LT3084B - Process for preparing 1-substituted-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid,a novel intermediate useful in said process, and a process for preparing said intermediate - Google Patents
Process for preparing 1-substituted-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid,a novel intermediate useful in said process, and a process for preparing said intermediate Download PDFInfo
- Publication number
- LT3084B LT3084B LTIP1558A LTIP1558A LT3084B LT 3084 B LT3084 B LT 3084B LT IP1558 A LTIP1558 A LT IP1558A LT IP1558 A LTIP1558 A LT IP1558A LT 3084 B LT3084 B LT 3084B
- Authority
- LT
- Lithuania
- Prior art keywords
- substituted
- fluoro
- oxy
- general formula
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- -1 1-substituted-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic Chemical class 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- RGVPOXRFEPSFGH-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 RGVPOXRFEPSFGH-UHFFFAOYSA-N 0.000 claims 1
- 241000272525 Anas platyrhynchos Species 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 150000001638 boron Chemical class 0.000 description 2
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000252073 Anguilliformes Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9200377A SI9200377A (en) | 1992-12-11 | 1992-12-11 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1558A LTIP1558A (en) | 1994-06-15 |
| LT3084B true LT3084B (en) | 1994-11-25 |
Family
ID=20431064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1558A LT3084B (en) | 1992-12-11 | 1993-12-07 | Process for preparing 1-substituted-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid,a novel intermediate useful in said process, and a process for preparing said intermediate |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT401648B (cs) |
| CA (1) | CA2111181A1 (cs) |
| CZ (1) | CZ284715B6 (cs) |
| EE (1) | EE9400277A (cs) |
| HR (1) | HRP931485A2 (cs) |
| HU (1) | HUT75319A (cs) |
| LT (1) | LT3084B (cs) |
| LV (1) | LV10863B (cs) |
| PL (1) | PL173784B1 (cs) |
| RU (1) | RU2127270C1 (cs) |
| SI (1) | SI9200377A (cs) |
| SK (1) | SK140093A3 (cs) |
| YU (1) | YU76593A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7452888B2 (en) * | 2002-03-27 | 2008-11-18 | Glaxo Group Limited | Quinoline derivatives and their use as 5-ht6 ligands |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840910A1 (de) | 1977-09-20 | 1979-04-05 | Bellon Labor Sa Roger | 7-dialkylamino-6-halogen-4-oxo-1,4- dihydro-3-chinolin-carbonsaeuren, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| JPS5466689A (en) | 1977-10-21 | 1979-05-29 | Bayer Ag | Novel substituted pyrimidinyl*thiono**thiol* phosphoric acid esters and esterramidos* their manufacture and use thereof as insecticide and tickicide |
| JPS5533453A (en) | 1978-08-31 | 1980-03-08 | Dainippon Pharmaceut Co Ltd | Preventive and remedy for infectious disease of fish |
| BE890223A (fr) | 1980-09-05 | 1982-01-04 | Kyorin Seiyaku Kk | Procede de preparation de derives de l'acide quinoleine-carboxylique |
| DE3308909A1 (de) | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel auf chinoloncarbonsaeure-basis |
| ES1014131U (es) | 1988-09-22 | 1991-02-16 | Amphora-Weinschlauch Gmbh. | Armario surtidor. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU198709B (en) * | 1987-04-08 | 1989-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| YU46099B (sh) * | 1987-12-31 | 1992-12-21 | Krka Tovarna Zdravil | Postopek za pripravo 1-supstituirane 6-fluoro-4-okso-7- 1-piperazinil)-1 |
-
1992
- 1992-12-11 SI SI9200377A patent/SI9200377A/sl unknown
-
1993
- 1993-10-18 HU HU9302940A patent/HUT75319A/hu unknown
- 1993-11-12 PL PL93301045A patent/PL173784B1/pl unknown
- 1993-12-06 CZ CZ932643A patent/CZ284715B6/cs not_active IP Right Cessation
- 1993-12-07 LT LTIP1558A patent/LT3084B/lt not_active IP Right Cessation
- 1993-12-10 SK SK140093A patent/SK140093A3/sk unknown
- 1993-12-10 AT AT249793A patent/AT401648B/de not_active IP Right Cessation
- 1993-12-10 LV LVP-93-1317A patent/LV10863B/en unknown
- 1993-12-10 HR HRP931485 patent/HRP931485A2/hr not_active Application Discontinuation
- 1993-12-10 YU YU76593A patent/YU76593A/sh unknown
- 1993-12-10 CA CA 2111181 patent/CA2111181A1/en not_active Abandoned
- 1993-12-10 RU RU93054527A patent/RU2127270C1/ru active
-
1994
- 1994-11-17 EE EE9400277A patent/EE9400277A/xx unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840910A1 (de) | 1977-09-20 | 1979-04-05 | Bellon Labor Sa Roger | 7-dialkylamino-6-halogen-4-oxo-1,4- dihydro-3-chinolin-carbonsaeuren, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| JPS5466689A (en) | 1977-10-21 | 1979-05-29 | Bayer Ag | Novel substituted pyrimidinyl*thiono**thiol* phosphoric acid esters and esterramidos* their manufacture and use thereof as insecticide and tickicide |
| JPS5533453A (en) | 1978-08-31 | 1980-03-08 | Dainippon Pharmaceut Co Ltd | Preventive and remedy for infectious disease of fish |
| BE890223A (fr) | 1980-09-05 | 1982-01-04 | Kyorin Seiyaku Kk | Procede de preparation de derives de l'acide quinoleine-carboxylique |
| DE3308909A1 (de) | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel auf chinoloncarbonsaeure-basis |
| ES1014131U (es) | 1988-09-22 | 1991-02-16 | Amphora-Weinschlauch Gmbh. | Armario surtidor. |
Also Published As
| Publication number | Publication date |
|---|---|
| HRP931485A2 (en) | 1995-04-30 |
| ATA249793A (de) | 1996-03-15 |
| SK140093A3 (en) | 1994-11-09 |
| AT401648B (de) | 1996-10-25 |
| YU76593A (sh) | 1996-07-24 |
| CZ264393A3 (en) | 1994-07-13 |
| SI9200377A (en) | 1994-06-30 |
| PL173784B1 (pl) | 1998-04-30 |
| HUT75319A (en) | 1997-05-28 |
| RU2127270C1 (ru) | 1999-03-10 |
| CA2111181A1 (en) | 1994-06-12 |
| LV10863B (en) | 1996-08-20 |
| PL301045A1 (en) | 1994-06-13 |
| LTIP1558A (en) | 1994-06-15 |
| HU9302940D0 (en) | 1993-12-28 |
| LV10863A (lv) | 1995-10-20 |
| CZ284715B6 (cs) | 1999-02-17 |
| EE9400277A (et) | 1996-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19971207 |