GB1528930A - Pseudotrisaccharides and methods for their production - Google Patents

Pseudotrisaccharides and methods for their production

Info

Publication number
GB1528930A
GB1528930A GB48412/75A GB4841275A GB1528930A GB 1528930 A GB1528930 A GB 1528930A GB 48412/75 A GB48412/75 A GB 48412/75A GB 4841275 A GB4841275 A GB 4841275A GB 1528930 A GB1528930 A GB 1528930A
Authority
GB
United Kingdom
Prior art keywords
gentamicin
antibiotic
deoxystreptamines
aminoglycosyl
kanamycin
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
GB48412/75A
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 US05/611,289 external-priority patent/US4000261A/en
Priority claimed from US05/611,290 external-priority patent/US4000262A/en
Application filed by Scherico Ltd filed Critical Scherico Ltd
Publication of GB1528930A publication Critical patent/GB1528930A/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
    • 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
    • C07H15/236—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 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

5-Epiderivatives of the 4,6-di-O-(aminoglycosyl)-2-deoxystreptamines gentamicin A, gentamicin B, gentamicin B1, gentamicin C1, gentamicin C1a, gentamicin C2, gentamicin C2a, gentamicin C2b, gentamicin X2, tobramycin, verdamicin, kanamycin A, kanamycin B, 3',4'-dideoxykanamycin B, antibiotic G-52, antigbiotic 66-40B, antibiotic 66-40D, antibiotic G-418, antibiotic JI-20A, antibiotic JI-20B and sisomicin and the corresponding 1-N-alkyl derivatives are obtained by reacting the above 4,6-di-O-(aminoglycosyl)-2-deoxystreptamines which have a hydrocarbon-sulphonyloxy group in position 5 with dimethylformamide at 80 - 155 DEG C, preferably in the presence of a tetraalkylammonium alkanoate. All the amino and hydroxyl groups not involved in the reaction are protected. The final products with antibiotic activity are obtained in good yields in the process.
GB48412/75A 1974-11-29 1975-11-25 Pseudotrisaccharides and methods for their production Expired GB1528930A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US52859374A 1974-11-29 1974-11-29
US52859274A 1974-11-29 1974-11-29
US05/611,289 US4000261A (en) 1974-11-29 1975-09-08 5-epi-4,6-di-o-(aminoglycosyl)-2-deoxystreptamines, methods for their manufacture and intermediates useful therein, methods for their use as antibacterial agents and compositions useful therefor
US05/611,290 US4000262A (en) 1974-11-29 1975-09-08 5-epi-amino and 5-epi-azido-4,6-di-o-(aminoglycosyl)-2,5-dideoxystreptamines 1-n-alkyl-5-epi-amino and 1-n-alkyl-5-epi-azido-4,6-di-o-(aminoglycosyl)-2,5-dideoxystreptamines

Publications (1)

Publication Number Publication Date
GB1528930A true GB1528930A (en) 1978-10-18

Family

ID=27504618

Family Applications (1)

Application Number Title Priority Date Filing Date
GB48412/75A Expired GB1528930A (en) 1974-11-29 1975-11-25 Pseudotrisaccharides and methods for their production

Country Status (17)

Country Link
JP (1) JPS52244A (en)
AR (1) AR215848A1 (en)
CA (1) CA1048020A (en)
CH (1) CH618986A5 (en)
DE (1) DE2552799A1 (en)
DK (1) DK531375A (en)
ES (1) ES442989A1 (en)
FI (1) FI753318A (en)
FR (1) FR2292482A1 (en)
GB (1) GB1528930A (en)
GR (1) GR58472B (en)
IE (1) IE43126B1 (en)
IL (1) IL48558A (en)
LU (1) LU73887A1 (en)
NL (1) NL7513737A (en)
NO (2) NO142080C (en)
SE (1) SE7513330L (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2832268A1 (en) * 1978-07-22 1980-01-31 Bayer Ag PSEUDOTRISACCHARIDE
DE2924659A1 (en) * 1979-06-19 1981-01-22 Bayer Ag PSEUDOTRISACCHARIDE, THEIR PRODUCTION AND USE AS A MEDICINAL PRODUCT
US20070161581A1 (en) * 2004-01-21 2007-07-12 Nobuto Minowa Novel aminoglycoside antibiotics effective against methicillin resistant staphylococcus auerus (mrsas)

Also Published As

Publication number Publication date
NL7513737A (en) 1976-06-01
FR2292482A1 (en) 1976-06-25
NO142080C (en) 1980-06-25
IE43126B1 (en) 1980-12-31
LU73887A1 (en) 1976-09-06
AR215848A1 (en) 1979-11-15
JPS52244A (en) 1977-01-05
FI753318A (en) 1976-05-30
IL48558A (en) 1980-07-31
GR58472B (en) 1977-10-14
IE43126L (en) 1976-05-29
FR2292482B1 (en) 1981-12-31
SE7513330L (en) 1976-05-31
IL48558A0 (en) 1976-01-30
AU8698875A (en) 1977-06-09
DK531375A (en) 1976-05-30
CA1048020A (en) 1979-02-06
CH618986A5 (en) 1980-08-29
DE2552799A1 (en) 1976-08-12
NO790908L (en) 1976-06-01
ES442989A1 (en) 1977-08-16
NO142080B (en) 1980-03-17
NO753969L (en) 1976-06-01

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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