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
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WO
WIPO (PCT)
Prior art keywords
alkyl
activityof
antimicrobial
synthesis
aryl
Prior art date
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
Original Assignee
Univ North Carolina
Univ Georgia State Res Found
David Boykin
Richard R Tidwell
W David Wilson
John R Perfect
Chad E Stephens
Univ Duke
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 Univ North Carolina, Univ Georgia State Res Found, David Boykin, Richard R Tidwell, W David Wilson, John R Perfect, Chad E Stephens, Univ Duke filed Critical Univ North Carolina
Priority to AU2002246600A priority Critical patent/AU2002246600B2/en
Priority to JP2002557905A priority patent/JP2004517889A/en
Priority to EP01994174A priority patent/EP1337510A4/en
Priority to CA002425135A priority patent/CA2425135A1/en
Publication of WO2002057224A2 publication Critical patent/WO2002057224A2/en
Publication of WO2002057224A3 publication Critical patent/WO2002057224A3/en

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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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (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' WO2002057224A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU2002246600A AU2002246600B2 (en) 2000-11-06 2001-11-06 Synthesis and antimicrobial activity of novel dicationic "Reversed amidines"
JP2002557905A JP2004517889A (en) 2000-11-06 2001-11-06 Synthesis and antibacterial activity of a novel dicationic "reverse amidine"
EP01994174A EP1337510A4 (en) 2000-11-06 2001-11-06 Synthesis and antimicrobial activityof 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 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”
WO2002036588A2 (en) * 2000-11-06 2002-05-10 U.S. Army Medical Research And Materiel Command Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis
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
EP1413301A1 (en) * 2002-10-24 2004-04-28 Bayer CropScience SA Antifungal medicaments comprising arylamidine derivatives
EP1565458A4 (en) * 2002-11-27 2010-06-02 Univ North Carolina Dicationic 2,5-diarylfuran aza-analogs as anti-protozoan agents
AU2006202040A1 (en) * 2005-05-20 2006-12-07 Reto Brun Novel biochalcophenes 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
US20230105108A1 (en) * 2019-12-19 2023-04-06 Georgia State University Research Foundation, Inc. Compounds for the treatment of bacterial infections and potentiation 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
WO2002036588A2 (en) * 2000-11-06 2002-05-10 U.S. Army Medical Research And Materiel Command Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis
US20030199521A1 (en) * 2001-01-13 2003-10-23 Dykstra Christine C. Compounds, methods and compositions useful for the treatment of bovine viral diarrhea virus (BVDV) infection and hepatitis C virus (HCV) infection
WO2003017994A1 (en) * 2001-08-31 2003-03-06 Neurochem (International) Limited 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
EP1337510A2 (en) 2003-08-27
AU2002246600B2 (en) 2005-08-25
JP2004517889A (en) 2004-06-17
WO2002057224A2 (en) 2002-07-25
EP1337510A4 (en) 2005-02-23

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