Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Azoxy doai
Patent
1994-05-10
1996-07-30
Powers, Fiona T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Azoxy doai
534566, 534572, A61K 31655, A01N 5100, C07C29108
Patent
active
055411690
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP93/01295 filed Sep. 10, 1993.
TECHNICAL FIELD
This invention relates to a novel antifungal compound, and more particularly relates to a novel azoxy compound, a preparation process thereof and a use thereof as an antifungal agent.
BACKGROUND ART
It is already known that Streptomyces sp. KC-7367 (FERM BP-1277), a microorganism isolated from soil in Maniwa-gun, Okayama-prefecture, Japan produces two substances which are represented by the following formulae ##STR2## and exhibit a strong antifungal activity against fungi (U.S. Pat. No. 4,981,954 and EP-B-282,001).
Further, it is also reported that the 2-imino derivative of KA-7367A obtained by imination of the carbonyl group at the 2-position of the above antifungal substance KA-7367A has a high antifungal activity (U.S. Pat. No. 5,093,480 and EP-B-396,769).
However, although the above compounds KA-7367A and B exhibit an excellent antifungal activity, KA-7367A is unstable, and although the 2-imino derivative of KA-7367A is improved in stability as a result of the imination, it has a difficulty that its antifungal activity is lowered compared with its parent compound KA-7367A.
As compounds to improve these problems, EP-A -443,513 (Japanese Laid-Open Patent Publication No. 240766/1991) discloses compounds represented by the following formula ##STR3## wherein R.sub.11, R.sub.21 and R.sub.31 are the same or different with one another, and each represent a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a haloalkyl group, an alkoxy group, an alkylthio group, an aryl or aralkyl group wherein the aromatic ring is optionally substituted by 1 to 3 substituents, or a hetero-cyclic group optionally substituted by 1 to 3 substituents, or R.sub.11 and R.sub.21 combine to form an alkylene group, Y denotes O or NOH provided that when R.sub.21 (or R.sub.11) and R.sub.31 denote hydrogen atoms simultaneously, R.sub.11 (or R.sub.21) cannot denote an n-butyl group.
DISCLOSURE OF INVENTION
This invention provides an azoxy compound represented by the following general formula ##STR4## wherein R.sub.1 denotes a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkoxy group, a lower alkoxy-lower alkoxy group or a group of the formula X.sub.1 --C.tbd.C--CH.sub.2 O-- wherein X.sub.1 is a hydrogen atom or a halogen atom; --C.tbd.C--CH.sub.2 -- wherein X.sub.2 is a hydrogen atom or a halogen atom;
In this description, the term "lower" means that a group or compound to which this term is attached has 6 or less, preferably 4 or less carbon atoms.
The "halogen atom" includes the four atoms of fluorine, chlorine, bromine and iodine.
The "alkyl group" is a straight-chain or branched chain saturated aliphatic hydrocarbon group, and there can, for example, be mentioned methyl, ethyl, n- or iso-propyl, n- or iso- or tert-butyl, n-pentyl, isoamyl, n-hexyl, etc.
The "alkoxy group" is an (alkyl)-O-group wherein the alkyl moiety has the above meaning, and there can, for example, be mentioned methoxy, ethoxy, n- or iso-proproxy, n- or iso- or tert-butoxy, etc.
The "lower alkoxy-lower alkoxy group" is a lower alkoxy group substituted by a lower alkoxy group, and there can, for example, be mentioned methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, etc.
As specific examples of the compounds of the above formula (I) provided by this invention, the following ones are mentioned besides those disclosed in the later-described examples.
3-(2-(2-hydroxyphenyl)-1-butenyl-ONN-azoxy)-2-butanol,
3-(2-(4-methoxyphenyl)-1-pentenyl-ONN-azoxy)-2-butanol,
3-(3-methyl-2-(4-tert-butoxyphenyl)-1-butenyl-Onn-azoxy)-2-butanol,
3-(2-phenyl-1-hexenyl-ONN-azoxy)-2-butanol,
3-(4-methyl-2-(4-ethoxyphenyl)-1-pentenyl-ONN-azoxy)-2-butanol,
3-(3,3-dimethyl-2-(4-n-propoxyphenyl)-1-butenyl-ONN-azoxy)-2-butanol,
3-(2-(4-iso-propoxyphenyl)-1-heptenyl-ONN-azoxy)-2-butanol,
3-(5-methyl-2-(4-n-butoxyphenyl)-1-hexenyl-ONN-azoxy)-2-butanol,
3-(2-(4-iso-butoxyphenyl)-1-octenyl-ONN-azoxy)-2-butanol,
1-(4-(3-bromo-2-propynyloxy)styryl-ONN-azoxy)-2-propanol,
3-(4-chl
REFERENCES:
patent: 4981954 (1991-01-01), Nakayama et al.
patent: 5093480 (1992-03-01), Nakayama et al.
patent: 5264559 (1993-11-01), Nakayama et al.
Nelson et al., "Regiospecific Synthesis of Unsymmetrical Azoxy Compounds (Diazene N-Oxides)", J. Org. Chem., vol. 41, No. 10, 1976, pp. 1751-1754.
Luk'yanov et al., Chemical Abstracts, 112:55114 b (1990).
Nakata et al., "Regioselective Oxidation of .beta.-Hydroxyazo Compounds to .beta.-Hydroxyazoxy Compounds and Its Application to Syntheses of Maniwamycins A and B", Tetrahedron Letters, vol. 34, No. 38, Sep. 17, 1993, pp. 6095-6098.
Luk'yanov et al., Izv. Akad. Nauk SSSR, Ser. Khim. (1989), (5), 1110-1115.
Deushi Takeo
Ishiwata Hiroyuki
Oda Toshiaki
Okuno Yukihiro
Shiratsuchi Masami
Kowa Company Ltd.
Powers Fiona T.
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