Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1999-03-06
2000-10-24
Owens, Amelia
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
562508, 514460, 549418, 549420, 549475, A01N 3734
Patent
active
061368539
DESCRIPTION:
BRIEF SUMMARY
SUMMARY OF THE INVENTION
The present invention relates to sordarin derivatives which are potent antifungal agents with a broad spectrum of activity, to processes for their preparation, to pharmaceutical and agricultural compositions containing the compounds, and to methods of controlling fungal infections in human, animals and plant materials using such compounds.
BACKGROUND OF THE INVENTION
Sordarin is an antifungal antibiotic isolated from the mould Sordaria araneosa (see GB 1,162,027 and Helvetica Chimica Acta, 1971, 51:119-20). Other compounds having the sordarin skeleton have also been reported as antifungal agents. Japanese Kokai J62040292 discloses the compound zofimarin isolated from Zofiela marina sp.; Japanese Kokai J06157582 discloses the compound BE-31405 isolated from Penicillium sp.; and SCH57404 is reported in J. Antibiotics, 1995, 48:1171-1172. Semi-synthetic sordarin derivatives are reported in PCT Applications WO96/14326 and WO96/14327.
Sordaricin, the aglycon, may be obtained from sordarin by acid hydrolysis (Hauser and Sigg, Helvetica Chimica Acta, 1971, 51:119-20); similarly sordaricin methyl ester is obtained from sordarin methyl ester. The total synthesis of sordaricin methyl ester is reported in Kato et al, J. Chem. Soc., Chem. Commun., 1993, 1002-1004, which also discloses O-methoxymethyl sordaricin methyl ester. The diacetate of 4-desformyl-4-hydroxymethyl sordaricin is disclosed in Mander and Robinson, J. Org. Chem., 1991, 56(11):3395-3601. Neither sordaricin nor the reported derivatives thereof has been shown to have biological activity.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides compounds having the formula I: ##STR1## wherein R is ##STR2## with the proviso that when R.sup.12 is CHO, R is not (g); R.sup.1 is ##STR3## R.sup.14 is (a) H,
One embodiment of the present invention provides compounds of formula I wherein ##STR4##
Another embodiment of the present invention provides compounds of formula I wherein
Another embodiment of the present invention provides compounds of formula I wherein
Another embodiment of the present invention provides compounds of formula I wherein
Another embodiment of the present invention provides compounds of formula I wherein
Another embodiment of the present invention provides compounds of formula I wherein
Another embodiment of the present invention provides compounds of formula I wherein ##STR5##
A preferred embodiment of the present invention provides compounds of formula I wherein
Another preferred embodiment of the present invention provides compounds of formula I wherein
A more preferred embodiment of the present invention provides compounds of formula I wherein
In another aspect of the present invention, there is provided a pharmaceutical composition which comprises an antifungal effective amount of a compound of formula I, and a pharmaceutically acceptable carrier. Also provided is a pharmaceutical composition which is made by combining a compound of formula I and a pharmaceutically acceptable carrier.
Another aspect of the present invention provides an agricultural composition which comprises an antifungal effective amount of a compound of formula I, and an agriculturally acceptable carrier thereof. Also provided is an agricultural composition which is made by combining a compound of formula I and an agriculturally acceptable carrier.
Yet another aspect of the present invention provides a method for treating fungal infection in an animal (including humans) which comprises administering to an animal in need of such treatment an antifungal effective amount of a compound of formula I.
A further aspect of the present invention provides a method for controlling phytopathogenic fungi in plants which comprises applying to said plant an antifungal effective amount of a compound of formula I.
As used herein, unless otherwise specified, the following terms have the indicated meanings.
The term "alkyl", alone or as part of a group (e.g. aralkyl), means a straight or branched chain alkyl moiety, optionally substituted wi
REFERENCES:
von D. Hauser, et al., Helvetica Chimica Acta, 54:119-20, (1971).
S. J. Coval, et al., J. Antibiotics, 48:1171-1172, (1995).
N. Kato, et al., J. Chem. Soc., Chem. Commun., 002-1004, (1993).
L. N. Mander, et al., J. Org. Chem. 56(11):3595-3601, (1991).
M. Dawson, et al., Chem. Abstr., vol. 125, No. 1996:479150 (1996).
M. Hayes, et al., Chem. Abstr., vol. 125, No. 1996:455761 (1996).
Patent Abstracts of Japan, vol. 11, No. 229 (C-436) Jul. 25, 1987.
Kato et al "Total Synthesis of Optically Active Sordaricin Methyl Ester and Its Delta 2-Derivative" CA 120:107383 (1993).
Mander et al "Studies on the Synthesis of the Diterpenoid Mold Metabolite Sordaricin . . . " CA 114:229179 1991.
Balkovec James M.
Tse Bruno
Lee Shu M.
Merck & Co. , Inc.
Owens Amelia
Rose David L.
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