JPS59122470A - キノリン−３−カルボン酸誘導体の製造法 - Google Patents
キノリン−３−カルボン酸誘導体の製造法Info
- Publication number
- JPS59122470A JPS59122470A JP23368482A JP23368482A JPS59122470A JP S59122470 A JPS59122470 A JP S59122470A JP 23368482 A JP23368482 A JP 23368482A JP 23368482 A JP23368482 A JP 23368482A JP S59122470 A JPS59122470 A JP S59122470A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- carboxylic acid
- ethyl
- formula
- dihydroquinoline
- 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.)
- Granted
Links
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 14
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract description 11
- 239000013522 chelant Substances 0.000 abstract description 11
- -1 piperazine compound Chemical class 0.000 abstract description 8
- 229910015900 BF3 Inorganic materials 0.000 abstract description 5
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- WNNSMMJBBOPPOT-UHFFFAOYSA-N 7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(Cl)C=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 WNNSMMJBBOPPOT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 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 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000001914 filtration 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 239000005973 Carvone Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 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 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910001853 inorganic hydroxide Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229940099765 pipracil Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23368482A JPS59122470A (ja) | 1982-12-27 | 1982-12-27 | キノリン−３−カルボン酸誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23368482A JPS59122470A (ja) | 1982-12-27 | 1982-12-27 | キノリン−３−カルボン酸誘導体の製造法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13400487A Division JPS62294689A (ja) | 1987-05-29 | 1987-05-29 | キノリン−３−カルボン酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59122470A true JPS59122470A (ja) | 1984-07-14 |
| JPH0240066B2 JPH0240066B2 (enrdf_load_stackoverflow) | 1990-09-10 |
Family
ID=16958915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23368482A Granted JPS59122470A (ja) | 1982-12-27 | 1982-12-27 | キノリン−３−カルボン酸誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59122470A (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987003595A1 (en) | 1985-12-09 | 1987-06-18 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Norfloxacin intermediate |
| WO1987003587A1 (en) | 1985-12-09 | 1987-06-18 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Process for the preparation of quinoline carboxylic acids |
| WO1988007998A1 (en) * | 1987-04-08 | 1988-10-20 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Quinoline carboxylic acid boric acid anhydrides and process for the preparation thereof |
| JPS6419069A (en) * | 1987-07-14 | 1989-01-23 | Dainippon Pharmaceutical Co | Production of polyhalogenoquinoline derivative |
| GR880100231A (en) * | 1987-04-08 | 1989-01-31 | Chinoin Gyogyszer Es Vegyeszet | Preparation method of quinoline carboxylic acids |
| JPH01503301A (ja) * | 1987-04-08 | 1989-11-09 | キノイン ギオギスゼル エス ベギエスゼチ テルメケク ギヤラ アール．ティー | キノリンカルボン酸の製造方法 |
| JPH02500366A (ja) * | 1987-06-24 | 1990-02-08 | キノイン ギオギスゼル エス ベギエスゼチ テルメケク ギヤラ アールティー． | キノリンカルボン酸誘導体の製造方法 |
| JPH02501839A (ja) * | 1986-12-04 | 1990-06-21 | アウディ アクチェンゲゼルシャフト | 二つのシリンダサポートを備える内燃機関用の排気ガス装置 |
| FR2640974A1 (enrdf_load_stackoverflow) * | 1988-12-22 | 1990-06-29 | Chinoin Gyogyszer Es Vegyeszet | |
| WO1993002055A1 (en) * | 1991-07-16 | 1993-02-04 | Chugai Seiyaku Kabushiki Kaisha | Process for producing quinolonecarboxylic acid derivative |
| US5284950A (en) * | 1985-12-09 | 1994-02-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Process for the preparation of quinoline carboxyolic acids |
| US5294712A (en) * | 1985-12-09 | 1994-03-15 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Process for the preparation of quinoline carboxylic acids |
| US5869661A (en) * | 1991-07-16 | 1999-02-09 | Chugai Seiyaku Kabushiki Kaisha | Method of producing a quinolonecarboxylic acid derivative |
| US7361780B2 (en) | 2003-01-31 | 2008-04-22 | Mitsubishi Rayon Co., Ltd. | Apparatus for producing hydroxyalkyl(meth)acrylate and process for producing the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53141286A (en) * | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| JPS54138582A (en) * | 1978-04-19 | 1979-10-27 | Kyorin Seiyaku Kk | Substituted quinolinecarboxylic acid |
| JPS5547658A (en) * | 1978-09-29 | 1980-04-04 | Kyorin Pharmaceut Co Ltd | Substituted quinolinecarboxylic acid derivative |
| JPS5762259A (en) * | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
-
1982
- 1982-12-27 JP JP23368482A patent/JPS59122470A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53141286A (en) * | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| JPS54138582A (en) * | 1978-04-19 | 1979-10-27 | Kyorin Seiyaku Kk | Substituted quinolinecarboxylic acid |
| JPS5547658A (en) * | 1978-09-29 | 1980-04-04 | Kyorin Pharmaceut Co Ltd | Substituted quinolinecarboxylic acid derivative |
| JPS5762259A (en) * | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0351889A1 (en) | 1985-12-09 | 1990-01-24 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Process for the preparation of a quinoline carboxylic acid |
| WO1987003587A1 (en) | 1985-12-09 | 1987-06-18 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Process for the preparation of quinoline carboxylic acids |
| US5294712A (en) * | 1985-12-09 | 1994-03-15 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Process for the preparation of quinoline carboxylic acids |
| US5284950A (en) * | 1985-12-09 | 1994-02-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Process for the preparation of quinoline carboxyolic acids |
| WO1987003595A1 (en) | 1985-12-09 | 1987-06-18 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Norfloxacin intermediate |
| JPH02501839A (ja) * | 1986-12-04 | 1990-06-21 | アウディ アクチェンゲゼルシャフト | 二つのシリンダサポートを備える内燃機関用の排気ガス装置 |
| GR880100232A (en) * | 1987-04-08 | 1989-01-31 | Chinoin Gyogyszer Es Vegyeszet | Quinoline carboxylic acid boric acid anhydrides and process for the preparation therefor |
| JPH01503301A (ja) * | 1987-04-08 | 1989-11-09 | キノイン ギオギスゼル エス ベギエスゼチ テルメケク ギヤラ アール．ティー | キノリンカルボン酸の製造方法 |
| JPH01503300A (ja) * | 1987-04-08 | 1989-11-09 | キノイン ギオギスゼル エス ベギエスゼチ テルメケク ギヤラ アール．ティー | キノリンカルボン酸ホウ酸無水物及びその製造方法 |
| GR880100231A (en) * | 1987-04-08 | 1989-01-31 | Chinoin Gyogyszer Es Vegyeszet | Preparation method of quinoline carboxylic acids |
| AU612648B2 (en) * | 1987-04-08 | 1991-07-18 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara | Process for the preparation of quinoline carboxylic acids |
| AU613035B2 (en) * | 1987-04-08 | 1991-07-25 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara | Quinoline carboxylic acid boric acid anhydrides and process for the preparation thereof |
| WO1988007998A1 (en) * | 1987-04-08 | 1988-10-20 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Quinoline carboxylic acid boric acid anhydrides and process for the preparation thereof |
| JPH02500366A (ja) * | 1987-06-24 | 1990-02-08 | キノイン ギオギスゼル エス ベギエスゼチ テルメケク ギヤラ アールティー． | キノリンカルボン酸誘導体の製造方法 |
| JPS6419069A (en) * | 1987-07-14 | 1989-01-23 | Dainippon Pharmaceutical Co | Production of polyhalogenoquinoline derivative |
| FR2640974A1 (enrdf_load_stackoverflow) * | 1988-12-22 | 1990-06-29 | Chinoin Gyogyszer Es Vegyeszet | |
| WO1993002055A1 (en) * | 1991-07-16 | 1993-02-04 | Chugai Seiyaku Kabushiki Kaisha | Process for producing quinolonecarboxylic acid derivative |
| US5869661A (en) * | 1991-07-16 | 1999-02-09 | Chugai Seiyaku Kabushiki Kaisha | Method of producing a quinolonecarboxylic acid derivative |
| US7361780B2 (en) | 2003-01-31 | 2008-04-22 | Mitsubishi Rayon Co., Ltd. | Apparatus for producing hydroxyalkyl(meth)acrylate and process for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0240066B2 (enrdf_load_stackoverflow) | 1990-09-10 |
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