CA2013449A1 - Antibacterial 5-alkylquinolonecarboxylic acids - Google Patents

Antibacterial 5-alkylquinolonecarboxylic acids

Info

Publication number
CA2013449A1
CA2013449A1 CA2013449A CA2013449A CA2013449A1 CA 2013449 A1 CA2013449 A1 CA 2013449A1 CA 2013449 A CA2013449 A CA 2013449A CA 2013449 A CA2013449 A CA 2013449A CA 2013449 A1 CA2013449 A1 CA 2013449A1
Authority
CA
Canada
Prior art keywords
alkylquinolonecarboxylic
antibacterial
acids
optionally substituted
hydrogen
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
CA2013449A
Other languages
French (fr)
Other versions
CA2013449C (en
Inventor
Michael Schriewer
Klaus Grohe
Andreas Krebs
Uwe Petersen
Thomas Schenke
Ingo Haller
Karl G. Metzger
Rainer Endermann
Hans-Joachim Zeiler
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of CA2013449A1 publication Critical patent/CA2013449A1/en
Application granted granted Critical
Publication of CA2013449C publication Critical patent/CA2013449C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • 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
    • 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
    • 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
    • C07D487/08—Bridged systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Antibacterial 5-alkylquinolonecarboxylic acids of the formula in which R3 is C1-C4-alkyl, R1 is optionally substituted alkyl or cycloalkyl, alkenyl, alkoxy, amino or alkylamino or optionally substituted phenyl, R2 is hydrogen or optionally substituted alkyl, R4 is a nitrogen-containing heterocyclic radical, and A is hydrogen, halogen, methyl, cyano or nitro, or forms a bridge with R1.
and hydrates and salts thereof.
CA002013449A 1989-04-03 1990-03-30 Antibacterial 5-alkylquinolonecarboxylic acids Expired - Fee Related CA2013449C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3910663.2 1989-04-03
DE3910663A DE3910663A1 (en) 1989-04-03 1989-04-03 5-ALKYLCHINOLON CARBONIC ACIDS

Publications (2)

Publication Number Publication Date
CA2013449A1 true CA2013449A1 (en) 1990-10-03
CA2013449C CA2013449C (en) 2001-01-02

Family

ID=6377683

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002013449A Expired - Fee Related CA2013449C (en) 1989-04-03 1990-03-30 Antibacterial 5-alkylquinolonecarboxylic acids

Country Status (16)

Country Link
EP (1) EP0391132A1 (en)
JP (1) JP3046035B2 (en)
KR (1) KR0156245B1 (en)
CN (1) CN1035945C (en)
AU (1) AU638005B2 (en)
CA (1) CA2013449C (en)
DD (1) DD298400A5 (en)
DE (1) DE3910663A1 (en)
FI (1) FI901615A7 (en)
HU (2) HU204811B (en)
IL (1) IL93954A0 (en)
NO (1) NO173547C (en)
NZ (1) NZ233142A (en)
PH (1) PH27364A (en)
PT (1) PT93639A (en)
ZA (1) ZA902510B (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4920120A (en) * 1988-01-25 1990-04-24 Warner-Lambert Company Antibacterial agents
MY105136A (en) * 1988-04-27 1994-08-30 Daiichi Seiyaku Co Optically active pyridonecarboxylic acid derivatives.
DD285601A5 (en) * 1988-07-15 1990-12-19 Bayer Ag,De PROCESS FOR PREPARING 7- (1-PYRROLIDINYL) -3-CHINOLONE AND NAPHTHYRIDONE CARBOXYLIC ACID DERIVATIVES
ES2079391T3 (en) * 1989-04-17 1996-01-16 Bayer Ag PROCEDURE FOR OBTAINING 2,7-DIAZABICICLO (3.3.0) OCTANES.
US5177210A (en) * 1989-04-17 1993-01-05 Bayer Aktiengesellschaft Preparation of 2,7-diazabicyclo(3.3.0)octanes
US5241076A (en) * 1989-04-17 1993-08-31 Bayer Aktiengesellschaft 1,4-diazatricyclo [6.3.0.0]undecanes
US5696132A (en) * 1991-05-28 1997-12-09 Daiichi Pharmaceutical Co., Ltd. Pyridonecarboxylic acid derivatives
DE4120646A1 (en) * 1991-06-22 1992-12-24 Bayer Ag 7-ISOINDOLINYL-CHINOLONE AND NAPHTHYRIDONE CARBONIC ACID DERIVATIVES
TW209865B (en) * 1992-01-10 1993-07-21 Bayer Ag
KR960003611B1 (en) * 1992-07-23 1996-03-20 재단법인 한국화학연구소 New diazabicyclo alkene derivatives and the preparation process thereof
DE4234078A1 (en) * 1992-10-09 1994-04-14 Bayer Ag Quinolonecarboxylic acids
DE4234330A1 (en) * 1992-10-12 1994-04-14 Bayer Ag Quinolonecarboxylic acids
JP3268098B2 (en) * 1992-12-25 2002-03-25 第一製薬株式会社 Bicyclic cyclic amine derivative
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
DE4329600A1 (en) * 1993-09-02 1995-03-09 Bayer Ag Pyrido [1,2,3-d, e] [1,3,4] benzoxadiazine derivatives
DE4339134A1 (en) * 1993-11-16 1995-05-18 Bayer Ag 1- (2-fluorocyclopropyl) quinolone and naphthyridonecarboxylic acid derivatives
DE4408212A1 (en) * 1994-03-11 1995-09-14 Bayer Ag 5-vinyl and 5-ethynyl quinolone and naphthyridone carboxylic acids
DE19546249A1 (en) * 1995-12-12 1997-06-19 Bayer Ag New crystal modification of 1-cyclopropyl-7 - ([S, S] -2,8-diazabicyclo [4,3,0] non-8-yl) -6-fluoro-1,4-dihydro-8-methoxy-4 -oxo-3-quinoline carboxylic acid hydrochloride (CDCH), process for its preparation and pharmaceutical preparations containing it
EP0882049B1 (en) * 1996-02-23 2002-11-20 Bayer Ag Possibly substituted 8-cyano-1-cyclopropyl-7-(2,8-diazabicyclo- 4.3.0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolin carboxylic acids and their derivatives
DE19633805A1 (en) * 1996-02-23 1997-08-28 Bayer Ag Optionally substituted 8-cyano-l-cyclopropyl-7- (2,8-diazabicyclo- [4.3.0] -nonan-8-yl) -6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids and their derivatives
DE19652239A1 (en) * 1996-12-16 1998-06-18 Bayer Ag Use of 7- (2-oxa-5,8-diazabicyclo [4.3.0] non-8-yl) -quinolone and naphthyridonecarboxylic acid derivatives for the therapy of Helicobacter pylori infections and the associated gastroduodenal diseases
DE19854355A1 (en) * 1998-11-25 2000-05-31 Bayer Ag Crystal modification B of 8-cyan-1-cyclopropyl-7- (1S, 6S-2,8-diazabicyclo- / 4.3.O / nonan-8-yl) -6-fluoro-1,4-dihydro-4-oxo 3-quinoline carboxylic acid
DE19854356A1 (en) * 1998-11-25 2000-05-31 Bayer Ag Crystal modification A of 8-cyan-1-cyclopropyl-7- (1S, 6S-2,8-diazabicyclo- / 4.3.0 / nonan-8-yl) -6-fluoro-1,4-dihydro-4-oxo 3-quinoline carboxylic acid
DE19854357A1 (en) * 1998-11-25 2000-05-31 Bayer Ag Semi-hydrochloride of 8-cyano-1-cyclopropyl-7- (1S, 6S-2,8-diazabicyclo / 4.3.0 / -nonan-8-yl) -6-fluoro-1,4-dihydro-4-oxo -3-quinoline carboxylic acid
WO2004024729A1 (en) * 2002-09-10 2004-03-25 Pfizer Products Inc. Diazabicyclic compounds useful in the treatment of cns and other disorders
SG144936A1 (en) 2003-09-10 2008-08-28 Kyorin Seiyaku Kk 7-(4-substituted-3-cyclopropylaminomethyl-1- pyrrolidinyl)quinolonecarboxylic acid derivative
CA2688008A1 (en) 2007-05-24 2008-11-27 Kyorin Pharmaceutical Co., Ltd. Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3522405A1 (en) * 1985-06-22 1987-01-02 Bayer Ag 1,8-BRIDGED 4-CHINOLON-3-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE MEDICINAL PRODUCTS CONTAINING THE SAME AND THE USE THEREOF FOR THE PRODUCTION OF MEDICINAL PRODUCTS
DE3543513A1 (en) * 1985-12-10 1987-06-11 Bayer Ag ENANTIOMER-PURE 1,8-BRIDGED 4-CHINOLON-3-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE MEDICINAL PRODUCTS CONTAINING THEM AND THEIR USE FOR THE PRODUCTION OF MEDICINAL PRODUCTS
DE3601567A1 (en) * 1986-01-21 1987-07-23 Bayer Ag 7- (AZABICYCLOALKYL) -CHINOLONCARBONIC ACID AND -NAPHTHYRIDON-CARBONIC ACID DERIVATIVES
DE3702393A1 (en) * 1987-01-28 1988-08-11 Bayer Ag 8-CYANO-1-CYCLOPROPYL-1,4-DIHYDRO-4-OXO- 3-CHINOLINE CARBONIC ACIDS, METHOD FOR THEIR PRODUCTION AND ANTIBACTERIAL AGENTS CONTAINING THEM
US5563138A (en) * 1987-04-16 1996-10-08 Otsuka Pharmaceutical Company, Limited Benzoheterocyclic compounds
US4920120A (en) * 1988-01-25 1990-04-24 Warner-Lambert Company Antibacterial agents

Also Published As

Publication number Publication date
HU902055D0 (en) 1990-08-28
FI901615A7 (en) 1990-10-04
KR900016186A (en) 1990-11-12
HU912263D0 (en) 1991-12-30
JPH02289583A (en) 1990-11-29
DE3910663A1 (en) 1990-10-04
NO901274L (en) 1990-10-04
KR0156245B1 (en) 1998-11-16
AU5231790A (en) 1990-10-04
NZ233142A (en) 1992-09-25
AU638005B2 (en) 1993-06-17
HU204811B (en) 1992-02-28
PH27364A (en) 1993-06-21
CA2013449C (en) 2001-01-02
PT93639A (en) 1990-11-20
CN1035945C (en) 1997-09-24
NO173547B (en) 1993-09-20
ZA902510B (en) 1991-01-30
NO901274D0 (en) 1990-03-20
FI901615A0 (en) 1990-03-30
HUT56563A (en) 1991-09-30
EP0391132A1 (en) 1990-10-10
JP3046035B2 (en) 2000-05-29
CN1046162A (en) 1990-10-17
DD298400A5 (en) 1992-02-20
IL93954A0 (en) 1990-12-23
NO173547C (en) 1993-12-29
HUT58056A (en) 1992-01-28

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