RU94043645A - Способ получения производных 3-хиннолонкарбоновой кислоты - Google Patents
Способ получения производных 3-хиннолонкарбоновой кислотыInfo
- Publication number
- RU94043645A RU94043645A RU94043645/04A RU94043645A RU94043645A RU 94043645 A RU94043645 A RU 94043645A RU 94043645/04 A RU94043645/04 A RU 94043645/04A RU 94043645 A RU94043645 A RU 94043645A RU 94043645 A RU94043645 A RU 94043645A
- Authority
- RU
- Russia
- Prior art keywords
- general formula
- formula
- acid ester
- compound
- acid
- Prior art date
Links
- 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 claims abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims abstract 3
- -1 aminoacrylic acid ester Chemical class 0.000 claims abstract 3
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract 2
- 239000013067 intermediate product Substances 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 238000007127 saponification reaction Methods 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Photolithography (AREA)
Abstract
Объектом изобретения является способ получения производных 3-хинолонкарбоновой кислоты общей формулы 1, приведенной в описании, который заключается в том, что галоидангидрид кислоты формулы 2 подвергают взаимодействию со сложным эфиром аминокриловой кислоты общей формулы 3RNH-CH=CH -COORИли же сначала со сложным эфиром диметиламиноакриловой кислоты общей формулы 4(CH)N-CH=CH-COORИ затем с амином формулы (5) R-NHполучаемое при этом соединении общей формулы (6) подвергают циклизации в присутствии щелочного средства с последующим взаимодействием получаемого при этом соединения общей формулы (7) с гетеро циклическим соединением общей формулы (8) и щелочным омылением получаемого при этом соединения формулы (9) причем каждую стадию проводят без предварительного выделения соответствующих промежуточных продуктов, и целевой продукт выделяют в свободном виде или в виде соли. Формулы 1,2,6,7,8 и 9 приведены в описании. Приведенные в формулах 1-9 радикалы A,R-R,X-Xи Hal имеют указанные в описании значения.
Claims (1)
- Объектом изобретения является способ получения производных 3-хинолонкарбоновой кислоты общей формулы 1, приведенной в описании, который заключается в том, что галоидангидрид кислоты формулы 2 подвергают взаимодействию со сложным эфиром аминокриловой кислоты общей формулы 3
R3NH-CH=CH -COOR4
Или же сначала со сложным эфиром диметиламиноакриловой кислоты общей формулы 4
(CH3)2N-CH=CH-COOR4
И затем с амином формулы (5) R3-NH2 получаемое при этом соединении общей формулы (6) подвергают циклизации в присутствии щелочного средства с последующим взаимодействием получаемого при этом соединения общей формулы (7) с гетеро циклическим соединением общей формулы (8) и щелочным омылением получаемого при этом соединения формулы (9) причем каждую стадию проводят без предварительного выделения соответствующих промежуточных продуктов, и целевой продукт выделяют в свободном виде или в виде соли. Формулы 1,2,6,7,8 и 9 приведены в описании. Приведенные в формулах 1-9 радикалы A,R1-R4,X1-X3 и Hal имеют указанные в описании значения.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4342186.5 | 1993-12-10 | ||
| DE4342186A DE4342186A1 (de) | 1993-12-10 | 1993-12-10 | Eintopfverfahren zur Herstellung von 3-Chinoloncarbonsäurederivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94043645A true RU94043645A (ru) | 1996-10-27 |
| RU2138483C1 RU2138483C1 (ru) | 1999-09-27 |
Family
ID=6504693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU94043645A RU2138483C1 (ru) | 1993-12-10 | 1994-12-09 | Способ получения производных 3-хинолонкарбоновой кислоты |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US5639886A (ru) |
| EP (1) | EP0657448B1 (ru) |
| JP (1) | JP3963490B2 (ru) |
| KR (1) | KR950018008A (ru) |
| CN (1) | CN1109877A (ru) |
| AT (1) | ATE163645T1 (ru) |
| AU (1) | AU693818B2 (ru) |
| BG (1) | BG61947B1 (ru) |
| CA (1) | CA2137523C (ru) |
| CO (1) | CO4180607A1 (ru) |
| CZ (1) | CZ288078B6 (ru) |
| DE (2) | DE4342186A1 (ru) |
| DK (1) | DK0657448T3 (ru) |
| EE (1) | EE03215B1 (ru) |
| ES (1) | ES2113040T3 (ru) |
| FI (1) | FI945776A (ru) |
| GR (1) | GR3026383T3 (ru) |
| HR (1) | HRP940950B1 (ru) |
| HU (1) | HU220597B1 (ru) |
| IL (1) | IL111921A (ru) |
| LV (1) | LV11470B (ru) |
| MY (1) | MY113302A (ru) |
| NO (1) | NO307180B1 (ru) |
| NZ (1) | NZ270086A (ru) |
| PE (1) | PE33795A1 (ru) |
| PL (1) | PL180022B1 (ru) |
| RO (1) | RO113345B1 (ru) |
| RU (1) | RU2138483C1 (ru) |
| SI (1) | SI0657448T1 (ru) |
| SK (1) | SK279950B6 (ru) |
| SV (1) | SV1994000071A (ru) |
| TW (1) | TW401412B (ru) |
| UA (1) | UA41323C2 (ru) |
| YU (1) | YU48865B (ru) |
| ZA (1) | ZA949830B (ru) |
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 |
| KR20020075447A (ko) * | 2000-02-25 | 2002-10-04 | 다이이찌 세이야꾸 가부시기가이샤 | 퀴놀론카복실산의 제조방법 및 이의 중간체 |
| 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 |
| ATE366734T1 (de) | 2003-09-04 | 2007-08-15 | Wockhardt Ltd | Benzochinolizin-2-carbonsäureargininsalz- tetrahydrat |
| 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 |
| AU2007320997B2 (en) | 2006-11-13 | 2012-11-08 | 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 |
| US9388178B2 (en) | 2012-12-04 | 2016-07-12 | Mankind Research Centre | Process for the preparation of moxifloxacin hydrochloride |
| UA106556C2 (ru) | 2013-05-13 | 2014-09-10 | Наталья Николаевна Деркач | Способ получения (1-циклопропил-6-фтор-1,4-дигидро-8-метокси-7-[(4as,7as)-октагидро-6н-пироло[3,4-b]пиридин-6-ил]-4-оксо-3-хнолинкарбонованой кислоты |
| US11059788B2 (en) | 2017-06-12 | 2021-07-13 | Virginia Commonwealth University | Streamlined syntheses of fluoroquinolones |
| 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 |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| TW209865B (ru) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| DE4208789A1 (de) | 1992-03-19 | 1993-09-23 | Bayer Ag | Enantiomerenreine chinolincarbonsaeure-derivate |
| DE4208792A1 (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 DK DK94118676T patent/DK0657448T3/da active
- 1994-11-28 CO CO94054149A patent/CO4180607A1/es unknown
- 1994-11-28 SI SI9430120T patent/SI0657448T1/xx unknown
- 1994-11-28 AT AT94118676T patent/ATE163645T1/de not_active IP Right Cessation
- 1994-11-28 ES ES94118676T patent/ES2113040T3/es not_active Expired - Lifetime
- 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 RO RO94-01949A patent/RO113345B1/ro unknown
- 1994-12-06 AU AU80244/94A patent/AU693818B2/en not_active Ceased
- 1994-12-07 SK SK1514-94A patent/SK279950B6/sk unknown
- 1994-12-07 PE PE1994256625A patent/PE33795A1/es not_active Application Discontinuation
- 1994-12-07 NZ NZ270086A patent/NZ270086A/en unknown
- 1994-12-07 IL IL11192194A patent/IL111921A/xx not_active IP Right Cessation
- 1994-12-07 CA CA002137523A patent/CA2137523C/en not_active Expired - Lifetime
- 1994-12-08 SV SV1994000071A patent/SV1994000071A/es not_active Application Discontinuation
- 1994-12-08 BG BG99248A patent/BG61947B1/bg unknown
- 1994-12-08 FI FI945776A patent/FI945776A/fi unknown
- 1994-12-08 YU YU71694A patent/YU48865B/sh unknown
- 1994-12-09 CZ CZ19943105A patent/CZ288078B6/cs not_active IP Right Cessation
- 1994-12-09 UA UA94129157A patent/UA41323C2/ru unknown
- 1994-12-09 KR KR1019940033433A patent/KR950018008A/ko not_active Application Discontinuation
- 1994-12-09 RU RU94043645A patent/RU2138483C1/ru active
- 1994-12-09 PL PL94306198A patent/PL180022B1/pl unknown
- 1994-12-09 MY MYPI94003290A patent/MY113302A/en unknown
- 1994-12-09 NO NO944786A patent/NO307180B1/no not_active IP Right Cessation
- 1994-12-09 ZA ZA949830A patent/ZA949830B/xx unknown
- 1994-12-09 LV LVP-94-241A patent/LV11470B/lv unknown
- 1994-12-09 CN CN94112890A patent/CN1109877A/zh active Pending
- 1994-12-09 HU HU9403553A patent/HU220597B1/hu not_active IP Right Cessation
-
1998
- 1998-03-17 GR GR980400579T patent/GR3026383T3/el unknown
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