DE3514076C2 - - Google Patents
Info
- Publication number
- DE3514076C2 DE3514076C2 DE3514076A DE3514076A DE3514076C2 DE 3514076 C2 DE3514076 C2 DE 3514076C2 DE 3514076 A DE3514076 A DE 3514076A DE 3514076 A DE3514076 A DE 3514076A DE 3514076 C2 DE3514076 C2 DE 3514076C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- salt
- acid
- dihydro
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/61—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
NMR (CDCl₃) δ: 1,25 (1,29 H, t, J = 7 Hz), 135 (1,71 H, t, J = 7 Hz), 4,07 (1,14 H, s), 4,28 (2 H, q, J = 7 Hz), 5,82 (0,43 H, s), 7,80 (1 H, d, J = 7 Hz). 12,62 (0,43 H, s).
NMR (CDCl₃) δ: 1,08 (3 H, t, J = 7 Hz), 4,10 (2 H, q, J = 7 Hz), 6,77-7,40 (4 H, m), 8,50 (1 H, d, J = 13 Hz), 12,70 (1 H, J = 13 Hz).
NMR (CDCl₃) δ: 1,36 (3 H, t, J = 7 Hz), 4,30 (2 H, q, J = 7 Hz), 6,80-7,60 (3 H, m), 8,27 (1 H, d, J = 7 Hz), 8,42 (1 H, s).
NMR (CDCl₃) δ: 1,38 (3 H, t, J = 7 Hz), 2,05 (3 H, s), 3,53 (8 H, bs), 4,30 (2 H, q, J = 7 Hz), 6,80-7,75 (3 H, m), 8,00 (1 H, d, J = 13 Hz), 8,30 (1 H, s).
NMR (CDCl₃) δ: 1,32 (3 H, t, J = 7 Hz), 1,77-2,27 (5 H, m), 2,08 (5 H, s), 3,12-3,74 (4 H, m), 4,02-4,74 (3 H, m), 4,29 (3 H, q, J = 7 Hz) 6,75-7,60 (4 H, m), 7,93 (1 H, d, J = 8 Hz), 8,24 (1 H, s).
NMR (DMSO-d₆) δ: 1,82-2,42 (5 H, m), 2,27 (5 H, s), 3,12-4,30 (5 H, m) 6,92-8,17 (8 H, m), 8,79 (1 H, s).
Oxalsäuresalz von 7-(3-Amino-1-pyrrolidinyl)-6- fluor-1-(2,4-difluorphenyl)-1,4-dihydro-4-oxo-1,8-naph thyridin-3-carbonsäure, Fp. 250 bis 253°C.
Schwefelsäuresalz von 7-(3-Amino-1-pyrrolidinyl)- 6-fluor-1-(2,4-diffluorphenyl)-1,4-dihydro-4-oxo-1,8- naphthyridin-3-carbonsäure, Fp. 220 bis 230°C.
Claims (3)
- entweder in an sich bekannter Weise eine Verbindung der allgemeinen Formel oder ein Salz derselben, worin R¹ für eine Carboxyl-Schutzgruppe steht und R³ die oben angegebene Bedeutung hat, einer Ringschlußreaktion unterwirft und anschließend die Carboxyl-Schutzgruppe entfernt, oder
- auf an sich bekannte Weise eine Verbindung der allgemeinen Formel
- oder ein Salz derselben, wobei R3a für ein Halogenatom steht; R1a für ein Wasserstofffatom oder eine Carboxyl-Schutzgruppe steht, mit einer Verbindung der allgemeinen Formel R³-Hoder einem Salz derselben, wobei R³ die oben angegebene Bedeutung hat, umsetzt und gegebenenfalls die so erhaltenen Verbindungen in deren Salze überführt.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59084963A JPS60228479A (ja) | 1984-04-26 | 1984-04-26 | 1,4−ジヒドロ−4−オキソナフチリジン誘導体およびその塩 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3514076A1 DE3514076A1 (de) | 1985-10-31 |
DE3514076C2 true DE3514076C2 (de) | 1989-03-30 |
Family
ID=13845280
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3546658A Expired - Lifetime DE3546658C2 (de) | 1984-04-26 | 1985-04-18 | |
DE19853514076 Granted DE3514076A1 (de) | 1984-04-26 | 1985-04-18 | 1,4-dihydro-4-oxonaphthyridin-derivate und salze derselben, verfahren zu ihrer herstellung und antibakterielle mittel mit einem gehalt derselben |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3546658A Expired - Lifetime DE3546658C2 (de) | 1984-04-26 | 1985-04-18 |
Country Status (30)
Country | Link |
---|---|
JP (1) | JPS60228479A (de) |
KR (1) | KR870001693B1 (de) |
AR (1) | AR241911A1 (de) |
AT (2) | AT389698B (de) |
AU (2) | AU565087B2 (de) |
BE (1) | BE902279A (de) |
CH (1) | CH673458A5 (de) |
CS (1) | CS250684B2 (de) |
DD (1) | DD238795A5 (de) |
DE (2) | DE3546658C2 (de) |
DK (1) | DK165877C (de) |
EG (1) | EG17339A (de) |
ES (2) | ES8700256A1 (de) |
FI (1) | FI80453C (de) |
FR (2) | FR2563521B1 (de) |
GB (2) | GB2158825B (de) |
HU (2) | HU194226B (de) |
ID (1) | ID21142A (de) |
IL (1) | IL75021A (de) |
IT (1) | IT1209953B (de) |
LU (1) | LU85871A1 (de) |
NL (2) | NL187314C (de) |
NO (1) | NO162238C (de) |
NZ (1) | NZ211895A (de) |
PH (3) | PH22801A (de) |
PL (1) | PL147392B1 (de) |
PT (1) | PT80349B (de) |
RO (2) | RO91871B (de) |
SE (2) | SE463102B (de) |
ZA (1) | ZA853102B (de) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6172753A (ja) * | 1984-09-18 | 1986-04-14 | Dainippon Pharmaceut Co Ltd | ピリジルケトン誘導体 |
AU576657B2 (en) * | 1985-01-23 | 1988-09-01 | Toyama Chemical Co. Ltd. | Naphthyridine and pyridine derivatives |
AT392789B (de) * | 1985-01-23 | 1991-06-10 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 1-substituierten aryl-1,4-dihydro-4-oxonaphthyridinderivaten |
DE3525108A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Antibakteriell wirksame chinoloncarbonsaeureester |
IL79189A (en) * | 1985-06-26 | 1990-07-12 | Daiichi Seiyaku Co | Quinoline and/or naphthyridine-4-oxo-3-carboxylic acid derivatives,process for their preparation and pharmaceutical compositions comprising them |
US4962112A (en) * | 1987-08-04 | 1990-10-09 | Abbott Laboratories | 7-(2-methyl-4-aminopyrrolidinyl)naphthryidine and quinoline compounds |
IE62600B1 (en) * | 1987-08-04 | 1995-02-22 | Abbott Lab | Naphtyridine antianaerobic compounds |
US4859776A (en) * | 1988-03-11 | 1989-08-22 | Abbott Laboratories | (S)-7-(3-aminopyrrolidin-1-yl)-1-(ortho, para-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid and method for its preparation |
JP2844079B2 (ja) * | 1988-05-23 | 1999-01-06 | 塩野義製薬株式会社 | ピリドンカルボン酸系抗菌剤 |
DE3934082A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Chinoloncarbonsaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung als antivirale mittel |
AU1161492A (en) * | 1991-01-14 | 1992-08-17 | Hanmi Pharmaceutical Co., Ltd. | Novel quinolone compounds and processes for preparation thereof |
FR2692577B1 (fr) * | 1992-05-26 | 1996-02-02 | Bouchara Sa | Nouvelles quinolones fluorees, leur procede de preparation et les compositions pharmaceutiques en renfermant. |
KR940014395A (ko) * | 1992-12-09 | 1994-07-18 | 강박광 | 신규한 퀴놀론 유도체 및 그의 제조방법 |
KR0148277B1 (ko) * | 1993-01-18 | 1998-11-02 | 채영복 | 신규한 플루오르퀴놀론계 유도체 및 그의 제조방법 |
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 |
KR950018003A (ko) * | 1993-12-09 | 1995-07-22 | 스미스클라인 비참 피엘씨 | 신규한 퀴놀론 유도체 및 그의 제조 방법 |
DE69531305T2 (de) * | 1994-10-20 | 2004-05-13 | Wakunaga Seiyaku K.K. | Pyridoncarboxylat- derivate oder salze davon und antibakterielle zusammensetzungen die diese als aktiven bestandteil enthalten |
US6211375B1 (en) | 1996-04-19 | 2001-04-03 | Wakunaga Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives or salts thereof and antibacterial agents containing the same as the active ingredient |
PL332941A1 (en) * | 1996-10-30 | 1999-10-25 | Bayer Ag | Method of obtaining naphtyridinic compounds and novel intermediate compounds |
DE19713506A1 (de) | 1997-04-01 | 1998-10-08 | Bayer Ag | Verfahren zur Herstellung von 2,6-Dichlor-5-fluornicotinonitril und die chemische Verbindung 3-Cyano-2-hydroxy-5-fluorpyrid-6-on-mononatriumsalz sowie dessen Tautomere |
KR100768034B1 (ko) | 1999-03-17 | 2007-10-17 | 다이이찌 세이야꾸 가부시기가이샤 | 의약 조성물 |
US6441182B1 (en) | 1999-06-10 | 2002-08-27 | Bayer Aktiengesellschaft | Method for the production of 2,6-dichloro-5-fluoro-nicotinic acid and coarse and particularly pure 2,6-dichloro-5-fluoro-nicotinic acid |
EP1219618A4 (de) | 1999-09-02 | 2002-09-18 | Wakunaga Pharma Co Ltd | Qunolin-carbonsäure-derivate oder ihre salze |
EP1313708A1 (de) * | 2000-08-29 | 2003-05-28 | Chiron Corporation | Antibakterielle chinolin verbindungen zu ihrer verwendung |
KR100981351B1 (ko) * | 2003-10-29 | 2010-09-10 | 주식회사 엘지생명과학 | 7-클로로-1-사이클로프로필-6-플루오로-4-옥소-1,4-디하이드로-1,8-나프티리딘-3-카복실산의 제조방법 |
CN101792443A (zh) * | 2010-03-09 | 2010-08-04 | 北京欧凯纳斯科技有限公司 | 氟代喹诺酮衍生物及其制备方法和用途 |
JOP20190045A1 (ar) | 2016-09-14 | 2019-03-14 | Bayer Ag | مركبات أميد حمض 1- أريل-نفثيريدين-3-كربوكسيليك مستبدلة في الموضع 7 واستخدامها. |
CN114369092A (zh) * | 2021-12-20 | 2022-04-19 | 赤峰万泽药业股份有限公司 | 甲苯磺酸妥舒沙星及其制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2125310A1 (en) * | 1971-05-21 | 1972-11-30 | Sterling Drug Inc , New York, NY (V St A) | 1-alkyl-1,4-dihydro-4-oxo-1,8-naphtyridine 3-carboxylic acids antibac |
AR223983A1 (es) * | 1978-08-25 | 1981-10-15 | Dainippon Pharmaceutical Co | Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico |
DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
US4382937A (en) | 1981-02-27 | 1983-05-10 | Dainippon Pharmaceutical Co., Ltd. | Naphthyridine derivatives and their use as anti-bacterials |
IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
NZ210847A (en) * | 1984-01-26 | 1988-02-29 | Abbott Lab | Naphthyridine and pyridopyrimidine derivatives and pharmaceutical compositions |
IL74064A (en) * | 1984-01-26 | 1988-09-30 | Abbott Lab | 1,7-disubstituted-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid derivatives and antibacterial compositions containing them |
AU576657B2 (en) * | 1985-01-23 | 1988-09-01 | Toyama Chemical Co. Ltd. | Naphthyridine and pyridine derivatives |
DE3525108A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Antibakteriell wirksame chinoloncarbonsaeureester |
-
1984
- 1984-04-26 JP JP59084963A patent/JPS60228479A/ja active Granted
-
1985
- 1985-04-18 DE DE3546658A patent/DE3546658C2/de not_active Expired - Lifetime
- 1985-04-18 DE DE19853514076 patent/DE3514076A1/de active Granted
- 1985-04-23 GB GB08510297A patent/GB2158825B/en not_active Expired
- 1985-04-23 PH PH32174A patent/PH22801A/en unknown
- 1985-04-23 NL NLAANVRAGE8501172,A patent/NL187314C/xx not_active IP Right Cessation
- 1985-04-24 RO RO118517A patent/RO91871B/ro unknown
- 1985-04-24 AU AU41650/85A patent/AU565087B2/en not_active Expired
- 1985-04-24 RO RO126286A patent/RO95509B/ro unknown
- 1985-04-24 DD DD85275518A patent/DD238795A5/de unknown
- 1985-04-24 PT PT80349A patent/PT80349B/pt unknown
- 1985-04-24 AT AT0122485A patent/AT389698B/de not_active IP Right Cessation
- 1985-04-24 NZ NZ211895A patent/NZ211895A/xx unknown
- 1985-04-24 IL IL7502185A patent/IL75021A/en not_active IP Right Cessation
- 1985-04-24 NO NO851643A patent/NO162238C/no not_active IP Right Cessation
- 1985-04-24 EG EG261/85A patent/EG17339A/xx active
- 1985-04-25 BE BE0/214909A patent/BE902279A/fr not_active IP Right Cessation
- 1985-04-25 CH CH1798/85A patent/CH673458A5/de not_active IP Right Cessation
- 1985-04-25 DK DK185685A patent/DK165877C/da not_active IP Right Cessation
- 1985-04-25 FI FI851637A patent/FI80453C/fi not_active IP Right Cessation
- 1985-04-25 FR FR858506327A patent/FR2563521B1/fr not_active Expired
- 1985-04-25 ES ES542584A patent/ES8700256A1/es not_active Expired
- 1985-04-25 ID IDP980525A patent/ID21142A/id unknown
- 1985-04-25 HU HU851599A patent/HU194226B/hu unknown
- 1985-04-25 ZA ZA853102A patent/ZA853102B/xx unknown
- 1985-04-25 CS CS853035A patent/CS250684B2/cs not_active IP Right Cessation
- 1985-04-25 AR AR85300190A patent/AR241911A1/es active
- 1985-04-25 SE SE8502017A patent/SE463102B/sv not_active IP Right Cessation
- 1985-04-25 HU HU873675A patent/HU197571B/hu unknown
- 1985-04-25 KR KR1019850002822A patent/KR870001693B1/ko not_active IP Right Cessation
- 1985-04-26 PL PL1985253108A patent/PL147392B1/pl unknown
- 1985-04-26 IT IT8548002A patent/IT1209953B/it active
- 1985-04-26 LU LU85871A patent/LU85871A1/en unknown
-
1986
- 1986-01-31 ES ES551538A patent/ES8706673A1/es not_active Expired
-
1987
- 1987-07-17 GB GB8716897A patent/GB2191776B/en not_active Expired - Lifetime
- 1987-10-20 PH PH35958A patent/PH25046A/en unknown
- 1987-10-20 PH PH35960A patent/PH25228A/en unknown
- 1987-11-25 AU AU81804/87A patent/AU612993B2/en not_active Expired
-
1988
- 1988-06-30 FR FR888808836A patent/FR2614620B1/fr not_active Expired - Lifetime
- 1988-10-31 AT AT0267888A patent/AT390258B/de not_active IP Right Cessation
- 1988-12-20 SE SE8804586A patent/SE501412C2/sv not_active IP Right Cessation
-
1991
- 1991-04-15 NL NL9100648A patent/NL9100648A/nl not_active Application Discontinuation
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