Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-05-18
2001-12-11
Chang, Ceila (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S319000, C514S579000, C514S647000, C514S649000, C514S650000, C514S657000, C546S205000, C546S229000, C546S235000, C546S237000, C564S316000, C564S321000, C564S347000, C558S411000, C558S415000
Reexamination Certificate
active
06329399
ABSTRACT:
TECHNICAL FIELD
The present invention relates to novel amine derivatives having an excellent antimycotic effect and to a method for producing the same.
BACKGROUND ART
An increasing number of patients are suffering from superficial mycosis, whose representative example is athlete's foot (tinea pedis), due to a prolonged time in which shoes are put on. However, no certain therapeutical method or remedy therefor has been found and currently it is enumerated as one of diseases that remain to be overcome. So far, great effort has been made to find their remedy and many compounds have been subjected to screening for their antimycotic effect. Although, some substances show antimycotic activity in vitro or vivo using animals, most of them do not show the antimycotic activity in real clinical tests, resulting in stopping the development of the remedy. Therefore, only a limited number of substances showed satisfactory antimycotic results.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide novel compounds having an excellent antimycotic effect and a pharmaceutical composition containing them.
Under the circumstances, the present inventors have made intensive investigation, and as a result of which, the present inventors have found that the amine derivatives represented by general formula (1) set forth below have an excellent antimycotic effect, thus completing the present invention.
That is, the present invention provides amine derivatives represented by general formula (1) below or salts thereof:
[in the formula (1) above, R
1
represents a linear C
1-5
alkyl group, a branched C
1-5
alkyl group, or a cyclic C
1-5
alkyl group, said C
1-5
alkyl group may be halogenated;
R
2
represents a group represented by the formula (a), (b), (c), (d), or (e)
(“
”) indicates that the arrangement of double bond may be either cis or trans) (provided that R
5
in the formula (a) is a linear C
1-4
alkyl group or a phenyl group and n in the formula (d) or (e) is an integer of 1 to 3);
R
3
is an oxygen atom or a group represented by the formula (f) below;
R
6
and R
7
independently represent a hydrogen atom, a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or a cyclic C
1-4
alkyl group; R
4
represents a group represented by the formula (g), (h), or (i),
in the formula (i), R
8
is a substituent group which substitutes a hydrogen atom in the phenyl group in the formula and represents a linear C
1-7
alkyl group, a branched C
1-7
alkyl group, a cyclic C
1-7
alkyl group, a halogen atom, a linear C
1-4
alkoxy group, a branched C
1-4
alkoxy group, a cyclic C
1-4
alkoxy group, a nitro group, an amino group may be substituted, a cyano group, a carboxyl group, a linear C
2-5
alkoxycarbonyl group, a branched C
2-5
alkoxycarbonyl group, a cyclic C
2-5
alkoxycarbonyl group, a hydroxyl group, or a group represented by R
9
3
SiO—; and R
9
represents a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or a cyclic C
1-4
alkyl group, in which three of R
9
may be the same or different; and m of R
8
may be the same or different; m is an integer of 0 to 5.].
The amine derivatives or salts thereof of the present invention specifically include: amine derivatives represented by the general formula (1) in which R
1
is a linear C
1-5
alkyl group, a branched C
1-5
alkyl group or a cyclic C
1-5
alkyl group; R
2
is a group represented by the formula (d) or (e); R
4
is a group represented by the formula (i); and R
3
, R
8
in the formula (i), m, and n in the formula (d) or (e) are as defined above (hereinafter, referred to as “the first amine derivatives of the invention”) or salts thereof; or amine derivatives represented by the general formula (1) in which R
1
is a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or a cyclic C
1-4
alkyl group, said C
1-4
alkyl group may be halogenated, R
2
is a group represented by the formula (a), (b) or (c); R
8
, when R
4
is represented by the formula (i), is a linear C
1-4
alkyl group, a branched C
1-4
alkyl group, a cyclic C
1-4
alkyl group, a halogen atom, a liner C
1-4
alkoxy group, a branched C
1-4
alkoxy group, a cyclic C
1-4
alkoxy group, a nitro group, an amino group may be substituted, a cyano group, a carboxyl group, a linear C
2-5
alkoxycarbonyl group, a branched C
2-5
alkoxycarbonyl group, a cyclic C
2-5
alkoxycarbonyl group, a hydroxyl group, or a group represented by R
9
3
SiO—, R
9
represents a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or a cyclic C
1-4
alkyl group, in which three of R
9
may be the same or different, m is an integer of 0 to 5, m of R
8
may be the same or different; R
3
, and R
5
in the formula (a) are as defined above (hereinafter, referred to as “the second amine derivatives of the invention”)
Further, the present invention provides a method for producing amine derivatives represented by general formula (1) or salts thereof.
(in the formula (1), R
1
, R
2
, R
3
, and R
4
represent the same meanings as those in formulae (2) and (3) below] comprising condensing a compound represented by general formula (2)
[in the formula (2), R
1
represents a linear C
1-5
alkyl group, a branched C
1-5
alkyl group, or a cyclic C
1-5
alkyl group, said C
1-5
alkyl group may be halogenated; R
3
represents an oxygen atom or a group represented by the formula (f) below;
R
6
and R
7
independently represent a hydrogen atom or a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or a cyclic C
1-4
alkyl group; R
4
represents a group represented by the formula (g), (h), or (i),
in the formula (i), R
8
is a substituent group which substitutes a hydrogen atom in the phenyl group in the formula and represents a linear C
1-7
alkyl group, a branched C
1-7
alkyl group, a cyclic C
1-7
alkyl group, a halogen atom, a liner C
1-4
alkoxy group, a branched C
1-4
alkoxy group, a cyclic C
1-4
alkoxy group, a nitro group, an amino group may be substituted, a cyano group, a carboxyl group, a linear C
2-5
alkoxycarbonyl group, a branched C
2-5
alkoxycarbonyl group, a cyclic C
2-5
alkoxycarbonyl group, a hydroxyl group, or a group represented by R
9
3
SiO—, R
9
represents a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or cyclic C
1-4
alkyl group, in which three of R
9
may be the same or different; and m of R
8
may be the same or different; m is an integer of 0 to 5.] with a compound represented by general formula (3)
[in the formula (3), R
2
represents a group represented by the formula (a), (b), (c), (d), or (e)
(“
”) indicates that the arrangement of double bond may be either cis or trans) (provided that R
5
in the formula (a) is a linear C
1-4
alkyl group or a phenyl group and n in the formula (d) or (e) is an integer of 1 to 3); and X represents a halogen atom].
Still further, the present invention provides a method for producing amine derivatives represented by general formula (1) or salts thereof
[in the formula (1), R
1
, R
2
, R
3
, and R
4
represent the same meanings as those in formulae (4) and (5)] comprising condensing a compound represented by general formula (4)
[in the formula (4), R
3
represents an oxygen atom or a group represented by the formula (f) below;
R
6
and R
7
independently represent a hydrogen atom, a linear C
1-4
alkyl group, a branched C
1-4
alkyl group or a cyclic C
1-4
alkyl group, R
4
is a group represented by the formula (g), (h), or (i),
in the formula (i), R
8
is a substituent group which substitutes a hydrogen atom in the phenyl group in the formula and represents a linear C
1-7
alkyl group, a branched C
1-7
alkyl group, a cyclic C
1-7
alkyl group, a halogen atom, a linear C
1-4
alkoxy group, a branched C
1-4
alkoxy group, a cyclic C
1-4
alkoxy group, a nitro group, an amino group which may be substituted, a cyano group, a carboxyl group, a linear C
2-5
alkoxycarbonyl group, a branched C
2-5
alkoxycarbonyl group, a cyclic C
2-5
alkoxycarbonyl group, a hydroxyl group, or a group represented by R
9
3
SiO—, R
9
represents a linear C
1
Itoh Takao
Kawazu Yukio
Majima Toshiro
Nakashima Takuji
Nozawa Akira
Chang Ceila
Knobbe Martens Olson & Bear LLP
Pola Chemical Industries Inc.
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