GB1445871A - Intermediates for the preparation of 2-deoxystreptamine-amino glycosides - Google Patents

Intermediates for the preparation of 2-deoxystreptamine-amino glycosides

Info

Publication number
GB1445871A
GB1445871A GB2671873A GB2671873A GB1445871A GB 1445871 A GB1445871 A GB 1445871A GB 2671873 A GB2671873 A GB 2671873A GB 2671873 A GB2671873 A GB 2671873A GB 1445871 A GB1445871 A GB 1445871A
Authority
GB
United Kingdom
Prior art keywords
protecting
group
optionally protected
benzyloxycarbonyl
prepared
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
GB2671873A
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 GB2671873A priority Critical patent/GB1445871A/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 BE145074A priority patent/BE815910A/en
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 GB1445871A publication Critical patent/GB1445871A/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
    • 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

1445871 2-Deoxy-streptamine-aminoglycosides PFIZER Ltd 4 June 1974 [5 June 1973] 26718/73 Divided out of 1445872 Heading C2C Novel compounds II in which R<SP>1</SP> is H or Me, R<SP>2</SP>' is optionally protected hydroxy or NHR<SP>4</SP>, R<SP>3</SP>' is H or optionally protected hydroxy, R<SP>4</SP> is a monovalent protecting group for a primary amino group, R<SP>6</SP> is optionally protected hydroxyl or OR<SP>5'</SP> (in which R<SP>5</SP>' is a hexapyranosyl group containing two or more optionally protected hydroxy radicals and optionally containing an NHR 4 or NHMe group) R<SP>7</SP> is optionally protected hydroxyl and the dotted line represents an optional bond when R<SP>3</SP>' is H; are prepared from compounds V in which R<SP>2</SP> is H 2 N or OH, R<SP>3</SP> is H or NH 2 and R<SP>5</SP> is H or R<SP>6</SP>' by protecting all primary amino groups with R<SP>4</SP> and, if desired, protecting any free hydroxyl groups and selectively deprotecting the 6<SP>1</SP>-amino group by controlled soloolysis. Compounds II are also prepared by selectively protecting the 61-amino group of a compound V with benzyloxycarbonyl, protecting the remaining primary amino groups with R<SP>4</SP> (other than benzyloxycarbonyl) and, if necessary, protecting some or all of the free hydroxyl groups present and selectively removing the 6<SP>1</SP>-N- benzyloxycarbonyl group. Methoxycarbonyl and t-butyloxycarbonyl protected derivatives of neamine, kanamycin A and kanamycin B are prepared.
GB2671873A 1973-06-05 1973-06-05 Intermediates for the preparation of 2-deoxystreptamine-amino glycosides Expired GB1445871A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB2671873A GB1445871A (en) 1973-06-05 1973-06-05 Intermediates for the preparation of 2-deoxystreptamine-amino glycosides
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
BE145074A BE815910A (en) 1973-06-05 1974-06-04 NEW 2-DEOXY-STREPTAMINE AMINOGLYCOSIDES WITH ANTIBACTERIAL PROPERTIES AND THEIR PREPARATION PROCESS
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
GB2671873A GB1445871A (en) 1973-06-05 1973-06-05 Intermediates for the preparation of 2-deoxystreptamine-amino glycosides

Publications (1)

Publication Number Publication Date
GB1445871A true GB1445871A (en) 1976-08-11

Family

ID=10248145

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2671873A Expired GB1445871A (en) 1973-06-05 1973-06-05 Intermediates for the preparation of 2-deoxystreptamine-amino glycosides

Country Status (2)

Country Link
BE (1) BE815910A (en)
GB (1) GB1445871A (en)

Also Published As

Publication number Publication date
BE815910A (en) 1974-12-04

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Legal Events

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