EP1337510A4 - SYNTHESIS AND ANTIMICROBIAL EFFECT OF NEW DIKATIONIC INVERT AMIDINE - Google Patents

SYNTHESIS AND ANTIMICROBIAL EFFECT OF NEW DIKATIONIC INVERT AMIDINE

Info

Publication number
EP1337510A4
EP1337510A4 EP01994174A EP01994174A EP1337510A4 EP 1337510 A4 EP1337510 A4 EP 1337510A4 EP 01994174 A EP01994174 A EP 01994174A EP 01994174 A EP01994174 A EP 01994174A EP 1337510 A4 EP1337510 A4 EP 1337510A4
Authority
EP
European Patent Office
Prior art keywords
alkyl
dikationic
amidine
invert
synthesis
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.)
Withdrawn
Application number
EP01994174A
Other languages
German (de)
French (fr)
Other versions
EP1337510A2 (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
Publication of EP1337510A2 publication Critical patent/EP1337510A2/en
Publication of EP1337510A4 publication Critical patent/EP1337510A4/en
Withdrawn legal-status Critical Current

Links

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.
EP01994174A 2000-11-06 2001-11-06 SYNTHESIS AND ANTIMICROBIAL EFFECT OF NEW DIKATIONIC INVERT AMIDINE Withdrawn EP1337510A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US24624400P 2000-11-06 2000-11-06
US246244P 2000-11-06
PCT/US2001/047238 WO2002057224A2 (en) 2000-11-06 2001-11-06 Synthesis and antimicrobial activityof novel dicationic 'reversed amidines'

Publications (2)

Publication Number Publication Date
EP1337510A2 EP1337510A2 (en) 2003-08-27
EP1337510A4 true EP1337510A4 (en) 2005-02-23

Family

ID=22929882

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01994174A Withdrawn EP1337510A4 (en) 2000-11-06 2001-11-06 SYNTHESIS AND ANTIMICROBIAL EFFECT OF NEW DIKATIONIC INVERT AMIDINE

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

Citations (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
WO2002055025A2 (en) * 2001-01-13 2002-07-18 Univ North Carolina 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

Patent Citations (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
WO2002055025A2 (en) * 2001-01-13 2002-07-18 Univ North Carolina 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 (4)

* Cited by examiner, † Cited by third party
Title
POETA DEL M ET AL: "IN VITRO ANTIFUNGAL ACTIVITIES OF A SERIES OF DICATION-SUBSTITUTED CARBAZOLES, FURANS, AND BENZIMIDAZOLES", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, AMERICAN SOCIETY FOR MICROBIOLOGY, WASHINGTON, DC, US, vol. 42, no. 10, October 1998 (1998-10-01), pages 2503 - 2510, XP000920943, ISSN: 0066-4804 *
POETA DEL M ET AL: "STRUCTURE-IN VITRO ACTIVITY RELATIONSHIPS OF PENTAMIDINE ANALOGUES AND DICATION-SUBSTITUTED BIS-BENZIMIDAZOLES AS NEW ANTIFUNGAL AGENTS", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, AMERICAN SOCIETY FOR MICROBIOLOGY, WASHINGTON, DC, US, vol. 42, no. 10, October 1998 (1998-10-01), pages 2495 - 2502, XP000920922, ISSN: 0066-4804 *
See also references of WO02057224A3 *
STECK E A ET AL: "LEISHMANIA DONOVANI, PLASMODIUM BERGHEI, TRYPANOSOMA RHODESIENSE: ANTIPROTOZOAL EFFECTS OF SOME AMIDINE TYPES", EXPERIMENTAL PARASITOLOGY, NEW YORK, NY, US, vol. 52, no. 3, 1981, pages 404 - 413, XP008014942, ISSN: 0014-4894 *

Also Published As

Publication number Publication date
WO2002057224A3 (en) 2003-03-06
CA2425135A1 (en) 2002-07-25
JP2004517889A (en) 2004-06-17
AU2002246600B2 (en) 2005-08-25
EP1337510A2 (en) 2003-08-27
WO2002057224A2 (en) 2002-07-25

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Legal Events

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Effective date: 20030521

AK Designated contracting states

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

RBV Designated contracting states (corrected)

Designated state(s): AT BE CH CY DE FR GB IT LI

A4 Supplementary search report drawn up and despatched

Effective date: 20050110

RIC1 Information provided on ipc code assigned before grant

Ipc: 7A 61P 31/04 B

Ipc: 7A 61K 31/341 B

Ipc: 7C 07D 405/12 B

Ipc: 7C 07D 207/32 B

Ipc: 7C 07D 333/20 B

Ipc: 7C 07D 307/52 A

17Q First examination report despatched

Effective date: 20070115

STAA Information on the status of an ep patent application or granted ep patent

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18D Application deemed to be withdrawn

Effective date: 20070526