Oxime derivatives, hydrazone derivatives and use thereof

Details Oxime derivatives, hydrazone derivatives and use thereof Oxime derivatives, hydrazone derivatives and use thereof

1999-12-09

2001-06-26

Lambkin, Deborah C. (Department: 1613)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S378000, C514S351000, C514S227500, C514S212010, C564S256000, C548S248000, C544S059000, C540S607000

Reexamination Certificate

active

06251949

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel oxime derivative and a novel hydrazone derivative as well as the use of the same.
BACKGROUND ART
While as oxime derivatives and hydrazone derivatives analogous to the present invention Japanese Patent Application Laid-Open Nos. 3-215464 and 7-309825, and WO 95/21153, WO 95/21154, WO 95/18789 and WO 96/11183 disclose compounds having fungicidal activities, a compound disclosed in the present invention is not included in these publications. In addition, none of these publications mentioned the tachykinin receptor antagonism of the compounds disclosed therein.
Tachykinin is a name which is used commonly in a group of the neuropeptides having 10 to 11 amino acids, and includes substance P, neurokinin A and neurokinin B which are known. Each of these substances binds to three receptors, namely NK1, NK2 and NK3, and is known to be involved in pain transmission, vasodilation, saliva secretion, increase in capillary vessel permeability, immunoregulation, nerve cell regulation and the like. Accordingly, a compound having a tachykinin receptor antagonistic effect is considered to have various biological activities, and each of EP 394989, EP 428434, EP 429366, EP 436334, EP 443132, EP 474561, EP 482 539, EP 499313, EP 512901, EP 512902, EP 514273, EP 514275, EP 515240, EP 517589, EP 520555, EP 522808, EP 528495, EP 532456, EP 533280, EP 536817, EP 545478, EP 559538, EP 585913, WO 90/05525, WO 90/05729, WO 91/09844, WO 91/18899, WO 92/01688, WO 92/06079, WO 92/12151, WO 95/15585, WO 92/19254, WO 92/20661, WO 92/20667, WO 93/00330, WO 93/00331, WO 93/01159, WO 93/01165, WO 93/01169, WO 93/01170, WO 93/06099, WO 93/09116, WO 93/10073, WO 93/14084, WO 93/18023, WO 93/19064, WO 93/21155, WO 93/21181, WO 93/23380, WO 94/16697, WO 94/17045, WO 94/19323, WO 94/20500, WO 94/26740, WO 94/29309, WO 95/02595, WO 95/04040, WO 95/04042, WO 95/18124, WO 95/18129, WO 95/28389, WO 96/29326, WO 96/30367, Japanese Patent Application Laid-Open Nos. 8-239323, 8-295667, 8-2301849 and 8-301871 discloses a compound having a tachykinin receptor antagonistic effect.
However, none of these publications describes an oxime derivative or a hydrazone derivative disclosed in the present invention.
DISCLOSURE OF INVENTION
An objective of the present invention is to provide a compound having a higher fungicidal effect and a higher tachykinin receptor antagonistic effect.
The present inventors made an effort to achieve the objective described above and finally found that a novel oxime derivative and a novel hydrazone derivative described below have a higher fungicidal effect and a higher tachykinin receptor antagonistic effect, whereby accomplishing the present invention.
Thus, the present invention is a compound represented by Formula (I):
wherein R
1
is an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl; R
2
is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted alkylsulfonyl, an optionally substituted aryl, an optionally substituted arylsulfonyl or an optionally substituted heterocyclic group; R
3
is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted alkylsulfonyl, an optionally substituted aryl, an optionally substituted arylsulfonyl or an optionally substituted heterocyclic group; R
4
and R
5
are the same or different from each other and each is a hydrogen atom, an optionally substituted alkyl, an optionally substituted cycloalkyl or an optionally substituted alkoxy, or R
4
and R
5
may be taken together with their adjacent nitrogen atom to form an optionally substituted monocyclic ring or polycyclic ring; X and Y are the same or different from each other and each is an oxygen atom or an NR
6
wherein R
6
is a hydrogen atom, an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted alkanoyl or an optionally substituted aroyl; Z is an oxygen atom or a sulfur atom; a wave-shaped line (~) represents the configuration of a E form or a Z form or a mixture thereof;
provided that when R
2
is an optionally substituted benzyl, then the substituent is not a group represented by formula:
 wherein (R
12
)
2
is H
2
, ═O, ═CH—OH, ═CHOCH
3
, ═N—OH or ═N—OCH
3
; and R
13
represents an alkoxy or a monoalkylamino;
and a salt or a hydrate thereof preferably a compound or a salt or a hydrate thereof described above wherein R
1
is an aryl or an alkyl; R
2
is an optionally substituted alkyl, alkenyl, alkynyl, aryl or heterocyclic group; R
3
is an optionally substituted alkyl, alkenyl, alkynyl, an optionally substituted aryl, an optionally substituted arylsulfonyl or heterocyclic group; R
4
and R
5
are the same or different from each other and each is a hydrogen atom, an alkyl or an alkoxy, or R
4
and R
5
may be taken together with their adjacent nitrogen atom to form an optionally substituted monocyclic ring; X and Y are the same or different from each other and each is an oxygen atom or a NR
6
wherein R
6
is a hydrogen atom, alkyl, aryl, alkanoyl or aroyl.
BEST MODE FOR CARRYING OUT THE INVENTION
In this specification, the term “lower” means a straight or branched chain group having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, unless otherwise specified.
The aryl in an optionally substituted aryl represented by R
1
may be an aryl having 6 to 14 carbon atoms, such as phenyl, naphthyl (e.g., 1-naphthyl, 2-naphthyl) and the like.
The substituent on an optionally substituted aryl represented by R
1
may for example be a lower alkyl (e.g., methyl, ethyl, propyl, butyl and the like), a lower alkenyl (e.g., vinyl, allyl, 2-butenyl and the like), a lower alkynyl (e.g., ethynyl, 2-propynyl, 3-butynyl and the like), a cycloalkyl (e.g., cyclopropyl, cyclopentyl, cyclohexyl and the like), a cycloalkenyl (e.g., cyclopentenyl, cyclohexenyl and the like), a halogenated lower alkyl (e.g., trifluoromethyl, trichloromethyl, difluoromethyl, chloromethyl, 2-bromoethyl, 1,2-dichloropropyl and the like), a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), nitro, cyano, a lower alkylthio (e.g., methylthio, ethylthio, propylthio and the like), —NR
8
R
9
wherein R
8
and R
9
are the same or different from each other and each is a hydrogen atom, an optionally substituted lower alkyl (e.g., methyl, ethyl, propyl, 2-chloroethyl, methoxymethyl, 2-ethoxyethyl, benzyl, 4-chlorobenzyl, 2-oxopropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, carbamoylmethyl and the like), formyl, a lower alkanoyl (e.g., acetyl, propionyl and the like), a lower alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl and the like), an optionally substituted aryl (e.g., phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 1-naphthyl, 2-naphthyl and the like), an optionally substituted aroyl (e.g., benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2-methylbenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 2-methoxybenzoyl, 3-methoxybenzoyl, 4-methoxybenzoyl and the like), an optionally substituted lower alkylsulfonyl (e.g., methanesulfonyl, ethanesulfonyl, trifluoromethanesulfonyl and the like), an optionally substituted arylsulfonyl (e.g., benzenesulfonyl, 4-chlorobenzenesulfonyl, 4-methylbenzenesulfonyl and the like); or alternatively R
8
and R
9
may be taken together to form a cyclic system such as pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and the like, —OR
10
wherein R
10
is a hydrogen atom, a lower alkyl (e.g., methyl, ethyl, propyl and the like), a lower alkenyl (e.g., vinyl, allyl, 2-butenyl and the like), a lower alkynyl (e.g., ethynyl, 2-propynyl, 3-butynyl and the like), an optionally substituted aryl (e.g., phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chloropheny

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