 N F.HC1.1/4 320 15 16 3 3 ï c H N Beräknat: 52,03 5.09 ' 12,14 Funnet: 52.23 4.99 12.03 Exemnel 10 1-propyl-6-f1uoro~7-(1-píperazínyl)-4-oxo-1.4-díhydrokínolín-3~ -karboxylsyra-hydrokloríd. Smp. 293 - 296°C (sönderdelníng).
Analys: C H O N F.HCl.l/4 H O 17 20 3 3 2 C H N Beräknat: 54.55 5.79 11.23 Funnet: 54.58 5,72 ' 11.01 Exemuel 11 1-allyl-6-fluoro-1.4-díhydro-4-oxo-7-(1-piperazinyl)-kínolín-3- -karboxylsyra-hydrokloríd. Smp. 290 - 293°C (sönderdelníng).
Analys: C H 0 N F.HCl 17 18 3 3 C H N Beräknat: 55.51 5.21 11.42 Funnet: 55,15 5.19 11.30 I nedanstående tabell 1 återges antíbakteríellt spektrum för föreningarna framställda i exempel 1 - 7 ovan. ~1 PD 790806 °~.o o~.@ mm~@ @M.@ m~_m 1 o~waHH mcwuwwoums .w mH_~ o~.@ mm_@ w~.o mm_@ m.- 1 @H@QHH mcwøwwuume .w m~.m o~.@ o-o mm.@ mm.@ m~_w 1 wHwoHH wcwuwmuums wflumwwm m~ m~.w wm.H m~.w wm1H mm 1 OMHHQHH mmocflmsuwfl .ß mw m~.@ -.~ mH_~ @m.H m~1 1 _ QHNHQHH mmøcfløøuwß .m m~ mH.m mH.m mH_m wm.H m~.w m~ 1 [email protected]:fl@:uwm .m m.~H ~H.m w>.o ~H.~ m~.Q mH.~ m-H 1 H1> mwocflvsuwm wmcoaowpwwß oH.ov oH.ov ow.o 1 mwmcwfi Hmccom mfiflwmflzw mfi~m æß.o w>.@ w>.O m.- 1 . QQQQHH wwøflufiumpcw mfifiwcoæflww QH.o oH.Qv oH~@v oH\@v @H~o mwo.ov OH.Q 1 -mmo@H wmflcoszwcm mfifimflwnwflx w~.o QH.ov @m.o o~.o mm.o ø~.@ mm~o 1 cwxcwn xx mHummH=> .Q w>~o oH.ov @~_o o~.o o~.o @~.@ w~_0 1 ~@~mo@H mH~mmH:> mnwßohß mm.o o~.@ o~.Q @~.o QH.o o~.@ m>.ø 1 wmmQHuoe< flflou .m m».o OH.Qv oH~Qv Q~.oV o~.@ oH.@ @~.O 1 ~1uw w=Hz flflou mflnoflnwzuwm mm~@ w>.0 m~.@ mH.~ m~.@ mmkc m~1@ + m~>«Huue< mswuzm .w mm.Q mm.o @m.H @m.H mfi_m mm1@ mH.m + mmow wswusw w=uuouoH>=@m»w Q~.o @~,@ @~.o @m1@ @m_@ @.~c w>.@ + mA~Hum mflfifiunsw wsfiflflomm ~.xm m.xm m.xm v.xm ~.xm ~.xm H.xm 1 Hwfifiw + 1 uwsmflcmwuo _. . , 1 Eæuo ^HE\mRV ccfivmnuflwunox wwcmnwflflscfi mvmcflz aøfißxmmm Qflfiwfiflmvxmnflpsæ w fiflwßmß 7908065-1 Tabell A Antibakteriellt spektrum M.I.c2_§ng/ml) O r g a n i s m e r Gram Förening A (Ex. 1) Bacillus subtilis PCI 219 + ~ 0,39 3,13 Staphylococcus aureus 209P + 0,78 25 Sta. apreus ATCC 14775 + 6,25 100 Streptococcus pyogenes IID 692 + 6,25 >100 St. pyogenes IID 689 + 6,25 >100 St. faecalis IID 682 + 25 >10Q Diplococcus pneumoniae IID 552 + 6,25 lgg Corynebacterium pyogenes IID 548 + 6,25 100 Escherichia coli NIHJ JC-2 - 0,20 1,56 E- coli Arcc 10536 - 0,39 1,s6 Proteus vulgaris IFO 3167 - 0,20 12,5 Pr. vulgaris XX Denken - 0,39 3,13 Klebsiella pneumoñiae :Fo 3512 - 0,20 1,56 Salmönella enteritidis IID 604 - 0.39 6,25 Pseudomonas aeruginosa V~1 - 3,13 25 Ps. aeruginosa IFO 12689 - 6,25 25 Ps. aeruginosa IID 1210 ,- 6,25 >l00 Ps. aeruginosa IID 1130 - 1,56 25 Serratia marcescens IID 618 1 0,39 3,13 S. marcescens IID 619 - 0,78 12,5 S. marcescens IID 620 - 0,39 3,13 Shigella sonnei IID 969 - 0,20 1,56 Yersinia enterocolitica IID 981 - 0,39 6,25 Förening (EX. 1): 1-etyl-1,4-aihyar0-e-f1uoro~7-(1-pipera2inyl> -4-oxo-1,8-naftyridin-3-karbøxylsyra-hydro~ klorid enligt föreliggande uppfinning. 1,4-dihyaro-1-ety1-4-oxo-7-X1-pipera2inyl>- -1,8-naftyridin-3-karboxylsyra, framställd enl. us-A-4 o17 622. smp.= 275 - 276°C- Analys för C15H18N403 C H Beräknat: 59,59 6,00 Funnet: 59,46 5,97 18,53 18,46

Claims (1)

7988065-1 9 Patentkrqq Kinolín- och 1.8-naftyrídin-3-karboxylsyraderívat med den all- männa_formeln i vilken A är en kol- eller kväveatom. Rl är lägre alkyl. lägre alkenyl eller halogenerad lägre alkyl och R2 är väte- atom. lägre alkyl eller p-amínobensyl samt hydrat och syraad- áítíonssalter därav, vilka derivat är valda bland följande föreningar, nämligen 1-etfl-1,4-díhydro-6-f1uoro-7-(1-píperazínyl)-4~oxo-l.8- -naftyrídín-3-karboxylsyrahydroklorid. 1-ety1-6-f1uoro-7-(4-etyl-1-píperazínyl)-4-oxo-l.4-díhydro- kínolín-3-karboxylsyra, l~vínyl-6-f1uoro-7-(1-píperäzínyl)-4-oxo-1.4-dihydrokíno1in-3- -karboxylsyra, 1-víny1-6~f1ucro-7-(4-metyl-1-píperazínyl)-4-oxo-1.4-díhydro- kinolín-3-karboxylsyra. 1-(2-fluoretyl)-6-fluoro-7-(1-píperazinyl)-4-oxo-1,4-dihydro- kinolín-3-karboxylsyra. 1-(2-fluoretyl)-6-fluoro-7-(4-metyl-1-piperazinyl)-4-oxo-1,4- -díhydrokínolin-3-karboxylsyra. 1-ety1-6-fluoro-7-[4-(p-amínobensyl)-1-piperazinyl]-4~oxo-l,4- -díhydrokínolin-3-karboxylsyra. l-etyl-6-f1uoro-7-(1-piperazinyl)-4-oxo-1.4-díhydrokinolin-3~ -karboxylsyraetylester. 1~mety1-6-f1uoro-7-(1-piperazinyl)-4-oxo-1.4-díhydzokino1ín-3- -karboxylsyrahydroklorid. 1~propy1-6-f1uoro-7-(1-píperazínyl)-4-oxo-1,4-díhydrokíno1ín-3- -karboxylsyrahydrokloríd och
1. -allyl-6~fluoro-7~(1-píperazinyl)-4-oxo-1.4-díhydrokíno1ín-3- -karboxylsyrahydrokloríd.
SE7908065A 1978-09-29 1979-09-28 Substituerade kinolinkarboxylsyraderivat SE441597B (sv)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP53120216A JPS5845426B2 (ja) 1978-09-29 1978-09-29 置換キノリンカルボン酸誘導体

Publications (2)

Publication Number Publication Date
SE7908065L SE7908065L (sv) 1980-03-30
SE441597B true SE441597B (sv) 1985-10-21

Family

ID=14780757

Family Applications (1)

Application Number Title Priority Date Filing Date
SE7908065A SE441597B (sv) 1978-09-29 1979-09-28 Substituerade kinolinkarboxylsyraderivat

Country Status (12)

Country Link
US (1) US4448962A (sv)
JP (1) JPS5845426B2 (sv)
AU (1) AU534089B2 (sv)
BE (1) BE879106A (sv)
CA (1) CA1214465A (sv)
DE (1) DE2939786C2 (sv)
ES (1) ES484578A1 (sv)
FR (1) FR2437406A1 (sv)
GB (1) GB2034698B (sv)
HU (1) HU179214B (sv)
IT (1) IT1166909B (sv)
SE (1) SE441597B (sv)

Families Citing this family (84)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR223983A1 (es) 1978-08-25 1981-10-15 Dainippon Pharmaceutical Co Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico
JPS604820B2 (ja) * 1979-02-26 1985-02-06 大塚製薬株式会社 キノリンカルボン酸誘導体
JPS5644066U (sv) * 1979-09-14 1981-04-21
JPS5746986A (en) * 1980-09-02 1982-03-17 Dai Ichi Seiyaku Co Ltd Pyrido(1,2,3-de)(1,4)benzoxazine derivative
DE3033157A1 (de) * 1980-09-03 1982-04-01 Bayer Ag, 5090 Leverkusen 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
US4670444B1 (en) * 1980-09-03 1999-02-09 Bayer Ag and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds
US4620007A (en) * 1980-09-03 1986-10-28 Bayer Aktiengesellschaft 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
JPS5762259A (en) * 1980-09-05 1982-04-15 Kyorin Pharmaceut Co Ltd Preparation of substituted quinolinecarboxylic acid derivative
JPS57106681A (en) * 1980-12-24 1982-07-02 Dainippon Pharmaceut Co Ltd 1,8-naphthyridine derivative and its salt
JPS57134482A (en) * 1981-02-13 1982-08-19 Dainippon Pharmaceut Co Ltd 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation
SE440354B (sv) * 1981-02-19 1985-07-29 Kyorin Seiyaku Kk Kinolinkarboxylsyraderivat
JPS57145862A (en) * 1981-03-06 1982-09-09 Kyorin Pharmaceut Co Ltd Quinolinecarboxylic acid derivative
JPS57203067A (en) * 1981-06-10 1982-12-13 Kanebo Ltd Novel quinolinecarboxylic acid derivatives, their preparations, and antibacterial agent comprising them as active ingredient
US4530928A (en) * 1982-01-13 1985-07-23 Merck & Co., Inc. Quinoline carboxylic acid complexes with guanidinium carbonate
US4665079A (en) * 1984-02-17 1987-05-12 Warner-Lambert Company Antibacterial agents
US5281612A (en) * 1982-09-09 1994-01-25 Warner-Lambert Company Naphthyridine antibacterial agents
JPS59122470A (ja) * 1982-12-27 1984-07-14 Dai Ichi Seiyaku Co Ltd キノリン−３−カルボン酸誘導体の製造法
DE3248505A1 (de) * 1982-12-29 1984-07-05 Bayer Ag, 5090 Leverkusen 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE3306771A1 (de) * 1983-02-25 1984-08-30 Bayer Ag, 5090 Leverkusen Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE3306772A1 (de) * 1983-02-25 1984-08-30 Bayer Ag, 5090 Leverkusen Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
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
US4730000A (en) * 1984-04-09 1988-03-08 Abbott Laboratories Quinoline antibacterial compounds
AU553415B2 (en) * 1983-09-19 1986-07-17 Abbott Japan Co., Ltd. 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids
US4774246A (en) * 1984-01-26 1988-09-27 Abbott Laboratories Quinoline antibacterial compounds
US4616019A (en) * 1984-01-26 1986-10-07 Abbott Laboratories Naphthyridine antibacterial compounds
IT1196051B (it) * 1984-03-16 1988-11-10 Schiena Ricerche Composti ad attivita' antibatterica
US4571396A (en) * 1984-04-16 1986-02-18 Warner-Lambert Company Antibacterial agents
DE3420743A1 (de) * 1984-06-04 1985-12-05 Bayer Ag, 5090 Leverkusen 7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE3420770A1 (de) * 1984-06-04 1985-12-05 Bayer Ag, 5090 Leverkusen 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
GB8414559D0 (en) * 1984-06-07 1984-07-11 Scras Pyridine derivatives
EP0181521A1 (en) * 1984-10-19 1986-05-21 Otsuka Pharmaceutical Co., Ltd. Antimicrobial 1-substituted Phenyl-4-oxoquinoline-3-carboxylic acid compounds
DE3443183A1 (de) * 1984-11-27 1986-05-28 Robert Bosch Gmbh, 7000 Stuttgart Verfahren und vorrichtung zum steuern der daempferhaerte eines stossdaempfers fuer fahrzeuge
DE3576335D1 (de) * 1984-12-14 1990-04-12 Daiichi Seiyaku Co Chinolincarbonsaeure-derivate.
DE3508816A1 (de) * 1985-01-10 1986-07-10 Bayer Ag, 5090 Leverkusen 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren
US4851535A (en) * 1985-01-23 1989-07-25 Toyama Chemical Co., Ltd. Nicotinic acid derivatives
US4755513A (en) * 1985-01-30 1988-07-05 Otsuka Pharmaceutical Company, Limited Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds
DE3509546A1 (de) * 1985-03-16 1986-09-25 Bayer Ag, 5090 Leverkusen 7-amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
US4657913A (en) * 1985-04-18 1987-04-14 Warner-Lambert Company Trifluoro- quinoline -3- carboxylic acids and their use as anti-bacterial agents
US4684648A (en) * 1985-05-10 1987-08-04 Otsuka Pharmaceutical Company Limited Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds and compositions thereof
DE3608745A1 (de) * 1985-07-24 1987-01-29 Bayer Ag Bakterizide zubereitungen zur anwendung auf dem gebiet der veterinaermedizin
IN166416B (sv) * 1985-09-18 1990-05-05 Pfizer
JPH0717642B2 (ja) * 1985-10-09 1995-03-01 富山化学工業株式会社 １，４―ジヒドロ―４―オキソナフチリジン誘導体またはその塩
DE3542002A1 (de) * 1985-11-28 1987-06-04 Bayer Ag 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
HU196218B (en) 1985-12-09 1988-10-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing quinoline carboxylic acid boric acid anhydrides
CA1306750C (en) 1985-12-09 1992-08-25 Istvan Hermecz Process for the preparation of quinoline carboxylic acide
US4689325A (en) * 1985-12-23 1987-08-25 Abbott Laboratories Isoxazolo-pyrido-phenoxazine and isothiazolo-pyrido-phenoxazine derivatives
US4687770A (en) * 1985-12-23 1987-08-18 Abbott Laboratories Isoxazolo-pyrido-benzoxazine and isothiazolo-pyrido-benzoxazine derivatives
US4940710A (en) * 1986-01-17 1990-07-10 American Cyanamid Company 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
US5210193A (en) * 1986-01-17 1993-05-11 American Cyanamid Company Piperazine derivatives
US4692454A (en) * 1986-02-03 1987-09-08 Warner-Lambert Company Opthalmic use of quinolone antibiotics
DE3705621C2 (de) * 1986-02-25 1997-01-09 Otsuka Pharma Co Ltd Heterocyclisch substituierte Chinoloncarbonsäurederivate
JPH0811749B2 (ja) * 1986-03-06 1996-02-07 富山化学工業株式会社 新規なキノリン誘導体およびその塩
US4963553A (en) * 1986-10-16 1990-10-16 American Cyanamid Co. 4-[(substituted) alkylcarbonyl]-4,5-dihydro- and -4,5,6,7-tetrahydro-7-[(substituted)phenyl]pyrazolo[1,5-a]pyrimidines
US5126340A (en) * 1986-10-16 1992-06-30 American Cyanamid Company 4-[(substituted)alkylcarbonyl]-4,5-dihydro and -4,5,6,7-tetrahydro-7-[(substituted)-phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitriles
DE3641312A1 (de) * 1986-12-03 1988-06-09 Bayer Ag Verfahren zur herstellung von chinolincarbonsaeuren
JPS6416767A (en) * 1987-07-09 1989-01-20 Dainippon Pharmaceutical Co 8-halogenoquinoline derivative, its ester and salt
SI8712447A8 (en) * 1987-12-31 1995-12-31 Krka Tovarna Zdravil Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl) -1,4-dihydroquinoline-3-carboxylic acid and new intermediate used in this process
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
IL90635A0 (en) * 1988-07-15 1990-01-18 Abbott Lab Process for the preparation of quinoline antibacterial compounds
WO1991001308A1 (fr) * 1989-07-21 1991-02-07 Ss Pharmaceutical Co., Ltd. Derives de l'acide quinolonecarboxylique
JPH01258666A (ja) * 1988-08-18 1989-10-16 Kyorin Pharmaceut Co Ltd 新規置換キノリンカルボン酸
JP2503547Y2 (ja) * 1989-03-13 1996-07-03 トヨタ自動車株式会社 ショックアブソ―バ
FR2655545B1 (fr) 1989-12-11 1994-06-10 Rhone Poulenc Sante Nouvelle application therapeutique des derives des fluoroquinolones.
JPH0411946U (sv) * 1990-05-18 1992-01-30
ES2050594B1 (es) * 1991-12-31 1994-12-16 Ind Quimica Agropecuaria S A Procedimiento para la obtencion de acidos 6-fluoro-1,4-dihidro-4-oxo-7-piperazino-quinolin-3-carboxilicos sustituidos en 1-n.
TW301607B (sv) * 1993-03-09 1997-04-01 Takeda Pharm Industry Co Ltd
US5532239A (en) * 1993-08-02 1996-07-02 Assistance Publique - Hopitaux De Paris Therapeutic application of fluoroquinolone derivatives
WO1996002512A1 (fr) * 1994-07-18 1996-02-01 Ube Industries, Ltd. Acide du type trifluoromethylquinoleinecarboxylique
US5626310A (en) * 1994-11-21 1997-05-06 Kelly Space & Technology, Inc. Space launch vehicles configured as gliders and towed to launch altitude by conventional aircraft
MY138335A (en) 1997-09-15 2009-05-29 Procter & Gamble Antimicrobial quinolones, their compositions and uses
US6387928B1 (en) 1997-09-15 2002-05-14 The Procter & Gamble Co. Antimicrobial quinolones, their compositions and uses
CA2353557A1 (en) 1998-12-04 2000-06-08 Influx, Inc. Inhibitors of multidrug transporters
US6957105B2 (en) * 2002-03-26 2005-10-18 Cardiac Pacemakers, Inc. Method and apparatus for detecting oscillations in cardiac rhythm with electrogram signals
WO2007067489A1 (en) * 2005-12-05 2007-06-14 Merck & Co., Inc. Quinolone m1 receptor positive allosteric modulators
US20070196398A1 (en) * 2006-02-17 2007-08-23 Murthy Yerramilli V S Fluoroquinolone fatty acid salt compositions
US7973022B2 (en) * 2006-02-17 2011-07-05 Idexx Laboratories, Inc. Fluoroquinolone carboxylic acid salt compositions
US20070197548A1 (en) * 2006-02-17 2007-08-23 Murthy Yerramilli V S Fluoroquinolone compositions
CA2647457C (en) * 2006-03-28 2011-05-24 The Procter & Gamble Company A hydride reduction process for preparing quinolone intermediates
MX2008012488A (es) * 2006-03-28 2008-10-10 Procter & Gamble Un proceso de acoplamiento para preparar intermedios de quinolona.
BRPI0709772B8 (pt) * 2006-03-28 2021-05-25 The Protecter & Gamble Company sais de malato e polimorfos do ácido (3s,5s)-7-[3-amino-5-metil-piperidinil]-1-ciclopropil-1,4-diidro-8-metóxi-4-oxo-3-quinolinocarboxílico
EP1845088B1 (en) * 2006-04-10 2009-07-22 Ranbaxy Laboratories Limited An improved process for the preparation of aripipirazole
US20100273787A1 (en) * 2007-11-15 2010-10-28 Robert Schwarcz Kynurenine-aminotransferase inhibitors
ES2383857B1 (es) 2010-11-23 2013-05-13 Consejo Superior De Investigaciones Científicas (Csic) Haptenos e inmunoreactivos y su uso en la obtención de anticuerpos de familia e inmunoensayos para quinolonas

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3149104A (en) * 1961-01-03 1964-09-15 Sterling Drug Inc 4-hydroxy-7-styryl-1, 8-naphthyridine-3-carboxylic acids and esters
US3590036A (en) * 1968-11-18 1971-06-29 George Y Lesher Naphthyridine-3-carboxylic acids,their derivatives and preparation thereof
DE2103805C3 (de) * 1970-01-28 1980-03-20 Sumitomo Chemical Co., Ltd., Osaka (Japan) Verfahren zur Herstellung von N-substituierten 6,7-Methylendioxy-4chinolonen
US4017622A (en) * 1972-12-18 1977-04-12 Dainippon Pharmaceutical Co., Ltd. Piperazine derivatives
HU168497B (sv) * 1972-12-18 1976-05-28
JPS5049286A (sv) * 1973-09-04 1975-05-01
JPS5732061B2 (sv) * 1974-06-17 1982-07-08
JPS5732060B2 (sv) * 1974-02-12 1982-07-08
JPS587626B2 (ja) * 1974-02-13 1983-02-10 大日本製薬株式会社 ナフチリジン オヨビ キノリンユウドウタイノセイホウ
JPS5157836A (sv) * 1974-11-13 1976-05-20 Dainippon Pharmaceutical Co
JPS5365887A (en) * 1976-11-22 1978-06-12 Kyorin Seiyaku Kk Substituted quinoline*arboxylate and process for preparing same
JPS53141286A (en) * 1977-05-16 1978-12-08 Kyorin Seiyaku Kk Novel substituted quinolinecarboxylic acid
US4264604A (en) * 1977-07-01 1981-04-28 Ciba-Geigy Corporation Quinolonecarboxylic acid derivatives as bactericides
SE444566B (sv) * 1977-09-20 1986-04-21 Bellon Labor Sa Roger 7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav
US4292315A (en) * 1977-12-30 1981-09-29 Nichols Vorys Follicular phase estrogen or progestin with physiologic estrogen/progestin luteal phase replacement drug delivery system
JPS54138582A (en) * 1978-04-19 1979-10-27 Kyorin Seiyaku Kk Substituted quinolinecarboxylic acid
AR223983A1 (es) * 1978-08-25 1981-10-15 Dainippon Pharmaceutical Co Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico
US4352808A (en) * 1980-12-12 1982-10-05 Schering Corporation 3-Aralkyloxy-2,3-dihydro-2-(imidazolylmethyl)benzo(b)thiophenes and related derivatives, their use as antimicrobials and pharmaceutical formulations useful therefore

Also Published As

Publication number Publication date
HU179214B (en) 1982-09-28
CA1214465A (en) 1986-11-25
US4448962A (en) 1984-05-15
FR2437406B1 (sv) 1983-06-03
BE879106A (fr) 1980-02-01
FR2437406A1 (fr) 1980-04-25
GB2034698A (en) 1980-06-11
ES484578A1 (es) 1980-05-16
JPS5547658A (en) 1980-04-04
AU534089B2 (en) 1984-01-05
IT7926120A0 (it) 1979-09-28
IT1166909B (it) 1987-05-06
JPS5845426B2 (ja) 1983-10-08
DE2939786A1 (de) 1980-04-10
AU5142179A (en) 1981-04-16
SE7908065L (sv) 1980-03-30
GB2034698B (en) 1982-11-17
DE2939786C2 (de) 1986-10-09

Similar Documents

Publication Publication Date Title
SE441597B (sv) Substituerade kinolinkarboxylsyraderivat
CA1175836A (en) Production of 1,4-dihydroquinoline-3-carboxylic acid derivatives
KR920005112B1 (ko) 7-아미노-1-시클로프로필-6,8-디할로게노-1,4-디히드로-4-옥소-3-퀴놀린카르복실산의 제조방법
SE440353B (sv) Kinolinkarboxylsyraderivat och sett for framstellning derav
HU177959B (en) Process for producing 1,2-dihydro-quinoline-2-one derivatives
HU187356B (en) Process for producing quinoline-carboxylic acid derivatives
CA1339373C (en) 6-7-disubstituted 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-c arboxylic acids
FI91400B (sv) Förfarande för framställning av kinolinkarboxylsyraderivat
DK175037B1 (da) Fremgangsmåde til fremstilling af quinolincarboxylsyrederivater samt mellemprodukt, der kan anvendes ved fremgangsmåden
CS264345B2 (en) Process for preparing quinolincarboxylic acids
IE61624B1 (en) Tricyclic compounds
JPH0717608B2 (ja) ６−アルコキシキノロンカルボン酸誘導体
US4720495A (en) Benzo[ij]quinolizine-2-carboxylic acids useful for treating bacterial infection
Yoon et al. Synthesis, pharmacokinetics, and biological activity of a series of new pyridonecarboxylic acid antibacterial agents bearing a 5‐fluoro‐2‐pyridyl group or a 3‐fluoro‐4‐pyridyl group at N‐1
CS261250B2 (en) Method of 1-methylaminoquinolinecarboxyl acid&#39;s and its derivatives production
RU2049783C1 (ru) Способ получения производных хинолинкарбоновых кислот или их фармацевтически приемлемых солей
JPS6185381A (ja) １−エチル−６，８−ジフルオロ−１，４−ジヒドロ−４−オキソ−７−ピペラジニルキノリン−３−カルボン酸誘導体の製造法
FI89045B (fi) Foerfarande foer framstaellning av kinolinkarboxylsyraderivat
KR960001919B1 (ko) 신규한 퀴놀론 카르복실산 유도체와 그의 제조방법
US5380845A (en) Process for the preparation of quinoline carboxylic acid derivatives
EP0195135B1 (en) A process for the preparation of quinoline carboxylic acid derivatives
KR870000894B1 (ko) 퀴놀론 카복실산의 제조방법
GB2093018A (en) 6,8-Difluoro-quinoline carboxylic acid derivatives
JPS6110574A (ja) ６−フルオロ−１，４−ジヒドロ−４−オキソ−７−置換ピペラジニルキノリン−３−カルボン酸誘導体
CZ284715B6 (cs) Způsob přípravy 6-fluor-4-oxo-7-(1-piperazinyl)-1 4-dihydrochinolin-3-karboxylové kyseliny substituované v poloze 1, nový intermediát uvedeného způsobu a způsob přípravy tohoto intermediátu

Legal Events

Date Code Title Description
NAL Patent in force

Ref document number: 7908065-1

Format of ref document f/p: F

NUG Patent has lapsed

Ref document number: 7908065-1

Format of ref document f/p: F

NUG Patent has lapsed

Ref document number: 7908065-1

Format of ref document f/p: F