YU48865B - Postupak prema kome se, bez izdvajanja međuproizvoda, pripremaju derivati 3-hinolon-karbonske kiseline - Google Patents
Postupak prema kome se, bez izdvajanja međuproizvoda, pripremaju derivati 3-hinolon-karbonske kiselineInfo
- Publication number
- YU48865B YU48865B YU71694A YU71694A YU48865B YU 48865 B YU48865 B YU 48865B YU 71694 A YU71694 A YU 71694A YU 71694 A YU71694 A YU 71694A YU 48865 B YU48865 B YU 48865B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- ester
- denotes
- acid derivatives
- general formula
- 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 abstract 3
- 238000005580 one pot reaction Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 4
- 150000001412 amines 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
- -1 FCH2CH2- Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006519 CCH3 Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Photolithography (AREA)
Abstract
Postupak prema kome se bez izdvajanja meduproizvoda pripremaju derivati 3-hinolon-karbonske kiseline, opste formule (Ia) u kojoj R' i R" zajedno sa atomom azota za koji su vezani, obrazuju mono ili bi-ciklican heteroprsten, koji eventualno u svim delovima prstena moze da sadrzi jos i druge hetero-atome, azota, kiseonika ili sumpora, a koji eventualno moze da bude supstituisan, a u kojoj A oznacava CH, CF, CCI, C-OCH3, C-CH3, X1 oznacava H, halogen, NH2. CH3, R1 oznacava C1-C3-alkil, FCH2CH2-, ciklopropil, eventualno jedanput do triput halogenom supstituisan fenil, ili ciklopropil, naznacen time, sto se bez izdvajanja meduproizvoda deluje na halogenid kiseline, formule (XXVI) u kojoj Hal, X2 i X3 oznacavaju fluor ili hlor, a A i X1 imaju gore navedeno znacenje, u nekom rastvaracu, ili sa estrom dimetilaminoakrilne kiseline, formule (CH3)2N-CH=CH-COOR, posle cega se, dodavanjem amina R1-NH2 uz izmenu amina u delu akrilestra primarnog proizvoda, dobija aminoakrilestar (XIII), ili se na halogenid kiseline odmah deluje aminoakrilestrom, formule R1NH-CH=CH-COOR, u kom slucaju otpada napred opisana izmena amina pa se odmah dobija jedinjenje (XIII) u kome A, X1 i R1 imaju znacenje navedeno za formulu (Ia), X2 i X3 oznacavaju halogen, a R oznacava uobicajeni ostatak pogodan za stvaranje estra, prvenstveno metil, etil ili propil, sto se u nekom rastvaracu zagreva sa nekom pomocnom bazom i pritom ciklizuje u jedinjenje opste formule (XIV), u kojoj A, R, R1 i X3 imaju gore navedeno znacenje,koja se, bez izdvajanja kao meduproizvod, pomocu heterociklicnih jedinjenja u kojima R' i R" imaju gore navedeno znacenje, prevode u estre, opste formule u kojoj A, R, R1, R', R" i X1 imaju gore pomenuto znacenje, iz kojih, alkalnim saponifikovanjem estarske funckije, nastaju derivati 3-hinolon-karbonske kiseline, formule (Ia), koji se iz reakcione smese taloze neutralisanjem. - Prijava sadrzi jos 8 zavisnih zahteva.
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 (2)
Publication Number | Publication Date |
---|---|
YU71694A YU71694A (sh) | 1996-10-18 |
YU48865B true YU48865B (sh) | 2002-08-12 |
Family
ID=6504693
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
YU71694A YU48865B (sh) | 1993-12-10 | 1994-12-08 | Postupak prema kome se, bez izdvajanja međuproizvoda, pripremaju derivati 3-hinolon-karbonske kiseline |
Country Status (35)
Country | Link |
---|---|
US (1) | US5639886A (sh) |
EP (1) | EP0657448B1 (sh) |
JP (1) | JP3963490B2 (sh) |
KR (1) | KR950018008A (sh) |
CN (1) | CN1109877A (sh) |
AT (1) | ATE163645T1 (sh) |
AU (1) | AU693818B2 (sh) |
BG (1) | BG61947B1 (sh) |
CA (1) | CA2137523C (sh) |
CO (1) | CO4180607A1 (sh) |
CZ (1) | CZ288078B6 (sh) |
DE (2) | DE4342186A1 (sh) |
DK (1) | DK0657448T3 (sh) |
EE (1) | EE03215B1 (sh) |
ES (1) | ES2113040T3 (sh) |
FI (1) | FI945776A (sh) |
GR (1) | GR3026383T3 (sh) |
HR (1) | HRP940950B1 (sh) |
HU (1) | HU220597B1 (sh) |
IL (1) | IL111921A (sh) |
LV (1) | LV11470B (sh) |
MY (1) | MY113302A (sh) |
NO (1) | NO307180B1 (sh) |
NZ (1) | NZ270086A (sh) |
PE (1) | PE33795A1 (sh) |
PL (1) | PL180022B1 (sh) |
RO (1) | RO113345B1 (sh) |
RU (1) | RU2138483C1 (sh) |
SI (1) | SI0657448T1 (sh) |
SK (1) | SK279950B6 (sh) |
SV (1) | SV1994000071A (sh) |
TW (1) | TW401412B (sh) |
UA (1) | UA41323C2 (sh) |
YU (1) | YU48865B (sh) |
ZA (1) | ZA949830B (sh) |
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 |
PL214849B1 (pl) * | 2003-09-04 | 2013-09-30 | Wockhardt Ltd | Tetrahydrat soli kwasu benzochinolizyno-2-karboksylowego z arginina, sposób jego wytwarzania, kompozycja zawierajaca przedmiotowy tetrahydrat soli oraz jego zastosowanie |
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 |
KR101539561B1 (ko) | 2006-11-13 | 2015-07-27 | 씨아이피엘에이 엘티디. | 목시플록사신 염산염의 합성방법 |
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 (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 |
WO2018231747A2 (en) * | 2017-06-12 | 2018-12-20 | 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 |
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 |
TW209865B (sh) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
WO1994025464A1 (en) * | 1993-04-24 | 1994-11-10 | Korea Research Institute Of Chemical Technology | Novel quinolone carboxylic acid derivatives and process for preparing the same |
BR9407283A (pt) * | 1993-08-13 | 1996-10-01 | Dong Wha Pharm Co Ltd | Derivados do ácido carboxílico quinolônico e processo de preparação |
-
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 SI SI9430120T patent/SI0657448T1/xx unknown
- 1994-11-28 AT AT94118676T patent/ATE163645T1/de not_active IP Right Cessation
- 1994-11-28 DE DE59405376T patent/DE59405376D1/de not_active Expired - Lifetime
- 1994-11-28 CO CO94054149A patent/CO4180607A1/es unknown
- 1994-11-28 EP EP94118676A patent/EP0657448B1/de not_active Expired - Lifetime
- 1994-11-28 ES ES94118676T patent/ES2113040T3/es not_active Expired - Lifetime
- 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 CA CA002137523A patent/CA2137523C/en not_active Expired - Lifetime
- 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 SK SK1514-94A patent/SK279950B6/sk unknown
- 1994-12-07 PE PE1994256625A patent/PE33795A1/es not_active Application Discontinuation
- 1994-12-08 YU YU71694A patent/YU48865B/sh unknown
- 1994-12-08 BG BG99248A patent/BG61947B1/bg unknown
- 1994-12-08 FI FI945776A patent/FI945776A/fi 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 UA UA94129157A patent/UA41323C2/uk unknown
- 1994-12-09 MY MYPI94003290A patent/MY113302A/en unknown
- 1994-12-09 HU HU9403553A patent/HU220597B1/hu not_active IP Right Cessation
- 1994-12-09 LV LVP-94-241A patent/LV11470B/lv unknown
- 1994-12-09 RU RU94043645A patent/RU2138483C1/ru active
- 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 ZA ZA949830A patent/ZA949830B/xx unknown
- 1994-12-09 KR KR1019940033433A patent/KR950018008A/ko not_active Application Discontinuation
- 1994-12-09 NO NO944786A patent/NO307180B1/no not_active IP Right Cessation
-
1998
- 1998-03-17 GR GR980400579T patent/GR3026383T3/el unknown
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