WO2002036588A3 - Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis - Google Patents

Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis Download PDF

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Publication number
WO2002036588A3
WO2002036588A3 PCT/US2001/042905 US0142905W WO0236588A3 WO 2002036588 A3 WO2002036588 A3 WO 2002036588A3 US 0142905 W US0142905 W US 0142905W WO 0236588 A3 WO0236588 A3 WO 0236588A3
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WO
WIPO (PCT)
Prior art keywords
treating
preventing
methods
leishmaniasis
inhibiting
Prior art date
Application number
PCT/US2001/042905
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French (fr)
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WO2002036588A2 (en
Inventor
Karl A Werbovetz
James J Brendle
David W Boykin
Chad E Stephens
Original Assignee
Us Army Med Res Mat Command
Karl A Werbovetz
James J Brendle
David W Boykin
Chad E Stephens
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.)
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Publication date
Application filed by Us Army Med Res Mat Command, Karl A Werbovetz, James J Brendle, David W Boykin, Chad E Stephens filed Critical Us Army Med Res Mat Command
Priority to AU2002232400A priority Critical patent/AU2002232400A1/en
Publication of WO2002036588A2 publication Critical patent/WO2002036588A2/en
Publication of WO2002036588A3 publication Critical patent/WO2002036588A3/en

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    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—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
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Methods for treating, preventing or inhibiting leishmaniasis in a subject comprising administering to the subject a therapeutically effective amount of at least one compound having the structural formula (I) wherein Y is a heteroatom; R?1 and R2¿ are independently H or an alkyl, cycloalkyl, heterocycloalkyl, aryl, amino or heteroaryl group; and X1, X2, and X¿3? are independently H or an alkyl, alkoxy, halo, amino, alkylamino, dialkylamino acylamino, alkylthio, sulfonyl, cyano, carboxy alkoxycarbonyl, or carbamoyl group are disclosed.
PCT/US2001/042905 2000-11-06 2001-11-05 Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis WO2002036588A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002232400A AU2002232400A1 (en) 2000-11-06 2001-11-05 Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US24627700P 2000-11-06 2000-11-06
US60/246,277 2000-11-06
US24633000P 2000-11-07 2000-11-07
US60/246,330 2000-11-07
US28842801P 2001-05-04 2001-05-04
US60/288,428 2001-05-04

Publications (2)

Publication Number Publication Date
WO2002036588A2 WO2002036588A2 (en) 2002-05-10
WO2002036588A3 true WO2002036588A3 (en) 2003-08-28

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PCT/US2001/042905 WO2002036588A2 (en) 2000-11-06 2001-11-05 Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis

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AU (1) AU2002232400A1 (en)
WO (1) WO2002036588A2 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2425135A1 (en) * 2000-11-06 2002-07-25 University Of North Carolina At Chapel Hill Synthesis and antimicrobial activity of novel dicationic "reversed amidines"
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”
EP1837024A3 (en) * 2001-01-13 2007-11-14 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
JP4368582B2 (en) * 2001-01-13 2009-11-18 ユニバーシティ オブ ノース カロライナ アット チャペル ヒル Compounds, methods, and compositions useful for treating bovine viral diarrhea virus (BVDV) infection and hepatitis C virus (HCV) infection
US7163955B2 (en) 2001-01-13 2007-01-16 The 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
DE10203195A1 (en) * 2002-01-25 2003-08-07 Zentaris Ag Use of alkylphosphocholines in the preventive treatment of protozoal diseases
US7887817B2 (en) 2002-01-25 2011-02-15 Aeterna Zentaris Gmbh Process for preventing protozoal diseases
JP2006508164A (en) * 2002-11-27 2006-03-09 ユニバーシティ オブ ノース カロライナ アット チャペル ヒル Divalent cationic 2,5-diarylfuranaza-analogs as antigenic animal agents
EP1663959A4 (en) * 2003-09-05 2007-10-31 Univ North Carolina Novel amidine compounds for treating microbial infections
AU2006201739A1 (en) 2005-05-05 2006-11-23 The University Of North Carolina At Chapel Hill Synthesis and antiprotozoal activity of dicationic 3,5-diphenylisoxazoles
AU2006202040A1 (en) * 2005-05-20 2006-12-07 Reto Brun Novel biochalcophenes and their prodrugs as antiprotozoal agents
WO2008029810A1 (en) * 2006-09-07 2008-03-13 Ishihara Sangyo Kaisha, Ltd. Phenylguanidine derivative or salt thereof, and pest control agent containing them as active ingredient
US20100331368A1 (en) * 2007-10-17 2010-12-30 Tidwell Richard R 2,5-diaryl selenophene compounds, aza 2,5-diaryl thiophene compounds, and their prodrugs as antiprotozoal agents
DE102008022221A1 (en) 2008-05-06 2009-11-12 Universität des Saarlandes Inhibitors of human aldosterone synthase CYP11B2
US8541404B2 (en) 2009-11-09 2013-09-24 Elexopharm Gmbh Inhibitors of the human aldosterone synthase CYP11B2
JP5936350B2 (en) * 2011-12-27 2016-06-22 キヤノン株式会社 New organic compounds

Citations (4)

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Publication number Priority date Publication date Assignee Title
US4622330A (en) * 1982-12-20 1986-11-11 Merck & Co., Inc. Antiprotozoal 3-amino or substituted amino pyrazoles
CA2057834A1 (en) * 1990-12-26 1992-06-27 Denis R. Wikel Pentamidine solution with neutral ph and method for administration thereof
WO1996040737A1 (en) * 1995-06-07 1996-12-19 Arris Pharmaceutical Corporation Reversible cysteine protease inhibitors
WO2002057224A2 (en) * 2000-11-06 2002-07-25 University Of North Carolina At Chapel Hill Synthesis and antimicrobial activityof novel dicationic 'reversed amidines'

Patent Citations (5)

* Cited by examiner, † Cited by third party
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US4622330A (en) * 1982-12-20 1986-11-11 Merck & Co., Inc. Antiprotozoal 3-amino or substituted amino pyrazoles
CA2057834A1 (en) * 1990-12-26 1992-06-27 Denis R. Wikel Pentamidine solution with neutral ph and method for administration thereof
WO1996040737A1 (en) * 1995-06-07 1996-12-19 Arris Pharmaceutical Corporation Reversible cysteine protease inhibitors
US6030946A (en) * 1995-06-07 2000-02-29 Axys Pharmaceuticals, Inc. Reversible cysteine protease inhibitors
WO2002057224A2 (en) * 2000-11-06 2002-07-25 University Of North Carolina At Chapel Hill Synthesis and antimicrobial activityof novel dicationic 'reversed amidines'

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BRENDLE JAMES J ET AL: "Antileishmanial activities of several classes of aromatic dications.", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY. UNITED STATES MAR 2002, vol. 46, no. 3, March 2002 (2002-03-01), pages 797 - 807, XP001148797, ISSN: 0066-4804 *
DATABASE WPI Section Ch Week 199237, Derwent World Patents Index; Class B05, AN 1992-300533, XP002230966 *
HOPKINS K T ET AL: "EXTENDED AROMATIC FURAN AMIDINO DERIVATIVES AS ANTI-PNEUMOCYSTIS CARINII AGENTS", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 41, no. 20, 1998, pages 3872 - 3878, XP000914716, ISSN: 0022-2623 *
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STECK E A ET AL: "LEISHMANIA-DONOVANI PLASMODIUM-BERGHEI TRYPANOSOMA-RHODESIENSE ANTI PROTOZOAL EFFECTS OF SOME AMIDINE TYPES", EXPERIMENTAL PARASITOLOGY, vol. 52, no. 3, 1981, pages 404 - 413, XP008014942, ISSN: 0014-4894 *
STEPHENS, CHAD E. ET AL: "Diguanidino and "Reversed" Diamidino 2,5-Diarylfurans as Antimicrobial Agents", JOURNAL OF MEDICINAL CHEMISTRY (2001), 44(11), 1741-1748, XP001134987 *

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WO2002036588A2 (en) 2002-05-10

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