CS271643B1 - 1-(4-aminophenyl)-6-fluoro-1,4-dihydro-4-oxo-7 piperazinylquinoline-3-carboxyl acid - Google Patents
1-(4-aminophenyl)-6-fluoro-1,4-dihydro-4-oxo-7 piperazinylquinoline-3-carboxyl acid Download PDFInfo
- Publication number
- CS271643B1 CS271643B1 CS89303A CS30389A CS271643B1 CS 271643 B1 CS271643 B1 CS 271643B1 CS 89303 A CS89303 A CS 89303A CS 30389 A CS30389 A CS 30389A CS 271643 B1 CS271643 B1 CS 271643B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dihydro
- oxo
- fluoro
- piperazinylquinoline
- aminophenyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- QUTYURKTSVKCFD-UHFFFAOYSA-N 1-(4-aminophenyl)-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=CC(N)=CC=C1N1C2=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(O)=O)=C1 QUTYURKTSVKCFD-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IALRJWRVDOXAQY-UHFFFAOYSA-N 6-fluoro-1-(4-nitrophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C([N+]([O-])=O)C=C1 IALRJWRVDOXAQY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Je známá vysoká účinnost řady substituovaných l-aryl-6-fluor-1,4-dihydro-4-oxochinolin-3-karboxylových kyselin proti širokému spektru bakterií (Chu,D.T.W. a spol.: J. Med. Chem. 28, 1558 /1985/).
' 1·(4—Aminofeny1)—6—fluor—1,4-dihydro-4-oxo-7-piperazinyl-chinolin-3-karboxylová kyselina vzorce I je nová, dosud nepopsaná látka, která má antibakteriální aktivitu srovnatelnou s nej účinnějšími látkami této skupiny. Minimální inhibicní koncentrace in vitro proti Streptococcus pyogenee, Escherichia coli a Próteus vulgaris byly zjištěny nižší nebo rovny 1 mg/1.
Sloučeninu vzorce I lze podle vynálezu připravit redukcí námi již dříve popsané 6-fluor-1,4-dihydro-l-(4-nitrofenyl)-4-oxo-7-piperazinylchinolin-3-karboxylove kyseliny. Redukci lze podle vynálezu provést síranem železnatým v prostředí vodného alkalického hydroxidu nebo vodného amoniaku.
Způsob přípravy látky vzorce I podle vynálezu je jednoduchý a poskytuje žádanou látku v uspokojivém výtěžku. Bližší podrobnosti vyplývají z následujících příkladů provedení. Uvedené příklady vynález pouze ilustrují, nikoliv omezují.
Příklad 1
К vroucímu roztoku 6-fluor-1,4-dihydro-l-(4-nitrofeny1)-4-oxo-7-piperazinylchinolin-3-karboxylové kyseliny (0.,82 g, 2 mmol) v 50 ml .4% vodného hydroxidu sodného byl přilit roztok 5,5 g heptahydrátu síranu železnatého ve 20 ml vody a vzniklá reakční směs byla vařena pod zpětným chladičem 30 minut. Horká reakční směs byla vakuově zfiltrována a filtrát byl okyselen octovou kyselinou a ochlazen. Nerozpustný podíl byl odsát a Dromyt chladnou vodou a překrystalován z 50% vodného methylalkoholu. Bylo získáno 0,42 g (55 %) látky o t.t. 256 až 259 °C.
Příklad 2
Pokus byl nroveden stejně jako v příkladu 1, místo 4% vodného roztoku hydroxidu sodr.ébo byl použit 10% vodný amoniak. Bylo získáno 0,37 g (48 %) látky o t.t. 256 až
259 0 C.
Claims (1)
- PŘEDMĚT VYNÁLEZU1-(4-Aminofeny1)-6-fluor-1, 4-dihydro-4-oxo-7-plperazinylchinolln-3-karboxylová kyselí НП V«ni'nn T
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS89303A CS271643B1 (en) | 1989-01-16 | 1989-01-16 | 1-(4-aminophenyl)-6-fluoro-1,4-dihydro-4-oxo-7 piperazinylquinoline-3-carboxyl acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS89303A CS271643B1 (en) | 1989-01-16 | 1989-01-16 | 1-(4-aminophenyl)-6-fluoro-1,4-dihydro-4-oxo-7 piperazinylquinoline-3-carboxyl acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS30389A1 CS30389A1 (en) | 1990-02-12 |
| CS271643B1 true CS271643B1 (en) | 1990-10-12 |
Family
ID=5334909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS89303A CS271643B1 (en) | 1989-01-16 | 1989-01-16 | 1-(4-aminophenyl)-6-fluoro-1,4-dihydro-4-oxo-7 piperazinylquinoline-3-carboxyl acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS271643B1 (cs) |
-
1989
- 1989-01-16 CS CS89303A patent/CS271643B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS30389A1 (en) | 1990-02-12 |
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