CA1271744C - Preparation of aminoglycosides - Google Patents

Preparation of aminoglycosides

Info

Publication number
CA1271744C
CA1271744C CA297395A CA297395A CA1271744C CA 1271744 C CA1271744 C CA 1271744C CA 297395 A CA297395 A CA 297395A CA 297395 A CA297395 A CA 297395A CA 1271744 C CA1271744 C CA 1271744C
Authority
CA
Canada
Prior art keywords
kanamycin
aminoglycosides
amino group
group
lividomycin
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.)
Expired
Application number
CA297395A
Other languages
French (fr)
Other versions
CA1271744A (en
Inventor
Stephen Hanessian
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 filed Critical
Priority to CA000297395A priority Critical patent/CA1271744A/en
Application granted granted Critical
Publication of CA1271744C publication Critical patent/CA1271744C/en
Publication of CA1271744A publication Critical patent/CA1271744A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE N-Substituted derivatives of aminoglycosides are prepared by (a) complexing an aminoglycoside with divalent metal ion selected from the group consisting of the cations of Fe, CO, Ni, Cu, Pd, Ag and Pt to form a protected species having at least one amino group bound as a metal ion chelate and at least one unbound amino group, (b) reacting the protected species with an N-acylating reagent selected from the group consisting of carboxylic and sulfonic acid anhydrides, halides and active esters to acylate at least one unbound amino group, and (c) removing the amino-protecting chelate groups. Among the aminoglycosides useful are kanamycin A, kanamycin B, kanamycin C, sisomicin, gentamicin B, tobramycin, ribostamycin, butirosin A, butirosin B, neomycin B, paromomycin I, lividomycin A and lividomycin B. The N-substituted derivatives possess utility as antibiotics or as intermediates in the preparation of aminoglycoside antibiotics.
CA000297395A 1978-02-21 1978-02-21 Preparation of aminoglycosides Expired CA1271744A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA000297395A CA1271744A (en) 1978-02-21 1978-02-21 Preparation of aminoglycosides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA000297395A CA1271744A (en) 1978-02-21 1978-02-21 Preparation of aminoglycosides

Publications (2)

Publication Number Publication Date
CA1271744C true CA1271744C (en) 1990-07-17
CA1271744A CA1271744A (en) 1990-07-17

Family

ID=4110829

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000297395A Expired CA1271744A (en) 1978-02-21 1978-02-21 Preparation of aminoglycosides

Country Status (1)

Country Link
CA (1) CA1271744A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007064954A2 (en) 2005-12-02 2007-06-07 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
WO2010030690A1 (en) 2008-09-10 2010-03-18 Isis Pharmaceuticals, Inc. Antibacterial 4,6-substituted 6', 6" and 1 modified aminoglycoside analogs
WO2010030704A2 (en) 2008-09-10 2010-03-18 Achaogen, Inc. Antibacterial aminoglycoside analogs
WO2010042850A1 (en) 2008-10-09 2010-04-15 Achaogen, Inc. Antibacterial aminoglycoside analogs
WO2010042851A1 (en) 2008-10-09 2010-04-15 Achaogen, Inc. Antibacterial aminoglycoside analogs
EP2486044A2 (en) 2009-10-09 2012-08-15 Achaogen, Inc. Antibacterial aminoglycoside analogs
TW201304784A (en) 2010-11-17 2013-02-01 Achaogen Inc Antibacterial aminoglycoside analogs

Also Published As

Publication number Publication date
CA1271744A (en) 1990-07-17

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Legal Events

Date Code Title Description
MKEX Expiry
MKEX Expiry

Effective date: 20070717