RO88915B - Process for the preparation of 1-ethyl-1,4-dihydro-4-oxo--quinoline-3-carboxylic and 1-ethyl-1, 4-dihydro-4-oxo-1, 8-naphtiridin-3-carboxylic acid derivatives - Google Patents
Process for the preparation of 1-ethyl-1,4-dihydro-4-oxo--quinoline-3-carboxylic and 1-ethyl-1, 4-dihydro-4-oxo-1, 8-naphtiridin-3-carboxylic acid derivativesInfo
- Publication number
- RO88915B RO88915B RO115120A RO11512084A RO88915B RO 88915 B RO88915 B RO 88915B RO 115120 A RO115120 A RO 115120A RO 11512084 A RO11512084 A RO 11512084A RO 88915 B RO88915 B RO 88915B
- Authority
- RO
- Romania
- Prior art keywords
- ethyl
- dihydro
- oxo
- carboxylic acid
- quinoline
- Prior art date
Links
- ZSEJADLCFCHIGX-UHFFFAOYSA-N 1-ethyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 ZSEJADLCFCHIGX-UHFFFAOYSA-N 0.000 title abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 1-ethyl-1,4- naphthyridine-3-carboxylic acid Chemical compound 0.000 abstract 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052757 nitrogen Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Inventia se refera la un procedeu pentru prepararea unor derivati ai acizilor 1-etil-1,4-dihidro-4-oxo-chinolin-3-carboxilic si 1-etil-1,4-dihidro-4-oxo-1,8-naftiridin-3-carboxilic cu formula generala I: (vezi formula) în care X reprezinta un atom de carbon sau de azot si R reprezinta un atom de hidrogen sau de fluor, constând din aceea ca un compus cu formula generala II: (vezi formula) în careX si R au semnificaâiile de mai sus, se trateaza cu 2,5-dimetil oxitetrahidrofuran, în mediu de acid acetic, eventual în amestec cu dimetilformaldehida în proportie de 1:1, dupa care compusi transformati, daca se doreste, în saruri de metale alcaline sau alcalino-pamântoase, acceptabile fiziologic, prin procedee în sine cunoscute.The invention relates to a process for the preparation of 1-ethyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives and 1-ethyl-1,4- naphthyridine-3-carboxylic acid of the general formula I wherein X represents a carbon or nitrogen atom and R represents a hydrogen or fluorine atom consisting of a compound of the general formula II: ) in which X and R have the above meanings are treated with 2,5-dimethyl oxytetrahydrofuran in acetic acid medium, optionally in admixture with dimethylformaldehyde in a ratio of 1: 1, after which the compounds are converted, if desired, into salts of alkaline or alkaline earth metals, physiologically acceptable, by processes known per se.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8311250A FR2548664B1 (en) | 1983-07-06 | 1983-07-06 | 7- (PYRROL-L-YL) DERIVATIVES OF L-ETHYL-1,4-DIHYDRO-4-OXOQUINOLEIN-3-CARBOXYLIC ACIDS AND L-ETHYL-1,4-DIHYDRO-4-OXO- (1,8-NAPHTYRIDINE) ) -3-SUBSTITUTED CARBOXYLICS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO88915A RO88915A (en) | 1987-06-30 |
| RO88915B true RO88915B (en) | 1987-07-01 |
Family
ID=9290571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO115120A RO88915B (en) | 1983-07-06 | 1984-07-03 | Process for the preparation of 1-ethyl-1,4-dihydro-4-oxo--quinoline-3-carboxylic and 1-ethyl-1, 4-dihydro-4-oxo-1, 8-naphtiridin-3-carboxylic acid derivatives |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6036482A (en) |
| FR (1) | FR2548664B1 (en) |
| IN (1) | IN161611B (en) |
| RO (1) | RO88915B (en) |
| SU (1) | SU1322980A3 (en) |
| ZA (1) | ZA844693B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1221492B (en) * | 1984-03-13 | 1990-07-06 | Biochem Design Srl | ACIDS 7- (1-PIRRIL) -E 7- (1-PIRROLI-DINIL) -6-FLUORO-1-ETHYL-1,4-DIIDRO-4-KETOCHINOLIN-3-CARBOXYLS WITH ANTI-MICROBIAL ACTIVITIES, THEIR PREPARATION PROCEDURE AND PHARMACEUTICAL COMPOUNDS THAT CONTAIN THEM |
| US6080756A (en) * | 1995-08-29 | 2000-06-27 | Pfizer Inc. | Polymorphs of the prodrug 6-N-(L-ALA-L-ALA)-trovafloxacin |
| DK0992501T3 (en) * | 1995-09-22 | 2002-10-28 | Wakunaga Pharma Co Ltd | Pyridonecarboxylic acid derivatives as antibacterial agents |
| SK286420B6 (en) * | 1997-09-15 | 2008-09-05 | The Procter & Gamble Company | Derivative of quinolone structure, pharmaceutical composition comprising the same and their use |
| AU3192700A (en) | 1999-03-17 | 2000-10-04 | Daiichi Pharmaceutical Co., Ltd. | Medicinal compositions |
| MXPA02000103A (en) * | 1999-07-01 | 2003-07-21 | Wakunaga Pharma Co Ltd | Quinolinecarboxylic acid derivative or salts thereof. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1006521A (en) * | 1972-12-18 | 1977-03-08 | Minoru Sugita | Piperazine derivatives and process for preparing them |
| JPS5233694A (en) * | 1975-09-09 | 1977-03-14 | Dai Ichi Seiyaku Co Ltd | Process for preparation of 6_nitro-1,8-naphthyridine derivatives |
| AR223983A1 (en) * | 1978-08-25 | 1981-10-15 | Dainippon Pharmaceutical Co | A PROCEDURE FOR PREPARING 6-HALOGEN-4-OXO-7- (1-PIPERAZINYL) -1,8-NAFTIRIDIN-3-CARBOXYLIC ACID DERIVATIVES |
-
1983
- 1983-07-06 FR FR8311250A patent/FR2548664B1/en not_active Expired
-
1984
- 1984-06-21 ZA ZA844693A patent/ZA844693B/en unknown
- 1984-07-03 IN IN536/DEL/84A patent/IN161611B/en unknown
- 1984-07-03 RO RO115120A patent/RO88915B/en unknown
- 1984-07-04 JP JP59138851A patent/JPS6036482A/en active Granted
- 1984-07-05 SU SU843759901A patent/SU1322980A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA844693B (en) | 1985-02-27 |
| JPS6036482A (en) | 1985-02-25 |
| RO88915A (en) | 1987-06-30 |
| IN161611B (en) | 1988-01-02 |
| FR2548664A1 (en) | 1985-01-11 |
| SU1322980A3 (en) | 1987-07-07 |
| FR2548664B1 (en) | 1986-03-21 |
| JPH026756B2 (en) | 1990-02-13 |
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