GB933702A - Process for the production of n-methanesulfonic acid derivatives of kanamycin - Google Patents

Process for the production of n-methanesulfonic acid derivatives of kanamycin

Info

Publication number
GB933702A
GB933702A GB39876/59A GB3987659A GB933702A GB 933702 A GB933702 A GB 933702A GB 39876/59 A GB39876/59 A GB 39876/59A GB 3987659 A GB3987659 A GB 3987659A GB 933702 A GB933702 A GB 933702A
Authority
GB
United Kingdom
Prior art keywords
kanamycin
methane
sodium
sulphonate
acid
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
GB39876/59A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB933702A publication Critical patent/GB933702A/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

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for the production of N-substituted derivatives of kanamycin and neomycin in which N-methane sulphonic acid groups and/or the sodium potassium or calcium salts thereof are introduced into the amino groups of the free base of the antibiotic or a salt thereof with an inorganic acid containing at least one free amino group, comprises (I) reacting the antibiotic with sodium potassium or calcium-hydroxymethane sulphonate or (II) formaldehyde and sodium potassium or calcium bisulphate and/or (III) sulphur dioxide and paraformaldehyde (or formalin). The antibiotic may be used in the form of the free antibiotic its sulphate or its salt with a weak acid such as carbonic acid. Specified derivatives of the antibiotics prepared are tetra-sodium kanamycin-tetra-N-methane sulphonate, disodium kanamycin-di-N-methane sulphonate, disodium kanamycin-di-N-methane sulphonate sulphate, kanamycin-di-N-methanesulphonic acid, kanamycin-mono-N-methane-sulphonic acid, trisodium salt of kanamycin-tetra-N-methanesulphonic acid, sodium kanamycin-mono-N-methane-sulphonate and sodium neomycin-mono-N-methanesulphonate.
GB39876/59A 1958-12-12 1959-11-24 Process for the production of n-methanesulfonic acid derivatives of kanamycin Expired GB933702A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP3554558 1958-12-12
JP962259 1959-03-28
JP1595559 1959-05-21
JP3384159 1959-10-29

Publications (1)

Publication Number Publication Date
GB933702A true GB933702A (en) 1963-08-08

Family

ID=27455216

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39876/59A Expired GB933702A (en) 1958-12-12 1959-11-24 Process for the production of n-methanesulfonic acid derivatives of kanamycin

Country Status (4)

Country Link
CH (1) CH421384A (en)
DK (1) DK118502B (en)
FR (1) FR435M (en)
GB (1) GB933702A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4091202A (en) * 1975-09-25 1978-05-23 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai N-methanesulfonic acid derivatives of 3',4'-dideoxykanamycin B

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4091202A (en) * 1975-09-25 1978-05-23 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai N-methanesulfonic acid derivatives of 3',4'-dideoxykanamycin B

Also Published As

Publication number Publication date
DE1418452A1 (en) 1968-10-24
CH421384A (en) 1966-09-30
DK118502B (en) 1970-08-31
FR435M (en) 1961-04-24

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