ES2006994A6 - PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF QUINOLINCARBOXILIC ACIDS. - Google Patents
PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF QUINOLINCARBOXILIC ACIDS.Info
- Publication number
- ES2006994A6 ES2006994A6 ES8801926A ES8801926A ES2006994A6 ES 2006994 A6 ES2006994 A6 ES 2006994A6 ES 8801926 A ES8801926 A ES 8801926A ES 8801926 A ES8801926 A ES 8801926A ES 2006994 A6 ES2006994 A6 ES 2006994A6
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- stands
- salt
- hydrogen
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- -1 4-methyl-piperazinyl Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000004885 piperazines Chemical class 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
The invention relates to a new process for the preparation of compounds of general formula (I) (wherein R<1> stands for phenyl being optionally substituted by 1 or 2 halogen atoms, or a group of the general formula CH2CR<6>R<7>R<8> (wherein R<6>, R<7> and R<8> stand for hydrogen or halogen) R<2> stands for piperazinyl or 4-methyl-piperazinyl R<3> stands for hydrogen or fluorine) and pharmaceutically acceptable salts thereof which comprises reacting a compound of general formula (II) (wherein R stands for halogen or an aliphatic acyloxy group containing 2 to 6 carbon atoms or an aromatic acyloxy group containing 7 to 11 carbon atoms, R<4> stands for fluorine or chlorine) with a piperazine derivative of general formula (III) (wherein R<5> stands for hydrogen or methyl) or a salt thereof and subjecting the compound of general formula (IV) thus obtained (wherein R, R<1>, R<2> and R<3> are as stated above) to hydrolysis after or without isolation and if desired converting the compound of general formula (I) thus obtained into a salt thereof or setting free the same from its salt. The compounds of general formula (I) are known antibacterial agents. The advantage of the process of the present invention is that it makes the desired compounds of general formula (I) available in a simple manner, with high yields and in a short reaction time.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU285887A HU200175B (en) | 1987-06-24 | 1987-06-24 | Process for producing quinolinecarboxylic acid derivatives |
| HU873146A HU199822B (en) | 1987-07-10 | 1987-07-10 | Process for production of derivatives of quinoline carbonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2006994A6 true ES2006994A6 (en) | 1989-05-16 |
Family
ID=26317564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8801926A Expired ES2006994A6 (en) | 1987-06-24 | 1988-06-21 | PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF QUINOLINCARBOXILIC ACIDS. |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0329719A1 (en) |
| JP (1) | JP2693988B2 (en) |
| KR (1) | KR970005911B1 (en) |
| CN (1) | CN1025028C (en) |
| CA (1) | CA1325010C (en) |
| CS (1) | CS274677B2 (en) |
| DK (1) | DK84089A (en) |
| ES (1) | ES2006994A6 (en) |
| FI (1) | FI91400C (en) |
| WO (1) | WO1988010253A1 (en) |
| YU (1) | YU46570B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2049636A1 (en) * | 1992-04-15 | 1994-04-16 | Genesis Para La Investigacion | Quinoline carboxylic acid deriv prepn - by reacting boron complex of quinoline deriv with nucleophilic cpd |
| ES2095809A1 (en) * | 1995-07-27 | 1997-02-16 | Sint Quimica Sa | PROCEDURE FOR THE PREPARATION OF NAFTIRIDIN CARBOXYLIC ACIDS AND THEIR SALTS. |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562852A (en) * | 1984-08-20 | 1986-01-07 | Britt Franklin J | Safety valve |
| US4606367A (en) * | 1985-04-04 | 1986-08-19 | Britt Franklin J | Apparatus and method for relieving pressure within a high pressure tank |
| HU198709B (en) * | 1987-04-08 | 1989-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| IL119476A (en) * | 1990-09-11 | 1999-10-28 | Schering Corp | Process for preparing acetals and hemi-acetals |
| US5869661A (en) * | 1991-07-16 | 1999-02-09 | Chugai Seiyaku Kabushiki Kaisha | Method of producing a quinolonecarboxylic acid derivative |
| JP3165742B2 (en) * | 1991-07-16 | 2001-05-14 | 中外製薬株式会社 | Method for producing quinolone carboxylic acid derivative |
| ES2077490B1 (en) * | 1992-11-18 | 1996-10-16 | Marga Investigacion | TRIMETILSILILIC ESTERS AND SOLVATES OF CHELATES OF QUINOLIN-3-CARBOXYL ACIDS. PREPARATION AND APPLICATION TO THE QUINOLON PROCESS. |
| ES2092963B1 (en) * | 1995-04-12 | 1997-12-16 | Sint Quimica Sa | PROCEDURE FOR THE PREPARATION OF ACID 1-CICLOPROPIL-6-FLUORO-1, 4-DIHIDRO-7- (1S, 4S) -5-METHYL-2,5-DIAZABICICLO (2.2.1) HEPT-2-IL) -4 -OXO-3-QUINOLINCARBOXILICO AND ITS SALTS. |
| FR2916446B1 (en) | 2007-05-24 | 2009-08-21 | Biocodex Sa | NOVEL PROCESS FOR SYNTHESIZING FLUOROQUINOLONES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59122470A (en) * | 1982-12-27 | 1984-07-14 | Dai Ichi Seiyaku Co Ltd | Preparation of quinoline-3-carboxylic acid derivative |
| NZ208470A (en) * | 1983-07-18 | 1988-06-30 | Abbott Lab | 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives and antibacterial compositions containing such |
-
1988
- 1988-05-20 KR KR1019890700325A patent/KR970005911B1/en not_active Expired - Fee Related
- 1988-05-20 EP EP88904603A patent/EP0329719A1/en not_active Ceased
- 1988-05-20 WO PCT/HU1988/000036 patent/WO1988010253A1/en not_active Ceased
- 1988-05-20 JP JP63504328A patent/JP2693988B2/en not_active Expired - Lifetime
- 1988-06-14 CS CS412388A patent/CS274677B2/en unknown
- 1988-06-21 ES ES8801926A patent/ES2006994A6/en not_active Expired
- 1988-06-23 YU YU121788A patent/YU46570B/en unknown
- 1988-06-23 CA CA000570183A patent/CA1325010C/en not_active Expired - Fee Related
- 1988-06-24 CN CN88103892A patent/CN1025028C/en not_active Expired - Fee Related
-
1989
- 1989-02-15 FI FI890723A patent/FI91400C/en not_active IP Right Cessation
- 1989-02-23 DK DK084089A patent/DK84089A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2049636A1 (en) * | 1992-04-15 | 1994-04-16 | Genesis Para La Investigacion | Quinoline carboxylic acid deriv prepn - by reacting boron complex of quinoline deriv with nucleophilic cpd |
| ES2095809A1 (en) * | 1995-07-27 | 1997-02-16 | Sint Quimica Sa | PROCEDURE FOR THE PREPARATION OF NAFTIRIDIN CARBOXYLIC ACIDS AND THEIR SALTS. |
Also Published As
| Publication number | Publication date |
|---|---|
| CS274677B2 (en) | 1991-09-15 |
| YU121788A (en) | 1989-12-31 |
| CA1325010C (en) | 1993-12-07 |
| KR890701564A (en) | 1989-12-21 |
| CN1032166A (en) | 1989-04-05 |
| JPH02500366A (en) | 1990-02-08 |
| CN1025028C (en) | 1994-06-15 |
| FI890723A7 (en) | 1989-02-15 |
| CS412388A2 (en) | 1990-11-14 |
| FI91400B (en) | 1994-03-15 |
| EP0329719A1 (en) | 1989-08-30 |
| WO1988010253A1 (en) | 1988-12-29 |
| DK84089D0 (en) | 1989-02-23 |
| JP2693988B2 (en) | 1997-12-24 |
| YU46570B (en) | 1993-11-16 |
| KR970005911B1 (en) | 1997-04-22 |
| FI91400C (en) | 1994-06-27 |
| DK84089A (en) | 1989-02-23 |
| FI890723A0 (en) | 1989-02-15 |
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