Title:
NAPHTHOQUINONE DERIVATIVES AND THEIR USE IN THE TREATMENT AND CONTROL OF TUBERCULOSIS
Document Type and Number:
WIPO Patent Application WO2001000554
Kind Code:
A3
Abstract:
Naphthoquinone derivatives of Formula (1): wherein, R represents an OH group, methyl ether, ethyl ether or a similar ether; R1 represents a methyl, ethyl or similar aliphatic hydrocarbon derivative; R2 and R3 each independently represent hydrogen or a group selected from: (A), (B), or (C) wherein R5 represents an OH group, methyl ether, ethyl ether or a similar ether and R6 represents a methyl, ethyl or similar aliphatic hydrocarbon derivative; R4 represents hydrogen or a group selected from: (D), (E) or (F) wherein R7 represents an OH group, methyl ether, ethyl ether or a similar ether and R8 represents a methyl, ethyl or similar aliphatic hydrocarbon derivative; or pharmaceutically acceptable salts thereof, are useful for the treatment and/or control of a tuberculosis in a patient caused by Mycobacterium tuberculosis.
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Inventors:
MEYER JACOBUS JOHANNES MARION (ZA)
LALL NAMRITA (ZA)
LALL NAMRITA (ZA)
Application Number:
PCT/IB2000/000837
Publication Date:
July 05, 2001
Filing Date:
June 22, 2000
Export Citation:
Assignee:
UNIV PRETORIA (ZA)
MEYER JACOBUS JOHANNES MARION (ZA)
LALL NAMRITA (ZA)
MEYER JACOBUS JOHANNES MARION (ZA)
LALL NAMRITA (ZA)
International Classes:
A61K31/122; C07C50/32; A61P31/06; (IPC1-7): A61K31/122; A61P31/06
Other References:
ADENIYI, B. A. ET AL: "Antibacterial activity of diospyrin, isodiospyrin and bisisodiospyrin from the root of Diospyros piscatoria (Gurke) (Ebenaceae)", PHYTOTHER. RES. (2000), 14(2), 112-117, XP000978371
KHAN M R ET AL: "ANTIBIOTIC ACTION OF CONSTITUENTS OF ROOT BARK OF EUCLEA-NATALENSIS.", PAK J SCI IND RES, (1978 (RECD 1979)) 21 (5-6), 197-199., XP000978450
KHAN, M. R. (1) ET AL: "Constituents of Diospyros lolin, D. maritima and D. novoguinensis.", FITOTERAPIA, (APRIL, 1999) VOL. 70, NO. 2, PP. 194-196., XP000978591
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; VICHKANOVA, S. A. ET AL: "Search for antimicrobial drugs among quinones of plant origin", XP002157353, retrieved from STN Database accession no. 91:83030
ROUSHDI I M ET AL: "Synthesis of 1.4-naphthoquinones-4-aryl(aroyl)hydrazones of potential antimicrobial activity.", PHARMAZIE, (1976) 31 (12) 856-9., XP000971908
HAZRA, BANASRI ET AL: "In vitro antiplasmodial effects of diospyrin, a plant-derived naphthoquinoid, and a novel series of derivatives", PHYTOTHER. RES. (1995), 9(1), 72-4, XP000978372
YARDLEY, VANESSA ET AL: "In vitro activity of diospyrin and derivatives against Leishmania donovani, Trypanosoma cruzi and Trypanosoma brucei brucei", PHYTOTHER. RES. (1996), 10(7), 559-562, XP000978369
HAZRA, BANASRI ET AL: "Biological activity of diospyrin towards Ehrlich ascites carcinoma in Swiss A mice", PLANTA MED. (1984), 50(4), 295-7, XP000978377
HAZRA, BANASRI ET AL: "New diospyrin derivatives with improved tumor inhibitory activity towards Ehrlich ascites carcinoma", MED. SCI. RES. (1994), 22(5), 351-3, XP000978374
OERIU I: "Relation between the chemical structure and the antitubercular effect of alpha-naphthoquinone derivatives substituted in 2 and 3 positions.", PHARMAZIE, (1961 MAY) 16 266-72., XP000971910
OERIU I: "Zusammenhänge zwischen der chemischen Struktur und der antituberkulösen Wirkung der in Stellung 2 und 3 substituieren Derivate des alpha-Naphthochinons", PHARMAZIE,DD,VEB VERLAG VOLK UND GESUNDHEIT. BERLIN, no. 16, 1961, pages 320 - 327, XP002078405, ISSN: 0031-7144
KHAN M R ET AL: "ANTIBIOTIC ACTION OF CONSTITUENTS OF ROOT BARK OF EUCLEA-NATALENSIS.", PAK J SCI IND RES, (1978 (RECD 1979)) 21 (5-6), 197-199., XP000978450
KHAN, M. R. (1) ET AL: "Constituents of Diospyros lolin, D. maritima and D. novoguinensis.", FITOTERAPIA, (APRIL, 1999) VOL. 70, NO. 2, PP. 194-196., XP000978591
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; VICHKANOVA, S. A. ET AL: "Search for antimicrobial drugs among quinones of plant origin", XP002157353, retrieved from STN Database accession no. 91:83030
ROUSHDI I M ET AL: "Synthesis of 1.4-naphthoquinones-4-aryl(aroyl)hydrazones of potential antimicrobial activity.", PHARMAZIE, (1976) 31 (12) 856-9., XP000971908
HAZRA, BANASRI ET AL: "In vitro antiplasmodial effects of diospyrin, a plant-derived naphthoquinoid, and a novel series of derivatives", PHYTOTHER. RES. (1995), 9(1), 72-4, XP000978372
YARDLEY, VANESSA ET AL: "In vitro activity of diospyrin and derivatives against Leishmania donovani, Trypanosoma cruzi and Trypanosoma brucei brucei", PHYTOTHER. RES. (1996), 10(7), 559-562, XP000978369
HAZRA, BANASRI ET AL: "Biological activity of diospyrin towards Ehrlich ascites carcinoma in Swiss A mice", PLANTA MED. (1984), 50(4), 295-7, XP000978377
HAZRA, BANASRI ET AL: "New diospyrin derivatives with improved tumor inhibitory activity towards Ehrlich ascites carcinoma", MED. SCI. RES. (1994), 22(5), 351-3, XP000978374
OERIU I: "Relation between the chemical structure and the antitubercular effect of alpha-naphthoquinone derivatives substituted in 2 and 3 positions.", PHARMAZIE, (1961 MAY) 16 266-72., XP000971910
OERIU I: "Zusammenhänge zwischen der chemischen Struktur und der antituberkulösen Wirkung der in Stellung 2 und 3 substituieren Derivate des alpha-Naphthochinons", PHARMAZIE,DD,VEB VERLAG VOLK UND GESUNDHEIT. BERLIN, no. 16, 1961, pages 320 - 327, XP002078405, ISSN: 0031-7144
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