IE40796B1 - Derivatives of diaminocyclitols and methods for their preparation - Google Patents

Derivatives of diaminocyclitols and methods for their preparation

Info

Publication number
IE40796B1
IE40796B1 IE115/75A IE11575A IE40796B1 IE 40796 B1 IE40796 B1 IE 40796B1 IE 115/75 A IE115/75 A IE 115/75A IE 11575 A IE11575 A IE 11575A IE 40796 B1 IE40796 B1 IE 40796B1
Authority
IE
Ireland
Prior art keywords
gentamicin
antibiotic
amino
diaminocyclitols
aminoglycosyl
Prior art date
Application number
IE115/75A
Other versions
IE40796L (en
Original Assignee
Scherico 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
Priority claimed from US05/452,586 external-priority patent/US4029882A/en
Application filed by Scherico Ltd filed Critical Scherico Ltd
Publication of IE40796L publication Critical patent/IE40796L/en
Publication of IE40796B1 publication Critical patent/IE40796B1/en

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
    • 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

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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The 1-N-X-substituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitols gentamicin A, gentamicin B, gentamicin B1, gentamicin C1, gentamicin C1a, gentamicin C2, gentamicin C2a, gentamicin X2, sisomicin, verdamicin, antibiotic G-418, antibiotic 66-40B, antibiotic 66-40D, antibiotic JI-20A, antibiotic JI-20B and antibiotic G-52, in which X is the S-3-amino-2-hydroxypropionyl or S-4-amino-2-hydroxybutyl group, are prepared. (In the case of gentamicins C1, C1a and C2, X is restricted to S-3-amino-2-hydroxypropionyl.) Owing to the presence of the 1-N-substituent, these compounds have greater activity. The process comprises reacting a 1-N-unsubstituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitol, which may be in the form of a partially neutralised acid addition salt, with an appropriate acid in the presence of a carbodiimide or with a functional derivative of this acid. During the process it is possible for amino groups and/or the hydroxyl group, with the exception of the 1-amino group, in the starting materials to undergo intermediate protection. [GB1494129A]
IE115/75A 1974-03-19 1975-01-21 Derivatives of diaminocyclitols and methods for their preparation IE40796B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45257174A 1974-03-19 1974-03-19
US05/452,586 US4029882A (en) 1974-03-19 1974-03-19 Selective acylation of the C-1 amino group of aminoglycoside antibiotics

Publications (2)

Publication Number Publication Date
IE40796L IE40796L (en) 1975-09-19
IE40796B1 true IE40796B1 (en) 1979-08-15

Family

ID=27036813

Family Applications (1)

Application Number Title Priority Date Filing Date
IE115/75A IE40796B1 (en) 1974-03-19 1975-01-21 Derivatives of diaminocyclitols and methods for their preparation

Country Status (10)

Country Link
AR (1) AR207582A1 (en)
BG (1) BG26400A3 (en)
CH (1) CH612946A5 (en)
DE (1) DE2502296C2 (en)
FR (1) FR2264553B1 (en)
GB (1) GB1494129A (en)
HK (1) HK7681A (en)
IE (1) IE40796B1 (en)
IL (1) IL46467A (en)
MY (1) MY8100350A (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4136254A (en) * 1976-06-17 1979-01-23 Schering Corporation Process of selectively blocking amino functions in aminoglycosides using transition metal salts and intermediates used thereby
DE2753769A1 (en) * 1977-12-02 1979-06-13 Bayer Ag 1-N-4,6-DI-O- (AMINOGLYCOSYL) -1,3-DIAMINO-CYCLITOL DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND USE
DE2921973A1 (en) * 1979-05-30 1980-12-11 Bayer Ag SISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
DE3101376A1 (en) * 1981-01-17 1982-09-02 Bayer Ag, 5090 Leverkusen SISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
EP2007783B1 (en) 2006-04-03 2018-07-11 Technion Research & Development Foundation Ltd. Novel aminoglycosides and uses thereof in the treatment of genetic disorders
EP3150617B1 (en) 2007-11-21 2020-04-08 Cipla USA, Inc. Antibacterial aminoglycoside analogs
WO2010132770A1 (en) * 2009-05-14 2010-11-18 Achaogen, Inc. Treatment of klebsiella pneumoniae infections with antibacterial aminoglycoside compounds
WO2010132759A1 (en) 2009-05-15 2010-11-18 Achaogen, Inc. Antibacterial derivatives of dibekacin
WO2010132760A1 (en) 2009-05-15 2010-11-18 Achaogen, Inc. Antibacterial derivatives of tobramycin
WO2010132757A2 (en) 2009-05-15 2010-11-18 Achaogen, Inc. Antibacterial aminoglycoside analogs
WO2010132768A1 (en) 2009-05-15 2010-11-18 Achaogen, Inc. Antibacterial derivatives of sisomicin
WO2010132765A2 (en) 2009-05-15 2010-11-18 Achaogen, Inc. Antibacterial aminoglycoside analogs

Also Published As

Publication number Publication date
MY8100350A (en) 1981-12-31
IE40796L (en) 1975-09-19
FR2264553B1 (en) 1978-12-01
DE2502296C2 (en) 1983-09-22
CH612946A5 (en) 1979-08-31
HK7681A (en) 1981-03-20
AR207582A1 (en) 1976-10-15
AU7747775A (en) 1976-07-22
FR2264553A1 (en) 1975-10-17
IL46467A (en) 1978-10-31
BG26400A3 (en) 1979-03-15
GB1494129A (en) 1977-12-07
DE2502296A1 (en) 1975-09-25
IL46467A0 (en) 1975-04-25

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