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WO2006032466A3 - New bicyclic antibiotics - Google Patents

New bicyclic antibiotics Download PDF

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Publication number
WO2006032466A3
WO2006032466A3 PCT/EP2005/010154 EP2005010154W WO2006032466A3 WO 2006032466 A3 WO2006032466 A3 WO 2006032466A3 EP 2005010154 W EP2005010154 W EP 2005010154W WO 2006032466 A3 WO2006032466 A3 WO 2006032466A3
Authority
WO
WIPO (PCT)
Prior art keywords
represent
halogen
new bicyclic
antibiotics
alkoxy
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.)
Ceased
Application number
PCT/EP2005/010154
Other languages
French (fr)
Other versions
WO2006032466A2 (en
Inventor
Christian Hubschwerlen
Jean-Philippe Surivet
Acklin Cornelia Zumbrunn
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.)
Actelion Pharmaceuticals Ltd
Original Assignee
Actelion Pharmaceuticals 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 Actelion Pharmaceuticals Ltd filed Critical Actelion Pharmaceuticals Ltd
Priority to CA002580621A priority Critical patent/CA2580621A1/en
Priority to JP2007532823A priority patent/JP4887297B2/en
Priority to EP05784860A priority patent/EP1799676A2/en
Publication of WO2006032466A2 publication Critical patent/WO2006032466A2/en
Publication of WO2006032466A3 publication Critical patent/WO2006032466A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04Ortho-condensed systems

Landscapes

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

Abstract

The invention relates to novel antibiotics of formula (I) wherein R1 represents alkyl, alkoxy, haloalkoxy, halogen or cyano; one or two of U, V, W and X represent(s) N, the remaining represent CH, or, in case of U, V and/or W, may also represent CRa and, in the case of X, may also represent CRb; Ra represents halogen; Rb represents halogen or alkoxy; M is a linking chain containing a non-aromatic cyclic or heterocyclic group, and D represents alkyl, aryl or heteroaryl.
PCT/EP2005/010154 2004-09-24 2005-09-20 New bicyclic antibiotics Ceased WO2006032466A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA002580621A CA2580621A1 (en) 2004-09-24 2005-09-20 New bicyclic antibiotics
JP2007532823A JP4887297B2 (en) 2004-09-24 2005-09-20 New bicyclic antibiotics
EP05784860A EP1799676A2 (en) 2004-09-24 2005-09-20 New bicyclic antibiotics

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP2004010762 2004-09-24
EPPCT/EP2004/010762 2004-09-24
EP2005007731 2005-07-15
EPPCT/EP2005/007731 2005-07-15

Publications (2)

Publication Number Publication Date
WO2006032466A2 WO2006032466A2 (en) 2006-03-30
WO2006032466A3 true WO2006032466A3 (en) 2006-12-14

Family

ID=36090370

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/010154 Ceased WO2006032466A2 (en) 2004-09-24 2005-09-20 New bicyclic antibiotics

Country Status (5)

Country Link
JP (1) JP4887297B2 (en)
AR (1) AR050958A1 (en)
CA (1) CA2580621A1 (en)
TW (1) TW200615267A (en)
WO (1) WO2006032466A2 (en)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7709472B2 (en) 2005-01-25 2010-05-04 Glaxo Group Limited Antibacterial agents
RU2007147413A (en) * 2005-05-24 2009-06-27 Астразенека Аб (Se) AMINOPIPERIDINCHINOLINS AND THEIR AZAISOSTERIC ANALOGUES WITH ANTIBACTERIAL ACTIVITY
MY150958A (en) 2005-06-16 2014-03-31 Astrazeneca Ab Compounds for the treatment of multi-drug resistant bacterial infections
CN101374831B (en) 2006-01-26 2011-04-27 埃科特莱茵药品有限公司 tetrahydropyran antibiotics
EP1987040B1 (en) 2006-02-15 2010-11-10 Actelion Pharmaceuticals Ltd. Ethanol or 1,2-ethanediol cyclohexyl antibiotic derivatives
CA2643962A1 (en) * 2006-03-10 2007-09-20 Actelion Pharmaceuticals Ltd Antibiotic compounds
WO2007115947A1 (en) 2006-04-06 2007-10-18 Glaxo Group Limited Pyrrolo-quinoxalinone derivatives as antibacterials
EP2044059A1 (en) * 2006-06-08 2009-04-08 Speedel Experimenta AG 2,5-disubstituted piperidines
EP1992628A1 (en) 2007-05-18 2008-11-19 Glaxo Group Limited Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones
TW200819457A (en) 2006-08-30 2008-05-01 Actelion Pharmaceuticals Ltd Spiro antibiotic derivatives
CL2007003693A1 (en) * 2006-12-22 2008-06-27 Actelion Pharmaceuticals Ltd COMPOUNDS DERIVED FROM PIRIDO [3,2-B] [1,4] THIAZINE; PHARMACEUTICAL COMPOSITION CONTAINING SUCH COMPOUNDS; AND ITS USE IN THE TREATMENT OF BACTERIAL INFECTIONS.
CL2008001002A1 (en) 2007-04-11 2008-10-17 Actelion Pharmaceuticals Ltd COMPOUNDS DERIVED FROM OXAZOLIDINONA; PHARMACEUTICAL COMPOSITION THAT INCLUDES SUCH COMPOUNDS; AND ITS USE TO PREPARE A MEDICINAL PRODUCT TO TREAT A BACTERIAL INFECTION.
CL2008001003A1 (en) 2007-04-11 2008-10-17 Actelion Pharmaceuticals Ltd COMPOUNDS DERIVED FROM OXAZOLIDINONA; PHARMACEUTICAL COMPOSITION THAT INCLUDES SUCH COMPOUNDS; AND ITS USE TO PREPARE A MEDICINAL PRODUCT TO TREAT A BACTERIAL INFECTION.
MY149347A (en) 2007-04-20 2013-08-30 Glaxo Group Ltd Tricyclic nitrogen containing compounds as antibacterial agents
ES2370123T3 (en) * 2007-06-15 2011-12-12 Actelion Pharmaceuticals Ltd. DERIVATIVES OF 3-AMINO-6- (1-AMINOETIL) -TETRAHYDROPIRANE.
EP2005995A1 (en) * 2007-06-22 2008-12-24 Glaxo Group Limited Heterocyclic compounds for the treatment of tuberculosis
CA2706837C (en) 2007-12-18 2016-05-03 Actelion Pharmaceuticals Ltd 5-aminocyclylmethyl-oxazolidin-2-one derivatives
EP2080761A1 (en) 2008-01-18 2009-07-22 Glaxo Group Limited Compounds
CA2713182C (en) 2008-02-20 2016-09-13 Actelion Pharmaceuticals Ltd Azatricyclic antibiotic compounds
JP2011518149A (en) 2008-04-15 2011-06-23 アクテリオン ファーマシューティカルズ リミテッド Tricyclic antibacterial agent
RU2515906C2 (en) 2008-06-03 2014-05-20 Актелион Фармасьютиклз Лтд [4-(1-aminoethyl)cyclohexyl]methylamine and [6-(1-aminoethyl)tetrahydropyran-3-yl]methylamine derivatives
KR20110036938A (en) 2008-08-04 2011-04-12 액테리온 파마슈티칼 리미티드 Tricyclic Alkylaminomethyloxazolidinone Derivatives
DK2344495T3 (en) 2008-10-07 2015-02-02 Actelion Pharmaceuticals Ltd TRICYCLIC OXAZOLIDINON ANTIBIOTIC COMPOUNDS
WO2010043714A1 (en) 2008-10-17 2010-04-22 Glaxo Group Limited Tricyclic nitrogen compounds used as antibacterials
US8642629B2 (en) 2008-11-17 2014-02-04 Hoffmann-La Roche Inc. Naphthylacetic acids
RU2525541C2 (en) 2008-12-12 2014-08-20 Актелион Фармасьютиклз Лтд 5-amino-2-(1-hydroxyethyl)tetrahydropyran derivatives
US8318940B2 (en) 2009-01-15 2012-11-27 Glaxo Group Limited Naphthyridin-2 (1 H)-one compounds useful as antibacterials
AU2010206161B2 (en) 2009-01-21 2014-08-07 Basilea Pharmaceutica Ag Novel bicyclic antibiotics
AR076222A1 (en) 2009-04-09 2011-05-26 Actelion Pharmaceuticals Ltd DERIVATIVES 2-HYDROXIETIL-1H-QUINOLIN-ONA AND ITS AZAISOTHERAL ANALOGS WITH ANTIBACTERIAL ACTIVITY AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
US9133116B2 (en) 2010-09-28 2015-09-15 Panacea Biotec Ltd. Bicyclic compounds
CA2829188C (en) 2011-03-10 2016-10-18 Daiichi Sankyo Company, Limited Dispiropyrrolidine derivatives
WO2012125661A1 (en) * 2011-03-17 2012-09-20 Merck Sharp & Dohme Corp. Substituted 3-azabicyclo[3.1.0]hexane derivatives useful as ccr2 antagonists
CA2780403C (en) * 2011-06-17 2020-04-21 Forest Laboratories Holdings Ltd. Processes for preparing heterocyclic compounds including trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide and salts thereof
US20140243302A1 (en) * 2011-06-27 2014-08-28 Merck Sharp & Dohme Corporation Bridged bicyclic compounds for the treatment of bacterial infections
US8470884B2 (en) 2011-11-09 2013-06-25 Hoffmann-La Roche Inc. Alkenyl naphthylacetic acids
US9029368B2 (en) 2011-11-30 2015-05-12 Actelion Pharmaceuticals Ltd. 3,7-disubstituted octahydro-2H-pyrido[4,3-E][1,3]oxazin-2-one antibiotics
SG11201700566SA (en) 2014-08-22 2017-03-30 Glaxosmithkline Ip Dev Ltd Tricyclic nitrogen containing compounds for treating neisseria gonorrhoea infection
TW201722965A (en) 2015-08-16 2017-07-01 葛蘭素史密斯克藍智慧財產發展有限公司 Compounds for use in antibacterial applications
CA3072057A1 (en) * 2017-09-01 2019-03-07 Denali Therapeutics Inc. Small molecule modulators of eukaryotic initiation factor 2b
WO2019054427A1 (en) 2017-09-14 2019-03-21 第一三共株式会社 Compound having cyclic structure
CN109082280B (en) * 2018-11-05 2020-07-28 宁夏中星显示材料有限公司 Preparation method of liquid crystal material
US12091392B2 (en) 2019-02-13 2024-09-17 Denali Therapeutics Inc. Compounds, compositions and methods

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003064421A1 (en) * 2002-01-29 2003-08-07 Glaxo Group Limited Aminopiperidine derivatives
WO2004002490A2 (en) * 2002-06-26 2004-01-08 Glaxo Group Limited Piperidine compounds as antibacterials
WO2004035569A2 (en) * 2002-10-10 2004-04-29 Morphochem Aktiengesellschaft für kombinatorische Chemie Novel compounds with antibacterial activity
DE10256405A1 (en) * 2002-12-02 2004-06-17 Morphochem Aktiengesellschaft für kombinatorische Chemie New 4-substituted quinoline derivatives, useful for treating bacterial infections, optionally including additional ring nitrogens
WO2004089947A2 (en) * 2003-04-08 2004-10-21 Morphochem Ag Novel compounds having an antibacterial activity

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004089942A2 (en) * 2001-10-02 2004-10-21 Acadia Pharmaceuticals Inc. Benzimidazolidinone derivatives as muscarinic agents
TW200406413A (en) * 2002-06-26 2004-05-01 Glaxo Group Ltd Compounds
WO2006012396A1 (en) * 2004-07-22 2006-02-02 Glaxo Group Limited Antibacterial agents
DE102004041163A1 (en) * 2004-08-25 2006-03-02 Morphochem Aktiengesellschaft für kombinatorische Chemie New compounds with antibacterial activity

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003064421A1 (en) * 2002-01-29 2003-08-07 Glaxo Group Limited Aminopiperidine derivatives
WO2004002490A2 (en) * 2002-06-26 2004-01-08 Glaxo Group Limited Piperidine compounds as antibacterials
WO2004035569A2 (en) * 2002-10-10 2004-04-29 Morphochem Aktiengesellschaft für kombinatorische Chemie Novel compounds with antibacterial activity
DE10256405A1 (en) * 2002-12-02 2004-06-17 Morphochem Aktiengesellschaft für kombinatorische Chemie New 4-substituted quinoline derivatives, useful for treating bacterial infections, optionally including additional ring nitrogens
WO2004089947A2 (en) * 2003-04-08 2004-10-21 Morphochem Ag Novel compounds having an antibacterial activity

Also Published As

Publication number Publication date
JP4887297B2 (en) 2012-02-29
WO2006032466A2 (en) 2006-03-30
JP2008514563A (en) 2008-05-08
CA2580621A1 (en) 2006-03-30
TW200615267A (en) 2006-05-16
AR050958A1 (en) 2006-12-06

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