GB1505852A - Deoxykanamycin b derivatives - Google Patents

Deoxykanamycin b derivatives

Info

Publication number
GB1505852A
GB1505852A GB43950/75A GB4395075A GB1505852A GB 1505852 A GB1505852 A GB 1505852A GB 43950/75 A GB43950/75 A GB 43950/75A GB 4395075 A GB4395075 A GB 4395075A GB 1505852 A GB1505852 A GB 1505852A
Authority
GB
United Kingdom
Prior art keywords
group
dideoxykanamycin
tobramycin
general formula
hydrogen atom
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
GB43950/75A
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.)
Pfizer Ltd
Original Assignee
Pfizer 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
Application filed by Pfizer Ltd filed Critical Pfizer Ltd
Priority to GB43950/75A priority Critical patent/GB1505852A/en
Publication of GB1505852A publication Critical patent/GB1505852A/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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)

Abstract

1505852 Tobramycin and 3<SP>1</SP>,4<SP>1</SP>-dideoxykanamycin B derivatives PFIZER Ltd 22 Oct 1976 [25 Oct 1975] 43950/75 Heading C2C Novel tobramycin and 3<SP>1</SP>,4<SP>1</SP>-dideoxykanamycin B derivatives of the general Formula I wherein R<SP>1</SP> and R<SP>2</SP> are each a hydrogen atom or C 1-6 alkyl group, R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom or hydroxyl group and n is 1-4, and pharmaceutically acceptable acid addition salts thereof are prepared (a) by reacting tobramycin, 3<SP>1</SP>,4<SP>1</SP>-dideoxykanamycin B or a protected amino derivative of the general Formula II wherein R<SP>5</SP> is a monovalent protecting group for a primary amino group, with an aldehyde of the general formula wherein R<SP>6</SP> and R<SP>7</SP> are each a C 1-6 alkyl group or R<SP>6</SP> is a protecting group for a primary or secondary amino group and R<SP>7</SP> is a hydrogen atom or C 1-6 alkyl group, and simultaneously or subsequently reducing the Schiffs base so formed to the corresponding secondary amine and then, if necessary, removing the protecting groups R<SP>6</SP> and/or R<SP>6</SP>, (b) by reacting tobramycin or 3<SP>1</SP>,4<SP>1</SP>-dideoxykanamycin B with an acylating agent of the general formula wherein R<SP>6</SP> is a protecting group for a primary or secondary amino group, R<SP>7</SP> is a hydrogen atom or C 1-6 alkyl group and X is a halogen atom of N-oxy-succinimide group, removing the protecting group and reducing the amide product; and (c) when R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are each hydrogen and n is 1, by reacting a compound II with acrylonitrile, removing the protecting group and reducing the 6<SP>1</SP>-N-cyanoalkyl product; followed optionally by salification of the product. Pharmaceutical compositions having antibacterial activity comprise, as active ingredient, a tobramycin or 3<SP>1</SP>,4<SP>1</SP>-dideoxykanamycin B derivative (I) or pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier.
GB43950/75A 1976-10-22 1976-10-22 Deoxykanamycin b derivatives Expired GB1505852A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB43950/75A GB1505852A (en) 1976-10-22 1976-10-22 Deoxykanamycin b derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB43950/75A GB1505852A (en) 1976-10-22 1976-10-22 Deoxykanamycin b derivatives

Publications (1)

Publication Number Publication Date
GB1505852A true GB1505852A (en) 1978-03-30

Family

ID=10431085

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43950/75A Expired GB1505852A (en) 1976-10-22 1976-10-22 Deoxykanamycin b derivatives

Country Status (1)

Country Link
GB (1) GB1505852A (en)

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee