JPS57176987A - Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative - Google Patents

Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative

Info

Publication number
JPS57176987A
JPS57176987A JP56063170A JP6317081A JPS57176987A JP S57176987 A JPS57176987 A JP S57176987A JP 56063170 A JP56063170 A JP 56063170A JP 6317081 A JP6317081 A JP 6317081A JP S57176987 A JPS57176987 A JP S57176987A
Authority
JP
Japan
Prior art keywords
compound shown
pyrrolo
quinoline
carboxylic acid
formulai
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.)
Granted
Application number
JP56063170A
Other languages
Japanese (ja)
Other versions
JPH0222074B2 (en
Inventor
Hiroshi Ishikawa
Tetsuyuki Uno
Masanobu Kano
Kazuyuki Nakagawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Otsuka Pharmaceutical Co Ltd
Original Assignee
Otsuka Pharmaceutical 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
Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd
Priority to JP56063170A priority Critical patent/JPS57176987A/en
Priority to NO813726A priority patent/NO156828C/en
Priority to AT0474881A priority patent/AT395150B/en
Priority to DE3153221A priority patent/DE3153221C2/de
Priority to PT73957A priority patent/PT73957B/en
Priority to FI813526A priority patent/FI71141C/en
Priority to DK495281A priority patent/DK160940C/en
Priority to DE19813144455 priority patent/DE3144455A1/en
Priority to SU813354800A priority patent/SU1366055A3/en
Priority to DE2000175035 priority patent/DE10075035I2/en
Priority to SE8106642A priority patent/SE448542B/en
Priority to IT49656/81A priority patent/IT1171646B/en
Priority to KR1019810004344A priority patent/KR880001625B1/en
Priority to GB8133890A priority patent/GB2086905B/en
Priority to NL8105075A priority patent/NL193457C/en
Priority to PH26477A priority patent/PH16685A/en
Priority to US06/320,027 priority patent/US4399134A/en
Priority to FR8121100A priority patent/FR2493849A1/en
Priority to AU77335/81A priority patent/AU546358B2/en
Priority to CH7200/81A priority patent/CH648845A5/en
Priority to MX785781A priority patent/MX155102A/en
Priority to ES507493A priority patent/ES8301981A1/en
Priority to CA000389769A priority patent/CA1179341A/en
Priority to ES516523A priority patent/ES8401035A1/en
Publication of JPS57176987A publication Critical patent/JPS57176987A/en
Priority to SU823527501A priority patent/SU1277896A3/en
Priority to US06/497,914 priority patent/US4552879A/en
Priority to AT2887/89A priority patent/AT393383B/en
Publication of JPH0222074B2 publication Critical patent/JPH0222074B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • 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
    • C07D471/06—Peri-condensed systems

Abstract

NEW MATERIAL:A compound shown by the formulaI(R1 is H, lower alkyl; R2 is H, halogen; R3 is 1-pyrrolidinyl, morpholino, thiomorpholino, 1,2,5,6-tetrahydro- 1-pyridyl, etc.) and its salt.
EXAMPLE: 9-(1-Pyrrolidinyl)-8-fluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij] quinoline-5-carboxylic acid.
USE: An antibacterial agent. Also useful as a germicide for external use and a disinfectant. Characteritically, effective against Gram-positive and Gram-negative bacteria, having low toxicity and extremely low side effects. Having strong activity on Pseudomonas aeruginosa and Proteus, and antifugal activity on a resistant fungus of penicillin, etc.
PROCESS: A compound shown by the formula II (X is halogen, lower alkanesulfonyloxy, etc.) is reacted with a compound such as pyrrolidine, morpholine, etc., to give a compound shown by the formulaI.
COPYRIGHT: (C)1982,JPO&Japio
JP56063170A 1980-11-10 1981-04-24 Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative Granted JPS57176987A (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
JP56063170A JPS57176987A (en) 1981-04-24 1981-04-24 Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative
NO813726A NO156828C (en) 1980-11-10 1981-11-04 ANALOGY PROCEDURE FOR THE PREPARATION OF ANTIBACTERYLY EFFECTIVE BENZOHETEROCYCLIC COMPOUNDS.
AT0474881A AT395150B (en) 1980-11-10 1981-11-05 METHOD FOR PRODUCING NEW BENZOHETEROCYCLIC COMPOUNDS
DE3153221A DE3153221C2 (en) 1981-04-24 1981-11-09
PT73957A PT73957B (en) 1980-11-10 1981-11-09 Process for preparing piperazinylbenzoheterocyclic compounds
FI813526A FI71141C (en) 1980-11-10 1981-11-09 FRUIT PROCESSING WITH ANTIBACTERIA AEMNEN ANVAENDBARA 6,7-DIHYDRO-1-OXO-BENZO / IJ / -QUINOLIZIN-2-CARBOXYLSYROR OCH 1,2-DIHYDRO-6-OXO-3,1-PYRROL quinoline-5-carboxylic acids
DK495281A DK160940C (en) 1980-11-10 1981-11-09 METHOD OF ANALOGUE FOR THE PREPARATION OF BENZOHETEROCYCLIC COMPOUNDS OR PHARMACEUTICAL ACCEPTABLE SALTS THEREOF
DE19813144455 DE3144455A1 (en) 1980-11-10 1981-11-09 BENZOHETEROCYCLIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND BACTERIOSTATIC AGENTS THAT CONTAIN THEM
SU813354800A SU1366055A3 (en) 1980-11-10 1981-11-09 Method of obtaining piperazinylbenzoheterocyclic compounds
DE2000175035 DE10075035I2 (en) 1980-11-10 1981-11-09 Benzo¬ij¾chinolizinderivate Process for their preparation and bacteriostatic agents containing them
SE8106642A SE448542B (en) 1980-11-10 1981-11-09 BENZOHETEROCYCLIC COMPOUNDS, PROCEDURES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION THEREOF
IT49656/81A IT1171646B (en) 1980-11-10 1981-11-09 BENZOETEROCYCLIC COMPOUNDS AND PROCEDURE TO PREPARE THEM
ES507493A ES8301981A1 (en) 1980-11-10 1981-11-10 Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions
KR1019810004344A KR880001625B1 (en) 1980-11-10 1981-11-10 Process for the preparation of benzoheterocyclic compounds
NL8105075A NL193457C (en) 1980-11-10 1981-11-10 Benzoheterocyclic compounds and pharmaceutical composition containing such a compound.
PH26477A PH16685A (en) 1980-11-10 1981-11-10 Benzoheterocyclic compounds and antibacterial composition containing same
US06/320,027 US4399134A (en) 1980-11-10 1981-11-10 Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions
FR8121100A FR2493849A1 (en) 1980-11-10 1981-11-10 BENZOHETEROCYCLIC COMPOUNDS USEFUL AS ANTIMICROBIAL MEDICAMENTS AND METHODS OF THEIR PREPARATION
AU77335/81A AU546358B2 (en) 1980-11-10 1981-11-10 Piperazinylbenzoheterocyclic compounds
CH7200/81A CH648845A5 (en) 1980-11-10 1981-11-10 BENZOHETEROCYCLIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND BACTERIOSTATIC AGENTS THAT CONTAIN THEM.
MX785781A MX155102A (en) 1980-11-10 1981-11-10 PROCEDURE FOR PREPARING DERIVATIVES OF BENZO (I J) -QUINOLIZINE-2-CARBOXYLIC ACID AND DERIVATIVES OF PYRROLYL ACID- (3,2,1-I J) -QUINOLIN-5-CARBOXYLIC
GB8133890A GB2086905B (en) 1980-11-10 1981-11-10 Benzoheterocyclic compounds and process for preparing same
CA000389769A CA1179341A (en) 1980-11-10 1981-11-10 Piperazinylbenzoheterocyclic compounds and process for preparing same
ES516523A ES8401035A1 (en) 1980-11-10 1982-10-15 Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions
SU823527501A SU1277896A3 (en) 1980-11-10 1982-12-27 Method of producing tetrahydroquinoline derivatives or pharmaceutically acceptable salts thereof
US06/497,914 US4552879A (en) 1980-11-10 1983-05-25 Benzoheterocyclic compounds and pharmaceutical composition thereof
AT2887/89A AT393383B (en) 1980-11-10 1989-12-20 Processes for the preparation of novel benzo heterocyclic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP56063170A JPS57176987A (en) 1981-04-24 1981-04-24 Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative

Publications (2)

Publication Number Publication Date
JPS57176987A true JPS57176987A (en) 1982-10-30
JPH0222074B2 JPH0222074B2 (en) 1990-05-17

Family

ID=13221505

Family Applications (1)

Application Number Title Priority Date Filing Date
JP56063170A Granted JPS57176987A (en) 1980-11-10 1981-04-24 Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative

Country Status (2)

Country Link
JP (1) JPS57176987A (en)
DE (1) DE3153221C2 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59137482A (en) * 1983-01-26 1984-08-07 Otsuka Pharmaceut Co Ltd Pyrrolo(3,2,1,-ij)quinoline-5-carboxylic acid derivative
US6514986B2 (en) 2000-11-22 2003-02-04 Wockhardt Limited Chiral fluoroquinolone arginine salt forms
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
US6664267B1 (en) 2002-05-28 2003-12-16 Wockhardt Limited Crystalline fluoroquinolone arginine salt form
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
US7098219B2 (en) 2000-08-01 2006-08-29 Wockhart Limited Inhibitors of cellular efflux pumps of microbes
US7164023B2 (en) 2003-09-04 2007-01-16 Wockhardt Limited Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate
US7247642B2 (en) 1999-05-07 2007-07-24 Wockhardt Limited Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55149284A (en) * 1980-05-02 1980-11-20 Otsuka Pharmaceut Co Ltd Piperazinylbenzo heterocyclic derivative

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2914258A1 (en) * 1978-04-12 1979-10-25 Otsuka Pharma Co Ltd PIPERAZINYLBENZOHETEROCYCLIC COMPOUNDS, METHODS OF PREPARING THEREOF, AND AGENTS CONTAINING THEM
JPS6019910B2 (en) * 1979-10-11 1985-05-18 大塚製薬株式会社 Benzo[ij]quinolidine-2-carboxylic acid derivative and method for producing the same
JPS5630964A (en) * 1979-08-22 1981-03-28 Kyorin Pharmaceut Co Ltd Novel substituted quinolinecarboxylic acid and its preparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55149284A (en) * 1980-05-02 1980-11-20 Otsuka Pharmaceut Co Ltd Piperazinylbenzo heterocyclic derivative

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0321031B2 (en) * 1983-01-26 1991-03-20 Otsuka Pharma Co Ltd
JPS59137482A (en) * 1983-01-26 1984-08-07 Otsuka Pharmaceut Co Ltd Pyrrolo(3,2,1,-ij)quinoline-5-carboxylic acid derivative
US7247642B2 (en) 1999-05-07 2007-07-24 Wockhardt Limited Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment
US6753333B2 (en) 1999-12-14 2004-06-22 Wockhardt Limited Chiral fluoroquinolone arginine salt forms
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
US7098219B2 (en) 2000-08-01 2006-08-29 Wockhart Limited Inhibitors of cellular efflux pumps of microbes
US6514986B2 (en) 2000-11-22 2003-02-04 Wockhardt Limited Chiral fluoroquinolone arginine salt forms
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
US7393957B2 (en) 2001-04-25 2008-07-01 Wockhardt Limited Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
US7626032B2 (en) 2001-04-25 2009-12-01 Wockhardt Limited Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
US7132541B2 (en) 2002-05-28 2006-11-07 Wockhardt Limited Crystalline fluoroquinolone arginine salt form
US6664267B1 (en) 2002-05-28 2003-12-16 Wockhardt Limited Crystalline fluoroquinolone arginine salt form
US7164023B2 (en) 2003-09-04 2007-01-16 Wockhardt Limited Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate

Also Published As

Publication number Publication date
JPH0222074B2 (en) 1990-05-17
DE3153221C2 (en) 1991-07-04

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