Organic compounds -- part of the class 532-570 series – Organic compounds – Azoxy
Patent
1990-06-21
1992-03-03
Cintins, Marianne
Organic compounds -- part of the class 532-570 series
Organic compounds
Azoxy
534567, 534570, 534572, C07C29100
Patent
active
050934805
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a novel azoxy compound, and more specifically to an azoxy compound which is a 2-imino derivative of an antifungal product KA-7367, a process for producing same and its use as an antifungal agent.
TECHNICAL BACKGROUND
The present inventors found before that Streptomyces sp. KC-7367 (FERM BP-1277) separated from a soil in Maniwa-gun, Okayama, Japan produces a product showing high antifunal activity, further isolated two antifungal products, KA-7367A and KA-7367B from the liquid culture medium, and identified and proposed them (refer to Japanese Laid-open Patent Application No. 6248/89, European Patent Laid-open Specification No. 282,001).
Said antifungal products KA-7367A and KA-7367B are represented by the following formula. ##STR2##
Though the antifungal products KA-7367A and KA-73676B themselves show quite excellent antifungal activity, the present inventors have eagerly made studies to synthesize stable derivatives having by far better antifungal activity, and consequently found that 2-imino derivatives formed by converting a carbonyl group in the 2-position of KA-7367A into an imino exhibit quite high antifungal activity and excellent stability and are useful as antifungal agents; as a result, they have completed this invention.
DISCLOSURE OF INVENTION
This invention is to provide an azoxy compound represented by formula ##STR3## wherein A denotes --O--, --OCO--, --NH--, --NHCO--, --HNCS-- or ##STR4## Y denotes a single bond or a linear or branched alkylene group with 1 to 6 carbon atoms or a linear or branched alkenylene group with 2 to 6 carbon atoms, and said alkylene or alkenylene group may optionally be substituted by a halogen atom, a phenyl group or a halophenyl group, carboxyl group, an alkoxycarbonyl group with 2 to 6 carbon atoms, a phenyl group that may optionally have 1 to 3 substituents selected from a halogen atom, an alkoxy group with 1 to 5 carbon atoms, a carboxyl group, a nitro group, a sulfonyl group and a N-methyl-N-alpha-naphthylmethylamino-methyl group, a phenoxy group in which a benzene ring may optionally be substituted by 1 to 3 halogen atoms, a naphthyl group, a cyano group, a pyridyl group, an oxopyridyl group, a imidazolyl group, a furyl group, a thienyl group or a group of formula ##STR5## R.sub.1 and R.sub.2 are the same or different and each denotes a hydrogen atom, an alkyl group with 1 to 3 carbon atoms, a phenyl group, a naphthyl alkyl group, a phenylalkyl group with 7 to 10 carbon atoms, a naphthylalkyl group with 11 to 14 carbon atoms or an amino group, and with 1 to 3 carbon atoms, a benzoyl group or an alkanoyl group with 2 to 6 carbon atoms that may optionally be substituted by a phenyl group or a halophenyl group, ##STR6## is a hydrogen atom, and its salt.
In the definitions of the substituents in the above formula (I), examples of the linear or branched alkylene group with 1 to 6 carbon atoms include methylene, ethylene, trimethylene, propylene, tetramethylene, ethylethylene, pentamethylene and hexamethylene. Examples of the linear or branched alkenylene group with 2 to 6 carbon atoms are vinylene, propenylene and isoprenylene.
Examples of the halogen atom include fluorine, chlorine, bromine and iodine. Examples of the halophenyl group include o-, m- and p-chlorophenyls, o-, m- and p-fluorophenyls, 2,6-dichlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-difluorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trichlorophenyl and 2,4,6-trifluorophenyl.
The alkyl group is linear or branched. Examples thereof include methyl, ethyl, n-propyl and isopropyl.
The alkoxy group is an alkyloxy group whose alkyl moiety is linear or branched. Examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy and tert-butoxy. The alkoxycarbonyl group is an alkyloxycarbonyl group whose alkoxy moiety has the above meaning. Examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl.
Examples of the phenylalkyl group with 7 to 10 carbon atoms
Deushi Takeo
Ito Hisakatsu
Kamiya Kazuhiro
Nakayama Masahito
Shiratsuchi Masami
Cintins Marianne
Kowa Company Ltd.
Nguyen Jessica H.
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