GB1456674A - Neomycin derivatives - Google Patents

Neomycin derivatives

Info

Publication number
GB1456674A
GB1456674A GB5642173A GB5642173A GB1456674A GB 1456674 A GB1456674 A GB 1456674A GB 5642173 A GB5642173 A GB 5642173A GB 5642173 A GB5642173 A GB 5642173A GB 1456674 A GB1456674 A GB 1456674A
Authority
GB
United Kingdom
Prior art keywords
neomycin
general formula
pharmaceutically acceptable
formulμ
toxic
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
GB5642173A
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 GB1456674A publication Critical patent/GB1456674A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1456674 Neomycin derivatives BRISTOLMYERS CO 5 Dec 1973 [6 Dec 1972] 56421/73 Heading C2C Novel neomycin derivatives of the general formula wherein one of R<SP>1</SP> and R<SP>2</SP> is -CH 2 NH 2 and the other is a hydrogen atom and R is a L-(-)-γ- amino-α-hydroxy-butyryl group, and non-toxic, pharmaceutically acceptable acid addition salts thereof are prepared by (a) acylating neomycin B or C with a compound having one of the following general formulµ or carbodiimides thereof in the case of the last two formulµ, wherein each of R<SP>6</SP> and R<SP>7</SP> is H, F, Cl, Br, NO 2 , OH, C 1-6 alkyl or C 1-6 alkoxy and X is Cl, Br or I, or a functional equivalent thereof, (b) acylating the resulting acylated neomycin of the general formula wherein one of R<SP>1</SP> and R<SP>2</SP> is -CH 2 NHY, in which Y is a group having one of the following formulµ and the other is a hydrogen atom (novel when Y is benzyloxycarbonyl), with a compound of the general formula wherein W is as Y above and M is a group having one of the following formulµ or a functional equivalent thereof, and (c) removing the blocking groups W and Y from the resulting acylated neomycin of the general formula (novel when Y and W are benzyloxycarbonyl) and optionally converting the product to a non- toxic, pharmaceutically acceptable acid addition salt thereof. N - (Benzyloxycarbonylozy)succinimide is prepared by reacting N-hydroxysuccinimide with carbobenzoxy chloride in aqueous NaOH. Pharmaceutical compositions having antibacterial activity comprise, as active ingredient, a neomycin derivative of the first general formula above or a non-toxic, pharmaceutically acceptable acid addition salt thereof, together with an inert, pharmaceutically acceptable carrier.
GB5642173A 1972-12-06 1973-12-05 Neomycin derivatives Expired GB1456674A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31245272A 1972-12-06 1972-12-06

Publications (1)

Publication Number Publication Date
GB1456674A true GB1456674A (en) 1976-11-24

Family

ID=23211510

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5642173A Expired GB1456674A (en) 1972-12-06 1973-12-05 Neomycin derivatives

Country Status (4)

Country Link
JP (1) JPS5719120B2 (en)
DE (1) DE2360946A1 (en)
FR (1) FR2209546B1 (en)
GB (1) GB1456674A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007064954A2 (en) * 2005-12-02 2007-06-07 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
US7943749B2 (en) 2004-11-05 2011-05-17 Isis Pharmaceuticals, Inc. Antimicrobial 2-deoxystreptamine compounds
US8318685B2 (en) 2010-11-17 2012-11-27 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8367625B2 (en) 2008-10-09 2013-02-05 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8372813B2 (en) 2008-10-09 2013-02-12 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8377896B2 (en) 2008-09-10 2013-02-19 Isis Pharmaceuticals, Inc Antibacterial 4,6-substituted 6′, 6″ and 1 modified aminoglycoside analogs
US8399419B2 (en) 2008-09-10 2013-03-19 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8481502B2 (en) 2009-10-09 2013-07-09 Achaogen, Inc. Antibacterial aminoglycoside analogs

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2331620A1 (en) * 1998-05-11 1999-11-18 The Endowment For Research In Human Biology, Inc. Use of neomycin for treating angiogenesis-related diseases
US20080300199A1 (en) * 2007-04-10 2008-12-04 Achaogen Inc. Antibacterial 1,4,5-substituted aminoglycoside analogs

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR6907429D0 (en) * 1968-03-25 1973-04-12 Parke Davis & Co PROCESS FOR THE PRODUCTION OF NEW AMINE COMPOUNDS

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7943749B2 (en) 2004-11-05 2011-05-17 Isis Pharmaceuticals, Inc. Antimicrobial 2-deoxystreptamine compounds
WO2007064954A2 (en) * 2005-12-02 2007-06-07 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
WO2007064954A3 (en) * 2005-12-02 2007-08-16 Isis Pharmaceuticals Inc Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
US7893039B2 (en) 2005-12-02 2011-02-22 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
US8114856B2 (en) 2005-12-02 2012-02-14 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
AU2006320374B2 (en) * 2005-12-02 2012-08-30 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
US8569264B2 (en) 2005-12-02 2013-10-29 Isis Pharmaceuticals, Inc. Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents
US8377896B2 (en) 2008-09-10 2013-02-19 Isis Pharmaceuticals, Inc Antibacterial 4,6-substituted 6′, 6″ and 1 modified aminoglycoside analogs
US8399419B2 (en) 2008-09-10 2013-03-19 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8742078B2 (en) 2008-09-10 2014-06-03 Isis Pharmaceuticals, Inc. Antibacterial 4,6-substituted 6′, 6″ and 1 modified aminoglycoside analogs
US8372813B2 (en) 2008-10-09 2013-02-12 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8367625B2 (en) 2008-10-09 2013-02-05 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8481502B2 (en) 2009-10-09 2013-07-09 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8318685B2 (en) 2010-11-17 2012-11-27 Achaogen, Inc. Antibacterial aminoglycoside analogs
US8653041B2 (en) 2010-11-17 2014-02-18 Achaogen, Inc. Antibacterial aminoglycoside analogs

Also Published As

Publication number Publication date
FR2209546A1 (en) 1974-07-05
FR2209546B1 (en) 1977-09-02
DE2360946A1 (en) 1974-06-20
JPS5719120B2 (en) 1982-04-20
JPS4992044A (en) 1974-09-03

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Legal Events

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