WO2002057224A3 - Synthesis and antimicrobial activityof novel dicationic 'reversed amidines' - Google Patents

Synthesis and antimicrobial activityof novel dicationic 'reversed amidines' Download PDF

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Publication number
WO2002057224A3
WO2002057224A3 PCT/US2001/047238 US0147238W WO02057224A3 WO 2002057224 A3 WO2002057224 A3 WO 2002057224A3 US 0147238 W US0147238 W US 0147238W WO 02057224 A3 WO02057224 A3 WO 02057224A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
activityof
antimicrobial
synthesis
aryl
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.)
Ceased
Application number
PCT/US2001/047238
Other languages
French (fr)
Other versions
WO2002057224A2 (en
Inventor
David Boykin
Richard R Tidwell
W David Wilson
John R Perfect
Chad E Stephens
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.)
University of North Carolina at Chapel Hill
Georgia State University Research Foundation Inc
Duke University
Original Assignee
University of North Carolina at Chapel Hill
Georgia State University Research Foundation Inc
Duke University
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 University of North Carolina at Chapel Hill, Georgia State University Research Foundation Inc, Duke University filed Critical University of North Carolina at Chapel Hill
Priority to EP01994174A priority Critical patent/EP1337510A4/en
Priority to JP2002557905A priority patent/JP2004517889A/en
Priority to AU2002246600A priority patent/AU2002246600B2/en
Priority to CA002425135A priority patent/CA2425135A1/en
Publication of WO2002057224A2 publication Critical patent/WO2002057224A2/en
Publication of WO2002057224A3 publication Critical patent/WO2002057224A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • 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
    • A61P33/08—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis for Pneumocystis carinii
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)

Abstract

The present invention relates to novel 2,5-bis{[alkyl (or aryl) imino] aminophenyl} furans and thiophenes of the general formula (I) in which R1, R2, R3 and R4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R5 is H, alkyl or aryl; R6 is H, alkyl, aryl, or NR7R8, in which R7 and R8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR9, in which R9 is H or alkyl, and to the use of such compounds.
PCT/US2001/047238 2000-11-06 2001-11-06 Synthesis and antimicrobial activityof novel dicationic 'reversed amidines' Ceased WO2002057224A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP01994174A EP1337510A4 (en) 2000-11-06 2001-11-06 SYNTHESIS AND ANTIMICROBIAL EFFECT OF NEW DIKATIONIC INVERT AMIDINE
JP2002557905A JP2004517889A (en) 2000-11-06 2001-11-06 Synthesis and antibacterial activity of a novel dicationic "reverse amidine"
AU2002246600A AU2002246600B2 (en) 2000-11-06 2001-11-06 Synthesis and antimicrobial activity of novel dicationic "Reversed amidines"
CA002425135A CA2425135A1 (en) 2000-11-06 2001-11-06 Synthesis and antimicrobial activity of novel dicationic "reversed amidines"

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US24624400P 2000-11-06 2000-11-06
US60/246,244 2000-11-06

Publications (2)

Publication Number Publication Date
WO2002057224A2 WO2002057224A2 (en) 2002-07-25
WO2002057224A3 true WO2002057224A3 (en) 2003-03-06

Family

ID=22929882

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/047238 Ceased WO2002057224A2 (en) 2000-11-06 2001-11-06 Synthesis and antimicrobial activityof novel dicationic 'reversed amidines'

Country Status (5)

Country Link
EP (1) EP1337510A4 (en)
JP (1) JP2004517889A (en)
AU (1) AU2002246600B2 (en)
CA (1) CA2425135A1 (en)
WO (1) WO2002057224A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6737440B2 (en) 2000-11-06 2004-05-18 The University Of North Carolina At Chapel Hill Synthesis and antimicrobial activity of novel dicationic “reversed amidines”
US6706754B2 (en) 2000-11-06 2004-03-16 The United States Of America As Represented By The Secretary Of The Army Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis
AU2002232400A1 (en) * 2000-11-06 2002-05-15 U.S. Army Medical Research And Materiel Command Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis
EP1413301A1 (en) * 2002-10-24 2004-04-28 Bayer CropScience SA Antifungal medicaments comprising arylamidine derivatives
US7256203B2 (en) * 2002-11-27 2007-08-14 The University Of North Carolina At Chapel Hill Dicationic 2,5-diarylfuran aza-analogs as anti-protozoan agents
US7517893B2 (en) 2005-05-20 2009-04-14 The University Of North Carolina At Chapel Hill Bichalcophenes and their prodrugs as antiprotozoal agents
US20100249175A1 (en) * 2005-12-02 2010-09-30 Wilson W David Dicationic compounds which selectively recognize G-quadruplex DNA
US9782388B2 (en) 2014-02-25 2017-10-10 University Of South Florida BIS-cyclic guanidine compound compositions, methods of use and treatment thereof
CN119837855A (en) * 2019-12-19 2025-04-18 乔治亚州大学研究基金会 Compounds for the treatment of bacterial infections and for the enhancement of antibiotics
CN111362834B (en) * 2020-02-26 2021-04-02 湖南大学 Antibacterial amidine oligomer with drug resistance and preparation method and application thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002232400A1 (en) * 2000-11-06 2002-05-15 U.S. Army Medical Research And Materiel Command Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis
EP1399163B1 (en) * 2001-01-13 2007-10-10 University Of North Carolina At Chapel Hill Compounds, methods and compositions useful for the treatment of bovine viral diarrhea virus (bvdv) infection and hepatitis c virus (hcv) infection
IL160208A0 (en) * 2001-08-31 2004-07-25 Neurochem Int Ltd Amidine derivatives for treating amyloidosis

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
See also references of EP1337510A4 *
STEPHENS C.E. ET AL.: "Diguanidino and 'reversed' diamidino 2,5-diarylfurans as antimicrobial agents", J. MED. CHEM., vol. 44, no. 11, 2001, pages 1741 - 1748, XP002955210 *

Also Published As

Publication number Publication date
CA2425135A1 (en) 2002-07-25
JP2004517889A (en) 2004-06-17
AU2002246600B2 (en) 2005-08-25
EP1337510A2 (en) 2003-08-27
EP1337510A4 (en) 2005-02-23
WO2002057224A2 (en) 2002-07-25

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