GB1485450A - Process for the preparation of a kanamycin derivative - Google Patents

Process for the preparation of a kanamycin derivative

Info

Publication number
GB1485450A
GB1485450A GB48641/74A GB4864174A GB1485450A GB 1485450 A GB1485450 A GB 1485450A GB 48641/74 A GB48641/74 A GB 48641/74A GB 4864174 A GB4864174 A GB 4864174A GB 1485450 A GB1485450 A GB 1485450A
Authority
GB
United Kingdom
Prior art keywords
kanamycin
compound
preparation
derivative
kanamycin derivative
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
GB48641/74A
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.)
Bristol Myers Co
Original Assignee
Bristol Myers Co
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 Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1485450A publication Critical patent/GB1485450A/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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A kanamycin derivative of the formula IV <IMAGE> is prepared by reacting 6-carbobenzoxykanamycin A with, for example, benzaldehyde to give the corresponding Schiff's base which, after reaction with the N-hydroxy-5-norbornene-2,3-dicarboximide ester of L- gamma -benzyloxycarbonylaminoalpha -hydroxybutyric acid and subsequent hydrogenation of the residue in situ, yields the compound IV. The process is more selective than known processes in respect of the acylation of the 1-amino group. The compound has excellent antibacterial activity exceeding that of kanamycin A.
GB48641/74A 1973-11-14 1974-11-11 Process for the preparation of a kanamycin derivative Expired GB1485450A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41558973A 1973-11-14 1973-11-14
US47278074A 1974-05-23 1974-05-23

Publications (1)

Publication Number Publication Date
GB1485450A true GB1485450A (en) 1977-09-14

Family

ID=27023027

Family Applications (1)

Application Number Title Priority Date Filing Date
GB48641/74A Expired GB1485450A (en) 1973-11-14 1974-11-11 Process for the preparation of a kanamycin derivative

Country Status (11)

Country Link
JP (1) JPS572719B2 (en)
CA (1) CA1030961A (en)
CH (1) CH617441A5 (en)
DK (1) DK142991C (en)
ES (1) ES431912A1 (en)
FI (1) FI60217C (en)
GB (1) GB1485450A (en)
NL (1) NL157910B (en)
NO (1) NO142785C (en)
SE (2) SE419649B (en)
YU (1) YU39655B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0317970A2 (en) * 1987-11-27 1989-05-31 GIST BROCADES ITALY S.p.A. A process for the synthesis of amikacin

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1139844B (en) * 1981-11-25 1986-09-24 Corvi Mora Paolo PROCESS FOR THE PREPARATION OF AMIKACINA

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0317970A2 (en) * 1987-11-27 1989-05-31 GIST BROCADES ITALY S.p.A. A process for the synthesis of amikacin
EP0317970A3 (en) * 1987-11-27 1991-08-28 GIST BROCADES ITALY S.p.A. A process for the synthesis of amikacin

Also Published As

Publication number Publication date
NO744064L (en) 1975-06-09
NO142785C (en) 1980-10-15
SE7414332L (en) 1975-05-15
YU39655B (en) 1985-03-20
JPS5077345A (en) 1975-06-24
DK142991B (en) 1981-03-09
ES431912A1 (en) 1977-01-01
NL7414668A (en) 1975-05-16
FI60217C (en) 1981-12-10
SE7706005L (en) 1977-05-23
FI60217B (en) 1981-08-31
JPS572719B2 (en) 1982-01-18
SE441272B (en) 1985-09-23
YU301774A (en) 1982-05-31
NO142785B (en) 1980-07-07
DK142991C (en) 1981-09-07
DK591674A (en) 1975-07-14
CA1030961A (en) 1978-05-09
NL157910B (en) 1978-09-15
FI327074A (en) 1975-05-15
CH617441A5 (en) 1980-05-30
SE419649B (en) 1981-08-17

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years

Effective date: 19941110