GB1445872A - 2-deoxystreptamine-aminoglycosides and methods for their preparation paration - Google Patents

2-deoxystreptamine-aminoglycosides and methods for their preparation paration

Info

Publication number
GB1445872A
GB1445872A GB2671973A GB2671973A GB1445872A GB 1445872 A GB1445872 A GB 1445872A GB 2671973 A GB2671973 A GB 2671973A GB 2671973 A GB2671973 A GB 2671973A GB 1445872 A GB1445872 A GB 1445872A
Authority
GB
United Kingdom
Prior art keywords
group
free
hydrogen
hydroxyl group
amino
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
GB2671973A
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 GB2671973A priority Critical patent/GB1445872A/en
Priority to US05/476,269 priority patent/US4024332A/en
Priority to NL7407483A priority patent/NL7407483A/xx
Priority to FR7419268A priority patent/FR2232326B1/fr
Priority to LU70223A priority patent/LU70223A1/xx
Priority to DE19742427096 priority patent/DE2427096A1/en
Priority to JP49063829A priority patent/JPS5035131A/ja
Priority to ES426998A priority patent/ES426998A1/en
Priority to DK304574A priority patent/DK304574A/da
Publication of GB1445872A publication Critical patent/GB1445872A/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
    • 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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

1445872 2-Deoxy-streptamine-aminoglycosides PFIZER Ltd 4 June 1974 [5 June 1973] 26719/73 Heading C2C Novel 2-dioxystreptamines and their acid addition salts in which R is an aromatic carboxylic or heterocyclic group, R<SP>1</SP> is hydrogen or methyl R<SP>2</SP> is amino or hydroxy, R<SP>3</SP> is hydrogen or hydroxy. R<SP>5</SP> is hydrogen or a group of Formulµ VI or VII and the dotted line represents an optional bond when each R<SP>3</SP> is hydrogen are prepared by reacting a compound II in which R<SP>2</SP>' is a free or protected hydroxyl group, R<SP>3'</SP> is hydrogen or a free or protected hydroxyl group, R<SP>4</SP> is a mono-valent protecting group for a primary amino group, and R<SP>6</SP> is a free or protected hydroxyl group or a group OR<SP>5'</SP> in which R<SP>5'</SP> is a Group VI or VII in which any free amino group is replaced by NHR<SP>4</SP> and any free hydroxyl group is optionally protected and R<SP>7</SP> is a free or protected hydroxyl group or a compound V with (1) an aldehyde R-CHO are simultaneously or subsequently reducing the Schiffs base so formed (2) a halide R-CH 2 -X where X is halogen or (3) an acylating agent derived from an acid R-COOH and reducing the R-CO group so formed, and thereafter removing any amino or hydroxyl protecting groups. Compounds I prepared are the 6<SP>1</SP>-(R-CH 2 ) derivatives of neamine, kanamycins A and B, tobramycin gentamycins C 1a and C 2 and 3,41- dideoxy-kanamycin B, in which R is phenyl (optionally substituted by Me, OH, NMe 2 , CF 3 , NH 2 , NH-COCH 3 , Ph, CH 2 OH, F, Br, OB 3 , COOH, NO 2 , mono- or di-Cl or mono-, di- or tri-MeO), naphthyl, phenanthryl, furyl, thienyl (optionally substituted by Me) pyrrolyl, indolyl or pyridinyl (optionally substituted by Cl). Compounds I have anti-bacterial activity and form with a carrier a pharmaceutical composition which may be administered orally or parenterally.
GB2671973A 1973-06-05 1973-06-05 2-deoxystreptamine-aminoglycosides and methods for their preparation paration Expired GB1445872A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB2671973A GB1445872A (en) 1973-06-05 1973-06-05 2-deoxystreptamine-aminoglycosides and methods for their preparation paration
US05/476,269 US4024332A (en) 1973-06-05 1974-06-04 Aminoglycoside antibiotics and intermediates therefor
NL7407483A NL7407483A (en) 1973-06-05 1974-06-04
FR7419268A FR2232326B1 (en) 1973-06-05 1974-06-04
LU70223A LU70223A1 (en) 1973-06-05 1974-06-04
DE19742427096 DE2427096A1 (en) 1973-06-05 1974-06-05 2-DEOXYSTREPTAMINE AMINOGLYCOSIDES AND THE METHOD OF MANUFACTURING THEREOF
JP49063829A JPS5035131A (en) 1973-06-05 1974-06-05
ES426998A ES426998A1 (en) 1973-06-05 1974-06-05 Aminoglycoside antibiotics and intermediates therefor
DK304574A DK304574A (en) 1973-06-05 1974-06-06

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2671973A GB1445872A (en) 1973-06-05 1973-06-05 2-deoxystreptamine-aminoglycosides and methods for their preparation paration

Publications (1)

Publication Number Publication Date
GB1445872A true GB1445872A (en) 1976-08-11

Family

ID=10248165

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2671973A Expired GB1445872A (en) 1973-06-05 1973-06-05 2-deoxystreptamine-aminoglycosides and methods for their preparation paration

Country Status (1)

Country Link
GB (1) GB1445872A (en)

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Legal Events

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