Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
1999-01-14
2001-06-05
Wilson, James O. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S027000, C514S311000, C514S312000, C536S004100, C536S008000, C424S078050
Reexamination Certificate
active
06242425
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to glycosides of quinolinone derivatives or physiologically acceptable salts of such glycosides; processes for producing them; and medicines, and in particular anti-allergic agents, comprising one of them as an active ingredient.
More specifically, the present invention relates to: glycosides represented by general formula (I), in which the glycosidic linkage is formed at a hydroxyl group of 7-(3,5-dimethoxy-4-hydroxycinnamoyl)amino-4-hydroxy-1-methyl-3-octyloxy-2(1H)-quinolinone, represented by general formula (VI), which is the aglycone moiety of the glycosides represented by general formula (I), and physiologically acceptable salts of such glycosides; glycosides represented by general formula (II) or (III), in which the glycosidic linkage is formed at a hydroxyl group portion of a quinolinone derivative, and physiologically acceptable salts of such glycosides; and processes for producing glycosides represented by general formulae (I), (II), (III) and (V). Glycosides represented by general formula (I) are useful as medicines, and particularly as agents for treating or alleviating allergic diseases.
This application is based on Patent Application No. Hei 10-007462 filed in Japan, the content of which is incorporated herein by reference.
2. Background Art
Japanese Patent Application, First Publication (Kokai), No. Hei 9-255659, which was filed by the present inventors, discloses that quinolinone derivative (VI), which is an aglycone moiety of a glycoside expressed by general formula (I) to which the present invention relates, or its physiologically acceptable salt is useful as an agent for treating or alleviating allergic diseases. However, no process for producing a quinolinone glycoside, in which the glycosidic linkage is formed at a hydroxyl group in the quinolinone derivative, and no use of such a quinolinone glycoside have been known. Moreover, the quinolinone glycoside expressed by general formula (II) or (III), which is an important intermediate produced when synthesizing a quinolinone glycoside to which the present invention relates and which is expressed by general formula (I), has also been hitherto unknown.
SUMMARY OF THE INVENTION
An object of the present invention is to provide: novel quinolinone glycosides which are useful as medicines; processes for producing the quinolinone glycosides; intermediates for synthesis; and medicines, and particularly anti-allergic agents, which comprise the quinolinone glycoside as an active ingredient.
The present inventors carried out diligent research in order to achieve the above object, and as a result, by synthesizing various glycosides in which the glycosidic linkage is formed at a hydroxyl group of a quinolinone derivative according to Japanese Patent Application, First Publication (Kokai), No. Hei 9-255659, and by examining the pharmacological action of each of them, the present inventors found such glycosides useful as medicines, and particularly as anti-allergic agents, and achieved the present invention.
That is, the present invention includes:
(1) a quinolinone glycoside or a physiologically acceptable salt thereof, expressed by general formula (I):
(wherein, each of R
1
and R
2
is a hydrogen atom or a glycosyl group selected from the group consisting of a glucuronyl group, a glucosyl group, a galactosyl group and a mannosyl group, and at least one of R
1
and R
2
is a glycosyl group in which a hydroxyl group is unprotected or protected with an acyl group having a carbon number of 2 to 7 or a benzyl group);
(2) a quinolinone glycoside or a physiologically acceptable salt thereof according to (1), wherein each of R
1
and R
2
is a hydrogen atom or a glycosyl group selected from the group consisting of a glucuronyl group, a glucosyl group, a galactosyl group and a mannosyl group, and at least one of R
1
and R
2
is a glycosyl group in which no hydroxyl group is protected;
(3) a quinolinone glycoside or a physiologically acceptable salt thereof according to (1), wherein each of R
1
and R
2
is a hydrogen atom or a glycosyl group selected from the group consisting of a glucuronyl group, a glucosyl group, a galactosyl group and a mannosyl group, and at least one of R
1
and R
2
is a glycosyl group in which a hydroxyl group is protected with an acyl group having a carbon number of 2 to 7 or a benzyl group;
(4) a quinolinone glycoside or a physiologically acceptable salt thereof according to (2), wherein each of R
1
and R
2
is a hydrogen atom or a glucuronyl group in which no hydroxyl group is protected;
(5) a quinolinone glycoside or a physiologically acceptable salt thereof according to (2), wherein each of R
1
and R
2
is a hydrogen atom or a glucosyl group in which no hydroxyl group is protected;
(6) a quinolinone glycoside or a physiologically acceptable salt thereof according to (2), wherein each of R
1
and R
2
is a hydrogen atom or a galactosyl group in which no hydroxyl group is protected;
(7) a quinolinone glycoside or a physiologically acceptable salt thereof according to (2), wherein each of R
1
and R
2
is a hydrogen atom or a mannosyl group in which no hydroxyl group is protected;
(8) a quinolinone glycoside or a physiologically acceptable salt thereof according to (4), wherein each of R
1
and R
2
is a glucuronyl group in which no hydroxyl group is protected;
(9) a quinolinone glycoside or a physiologically acceptable salt thereof according to (4), wherein R
1
is a hydrogen atom, and R
2
is a glucuronyl group in which no hydroxyl group is protected;
(10) a quinolinone glycoside or a physiologically acceptable salt thereof according to (4), wherein R
1
is a glucuronyl group in which no hydroxyl group is protected, and R
2
is a hydrogen atom;
(11) a medicine comprising, as an active ingredient, a quinolinone glycoside or a physiologically acceptable salt thereof as in any one of (2) and (4) to (10);
(12) an anti-allergic agent comprising, as an active ingredient, a quinolinone glycoside or a physiologically acceptable salt thereof as in any one of (2) and (4) to (10);
(13) a quinolinone glycoside or a physiologically acceptable salt thereof, expressed by general formula (II):
(wherein R
1
is a glycosyl group selected from the group consisting of a glucuronyl group, a glucosyl group, a galactosyl group and a mannosyl group, in which a hydroxyl group is unprotected or protected with an acyl group having a carbon number of 2 to 7 or a benzyl group);
(14) a quinolinone glycoside or a physiologically acceptable salt thereof, expressed by general formula (III):
(wherein R
1
is a glycosyl group selected from the group consisting of a glucuronyl group, a glucosyl group, a galactosyl group and a mannosyl group, in which a hydroxyl group is unprotected or protected with an acyl group having a carbon number of 2 to 7 or a benzyl group);
(15) a quinolinone glycoside or a physiologically acceptable salt thereof according to (13), wherein R
1
is a glucuronyl group in which a hydroxyl group is protected or unprotected;
(16) a quinolinone glycoside or a physiologically acceptable salt thereof according to (14), wherein R
1
is a glucuronyl group in which a hydroxyl group is protected or unprotected;
(17) a process for producing a quinolinone glycoside expressed by general formula (II):
(wherein R
1
is a glycosyl group selected from the group consisting of a glucuronyl group, a glucosyl group, a galactosyl group and a mannosyl group, in which a hydroxyl group is unprotected or protected with an acyl group having a carbon number of 2 to 7 or a benzyl group),
comprising the steps of:
reacting a quinolinone derivative expressed by general formula (IV):
with a basic substance; and
then conducting a glycosylation reaction with a glycosyl halide, which is obtained by substituting a hydrogen atom at 1-position of a hexose, selected from the group consisting of, glucuronic acid, glucose, galactose and mannose, by a halogen atom, and in which a hydroxyl group is protected with an acyl group having a carbon
Aoki Yasuo
Kimura Nobuyuki
Nakanishi Shigenori
Takagaki Hidetsugu
Yamaguchi Shinobu
Armstrong Westerman Hattori McLeland & Naughton LLP
Dainippon Ink and Chemicals Inc.
Owens Howard
Wilson James O.
LandOfFree
Quinolinone glycoside, production process, and anti-allergic... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Quinolinone glycoside, production process, and anti-allergic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Quinolinone glycoside, production process, and anti-allergic... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2477729