Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-10-11
1994-02-01
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 41, C07H 1504
Patent
active
052833283
DESCRIPTION:
BRIEF SUMMARY
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a national phase of PCT/HU90/00082 filed Dec. 18, 1990 and based upon Hungarian National Application 6646/89 filed Dec. 18, 1989.
FIELD OF THE INVENTION
The present invention relates to novel 1-triacontanyl glycosides of formula I removing the hydrogen atom from the hydroxyl group being in the 1(alpha) or 1(beta) position, or the O-protected, preferably acetylated derivative thereof, carbon atom being in position 1 of the reaction product of glucose and mono-, di- or triethylene glycol or the O-protected, preferably O-acetylated derivative thereof.
The compounds of formula I of the invention are biologically active compounds and they are especially useful for the prevention and treatment of different diseases connected to aging.
BACKGROUND OF THE INVENTION
1-Triacontanol, the primary alcohol having 30 carbon atoms, was separated and identified by Chibnall in 1933.
According to U.S. Pat. No. 4,150,970, 1-triacontanol is a growth regulator for plants. This activity is also supported by Science, Vol. 195, pages 1339 to 1341.
According to published European patent application No. 78,533 a topical pharmaceutical composition comprising 1-triacontanol as active ingredient is useful for treating skin disorders.
No reference has been made so far to the different sugar derivatives of 1-triacontanol.
The use of 1-triacontanol and the examination of the mechanism of its activity is very difficult as this compound is highly lipophylic and hardly dissolves in water.
OBJECT OF THE INVENTION
It is an object of the invention to provide improved 1-triacontonyl compounds free from drawbacks of earlier 1-triacontonyl compounds.
DESCRIPTION OF THE INVENTION
We have found that the 1-tricontanol glycosides, according to the present invention dissolve well in water and have a less apolar character. The compounds have the formula I as defined above.
DETAILED DESCRIPTION OF THE INVENTION
In the description under the term "monosaccharide" the aldopentoses and aldohexoses are understood. When, in the formula I, m is 1, then the group derived from a monosaccharide by removing the hydrogen atom from the hydroxyl group being in the 1(alpha) or 1(beta) position may be a ribosyl, arabinosyl, xylosyl, lixosyl, allosyl, altrosyl, glucosyl, mannosyl, gulosyl, idosyl, galactosyl, talosyl group from which the glucosyl group is preferred.
The protected derivatives thereof may be such groups wherein one or more, preferably all of the free hydroxy groups are substituted by a conventional protecting group. The most preferred protecting group is the acetyl group. The most preferred protected monosaccharide residue represented by R when m=1 is glucosyl tetraacetate.
Under the term "oligosaccharides" the bioses, such as lactose, genciobiose, laminaribiose, maltose, cellobiose and the maltoligomers, such as maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, maltooctaose are understood. When m is 1, then the group derived from an oligosaccharide by removing the hydrogen atom from the hydroxyl group being in the 1(alpha) or 1(beta) position is preferably lactosyl, cellobiosyl, maltosyl, maltotriosyl, maltotetraosyl, matopentaosyl, maltohexaosyl, maltoheptaosyl or maltooctaosyl group.
The protected derivatives thereof may be such groups wherein one or more, and preferably all of the free hydroxy groups are substituted by a conventional protecting group. The most preferred protecting group is the acetyl group. The most preferred acetylated oligosaccharide residues represented by R when m=1 are cellobiosyl heptaacetate, lactosyl heptaacetate, maaltosyl heptaacetate, maltotriosyl decaacetate, maltotetraosyl tridecaacetate, maltohexaosyl nonadecaacetate, and maltoheptaosyl docosaacetate.
Thus a preferred group of compounds of formula I is that wherein the acetylated derivative thereof. A more preferred group of compounds of formula I is wherein group or the acetylated derivative thereof. The most preferred group of formula I is wherein maltotetraosyl, maltopentao
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Csernus Istvan
Emri-Harsi Zsuzsa
Gombos-Nemeti Ildiko
Kovacs Antal
Kovacs-Hadadi Katalin
Biogal Gyogyszergyar Rt.
Brown Johnnie R.
Dubno Herbert
Myers Jonathan
White Everett
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