RO91871B - Process for preparing 1,4-dihydro-4-oxonaphtiridine derivatives - Google Patents

Process for preparing 1,4-dihydro-4-oxonaphtiridine derivatives

Info

Publication number
RO91871B
RO91871B RO118517A RO11851785A RO91871B RO 91871 B RO91871 B RO 91871B RO 118517 A RO118517 A RO 118517A RO 11851785 A RO11851785 A RO 11851785A RO 91871 B RO91871 B RO 91871B
Authority
RO
Romania
Prior art keywords
lower alkoxy
alkoxy
dihydro
alkyl
derivatives
Prior art date
Application number
RO118517A
Other languages
Romanian (ro)
Other versions
RO91871A (en
Inventor
Narita Hirokazu
Konishi Yoshinori
Nitta Jun
Nagaki Hideyoshi
Kitayama Isao
Kobayashi Yoriko
Shinagawa Mikako
Watanabe Yasuo
Yotsuji Akira
Minami Shinzaburo
Saikawa Isamu
Original Assignee
Toyama Chemical Co. Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=13845280&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RO91871(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Toyama Chemical Co. Ltd. filed Critical Toyama Chemical Co. Ltd.
Publication of RO91871A publication Critical patent/RO91871A/en
Publication of RO91871B publication Critical patent/RO91871B/en

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)

Abstract

Inventia se refera la un procedeu pentru prepararea unor derivati de 1,4-dihidro-4-oxonaftiridina cu formula generala I : sau o sare a acesteia în care R reprezinta o grupa fenol, eventual substituita cu atomul de halogen, hidroxi, alchil, alcoxi inferior, clano, acilamino sau trihalogen alchil si R1 reprezinta o amina ciclica aleasa dintre 1-pirolidinil, piperidini, 1-piperazinil, sau morfolil eventual substituita cu hidroxialchil, hidroxil, alchenil, acil, alcilamino, diaschilamino, acilamino, alcoxicarbonil si N-acid-N-alchilamino. Procedeul consta în tratarea unui compus cu formula generala II : în care Ra reprezinta hidrogen sau o grupa de protectie carboxilic cu compusi cu formula III : în care R1 are semnificatiile de mai sus, în mediul de cloroform sau dimetilsufoxid în prezenta trietilaminei sau al unui exces din compusul cu formula III ca agent de legare a acidului la temperaturi de 30..70 degree C, urmata de tratare cu acid clorhidric, acid bromhidric sau hidrixid de sodiu la temperaturi de 40..125 degree C.The invention relates to a process for the preparation of 1,4-dihydro-4-oxonaphthyridine derivatives of the general formula I: or a salt thereof wherein R represents a phenol group optionally substituted with a halogen atom, hydroxy, alkyl, alkoxy lower alkyl, haloalkyl, lower alkyl, lower alkoxy, lower alkyl, lower alkoxy, lower alkoxy, lower alkoxy, lower alkoxy, lower alkoxy, -N-alkylamino. The process consists in treating a compound of general formula II: wherein Ra represents hydrogen or a carboxylic acid protecting group with compounds of formula III: wherein R1 has the above meaning in chloroform or dimethylsulfoxide in the presence of triethylamine or an excess of the compound of formula III as an acid-binding agent at temperatures of 30-70 ° C, followed by treatment with hydrochloric acid, hydrobromic acid or sodium hydride at temperatures of 40 to 125 ° C.

RO118517A 1984-04-26 1985-04-24 Process for preparing 1,4-dihydro-4-oxonaphtiridine derivatives RO91871B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP59084963A JPS60228479A (en) 1984-04-26 1984-04-26 1,4-dihydro-4-oxonaphthyridine derivative and salt thereof

Publications (2)

Publication Number Publication Date
RO91871A RO91871A (en) 1987-07-30
RO91871B true RO91871B (en) 1987-07-31

Family

ID=13845280

Family Applications (2)

Application Number Title Priority Date Filing Date
RO118517A RO91871B (en) 1984-04-26 1985-04-24 Process for preparing 1,4-dihydro-4-oxonaphtiridine derivatives
RO126286A RO95509B (en) 1984-04-26 1985-04-24 Process for preparing 1,4-dihydro-4-oxonaphthyridine derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
RO126286A RO95509B (en) 1984-04-26 1985-04-24 Process for preparing 1,4-dihydro-4-oxonaphthyridine derivatives

Country Status (30)

Country Link
JP (1) JPS60228479A (en)
KR (1) KR870001693B1 (en)
AR (1) AR241911A1 (en)
AT (2) AT389698B (en)
AU (2) AU565087B2 (en)
BE (1) BE902279A (en)
CH (1) CH673458A5 (en)
CS (1) CS250684B2 (en)
DD (1) DD238795A5 (en)
DE (2) DE3546658C2 (en)
DK (1) DK165877C (en)
EG (1) EG17339A (en)
ES (2) ES8700256A1 (en)
FI (1) FI80453C (en)
FR (2) FR2563521B1 (en)
GB (2) GB2158825B (en)
HU (2) HU197571B (en)
ID (1) ID21142A (en)
IL (1) IL75021A (en)
IT (1) IT1209953B (en)
LU (1) LU85871A1 (en)
NL (2) NL187314C (en)
NO (1) NO162238C (en)
NZ (1) NZ211895A (en)
PH (3) PH22801A (en)
PL (1) PL147392B1 (en)
PT (1) PT80349B (en)
RO (2) RO91871B (en)
SE (2) SE463102B (en)
ZA (1) ZA853102B (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6172753A (en) * 1984-09-18 1986-04-14 Dainippon Pharmaceut Co Ltd Pyridyl ketone derivative
AT392789B (en) * 1985-01-23 1991-06-10 Toyama Chemical Co Ltd METHOD FOR PRODUCING 1-SUBSTITUTED ARYL-1,4-DIHYDRO-4-OXONAPHTHYRIDINE DERIVATIVES
AU576657B2 (en) * 1985-01-23 1988-09-01 Toyama Chemical Co. Ltd. Naphthyridine and pyridine derivatives
DE3525108A1 (en) * 1985-06-07 1986-12-11 Bayer Ag, 5090 Leverkusen ANTIBACTERIAL EFFECT OF CHINOLON CARBON ACID ESTERS
DE3685157D1 (en) * 1985-06-26 1992-06-11 Daiichi Seiyaku Co PYRIDON CARBON ACID DERIVATIVES.
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 (en) * 1988-05-23 1999-01-06 塩野義製薬株式会社 Pyridonecarboxylic acid antibacterial agent
DE3934082A1 (en) * 1989-10-12 1991-04-18 Bayer Ag CHINOLON CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS AN ANTIVIRAL AGENT
CA2100242A1 (en) * 1991-01-14 1992-07-15 Soon K. Moon Quinolone compounds and processes for preparation thereof
FR2692577B1 (en) * 1992-05-26 1996-02-02 Bouchara Sa NOVEL FLUORINATED QUINOLONES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME.
KR940014395A (en) * 1992-12-09 1994-07-18 강박광 Novel quinolone derivatives and preparation methods thereof
KR0148277B1 (en) * 1993-01-18 1998-11-02 채영복 Novel fluoroquinolone derivatives and process for the preparation thereof
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 (en) * 1993-12-09 1995-07-22 스미스클라인 비참 피엘씨 Novel quinolone derivatives and methods for their preparation
US5910498A (en) * 1994-10-20 1999-06-08 Wakunaga Seiyaku Kabushiki Kaisha Pyridonecarboxylic acid derivatives or salts thereof and antibacterial agents comprising the same as active ingredient
PT897919E (en) 1996-04-19 2004-11-30 Wakunaga Pharma Co Ltd NEW DERIVATIVES OF PYRIDONACARBOXYLIC ACID OR ITS SATISTS AND ANTI-BACTERIAL AGENTS CONTAINING THEM AS AN ACTIVE INGREDIENT
KR20000052892A (en) * 1996-10-30 2000-08-25 빌프리더 하이더 Method of producing naphthyridine compounds and novel intermediate products
DE19713506A1 (en) 1997-04-01 1998-10-08 Bayer Ag Process for the preparation of 2,6-dichloro-5-fluoronicotinonitrile and the chemical compound 3-cyano-2-hydroxy-5-fluoropyrid-6-one monosodium salt and its tautomers
RU2270695C2 (en) 1999-03-17 2006-02-27 Дайити Фармасьютикал Ко., Лтд. Pharmaceutical composition
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
JP3477466B2 (en) 1999-09-02 2003-12-10 湧永製薬株式会社 Quinolinecarboxylic acid derivatives or salts thereof
AU2001286852A1 (en) * 2000-08-29 2002-03-13 Chiron Corporation Quinoline antibacterial compounds and methods of use thereof
KR100981351B1 (en) * 2003-10-29 2010-09-10 주식회사 엘지생명과학 Process for preparing 7-chloro-1-cyclopropyl-6- fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
CN101792443A (en) * 2010-03-09 2010-08-04 北京欧凯纳斯科技有限公司 Fluoro-carbostyril derivative as well as preparation method and application thereof
JOP20190045A1 (en) 2016-09-14 2019-03-14 Bayer Ag 7-substituted 1-aryl-naphthyridine-3-carboxylic acid amides and use thereof
CN114369092A (en) * 2021-12-20 2022-04-19 赤峰万泽药业股份有限公司 Tosufloxacin tosylate and preparation method thereof

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* Cited by examiner, † Cited by third party
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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 (en) * 1978-08-25 1981-10-15 Dainippon Pharmaceutical Co A PROCEDURE FOR PREPARING 6-HALOGEN-4-OXO-7- (1-PIPERAZINYL) -1,8-NAFTIRIDIN-3-CARBOXYLIC ACID DERIVATIVES
DE3033157A1 (en) * 1980-09-03 1982-04-01 Bayer Ag, 5090 Leverkusen 7-AMINO-1-CYCLOPROPYL-4-OXO-1,4-DIHYDRO-NAPHTHYRIDINE-3-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE ANTIBACTERIAL AGENTS CONTAINING THEM
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 (en) * 1985-06-07 1986-12-11 Bayer Ag, 5090 Leverkusen ANTIBACTERIAL EFFECT OF CHINOLON CARBON ACID ESTERS

Also Published As

Publication number Publication date
CH673458A5 (en) 1990-03-15
FR2614620A1 (en) 1988-11-04
GB8510297D0 (en) 1985-05-30
NL187314C (en) 1991-08-16
HUT38634A (en) 1986-06-30
DK165877B (en) 1993-02-01
IL75021A (en) 1994-01-25
HU194226B (en) 1988-01-28
FI80453C (en) 1990-06-11
RO95509B (en) 1988-10-01
DD238795A5 (en) 1986-09-03
NO162238C (en) 1989-12-06
DE3514076C2 (en) 1989-03-30
IT8548002A0 (en) 1985-04-26
ES8700256A1 (en) 1986-09-16
JPS6320828B2 (en) 1988-04-30
FR2563521B1 (en) 1989-02-03
SE8804586L (en) 1988-12-20
ES542584A0 (en) 1986-09-16
SE463102B (en) 1990-10-08
SE501412C2 (en) 1995-02-13
PH22801A (en) 1988-12-12
DK185685A (en) 1985-10-27
DK165877C (en) 1993-06-21
ATA267888A (en) 1989-09-15
AU612993B2 (en) 1991-07-25
ID21142A (en) 1999-04-29
FI80453B (en) 1990-02-28
AU8180487A (en) 1988-03-24
AT389698B (en) 1990-01-10
AT390258B (en) 1990-04-10
EG17339A (en) 1989-06-30
NL9100648A (en) 1991-08-01
NO162238B (en) 1989-08-21
GB2158825A (en) 1985-11-20
PT80349B (en) 1987-09-30
PL253108A1 (en) 1985-12-17
ES8706673A1 (en) 1987-07-01
GB2191776A (en) 1987-12-23
FR2563521A1 (en) 1985-10-31
PT80349A (en) 1985-05-01
SE8502017D0 (en) 1985-04-25
DK185685D0 (en) 1985-04-25
DE3514076A1 (en) 1985-10-31
RO91871A (en) 1987-07-30
IT1209953B (en) 1989-08-30
FR2614620B1 (en) 1990-03-09
JPS60228479A (en) 1985-11-13
AR241911A1 (en) 1993-01-29
DE3546658C2 (en) 1992-04-02
NL8501172A (en) 1985-11-18
ES551538A0 (en) 1987-07-01
LU85871A1 (en) 1985-12-16
PH25228A (en) 1991-03-27
SE8804586D0 (en) 1988-12-20
GB2191776B (en) 1990-03-28
NZ211895A (en) 1988-07-28
HU197571B (en) 1989-04-28
PL147392B1 (en) 1989-05-31
BE902279A (en) 1985-10-25
AU565087B2 (en) 1987-09-03
AU4165085A (en) 1985-10-31
GB8716897D0 (en) 1987-08-26
NO851643L (en) 1985-10-28
KR870001693B1 (en) 1987-09-24
GB2158825B (en) 1989-01-25
FI851637A0 (en) 1985-04-25
IL75021A0 (en) 1985-08-30
KR850007596A (en) 1985-12-07
ZA853102B (en) 1986-12-30
RO95509A (en) 1988-09-30
ATA122485A (en) 1989-06-15
CS250684B2 (en) 1987-05-14
PH25046A (en) 1991-01-28
FI851637L (en) 1985-10-27
SE8502017L (en) 1985-10-27

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