Glycoside derivatives, polymers containing glycoside derivatives

Details Glycoside derivatives, polymers containing glycoside derivatives Glycoside derivatives, polymers containing glycoside derivatives

1990-06-26

1992-11-17

Schofer, Joseph L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

52623823, C07H 1504, C08F12400

Patent

active

051644924

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to glycoside derivatives, polymers containing the glycoside derivatives, a process for their preparation and the use of said polymers.


PRIOR ART

Polymers having saccharide residues at side chains are increasingly used for various applications utilizing their hydrophilic property and compatibility with organisms, for example, as medical materials including those compatible with blood, surface-treating agents, etc.
The heretofore proposed polymers having saccharide residues at side chains are generally classified into the following two types.
(i) Polymers having saccharide residues obtained by the reaction of known polymers with sugar derivatives
For example, Japanese Unexamined Patent Publications No.106802/1985 and No.192704/1985 disclose the preparation of such polymers by reacting a hydroxymethylated polystyrene with a sugar having hydroxyl groups protected with protective groups such as acetyl groups, halogen atoms or the like, followed by saponification of protective groups of the sugar with an alkali. These polymers, however, have a poor hydrophilic property and a low compatibility with organisms because the protective groups on saccharide residues are not completely removed and the saccharide residues are not uniformly added to the polymers. Further this process can not regulate as desired the amount of the sugar to be added and entails difficulties in removing the reagent used and purifying the polymer thus formed.
(ii) Polymers formed by reacting a vinyl monomer with a saccharide having hydroxyl groups protected with protective groups such as acetyl groups, isopropylidene groups or the like and removing the protective groups after polymerization
For example, U.S. Pat. No.3,225,012 discloses a polymer represented by the formula ##STR2## the polymer being one prepared by polymerizing 1,2: 5,6 -di-O-isopropylidene-3-O-methacryloyl-D-glucose and removing the isopropylidene groups from the glucose by acid hydrolysis.
U.S. Pat. No.3,356,652 describes a polymer having structural units represented by the formula ##STR3##
As further example, Japanese Examined Patent Publication No.42641/1982 discloses a homopolymer represented by the formula ##STR4## wherein R is a hydrogen atom or a methyl group, R' is a sugar residue attached with the acyl linkage at the 1-position and n is 10 to 1000, the homopolymer being one formed from a monomer which is a sugar derivative having a monosaccharide or disaccharide and an acrylate or methacrylate directly attached to each other with the glycoside linkage.
These publications set forth techniques intended to remove the protective groups with an alkali or acid from the hydroxyl groups of the sugar in the obtained polymer. However, the currently available art can not completely remove the protective groups in polymers. Actually U.S. Pat. No.3,356,652 teaches that it is impossible to completely remove the acetyl groups in a copolymer containing a hydrophobic monomer. Thus the obtained polymer contains a substantial number of protected hydroxyl groups and is unsatisfactory in hydrophilic property and compatibility with organisms. The treatment of polymers with an alkali or acid impairs the properties of the resulting polymer. Moreover such methods necessitate the neutralization of alkali or acid after removal of protective groups from hydroxyl groups and the washing by water of the salt resulting from neutralization for elimination. The removal of protective groups renders the polymer hydrophilic to give an aqueous viscous solution or water-swollen gel, resulting in incomplete neutralization and desalting. Consequently the polymers formed by the methods are not suitable for use as medical materials.
As described above, polymers with saccharide residues at side chains having no protective group have not been heretofore obtained.


BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the IR spectrum of glucosyloxyethyl methacrylate.
FIG. 2 shows the .sup.1 H-NMR spectrum of glucosyloxyethyl methacrylate.
FIG. 3 shows the IR spe

REFERENCES:
patent: 3356652 (1967-12-01), Ray-Chaudhuri
Carl R. Noller, Chemistry of Organic Compounds, 1965 [W. B. Saunders], p. 159.

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