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WO1998027969A3 - Antimicrobial phenazine compounds - Google Patents

Antimicrobial phenazine compounds

Info

Publication number
WO1998027969A3
WO1998027969A3 PCT/CA1997/000978 CA9700978W WO1998027969A3 WO 1998027969 A3 WO1998027969 A3 WO 1998027969A3 CA 9700978 W CA9700978 W CA 9700978W WO 1998027969 A3 WO1998027969 A3 WO 1998027969A3
Authority
WO
Grant status
Application
Patent type
Prior art keywords
phenazine
compounds
positions
growth
microbial
Prior art date
Application number
PCT/CA1997/000978
Other languages
French (fr)
Other versions
WO1998027969A2 (en )
Inventor
Dick Zoutman
Kanji Nakatsu
Dragic Vukomanovic
Gerald Marks
James Brien
Original Assignee
Univ Kingston
Dick Zoutman
Kanji Nakatsu
Dragic Vukomanovic
Gerald Marks
James Brien
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

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine

Abstract

Phenazine compounds having antimicrobial activity are described. The phenazine compounds can be phenazine N-oxides, including phenazine-5,10-dioxides, which may optionally be substituted at one or more positions, preferably the 7- and/or 8-positions of the phenazine nucleus. Also described are methods for treating microbial infections, and methods for inhibiting the growth of a microbial cell. The microbes treated or inhibited can be multidrug resistant. These compounds also inhibit the growth of tumor cells.
PCT/CA1997/000978 1996-12-24 1997-12-24 Antimicrobial phenazine compounds WO1998027969A3 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US3403596 true 1996-12-24 1996-12-24
US60/034,035 1996-12-24

Publications (2)

Publication Number Publication Date
WO1998027969A2 true WO1998027969A2 (en) 1998-07-02
WO1998027969A3 true true WO1998027969A3 (en) 1998-10-01

Family

ID=21873904

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1997/000978 WO1998027969A3 (en) 1996-12-24 1997-12-24 Antimicrobial phenazine compounds

Country Status (2)

Country Link
CA (1) CA2247348A1 (en)
WO (1) WO1998027969A3 (en)

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1103137A (en) * 1965-10-22 1968-02-14 Pfizer & Co C 1,2,3,4-tetrahydrophenazine-5,10-dioxides, and derivatives thereof useful in veterinary applications
GB1182617A (en) * 1967-06-09 1970-02-25 Shell Int Research Phenazine di-N-Oxides and Compositions containing them
US3530130A (en) * 1967-09-14 1970-09-22 Hoffmann La Roche 1-acylated-6-methoxyphenazine 5,10-dioxides
US3567728A (en) * 1968-07-05 1971-03-02 Pfizer Process for the preparation of phenazine di-n-oxides and related compounds
DE1695429A1 (en) * 1967-06-08 1971-04-15 Merck Patent Gmbh A process for the preparation of 1-methoxy-phenazine-5,10-dioxide
US3586674A (en) * 1969-04-08 1971-06-22 Hoffmann La Roche Organometallic derivatives of 6-lower alkoxy 1-phenazinol 5,10-dioxide
US3609153A (en) * 1967-04-20 1971-09-28 Canadian Patents Dev 1 hydroxy 6 methoxy phenazines
GB1271194A (en) * 1970-04-03 1972-04-19 Pfizer PREPARATION OF QUINOXALINE-DI-N-OXIDES FROM o-QUINONEDIOXIME AND BUTENE-1,4 DIONES
US3678051A (en) * 1970-04-02 1972-07-18 Hoffmann La Roche Derivatives of 1,6-phenazinediol 5,10-dioxide
GB1285010A (en) * 1970-04-02 1972-08-09 Hoffmann La Roche Phenazine derivatives and a process for the manufacture thereof
US3700679A (en) * 1970-06-08 1972-10-24 Hoffmann La Roche Nuclear substituted derivatives of 1-hydroxy-6-methoxyphenazine 5,10-dioxide
FR2134012A1 (en) * 1971-04-23 1972-12-01 Hoffmann La Roche Myxin-metal complexes prodn - by reaction in aq suspension, having broad-sprectum antimicrobial activity
US3822265A (en) * 1966-11-25 1974-07-02 Hoffmann La Roche Phenazine derivatives
US3937707A (en) * 1972-05-01 1976-02-10 Hoffmann-La Roche Inc. 6-substituted 1-phenazinol 5,10-dioxide derivatives
US3985734A (en) * 1971-04-23 1976-10-12 Hoffmann-La Roche Inc. Method for the preparation of the copper complex of 6-methoxy-1-phenazinol 5,10-dioxide
US5637591A (en) * 1995-06-02 1997-06-10 Fuji Immunopharmaceuticals Corp. Antimicrobial and anticollagenase activity of phenazine-5, 10-dioxide and derivatives

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1103137A (en) * 1965-10-22 1968-02-14 Pfizer & Co C 1,2,3,4-tetrahydrophenazine-5,10-dioxides, and derivatives thereof useful in veterinary applications
US3822265A (en) * 1966-11-25 1974-07-02 Hoffmann La Roche Phenazine derivatives
US3609153A (en) * 1967-04-20 1971-09-28 Canadian Patents Dev 1 hydroxy 6 methoxy phenazines
DE1695429A1 (en) * 1967-06-08 1971-04-15 Merck Patent Gmbh A process for the preparation of 1-methoxy-phenazine-5,10-dioxide
GB1182617A (en) * 1967-06-09 1970-02-25 Shell Int Research Phenazine di-N-Oxides and Compositions containing them
US3530130A (en) * 1967-09-14 1970-09-22 Hoffmann La Roche 1-acylated-6-methoxyphenazine 5,10-dioxides
US3567728A (en) * 1968-07-05 1971-03-02 Pfizer Process for the preparation of phenazine di-n-oxides and related compounds
US3586674A (en) * 1969-04-08 1971-06-22 Hoffmann La Roche Organometallic derivatives of 6-lower alkoxy 1-phenazinol 5,10-dioxide
GB1285010A (en) * 1970-04-02 1972-08-09 Hoffmann La Roche Phenazine derivatives and a process for the manufacture thereof
US3678051A (en) * 1970-04-02 1972-07-18 Hoffmann La Roche Derivatives of 1,6-phenazinediol 5,10-dioxide
GB1271194A (en) * 1970-04-03 1972-04-19 Pfizer PREPARATION OF QUINOXALINE-DI-N-OXIDES FROM o-QUINONEDIOXIME AND BUTENE-1,4 DIONES
US3700679A (en) * 1970-06-08 1972-10-24 Hoffmann La Roche Nuclear substituted derivatives of 1-hydroxy-6-methoxyphenazine 5,10-dioxide
FR2134012A1 (en) * 1971-04-23 1972-12-01 Hoffmann La Roche Myxin-metal complexes prodn - by reaction in aq suspension, having broad-sprectum antimicrobial activity
US3985734A (en) * 1971-04-23 1976-10-12 Hoffmann-La Roche Inc. Method for the preparation of the copper complex of 6-methoxy-1-phenazinol 5,10-dioxide
US3937707A (en) * 1972-05-01 1976-02-10 Hoffmann-La Roche Inc. 6-substituted 1-phenazinol 5,10-dioxide derivatives
US5637591A (en) * 1995-06-02 1997-06-10 Fuji Immunopharmaceuticals Corp. Antimicrobial and anticollagenase activity of phenazine-5, 10-dioxide and derivatives

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
GRUNBERG ET AL.: "Studies on the in vitro and in vivo chemotherapeutic properties of the antibiotic Myxin", CHEMOTHERAPIA, vol. 12, no. 5, 1967, pages 272 - 281, XP002062758 *
MAESTRONE ET AL.: "Chemotherapeutic activity of 6-methoxy-1-phenazinol 5,10-dioxide, cupric complex in experimentally induced local microbial infections in dogs", AM. J. VET. RES., vol. 35, no. 2, 1974, pages 281 - 284, XP002062759 *
MAESTRONE ET AL.: "Topical antimicrobial activity of 6-Methoxy-1-Phenazinol 5,10-dioxide, cupric complex", AM. J. VET. RES., vol. 33, no. 1, 1972, pages 185 - 193, XP002062754 *
MAESTRONE TE AL.: "Evaluation of Cuprimyxin-hydrocortisone acetate suspension in the treatment of otitis externa in dogs and cats", AM. J. VET. RES., vol. 40, no. 2, 1979, pages 285 - 287, XP002062755 *
MCDONALD ET AL.: "Antimicrobial susceptibility of Prototheca zopfii isolated from bovine intramammary infections", AM. J. VET. RES., vol. 45, no. 6, 1984, pages 1079- - 1080, XP002062756 *
SEKHON ET AL.: "Sensitivity of some human pathogenic yeasts and systemic fungi to myxin", ABSTR. ANNU. MEET. AM. SOC. MICROBIOL., vol. 75, 1975, pages 44, XP002062757 *

Also Published As

Publication number Publication date Type
WO1998027969A2 (en) 1998-07-02 application
CA2247348A1 (en) 1998-07-02 application

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