GB1055616A - N-methylated derivatives of basic antibiotics - Google Patents

N-methylated derivatives of basic antibiotics

Info

Publication number
GB1055616A
GB1055616A GB4378564A GB4378564A GB1055616A GB 1055616 A GB1055616 A GB 1055616A GB 4378564 A GB4378564 A GB 4378564A GB 4378564 A GB4378564 A GB 4378564A GB 1055616 A GB1055616 A GB 1055616A
Authority
GB
United Kingdom
Prior art keywords
methylated derivatives
basic antibiotics
antibiotic
formaldehyde
antibiotics
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
GB4378564A
Inventor
Pierre Crooij
Hubert Vanderhaeghe
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.)
RIT RECH IND THERAPEUT
Original Assignee
RIT RECH IND THERAPEUT
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 to FR90368D priority Critical patent/FR90368E/fr
Priority claimed from GB1279062A external-priority patent/GB1033394A/en
Priority to GB4378564A priority patent/GB1055616A/en
Application filed by RIT RECH IND THERAPEUT filed Critical RIT RECH IND THERAPEUT
Priority to NO159978A priority patent/NO117363B/no
Priority to CH1386365A priority patent/CH429025A/en
Priority to SE13141/65A priority patent/SE324858B/xx
Priority to DE19651468937 priority patent/DE1468937A1/en
Priority to NL6513380A priority patent/NL6513380A/xx
Priority to BE671195A priority patent/BE671195A/xx
Priority to AT959865A priority patent/AT265516B/en
Publication of GB1055616A publication Critical patent/GB1055616A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
    • C07H15/232—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with at least three saccharide radicals in the molecule, e.g. lividomycin, neomycin, paromomycin
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

N-Methylated derivatives of the neomycins, kanamycins and paromomycins are prepared by reacting said basic antibiotics with formaldehyde in an aqueous acidic medium without the addition of an external reducing agent. The antibiotic is preferably in the form of the acid addition salt and at least 1.5 moles of formaldehyde is used per amino group of the antibiotic. The compounds have hypocholesterolemic activity.
GB4378564A 1962-04-03 1964-10-27 N-methylated derivatives of basic antibiotics Expired GB1055616A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
FR90368D FR90368E (en) 1962-04-03
GB4378564A GB1055616A (en) 1962-04-03 1964-10-27 N-methylated derivatives of basic antibiotics
NO159978A NO117363B (en) 1964-10-27 1965-10-06
CH1386365A CH429025A (en) 1962-04-03 1965-10-08 Process for the preparation of N-methylated derivatives of basic antibiotics
SE13141/65A SE324858B (en) 1964-10-27 1965-10-11
DE19651468937 DE1468937A1 (en) 1962-04-03 1965-10-15 Process for the preparation of derivatives of antibiotics
NL6513380A NL6513380A (en) 1962-04-03 1965-10-15
BE671195A BE671195A (en) 1962-04-03 1965-10-21
AT959865A AT265516B (en) 1964-10-27 1965-10-22 Process for the preparation of new N-methyl derivatives of neomycins, kanamycins and paromomycins

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1279062A GB1033394A (en) 1962-04-03 1962-04-03 New therapeutic agents
GB3895362 1962-10-15
GB4378564A GB1055616A (en) 1962-04-03 1964-10-27 N-methylated derivatives of basic antibiotics

Publications (1)

Publication Number Publication Date
GB1055616A true GB1055616A (en) 1967-01-18

Family

ID=27256888

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4378564A Expired GB1055616A (en) 1962-04-03 1964-10-27 N-methylated derivatives of basic antibiotics

Country Status (6)

Country Link
BE (1) BE671195A (en)
CH (1) CH429025A (en)
DE (1) DE1468937A1 (en)
FR (1) FR90368E (en)
GB (1) GB1055616A (en)
NL (1) NL6513380A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0587534A1 (en) * 1992-09-11 1994-03-16 Ciba-Geigy Ag Process for the preparation of amines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0587534A1 (en) * 1992-09-11 1994-03-16 Ciba-Geigy Ag Process for the preparation of amines
US5457233A (en) * 1992-09-11 1995-10-10 Ciba-Geigy Corporation Process for the preparation of amines

Also Published As

Publication number Publication date
BE671195A (en) 1966-04-21
CH429025A (en) 1967-01-31
NL6513380A (en) 1966-04-28
DE1468937A1 (en) 1969-07-31
FR90368E (en) 1968-02-14

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