WO2010030808A3 - Novel antibiotics against resistant bacteria - Google Patents

Novel antibiotics against resistant bacteria Download PDF

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Publication number
WO2010030808A3
WO2010030808A3 PCT/US2009/056552 US2009056552W WO2010030808A3 WO 2010030808 A3 WO2010030808 A3 WO 2010030808A3 US 2009056552 W US2009056552 W US 2009056552W WO 2010030808 A3 WO2010030808 A3 WO 2010030808A3
Authority
WO
WIPO (PCT)
Prior art keywords
present
antimicrobials
aminoglycosides
novel
useful
Prior art date
Application number
PCT/US2009/056552
Other languages
French (fr)
Other versions
WO2010030808A2 (en
Inventor
Cheng-Wei T. Chang
Original Assignee
Utah State University
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 Utah State University filed Critical Utah State University
Publication of WO2010030808A2 publication Critical patent/WO2010030808A2/en
Publication of WO2010030808A3 publication Critical patent/WO2010030808A3/en

Links

Classifications

    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/7036—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
    • 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
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
    • C07H15/232—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with at least three saccharide radicals in the molecule, e.g. lividomycin, neomycin, paromomycin
    • 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

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

The present invention is in the technical field of antimicrobials. More particularly, the present invention is in the technical field of aminoglycoside antimicrobials. In one aspect the present invention provides novel methods of synthesizing new classes of antimicrobial aminoglycosides. In a second aspect the present invention also provides two novel aminoglycosides useful as antimicrobials. The present invention relates to novel antibacterial aminoglycoside derivatives that exhibit improved antimicrobial properties. One advantage of the present invention is a facile synthetic protocol for the production of neomycin B derivatives with various modifications at the 5" position, which enables the direct modification of commercially available aminoglycosides using carbamate type protecting groups. Also provided are methods of using the compound of the present invention. The compounds of the present invention are useful in treating or preventing bacterial infection and may be especially useful in the treatment of infections with MRSA and VRE.
PCT/US2009/056552 2008-09-11 2009-09-10 Novel antibiotics against resistant bacteria WO2010030808A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9620308P 2008-09-11 2008-09-11
US61/096,203 2008-09-11

Publications (2)

Publication Number Publication Date
WO2010030808A2 WO2010030808A2 (en) 2010-03-18
WO2010030808A3 true WO2010030808A3 (en) 2010-08-12

Family

ID=42005746

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/056552 WO2010030808A2 (en) 2008-09-11 2009-09-10 Novel antibiotics against resistant bacteria

Country Status (1)

Country Link
WO (1) WO2010030808A2 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001039726A2 (en) * 1999-12-01 2001-06-07 Isis Pharmaceuticals, Inc. Antimicrobial 2-deoxystreptamine compounds
US20040204378A1 (en) * 2003-01-07 2004-10-14 Paratek Pharmaceuticals, Inc. Substituted polyamines as inhibitors of bacterial efflux pumps
US20040229265A1 (en) * 2003-04-28 2004-11-18 Aviva Lapidot Amino-modified polysaccharides and methods of generating and using same
WO2007028012A2 (en) * 2005-09-01 2007-03-08 Isis Pharmaceuticals, Inc. Antibacterial 6'-n-modified 4,5-substituted aminoglycoside analogs
WO2007064954A2 (en) * 2005-12-02 2007-06-07 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001039726A2 (en) * 1999-12-01 2001-06-07 Isis Pharmaceuticals, Inc. Antimicrobial 2-deoxystreptamine compounds
US20040204378A1 (en) * 2003-01-07 2004-10-14 Paratek Pharmaceuticals, Inc. Substituted polyamines as inhibitors of bacterial efflux pumps
US20040229265A1 (en) * 2003-04-28 2004-11-18 Aviva Lapidot Amino-modified polysaccharides and methods of generating and using same
WO2007028012A2 (en) * 2005-09-01 2007-03-08 Isis Pharmaceuticals, Inc. Antibacterial 6'-n-modified 4,5-substituted aminoglycoside analogs
WO2007064954A2 (en) * 2005-12-02 2007-06-07 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NARITA, Y. ET AL.: ""SYNTHESIS AND ACTIVITY OF BUTIROSIN DERIVATIVES WITH 5"-AMIDINO AND 5"-GUANIDINO SUBSTITUENTS"", THE JOURNAL OF ANTIBIOTICS, vol. 44, no. L, 1991, pages 86 - 92 *

Also Published As

Publication number Publication date
WO2010030808A2 (en) 2010-03-18

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