CA2343113A1 - Anionic or cationic dendrimer antimicrobial or antiparasitic compositions - Google Patents

Anionic or cationic dendrimer antimicrobial or antiparasitic compositions Download PDF

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Publication number
CA2343113A1
CA2343113A1 CA002343113A CA2343113A CA2343113A1 CA 2343113 A1 CA2343113 A1 CA 2343113A1 CA 002343113 A CA002343113 A CA 002343113A CA 2343113 A CA2343113 A CA 2343113A CA 2343113 A1 CA2343113 A1 CA 2343113A1
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Prior art keywords
terminated dendrimers
dendrimer
dendrimers
acid
terminated
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Granted
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CA002343113A
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French (fr)
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CA2343113C (en
Inventor
Barry Ross Matthews
George Holan
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Starpharma Pty Ltd
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Individual
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Publication of CA2343113A1 publication Critical patent/CA2343113A1/en
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Publication of CA2343113C publication Critical patent/CA2343113C/en
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Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • 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
    • 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
    • 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
    • A61P31/06—Antibacterial agents for tuberculosis
    • 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
    • A61P31/08—Antibacterial agents for leprosy
    • 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
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/04—Amoebicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/16—Dendrimers and dendritic polymers

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Polyamides (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

A method of prophylactic or therapeutic inhibition of a microbial or parasit ic agent in a human or non-human animal patient, comprises administration to th e patient of an effective amount of a dendrimer having a plurality of terminal groups wherein at least one of the terminal groups has an anionic- or cation ic- moiety bonded or linked thereto.

Claims (14)

1. (Amended) A method of prophylactic or therapeutic inhibition of a bacterial, yeast, fungal or parasitic agent in a human or non-human animal patient, which comprises administration to the patient of an effective amount of a dendrimer having a plurality of terminal groups wherein at least one of said terminal groups has an anionic- or cationic-containing moiety bonded or linked thereto.
2. A method according to claim 1, wherein said compound is a dendrimer which comprises a polyvalent core covalently bonded to at least two dendritic branches, and extends through at least two generations.
3. A method according to claim 2 wherein said dendrimer is a polyamidoamine dendrimer based on an ammonia core.
4. A method according to claim 2 wherein said dendrimer is a polyamidoamine dendrimer based on an ethylene diamine core.
5. A method according to claim 2 wherein said dendrimer is a polylysine dendrimer based on a benzhydrylamine or other suitable core.
6. A method according to claim 2 wherein said dendrimer is a poly(propyleneimine) dendrimer.
7. A method according to claim 2 wherein said compound is a polyionic dendrimer of the general formula I:

wherein:
I is an initiator core;
Z is an interior branching unit;
n is an integer which represents the number of generations of the dendrimer;
and A is an anionic- or cationic- containing moiety which may be linked to interior branching unit Z through an optional linking group X.
8. A method according to any of claims 1 to 7 wherein in said compound said anionic- or cationic-containing moiety or moieties are bonded to amine, sulfhydryl, hydroxy or other reactive terminal groups of the dendrimer by amide or thiourea linkages.
9. A method according to any of claims 1 to 8, wherein in said compound said anionic- or cationic-containing moieties are selected from the group consisting of sulfonic acid-containing moieties, carboxylic acid-containing moieties (including neuraminic and sialic acid-containing moieties and modified neuraminic and sialic acid-containing moieties), boronic acid-containing moieties, phosphoric and phosphoric acid-containing moieties (including esterified phosphoric and phosphoric acid-containing moieties), primary, secondary, tertiary or quaternary amino-containing moieties, pyridinium-containing moieties, guanidinium-containing moieties, amidinium-containing moieties, phenol-containing moieties, heterocycles possessing acidic or basic hydrogens, and zwitterionic-containing moieties.
10. A method according to any of claims 1 to 9 wherein in said compound the moiety or moieties which are bonded to amino or other reactive terminal groups of the dendrimer are selected from the following groups, in which n is zero or a positive integer:

---NH(CH2)nSO3- ---(CH2)nSO3 ---Ar(SO3)n ---CH2CH(SO3)COOH CH(SO3)CH2COOH ---ArX(CH2)nSO3- X = O, S, NH
+ + +
---(CH2)nNMe3 ---Ar(NMe3)n ---Ar(CH2NMe3)n ArXP(=O)(OR)2 X=O, CH2, CHF, CF2 R=alkyl, aryl, H, Na.
ArXP(=O)(OR1)(NR2R3) X=O, CH2, CHF, CF2 R1=alkyl, aryl, H, Na R2, R3=alkyl, aryl Ar[P(=O)(OR)2]n R=alkyl, aryl, H, Na n=1-3 Ar[B(OH)2]n n=1-3 ---Ar[COOH]n n=1-3 R= alkyl or arylalkyl; R1, R2, R3 (which may be same or different) = alkyl or arylalkyl
11. A method according to any of claims 1 to 10, wherein said compound is selected from the group consisting of:

i. alkylsulfonic acid terminated dendrimers;

ii. sulfoacetamide terminated dendrimers;

iii. sulfosuccinamic acid terminated dendrimers;

iv. N-(2-sulfoethyl) succinamide terminated dendrimers;

v. 4-sulfophenylthiourea terminated dendrimers;

vi. 3,6-di-sulfonaphthylthiourea terminated dendrimers;

vii. 4-sulfonaphthylthiourea terminated dendrimers;

viii. 3,5-di-sulfophenylthiourea terminated dendrimers;

ix. 3,6,8-tri-sulfonaphthylthiourea terminated dendrimers;

x. 4-(sulfomethyl) benzamide terminated dendrimers;

xi. 4-sulfabenzamide terminated dendrimers;

xii. N-(4-sulfophenyl) propanamide terminated dendrimers;

xiii. 4-sulfophenylurea terminated dendrimers;

xiv. N,N,N-tri-methylglycinamide terminated dendrimers;

xv. 4-trimethylammonium benzamide terminated dendrimers;

xvi. 4-(trimethylammoniummethyl)benzamide terminated dendrimers;

xvii. N-(2-acetoxyethyl)-N,N-(dimethylammonium)methyl-carboxamide terminated dendrimers;

xviii. guanidino terminated dendrimers;

xix. 4-([1,4,8,11-tetraazacyclotetradecane]methyl)benzamide terminated dendrimers;

xx. 4-carboxy-3-hydroxy-benzylamine terminated dendrimers;

xxi. 4-carboxyphenylarnide terminated dendrimers;

xxii. 3,5-dicarboxyphenylamide terminated dendrimers;

xxiii. 4-phosphonooxyphenylthiourea terminated dendrimers;

xxiv. 4-(phosphonomethyl)phenylthiourea terminated dendrimers;

xxv. ethyl-4-(phosphonomethyl)phenylthiourea terminated dendrimers;

xxvi. (8-octanamido)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-.alpha.-D
galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxvii. (11-undecanamido)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-.alpha.-D-galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxviii. (acetamido)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-.alpha.-D-galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxix. (4-butanarnido)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-.alpha.-D
galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxx. (4-methylbenzamido)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-.alpha.-D-galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxxi. (8-octanamido)-4-azido-5-acetamido-3,4,5-trideoxy-2-thio-D-glycero-.alpha.-D-galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxxii. (8-octanamido)-4-amino-5-acetamido-3,4,5-trideoxy-2-thio-D-glycero-.alpha.-D-galacto-2-nonulopyranosidoic acid terminated dendrimers;

xxxiii. 4-benzamidoboronic acid terminated dendrimers;

xxxiv. 3,5-dicarboxyphenylthiourea terminated dendrimers;

xxxv. 4-phosphonooxyphenylthiourea terminated dendrimers;

xxxvi. 4-phosphonophenylthiourea terminated dendrimers;

xxxvii. 4,6-diphosphononaphthylthiourea terminated dendrimers, xxxviii fluoresceinthiourea terminated dendrimers;

xxxix. (phenyl-3-boronic acid)-thiourea terminated dendrimers;

xl. pyridinium dodecylcarboxamide terminated dendrimers; and xii. saccharin terminated dendrimers.
12. A method according to any of claims 1 to 11, wherein said treatment comprises inhibition of bacterial, yeast or fungal pathogens, or parasitic pathogens.
13. A pharmaceutical or veterinary composition for prophylactic or therapeutic inhibition of a bacterial, yeast, fungal or parasitic agent in a human or non-human animal, which comprises an anionic or cationic dendrimer as defined in any of claims 1 to 11, in association with at least one pharmaceutically or veterinarily acceptable carrier or diluent.
14. Use of an anionic or cationic dendrimer as defined in any of claims 1 to 11, in, or in the manufacture of a medicament for, prophylactic or therapeutic inhibition of a bacterial, yeast, fungal or parasitic agent in a human or non-human animal.
CA002343113A 1998-09-14 1999-09-13 Anionic or cationic dendrimer antimicrobial or antiparasitic compositions Expired - Lifetime CA2343113C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AUPP5842A AUPP584298A0 (en) 1998-09-14 1998-09-14 Antimicrobial and antiparasitic agents
AUPP5842 1998-09-14
PCT/AU1999/000763 WO2000015240A1 (en) 1998-09-14 1999-09-13 Anionic or cationic dendrimer antimicrobial or antiparasitic compositions

Publications (2)

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CA2343113A1 true CA2343113A1 (en) 2000-03-23
CA2343113C CA2343113C (en) 2009-11-24

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CA002343113A Expired - Lifetime CA2343113C (en) 1998-09-14 1999-09-13 Anionic or cationic dendrimer antimicrobial or antiparasitic compositions

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US (1) US6464971B1 (en)
EP (1) EP1113806B1 (en)
JP (1) JP4979848B2 (en)
KR (1) KR100720905B1 (en)
CN (2) CN101352451A (en)
AT (1) ATE372123T1 (en)
AU (1) AUPP584298A0 (en)
BR (1) BR9913712A (en)
CA (1) CA2343113C (en)
DE (1) DE69937059T2 (en)
NZ (1) NZ510289A (en)
WO (1) WO2000015240A1 (en)

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Publication number Publication date
WO2000015240A1 (en) 2000-03-23
AUPP584298A0 (en) 1998-10-08
JP2002524524A (en) 2002-08-06
CN101352451A (en) 2009-01-28
KR20010075066A (en) 2001-08-09
DE69937059D1 (en) 2007-10-18
JP4979848B2 (en) 2012-07-18
BR9913712A (en) 2001-05-29
EP1113806A4 (en) 2003-06-25
CN1323214A (en) 2001-11-21
NZ510289A (en) 2002-10-25
US6464971B1 (en) 2002-10-15
EP1113806A1 (en) 2001-07-11
DE69937059T2 (en) 2008-05-29
KR100720905B1 (en) 2007-05-25
EP1113806B1 (en) 2007-09-05
CA2343113C (en) 2009-11-24
ATE372123T1 (en) 2007-09-15

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