GB1494129A - Derivatives of diaminocyclitols and methods for their preparation - Google Patents

Derivatives of diaminocyclitols and methods for their preparation

Info

Publication number
GB1494129A
GB1494129A GB2653/75A GB265375A GB1494129A GB 1494129 A GB1494129 A GB 1494129A GB 2653/75 A GB2653/75 A GB 2653/75A GB 265375 A GB265375 A GB 265375A GB 1494129 A GB1494129 A GB 1494129A
Authority
GB
United Kingdom
Prior art keywords
gentamicin
antibiotic
amino
diaminocyclitols
aminoglycosyl
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
GB2653/75A
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.)
Scherico Ltd
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 GB1494129A publication Critical patent/GB1494129A/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
    • 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.
GB2653/75A 1974-03-19 1975-01-21 Derivatives of diaminocyclitols and methods for their preparation Expired GB1494129A (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 (1)

Publication Number Publication Date
GB1494129A true GB1494129A (en) 1977-12-07

Family

ID=27036813

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2653/75A Expired GB1494129A (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)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010132770A1 (en) * 2009-05-14 2010-11-18 Achaogen, Inc. Treatment of klebsiella pneumoniae infections with antibacterial aminoglycoside compounds
US8383596B2 (en) 2007-11-21 2013-02-26 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8492354B2 (en) 2009-05-15 2013-07-23 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8524689B2 (en) 2009-05-15 2013-09-03 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8524675B2 (en) 2009-05-15 2013-09-03 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8653042B2 (en) 2009-05-15 2014-02-18 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8658606B2 (en) 2009-05-15 2014-02-25 Achaogen, Inc. Antibacterial aminoglycoside analogs
US9073958B2 (en) 2006-04-03 2015-07-07 Technion Research & Development Foundation Limited Aminoglycosides and uses thereof in the treatment of genetic disorders

Families Citing this family (4)

* 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

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10159689B2 (en) 2006-04-03 2018-12-25 Technion Research & Development Foundation Limited Aminoglycosides and uses thereof in the treatment of genetic disorders
US9821001B2 (en) 2006-04-03 2017-11-21 Technion Research & Development Foundation Limited Aminoglycosides and uses thereof in the treatment of genetic disorders
US9073958B2 (en) 2006-04-03 2015-07-07 Technion Research & Development Foundation Limited Aminoglycosides and uses thereof in the treatment of genetic disorders
US9266919B2 (en) 2007-11-21 2016-02-23 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8383596B2 (en) 2007-11-21 2013-02-26 Achaogen, Inc. Antibacterial aminoglycoside analogs
US11117915B2 (en) 2007-11-21 2021-09-14 Cipla USA, Inc. Antibacterial aminoglycoside analogs
US9688711B2 (en) 2007-11-21 2017-06-27 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8822424B2 (en) 2007-11-21 2014-09-02 Achaogen, Inc. Antibacterial aminoglycoside analogs
WO2010132770A1 (en) * 2009-05-14 2010-11-18 Achaogen, Inc. Treatment of klebsiella pneumoniae infections with antibacterial aminoglycoside compounds
US8524689B2 (en) 2009-05-15 2013-09-03 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8658606B2 (en) 2009-05-15 2014-02-25 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8653042B2 (en) 2009-05-15 2014-02-18 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8524675B2 (en) 2009-05-15 2013-09-03 Achaogen, Inc. Antibacterial aminoglycoside analogs
USRE47741E1 (en) 2009-05-15 2019-11-26 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8492354B2 (en) 2009-05-15 2013-07-23 Achaogen, Inc. Antibacterial aminoglycoside analogs

Also Published As

Publication number Publication date
AR207582A1 (en) 1976-10-15
MY8100350A (en) 1981-12-31
IE40796B1 (en) 1979-08-15
IL46467A0 (en) 1975-04-25
IL46467A (en) 1978-10-31
AU7747775A (en) 1976-07-22
IE40796L (en) 1975-09-19
CH612946A5 (en) 1979-08-31
FR2264553A1 (en) 1975-10-17
DE2502296C2 (en) 1983-09-22
HK7681A (en) 1981-03-20
FR2264553B1 (en) 1978-12-01
DE2502296A1 (en) 1975-09-25
BG26400A3 (en) 1979-03-15

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19950120