Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-08-24
2003-08-26
Aulakh, Charanjit S. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S221000, C546S216000
Reexamination Certificate
active
06610708
ABSTRACT:
TECHNICAL FIELD
The present invention relates to cyclic amino compounds or pharmacologically acceptable salts thereof each having excellent platelet aggregation inhibitory action and inhibitory action against the advance of arteriosclerosis, to compositions for the prevention or treatment of embolism, thrombosis or arteriosclerosis each of which comprises any one of said compounds, to use of said compounds for the preparation of a medicament for the prevention or treatment of embolism, thrombosis or arteriosclerosis, to a method for the prevention or treatment of embolism, thrombosis or arteriosclerosis, which comprises administering a pharmacologically effective amount of any one of said compounds to warm-blooded animals, and to a process for the preparation of said compounds.
BACKGROUND ART
As cyclic amino compounds having platelet aggregation inhibitory action, known are, for example, hydropyridine derivatives [ex. U.S. Pat. No. 4,051,141, Japanese Patent Application Kokai No. Sho 59-27895 (EP 99802), Japanese Patent Application Kokai No. Hei 6-41139 (EP 542411), WO 98/08811, etc.].
DISCLOSURE OF INVENTION
As a result of investigation on the pharmacological action of cyclic amino compounds for many years, the present inventors have found that specific cyclic amino compounds have excellent platelet aggregation inhibitory action and inhibitory action against the advance of arteriosclerosis (particularly, the platelet aggregation inhibitory action) and is useful as a preventive agent or remedy (particularly, as a remedy) for embolism, thrombosis and arteriosclerosis (particularly, embolism or thrombosis), leading to the completion of the present invention.
The present invention provides cyclic amino compounds or pharmacologically acceptable salts thereof having excellent platelet aggregation inhibitory action and inhibitory action against the advance of arteriosclerosis, compositions for the prevention or treatment of embolism, thrombosis or arteriosclerosis each of which comprises any one of said compounds, use of said compounds for the preparation of a medicament for the prevention or treatment of embolism, thrombosis or arteriosclerosis, a method for the prevention or treatment of embolism, thrombosis or arteriosclerosis, which comprises administering a pharmacologically effective amount of any one of said compounds to warm-blooded animals, and a process for the preparation of said compounds.
The cyclic amino compounds according to the present invention have the following formula:
In the above-described formula,
R
1
represents a substituted or unsubstituted phenyl group (the substituted of said group being a halogen atom, a C
1
-C
4
alkyl group, a fluoro-substituted-(C
1
-C
4
alkyl) group, a C
1
-C
4
alkoxy group, a fluoro-substituted-(C
1
-C
4
alkoxy) group, a cyano group or a nitro group);
R
2
represents a substituted or unsubstituted C
1
-C
8
aliphatic acyl group (the substituent of said group being a halogen atom, a C
1
-C
4
alkoxy group or a cyano group), a substituted or unsubstituted benzoyl group (the substituent of said group being a halogen atom, a C
1
-C
4
alkyl group or a C
1
-C
4
alkoxy group), or a (C
1
-C
4
alkoxy)carbonyl group; and
R
3
represents a substituted, 3- to 7-membered, saturated cyclic amino group which may optionally have a fused ring {said cyclic amino group is substituted with a group having the formula of —S—X—R
4
[wherein, R
4
represents a substituted or unsubstituted phenyl group (the substituent of said group being a halogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a nitro group or a cyano group), a substituted or unsubstituted C
1
-C
6
alkyl group [the substituent of said group being an amino group, a hydroxyl group, a carboxyl group, a (C
1
-C
4
alkoxy)carbonyl group, a group having the formula of —NH—A
1
(wherein, A
1
represents an &agr;-amino acid residue) or group having the formula of —CO—A
2
(wherein, A
2
represents an &agr;-amino acid residue)], or a C
3
-C
8
cycloalkyl group, and X represents a sulfur atom, a sulfinyl group or a sulfonyl group], and said cyclic amino group may optionally be further substituted with a group having the formula of ═CR
5
R
6
[wherein, R
5
and R
6
are the same or different and each independently represents a hydrogen atom, a C
1
-C
4
alkyl group, a carboxyl group, a (C
1
-C
4
alkoxy)carbonyl group, a carbamoyl group, a (C
1
-C
4
alkyl)carbamoyl group or a di-(C
1
-C
4
alkyl)carbamoyl group]}.
In the above-described definition of R
1
, examples of the “halogen atom” serving as a substituent for the substituted phenyl group include fluorine, chlorine, bromine and iodine atoms, of which the fluorine, chlorine and bromine atoms are preferred, and the fluorine and chlorine atoms are particularly preferred.
In the definition of R
1
, examples of the “C
1
-C
4
alkyl group” serving as a substituent for the substituted phenyl group include straight or branched C
1
-C
4
alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl and t-butyl groups, of which the methyl and ethyl groups are preferred, and the methyl group is most preferred.
In the definition of R
1
, examples of the “fluoro-substituted-(C
1
-C
4
alkyl) group” serving as a substituent for the substituted phenyl group include straight or branched fluoro-substituted-(C
1
-C
4
alkyl) groups such as fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2-fluorobutyl, 3-fluorobutyl and 4-fluorobutyl groups, of which the difluoromethyl and trifluoromethyl groups are preferred, and the trifluoromethyl group is most preferred.
In the definition of R
1
, examples of the “C
1
-C
4
alkoxy group” serving as a substituent for the substituted phenyl group include straight or branched C
1
-C
4
alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy groups, of which the methoxy and ethoxy groups are preferred, and the methoxy group is most preferred.
In the definition of R
1
, examples of the “fluoro-substituted-C
1
-C
4
alkoxy) group” serving as a substituent for the substituted phenyl group include straight or branched fluoro-substituted-(C
1
-C
4
alkoxy) groups such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-fluoroisopropoxy and 4-fluorobutoxy groups, of which the difluoromethoxy and trifluoromethoxy groups are preferred, and the trifluoromethoxy group is most preferred.
In the definition of R
1
, preferred examples of the substituent for the substituted phenyl group include the halogen atoms, methyl group, ethyl group, difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, difluoromethoxy group, trifluoromethoxy group, cyano group and nitro group, or which the fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, difluoromethoxy group, trifluoromethoxy group, cyano group and nitro group are more preferred, and the fluorine and chlorine atoms are particularly preferred. The number of substituents preferably ranges from 1 to 3, of which 1 or 2 are more preferred, and 1 is most preferred. The position of the substituent is preferably the 2- or 4-position, of which the 2-position is most preferred.
In the definition of R
2
, examples of the “aliphatic acyl” part of the substituted or unsubstituted C
1
-C
8
aliphatic acyl group include straight or branched C
1
-C
8
alkanoyl groups such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, heptanoyl and octanoyl groups, and (C
3
-C
7
cycloalkyl)carbonyl groups such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl and cycloheptylcarbonyl groups, of which C
2
-C
4
alkanoyl groups and (C
3
-C
6
cycloalkyl)carbonyl groups are preferred; the acetyl, propionyl, isobutyryl, cyclopropylcarbonyl and cyclobutylcarbonyl groups are more preferred; the propionyl and cyclopropylcarbonyl groups are still more preferred; and the cyclopropylcarbonyl group
Asai Fumitoshi
Ikeda Toshihiko
Inoue Teruhiko
Iwabuchi Haruo
Iwamura Ryo
Aulakh Charanjit S.
Frishauf Holtz Goodman & Chick P.C.
Sankyo Company Limited
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