CO4180607A1 - Procedimiento de una etapa para la fabricacion de derivados de acido 3-quinoloncarboxilico - Google Patents
Procedimiento de una etapa para la fabricacion de derivados de acido 3-quinoloncarboxilicoInfo
- Publication number
- CO4180607A1 CO4180607A1 CO94054149A CO94054149A CO4180607A1 CO 4180607 A1 CO4180607 A1 CO 4180607A1 CO 94054149 A CO94054149 A CO 94054149A CO 94054149 A CO94054149 A CO 94054149A CO 4180607 A1 CO4180607 A1 CO 4180607A1
- Authority
- CO
- Colombia
- Prior art keywords
- formula
- case
- ester
- acid
- halogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- UBIKHJZIEKPIBU-UHFFFAOYSA-N 3-oxo-2h-quinoline-2-carboxylic acid Chemical class C1=CC=CC2=CC(=O)C(C(=O)O)N=C21 UBIKHJZIEKPIBU-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical group [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- OITDPRAMDXERDT-DOFZRALJSA-N (5Z,8Z,11Z,14Z)-N-(3-nitrophenyl)icosa-5,8,11,14-tetraenamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC1=CC=CC([N+]([O-])=O)=C1 OITDPRAMDXERDT-DOFZRALJSA-N 0.000 abstract 1
- 125000006519 CCH3 Chemical group 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- -1 DIMETHYLAMIN ACRYLIC ACID ESTER Chemical class 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 238000009413 insulation Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
Abstract
1. UN PROCEDIMEINTO DE UNA SOLA ETAPA PARA LA FABRICACION DE DERIVADOS DE ACIDO 3-QUINOLOCARBO- XILICO, QUE PUEDE CONTENER DADO EL CASO EN TODAS LAS PARTES DEL ANILLO OTROS ATOMOS DE NITROGENO, DE OXIGENO O DE AZUFRE Y DADO EL CASO PUEDE ESTAR SUBSTITUIDO Y A REPRESENTACH, CF, CCl, C-OCH3, C-CH3, X1 REPRESENTA H, HALOGENO, NH2, CH3, R1 REPRESENTA ALQUILO DE C1-C3, FCH2CH2-, CICLOPROPILO, FENILO O CICLOPROPILO SUBSTITUIDO DADO EL CASO DE UNA A TRES VECES POR HALOGENO, CARACTERIZADO PORQUE SIN UN AISLAMIENTO DE LAS ETAPAS INTERMEDIAS, O BIEN SE HACE REACCIONAR HA- LOGENURO DE ACIDO DE LA FORMULA (XXVI) EN LA QUE Hal, X2 Y X3 REPRESENTAN FLUOR O CLORO, Y A Y X1 TIENEN EL SIGNIFICADO INDICADO ANTERIORMENTE, CON UN ESTER DE ACIDO DIMETILAMINOACRILICO DE LA FOR- MULA (CH3)2N-CH=CH-COOR EN UN DISOLVENTE, DESPUES DE LO CUAL SE GENERA EL AMONOACRILESTER (XIII) MEDIANTE ADICION DE UNA AMNA R1-NH2 BAJO INTER- CAMBIO DE AMINA EN LA PARTE DE ACRILESTER DEL PRODUCTO PRIMARIO, O EL HALOGENURO DE ACIDO SE HACE REACCIONAR IGUALMENTE CON UN AMINOACRILESTER DE LA FORMULA R1NH-CH=CH-COOR, EN CUYO CASO SE SUPRIME EL INTERCAMBIO DE AMINA DESCRITO ANTERIOR- MENTE Y SE GENERA INMEDIATAMENTE EL COMPUESTO (XIII) EL EL QUE A, X1 Y R1 TIENEN EL SIGNIFICADO INDICADO PARA LA FORMULA (Ia), X2 Y X3 REPRESENTAN HALOGENO Y R REPRESENTA UN RESTO ORGANICO USUAL APROPIADO PARA LA FORMAION DE ESTER, PREFERENTE- MENTE METILO, ETILO O PROPILO, SE CALIENTA EN UN DISOLVENTE CON UNA BASE AUXILIAR Y EN ESTE CASO SE CICLA DANDO COMPUESTOS DE LA FORMULA GENERAL (XIV), EN LA QUE A, R, R1 Y X32 TIENEN EL SIGNIFICADO MENCIONADO ANTERIORMENTE, QUE SE TRANSFORMAN SIN AISLAMIENTO INTERMEDIO MEDIANTE REACCION CON COMPUESTOS HETEROCICLICOS EN LA QUE R1 Y R" TIENEN EL SIGNIFICADO INDICADO ANTERIOR- MENTE EN ESTER DE LA FORMULA GENERAL EN LA QUE A, R, R1, R" Y X1 TIENEN EL SIGNIFICADO MENCIONADO ANTERIORMENTE, A PARTIR DE LOS CUALES SE OBTIENEN, MEDIANTE SAPONIFICACION ALCALINA DE LA FUNCION ESTER, LOS DERIVADOS DE ACIDO 3-QUINO- LONCARBOXILICO DE LA FORMULA (Ia), QUE SE PRECI- PITAN MEDIANTE NEUTRALIZACION DE LA MEZCLA DE REACCION.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4342186A DE4342186A1 (de) | 1993-12-10 | 1993-12-10 | Eintopfverfahren zur Herstellung von 3-Chinoloncarbonsäurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO4180607A1 true CO4180607A1 (es) | 1995-06-07 |
Family
ID=6504693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO94054149A CO4180607A1 (es) | 1993-12-10 | 1994-11-28 | Procedimiento de una etapa para la fabricacion de derivados de acido 3-quinoloncarboxilico |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US5639886A (es) |
| EP (1) | EP0657448B1 (es) |
| JP (1) | JP3963490B2 (es) |
| KR (1) | KR950018008A (es) |
| CN (1) | CN1109877A (es) |
| AT (1) | ATE163645T1 (es) |
| AU (1) | AU693818B2 (es) |
| BG (1) | BG61947B1 (es) |
| CA (1) | CA2137523C (es) |
| CO (1) | CO4180607A1 (es) |
| CZ (1) | CZ288078B6 (es) |
| DE (2) | DE4342186A1 (es) |
| DK (1) | DK0657448T3 (es) |
| EE (1) | EE03215B1 (es) |
| ES (1) | ES2113040T3 (es) |
| FI (1) | FI945776A (es) |
| GR (1) | GR3026383T3 (es) |
| HR (1) | HRP940950B1 (es) |
| HU (1) | HU220597B1 (es) |
| IL (1) | IL111921A (es) |
| LV (1) | LV11470B (es) |
| MY (1) | MY113302A (es) |
| NO (1) | NO307180B1 (es) |
| NZ (1) | NZ270086A (es) |
| PE (1) | PE33795A1 (es) |
| PL (1) | PL180022B1 (es) |
| RO (1) | RO113345B1 (es) |
| RU (1) | RU2138483C1 (es) |
| SI (1) | SI0657448T1 (es) |
| SK (1) | SK279950B6 (es) |
| SV (1) | SV1994000071A (es) |
| TW (1) | TW401412B (es) |
| UA (1) | UA41323C2 (es) |
| YU (1) | YU48865B (es) |
| ZA (1) | ZA949830B (es) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19826050A1 (de) * | 1998-06-12 | 1999-12-16 | Bayer Ag | Verfahren zur Herstellung von Chinolon- und Naphthyridoncarbonsäuren und deren Ester |
| WO2001062734A1 (fr) * | 2000-02-25 | 2001-08-30 | Daiichi Pharmaceutical Co., Ltd. | Procede de production d'acides quinolonecarboxyliques et de leurs intermediaires |
| US6608078B2 (en) | 2000-05-08 | 2003-08-19 | Wockhardt Limited | Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment |
| DE10026903A1 (de) * | 2000-06-03 | 2002-01-10 | Cpc Cellular Process Chemistry | Verfahren zur Herstellung von Chinolon-3-carbonsäuren |
| US7098219B2 (en) | 2000-08-01 | 2006-08-29 | Wockhart Limited | Inhibitors of cellular efflux pumps of microbes |
| US6878713B2 (en) | 2001-04-25 | 2005-04-12 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| US6964966B2 (en) | 2001-04-25 | 2005-11-15 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| WO2003099815A1 (en) | 2002-05-28 | 2003-12-04 | Wockhardt Limited | Crystalline fluoroquinolone arginine salt form |
| KR100519158B1 (ko) * | 2002-12-21 | 2005-10-06 | 주식회사유한양행 | 퀴놀론 카르복실레이트 유도체의 제조방법 |
| AU2003304460A1 (en) * | 2003-09-04 | 2005-03-29 | Wockhardt Limited | Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate |
| WO2005026145A2 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Quinolone antibacterial agents |
| CN100412075C (zh) * | 2004-06-22 | 2008-08-20 | 浙江医药股份有限公司新昌制药厂 | 左旋氧氟沙星和氧氟沙星的制备方法 |
| EP2089388B1 (en) | 2006-11-13 | 2014-01-29 | Cipla Limited | Process for the synthesis of moxifloxacin hydrochloride |
| EP1992626A1 (en) * | 2007-05-10 | 2008-11-19 | Sandoz AG | Process for the preparation of moxifloxacin hydrochloride |
| FR2916446B1 (fr) * | 2007-05-24 | 2009-08-21 | Biocodex Sa | Nouveau procede de synthese de fluoroquinolones |
| EP2083010A1 (en) | 2008-01-08 | 2009-07-29 | Chemo Ibérica, S.A. | Polymorphic Forms of Moxifloxacin hydrochloride and processes for preparation thereof |
| CN101781299B (zh) * | 2010-01-13 | 2012-06-27 | 杭州师范大学 | 一种喹诺酮类药物关键中间体的一锅法合成方法 |
| IT1398952B1 (it) * | 2010-03-19 | 2013-03-28 | F S I Fabbrica Italiana Sint | Processo di preparazione della moxifloxacina e suoi sali |
| CN102675306A (zh) * | 2011-03-17 | 2012-09-19 | 苏州中科天马肽工程中心有限公司 | 一种莫西沙星或其盐的制备方法 |
| CN102267994B (zh) * | 2011-06-17 | 2013-01-30 | 江苏正大丰海制药有限公司 | 一种盐酸莫西沙星已知杂质的制备方法 |
| WO2013157018A1 (en) | 2012-04-18 | 2013-10-24 | Indian Institute Of Technology Madras | A process for the preparation of the core structure in quinolone and napthyridone class of antibiotics |
| WO2014087292A1 (en) | 2012-12-04 | 2014-06-12 | Mankind Research Centre | An improved process for the preparation of moxifloxacin hydrochloride |
| UA106556C2 (uk) | 2013-05-13 | 2014-09-10 | Наталья Николаевна Деркач | СПОСІБ ОДЕРЖАННЯ (1-ЦИКЛОПРОПІЛ-6-ФТОР-1,4-ДИГІДРО-8-МЕТОКСІ-7-[(4aS,7aS)-ОКТАГІДРО-6Н-ПІРОЛО[3,4-b]-4-ОКСО-3-ХІНОЛІНКАРБОНОВОЇ КИСЛОТИ |
| EP3638648A4 (en) | 2017-06-12 | 2021-02-17 | Virginia Commonwealth University | STREAMLINED SYNTHESES OF FLUORCHINOLONES |
| CN115385856A (zh) * | 2022-09-05 | 2022-11-25 | 常州大学 | 一锅法合成诺氟沙星中间体的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420743A1 (de) | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US5468861A (en) * | 1984-06-04 | 1995-11-21 | Bayer Aktiengesellschaft | 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and alkyl esters thereof |
| JPS62215572A (ja) * | 1986-03-17 | 1987-09-22 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| JPS63179856A (ja) | 1987-01-21 | 1988-07-23 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体の製造方法並びにその中間体 |
| DE3724466A1 (de) | 1987-07-24 | 1989-02-02 | Bayer Ag | Verfahren zur herstellung von chinoloncarbonsaeuren |
| US4780468A (en) * | 1987-08-07 | 1988-10-25 | Warner-Lambert Company | 8-trifluoromethyl quinolones as antibacterial agents |
| WO1989005643A1 (en) * | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Heterocyclic-substituted quinoline-carboxylic acids |
| DE3906365A1 (de) | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| DE4208792A1 (de) | 1992-03-19 | 1993-09-23 | Bayer Ag | Enantiomerenreine chinolincarbonsaeure-derivate |
| TW209865B (es) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| DE4208789A1 (de) | 1992-03-19 | 1993-09-23 | Bayer Ag | Enantiomerenreine chinolincarbonsaeure-derivate |
| AU4272793A (en) * | 1993-04-24 | 1994-11-21 | Korea Research Institute Of Chemical Technology | Novel quinolone carboxylic acid derivatives and process for preparing the same |
| JP2758722B2 (ja) * | 1993-08-13 | 1998-05-28 | ドング ホワ ファーマシューチカル インダストリアル カンパニー，リミテッド | 新規キノロンカルボン酸誘導体 |
-
1993
- 1993-12-10 DE DE4342186A patent/DE4342186A1/de not_active Withdrawn
-
1994
- 1994-11-18 EE EE9400332A patent/EE03215B1/xx not_active IP Right Cessation
- 1994-11-21 TW TW083110792A patent/TW401412B/zh not_active IP Right Cessation
- 1994-11-23 HR HRP4342186.5A patent/HRP940950B1/xx not_active IP Right Cessation
- 1994-11-28 EP EP94118676A patent/EP0657448B1/de not_active Expired - Lifetime
- 1994-11-28 DE DE59405376T patent/DE59405376D1/de not_active Expired - Lifetime
- 1994-11-28 ES ES94118676T patent/ES2113040T3/es not_active Expired - Lifetime
- 1994-11-28 AT AT94118676T patent/ATE163645T1/de not_active IP Right Cessation
- 1994-11-28 CO CO94054149A patent/CO4180607A1/es unknown
- 1994-11-28 SI SI9430120T patent/SI0657448T1/xx unknown
- 1994-11-28 DK DK94118676T patent/DK0657448T3/da active
- 1994-12-02 US US08/348,400 patent/US5639886A/en not_active Expired - Lifetime
- 1994-12-05 JP JP32920694A patent/JP3963490B2/ja not_active Expired - Lifetime
- 1994-12-06 AU AU80244/94A patent/AU693818B2/en not_active Ceased
- 1994-12-06 RO RO94-01949A patent/RO113345B1/ro unknown
- 1994-12-07 NZ NZ270086A patent/NZ270086A/en unknown
- 1994-12-07 SK SK1514-94A patent/SK279950B6/sk unknown
- 1994-12-07 CA CA002137523A patent/CA2137523C/en not_active Expired - Lifetime
- 1994-12-07 PE PE1994256625A patent/PE33795A1/es not_active Application Discontinuation
- 1994-12-07 IL IL11192194A patent/IL111921A/xx not_active IP Right Cessation
- 1994-12-08 FI FI945776A patent/FI945776A/fi unknown
- 1994-12-08 BG BG99248A patent/BG61947B1/bg unknown
- 1994-12-08 YU YU71694A patent/YU48865B/sh unknown
- 1994-12-08 SV SV1994000071A patent/SV1994000071A/es not_active Application Discontinuation
- 1994-12-09 CN CN94112890A patent/CN1109877A/zh active Pending
- 1994-12-09 PL PL94306198A patent/PL180022B1/pl unknown
- 1994-12-09 CZ CZ19943105A patent/CZ288078B6/cs not_active IP Right Cessation
- 1994-12-09 NO NO944786A patent/NO307180B1/no not_active IP Right Cessation
- 1994-12-09 HU HU9403553A patent/HU220597B1/hu not_active IP Right Cessation
- 1994-12-09 KR KR1019940033433A patent/KR950018008A/ko not_active Application Discontinuation
- 1994-12-09 RU RU94043645A patent/RU2138483C1/ru active
- 1994-12-09 LV LVP-94-241A patent/LV11470B/lv unknown
- 1994-12-09 UA UA94129157A patent/UA41323C2/uk unknown
- 1994-12-09 MY MYPI94003290A patent/MY113302A/en unknown
- 1994-12-09 ZA ZA949830A patent/ZA949830B/xx unknown
-
1998
- 1998-03-17 GR GR980400579T patent/GR3026383T3/el unknown
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