Choay, S.a.

Sanofi

Sanofi Sa

D.r.o.p.i.c.

Jean-Claude Lormeau

Jean Choay

Maurice Petitou

Pierre G Sinay

Jean Goulay

Jean-Claude Jacquinet

Edmond G Vairel

Francis Toulemonde

Mahmoud Nassr

The oligosaccharides of the invention are composed essentially of chains:

Process for recovering heparinic oligosaccharides with an affinity for

Method for obtaining biologically active mucopolysaccharides by controlled depolymerization of heparin, wherein the quantity of products generating nitrous acid is selected so that those products are totally consumed when the desired depolymerization degree is reached.

Method for obtaining biologically active mucopolysaccharides of high

The compositions of the invention are composed of fragments of heparin consisting essentially of repeated disaccharide sequences corresponding to the regular regions of heparin and possessing a MW between 4,800 and 9,000. These compositions can be used for the regulation of physiological systems.

Low molecular weight heparins of regular structure, their preparation

Short chained ligosaccharides of high structural homogeneity constituted essentially by hexasaccharides of the formula: ##STR1## in which R represents a hydrogen atom or the --SO.sub.3.sup.31 group. These hexasaccharides have a highly selective activity on certain steps in blood coagulation and are useful as anti-thrombotic medicaments.

Short chained oligosaccharides having biological properties, a process

The invention relates to a process for the organic synthesis of oligosaccharides constituting or comprising fragments of acid mucopolysaccharides comprising the reaction of two compounds constituted or terminated by units of glucosamine structure and of uronic acid structure respectively, said units being specifically substituted. This process particularly enables valuable anticoagulant drugs to be obtained.

Process for the organic synthesis of oligosaccharides and derivatives

Mucopolysaccharides biologically active and more specific than heparin, particularly with respect to the blood factor Xa. These mucopolysaccharides may be obtained by partial depolymerization, under controlled conditions, of heparin, by the action of a chemical agent such as nitrous acid. The conditions implemented allow the preparation of mucopolysaccharides having a USP titer lower than that of the starting heparin and a Yin-Wessler titer at least equal to that of said heparin. These products may be used particularly as antithrombotic drugs.

Mucopolysaccharides having biological properties, preparation and

The oligosaccharides of the invention contain or are constituted by a tetrasaccharide enchainment of the formula: ##STR1## in which R.sub.1 represents an organic anion, R.sub.2 is identical to R.sub.1 or represents a hydrogen atom, N.sub.1 and N.sub.2 represent a functional amino group.

Oligosaccharides and their biological applications

The oligosaccharidic fractions of the invention are soluble in an hydro-alcoholic mixture 50/50 (v/v) in which is added 0.5% NaCl, at pH 3.8, are constituted by chains the majority of which have 2 to 14 sugar units, are terminated by end units with a 2,5-anhydromanno structure and are devoid or practically devoid of anti-thrombotic activity.

Oligosaccharidic fractions devoid or practically devoid of

The medicaments of the invention contain in their active principle, oligosaccharides of low molecular weight corresponding to or including heparin fragments.

Medicaments favoring the properties of blood flow and their use in

1,4.alpha.disaccharides of formula: ##STR1## with Z representing a nitrogenous functional group,

Disaccharides formed by patterns having a glucosamine and uronic acid

The invention pertains to a mucopolysaccharide fraction obtainable from heparin or from fractions including heparinic constituents of molecular weights from 2000 to 50,000, which has a Yin-Wessler titer which is high relative to the USP titer. It contains components whose molecular weights are less than 10,000, particularly oligosaccharides in the area of 2000-3000, comprising from 8 to 12, notably 10 monosaccharide units, among which glucosamine units whose primary positions are sulphated. The last mentioned oligosaccharides include one N-acetyl-glucosamine unit per two units of 2-O-sulphate iduronic acid and per two N-sulphate-glucosamine units, the other saccharide units being of a different nature and including distinct substituents.

Mucopolysaccharide composition having a regulatory action on

The invention relates to a process for preparing mucopolysaccharides having high anti-thrombotic activity compared to heparin. The mucopolysaccharides are obtained from a mucopolysaccharide composition having high anti-thrombotic activity and a ratio of YW/USP Titer higher than that of heparin by fractionation to remove, selectively, the mucopolysaccharide chains having less than six saccharide units.

Process for preparing mucopolysaccharide compositions having high

1,4 .alpha. disaccharides of formula: ##STR1## with Z representing a nitrogenous functional group,

Disaccharides having a glucosamine and uronic acid structure, and

Mucopolysaccharides biologically active and more specific than heparin, particularly with respect to the blood factor Xa. These mucopolysaccharides may be obtained by partial depolymerisation, under controlled conditions, of heparin, by the action of a chemical agent such as nitrous acid. The conditions implemented allow the preparation of mucopolysaccharides having a USP titer lower than that of the starting heparin and a Yin-Wessler titer at least equal to that of said heparin. These products may be used particularly as antithrombotic drugs.

Mucopolysaccharides having biological properties, preparation and method

Oligosaccharides obtainable from heparin including heparinic constituents of molecular weights ranging from 2000 to 50,000. Said fractions have a Yin-Wessler titer and a U.S.P. titer in a ratio of at least 30. They consist of chains constituted by no more than 8 saccharidic moities. They possess a strong antithrombotic activity and are then useful as antithrombotic drugs.

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Maromme, France

Jean-Claude Lormeau