PT78926B - A process for the preparation of 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxoquinoline-3-carboxylic acid - Google Patents
A process for the preparation of 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxoquinoline-3-carboxylic acid Download PDFInfo
- Publication number
- PT78926B PT78926B PT78926A PT7892684A PT78926B PT 78926 B PT78926 B PT 78926B PT 78926 A PT78926 A PT 78926A PT 7892684 A PT7892684 A PT 7892684A PT 78926 B PT78926 B PT 78926B
- Authority
- PT
- Portugal
- Prior art keywords
- fluoro
- ethyl
- piperazinyl
- oxo
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 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 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 229960001180 norfloxacin Drugs 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 6
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- NGBZZCXZVDYZQK-UHFFFAOYSA-N ethyl 7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound ClC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 NGBZZCXZVDYZQK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- FKGHGICVSSHGDP-UHFFFAOYSA-N C(C)N1C=C(C(C2=CC(=C(C=C12)N1CCNCC1)F)=O)C(=O)N1CCNCC1 Chemical compound C(C)N1C=C(C(C2=CC(=C(C=C12)N1CCNCC1)F)=O)C(=O)N1CCNCC1 FKGHGICVSSHGDP-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- -1 1-piperazinyl-4-oxo-1,4-dihydroquinoline-3-carbonylpiperazine Chemical compound 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- QYUFLWMYQNOLKA-UHFFFAOYSA-N piperazin-1-yl(quinolin-3-yl)methanone Chemical compound C=1N=C2C=CC=CC2=CC=1C(=O)N1CCNCC1 QYUFLWMYQNOLKA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES524358A ES8501391A1 (es) | 1983-07-22 | 1983-07-22 | Procedimiento de preparar acido 1-etil-6-fluo-1,4-dihidro-7-(1-piperacinil)-4-oxoquinolin-3-carboxilico. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT78926A PT78926A (en) | 1984-08-01 |
| PT78926B true PT78926B (en) | 1986-06-02 |
Family
ID=8486067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT78926A PT78926B (en) | 1983-07-22 | 1984-07-17 | A process for the preparation of 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxoquinoline-3-carboxylic acid |
Country Status (8)
| Country | Link |
|---|---|
| KR (1) | KR850001190A (en, 2012) |
| DK (1) | DK355884A (en, 2012) |
| ES (1) | ES8501391A1 (en, 2012) |
| FI (1) | FI842687A7 (en, 2012) |
| GR (1) | GR79960B (en, 2012) |
| IT (1) | IT1178493B (en, 2012) |
| NO (1) | NO842941L (en, 2012) |
| PT (1) | PT78926B (en, 2012) |
-
1983
- 1983-07-22 ES ES524358A patent/ES8501391A1/es not_active Expired
- 1983-11-07 KR KR1019830005273A patent/KR850001190A/ko not_active Withdrawn
-
1984
- 1984-07-04 FI FI842687A patent/FI842687A7/fi not_active Application Discontinuation
- 1984-07-12 IT IT21854/84A patent/IT1178493B/it active
- 1984-07-16 GR GR75320A patent/GR79960B/el unknown
- 1984-07-17 PT PT78926A patent/PT78926B/pt not_active IP Right Cessation
- 1984-07-18 NO NO842941A patent/NO842941L/no unknown
- 1984-07-20 DK DK355884A patent/DK355884A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GR79960B (en, 2012) | 1984-10-31 |
| IT8421854A1 (it) | 1986-01-12 |
| FI842687A0 (fi) | 1984-07-04 |
| KR850001190A (ko) | 1985-03-16 |
| FI842687A7 (fi) | 1985-01-23 |
| NO842941L (no) | 1985-01-23 |
| DK355884D0 (da) | 1984-07-20 |
| ES524358A0 (es) | 1984-12-16 |
| ES8501391A1 (es) | 1984-12-16 |
| PT78926A (en) | 1984-08-01 |
| IT8421854A0 (it) | 1984-07-12 |
| DK355884A (da) | 1985-01-23 |
| IT1178493B (it) | 1987-09-09 |
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|---|---|---|---|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19991231 |