DD283386B5 - Verfahren zur Herstellung von 1-substituierter 6-Fluor-4-oxo-7-(1-piperazinyl)-1,4-dihydrochinolin-3-carbonsaeure - Google Patents
Verfahren zur Herstellung von 1-substituierter 6-Fluor-4-oxo-7-(1-piperazinyl)-1,4-dihydrochinolin-3-carbonsaeure Download PDFInfo
- Publication number
- DD283386B5 DD283386B5 DD32470388A DD32470388A DD283386B5 DD 283386 B5 DD283386 B5 DD 283386B5 DD 32470388 A DD32470388 A DD 32470388A DD 32470388 A DD32470388 A DD 32470388A DD 283386 B5 DD283386 B5 DD 283386B5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- carboxylic acid
- fluoro
- dihydroquinoline
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- -1 1-substituted 6-fluoro-4-oxo-7- (1-piperazinyl) -1,4-dihydroquinoline-3-carboxylic acid Chemical class 0.000 title abstract 3
- 125000004494 ethyl ester group Chemical group 0.000 claims abstract description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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 8
- 238000004611 spectroscopical analysis Methods 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- GGWLGDBEMJWMAH-UHFFFAOYSA-N ethyl 1-cyclopropyl-7-(4-ethoxycarbonylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)N1CCN(CC1)C(=O)OCC)C1CC1 GGWLGDBEMJWMAH-UHFFFAOYSA-N 0.000 description 3
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- SIZQHYOHXHCYHI-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethoxycarbonylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SIZQHYOHXHCYHI-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- GZDOLMHJYOJBDF-UHFFFAOYSA-N 6-fluoro-1-(2-hydroxyethyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=C2N(CCO)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 GZDOLMHJYOJBDF-UHFFFAOYSA-N 0.000 description 2
- RSAMZLZRMSYMNT-UHFFFAOYSA-N 7-(4-ethoxycarbonylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound CCOC(=O)N1CCN(CC1)c1cc2n(CC)cc(C(O)=O)c(=O)c2cc1F RSAMZLZRMSYMNT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- OIAHODUMUYMPHR-UHFFFAOYSA-N CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCN(CC3)C(=O)OCC)F)C(=O)OCC Chemical compound CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCN(CC3)C(=O)OCC)F)C(=O)OCC OIAHODUMUYMPHR-UHFFFAOYSA-N 0.000 description 1
- GKSGTZQIYKVHCQ-UHFFFAOYSA-N CCOC(=O)N1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)CCO)F Chemical compound CCOC(=O)N1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)CCO)F GKSGTZQIYKVHCQ-UHFFFAOYSA-N 0.000 description 1
- QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 description 1
- 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 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU244787A YU46099B (sh) | 1987-12-31 | 1987-12-31 | Postopek za pripravo 1-supstituirane 6-fluoro-4-okso-7- 1-piperazinil)-1 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD283386B5 true DD283386B5 (de) | 1997-10-30 |
Family
ID=25557985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD32470388A DD283386B5 (de) | 1987-12-31 | 1988-12-30 | Verfahren zur Herstellung von 1-substituierter 6-Fluor-4-oxo-7-(1-piperazinyl)-1,4-dihydrochinolin-3-carbonsaeure |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT396105B (cs) |
| CS (1) | CS274635B2 (cs) |
| DD (1) | DD283386B5 (cs) |
| HU (1) | HU200454B (cs) |
| LT (1) | LT3274B (cs) |
| LV (1) | LV10774B (cs) |
| NO (1) | NO885666L (cs) |
| PL (1) | PL163337B1 (cs) |
| PT (1) | PT89359B (cs) |
| RU (1) | RU2002744C1 (cs) |
| SI (1) | SI8712447A8 (cs) |
| YU (1) | YU46099B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9200377A (en) * | 1992-12-11 | 1994-06-30 | Krka | Process for the preparation of 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxilic acid, novel intermediate used in this process and process for its preparation |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
| 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 |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| JPS5762259A (en) * | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3308909A1 (de) | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel auf chinoloncarbonsaeure-basis |
| 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 |
| JPH06103891B2 (ja) | 1989-05-31 | 1994-12-14 | 日本電信電話株式会社 | パケット交換網用ルーチング方法 |
| JPH066686A (ja) | 1992-06-17 | 1994-01-14 | Ricoh Co Ltd | 撮像装置 |
-
1987
- 1987-12-31 YU YU244787A patent/YU46099B/sh unknown
- 1987-12-31 SI SI8712447A patent/SI8712447A8/sl unknown
-
1988
- 1988-12-21 NO NO88885666A patent/NO885666L/no unknown
- 1988-12-28 PT PT8935988A patent/PT89359B/pt not_active IP Right Cessation
- 1988-12-29 CS CS903288A patent/CS274635B2/cs unknown
- 1988-12-30 HU HU667788A patent/HU200454B/hu not_active IP Right Cessation
- 1988-12-30 AT AT320688A patent/AT396105B/de not_active IP Right Cessation
- 1988-12-30 PL PL27689088A patent/PL163337B1/pl unknown
- 1988-12-30 DD DD32470388A patent/DD283386B5/de active IP Right Maintenance
- 1988-12-30 RU SU4613227 patent/RU2002744C1/ru active
-
1993
- 1993-05-05 LT LTIP510A patent/LT3274B/lt not_active IP Right Cessation
- 1993-06-30 LV LVP-93-828A patent/LV10774B/lv unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU200454B (en) | 1990-06-28 |
| LTIP510A (en) | 1994-11-25 |
| YU46099B (sh) | 1992-12-21 |
| LV10774A (lv) | 1995-08-20 |
| HUT49129A (en) | 1989-08-28 |
| PT89359B (pt) | 1993-08-31 |
| NO885666L (no) | 1989-07-03 |
| NO885666D0 (no) | 1988-12-21 |
| YU244787A (en) | 1990-06-30 |
| LT3274B (en) | 1995-05-25 |
| LV10774B (en) | 1996-08-20 |
| PL163337B1 (pl) | 1994-03-31 |
| PT89359A (pt) | 1989-12-29 |
| CS903288A2 (en) | 1990-12-13 |
| RU2002744C1 (ru) | 1993-11-15 |
| SI8712447A8 (en) | 1995-12-31 |
| ATA320688A (de) | 1992-10-15 |
| PL276890A1 (en) | 1989-10-16 |
| CS274635B2 (en) | 1991-09-15 |
| AT396105B (de) | 1993-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EP | Request for examination under paragraph 12(1) filed | ||
| EP | Request for examination under paragraph 12(1) filed | ||
| AUF | Maintained (sect. 12/3 extension act |
Free format text: SPC/GB97/080, 970925 |
|
| B5 | Patent specification, 2nd publ. accord. to extension act | ||
| IF04 | In force in the year 2004 |
Expiry date: 20081231 |