Zyma Sa

Ciba-geigy Corporation

Pierre Courbat

Alban I Albert

Andre J Weith

Robert G Tyson

Christian G Rimbault

Marc E Ballenegger

Derek R Palmer

David G Thompson

Pharmaceutical preparations containing (+)-cyanidan-3-ol derivatives of the formula I ##STR1## wherein R' and R' are hydrogen, an unsubstituted or substituted hydrocarbon radical, or heterocyclic radical, halogen, formyl, free or functionally modified carboxyl, free or etherified or esterified hydroxyl, free, etherified or oxidized mercapto, unsubstituted or substituted sulfamoyl, acyl or unsubstituted or substituted amino, where however R' and R' cannot both be hydrogen simultaneously, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen or an unsubstituted or substituted hydrocarbon radical, and R.sub.2 and R.sub.3 together can also be an unsubstituted or substituted methylene group, and R.sub.1 also an acyl group or an amidated carboxyl group; and therapeutically applicable salts of these compounds, as well as new compounds of these preparations. These pharmaceutical preparations are particularly valuable for treating liver and venous diseases.

Pharmaceutical preparations containing (+)-cyanidan-3-ol derivatives,

The present invention relates to the use of O-substituted derivatives of (+)-cyanidan-3-ol corresponding to the formula ##STR1## and their addition salts, in which R represents an optionally substituted hydrocarbon radical, an acyl radical of an organic carboxylic acid containing at least 2 carbon atoms, of a carbonic acid, or of an organic sulphonic acid, of a radical of an inorganic acid containing at least one oxygen atom, as compounds having immunomodulating properties, and pharmaceutical compositions for this purpose.

Use of O-substituted derivatives of (+)-cyanidan-3-ol as compounds

The subject of the present invention is new O-substituted derivatives of (+)-cyanidan-3-ol corresponding to the general formula I ##STR1## in which R represents an optionally substituted hydrocarbon radical; an acyl radical of an organic carboxylic acid containing at least 2 carbon atoms, of a carbonic acid or of an organic sulphonic acid; or a radical of an inorganic acid containing at least one oxygen atom, with the exception of a glucosidic radical, and the salts thereof, a process for the preparation thereof as well as their application in therapeutics and medicaments containing these new products. These compounds have a valuable activity in the prevention of hepatic necrosis and also inhibit lipoperoxidation. In addition, they are capable of acting on the fibrillation of collagen.

3-O-acylated derivatives of (+)-cyanidan-3-ol

Process for the preparation of O-substituted derivatives of

A process is provided for preparing mono-O-.beta.-hydroxyethyl-7-rutoside of the formula: ##STR1## which comprises contacting rutoside of the formula: ##STR2## in a solvent which is an at least partially aqueous medium with a boric acid alkali salt in an amount substantially not exceeding the amount necessary to form a boron complex of formula: reacting said boron complex with ethylene oxide to form a hydroxyethoxy compound of the formula ##STR3## and treating said hydroxyethoxy compound in an at least partially aqueous acid medium, whereby there is produced said mono-O-.beta.-hydroxyethyl-7-rutoside.

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Nyon, Switzerland

Pierre Courbat