Materials

Details Materials Materials

1995-06-07

1998-02-10

Schofer, Joseph L.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

526287, 526310, 5263031, 526328, 526346, 526332, C08F13002, C08F12802, C08F12056, C08F12018, C08F11612, C08F11208

Patent

active

057170479

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new materials which comprise a surface having pendent zwitterionic groups processes for producing the materials, the use of compounds to provide such a material and to improve biocompatibility and to a device having such a surface. It also relates to new compounds useful in providing such materials.
Our earlier patent applications WO-A-92/06719, EP-A-32622 and WO-A-92/21386 disclose that natural and synthetic phospholipids coated on a surface show improved biocompatibility and in particular haemocompatibility compared to an untreated surface. Thus, materials coated with such phospholipids are proposed as suitable for use in applications where they come into contact with body fluids, such as blood, or protein-containing fluids generally, so as to reduce protein adsorption and/or reduce activation of blood platelets. These materials may therefore be used to treat devices to be implanted into the body or apparatus or which comes into contact with such fluids extra-corporeally such as separation apparatus and in particular separation membranes. Such compounds may also be used to form liposomes as described in EP-A-32622 and EP-A-161759, which may for example be used to administer substances encapsulated within them.
The compounds disclosed in the above applications are phospholipids which comprise a glycerol-type structure as shown below: ##STR1## in which the two groups A are long-chain acyl groups and PC is a phosphoryl choline group or analogue thereof.
The compounds however possess a chiral carbon atom which can render them difficult to purify. In addition, the etheric oxygen linkages to the groups A are derived from primary and secondary alcohol groups. The difference in the reactivity of these two hydroxyl groups can lead to problems in the efficient preparation of the compounds.
Other glycerophosphatidyl choline (GPC) derivatives have also been used in a number of techniques for producing biocompatible articles, for instance, WO-A-86/02933 and WO-A-88/00956 disclose polyurethanes and polyesters respectively obtainable by copolymerisation using a GPC derivative as one of the comonomers. Other such polymerisable derivatives have been disclosed in WO-A-92/07885, which discloses crosslinked copolymers of such derivatives suitable for use in making contact lenses, WO-A-93/01221 which discloses copolymers of such derivatives, suitable for use as surface treatments, and our unpublished application PCT/GB92/01580 which discloses graft polymers of such derivatives suitable for use as surface treatments. In addition, WO-A-91/13639 discloses the treatment of a surface with an activated derivative of GPC, so as to bind covalently to the surface. Finally, WO-A-87/0284 discloses the use of GPC derivatives an additive for thermopolymers which render the polymers biocompatible.
We have also found that compounds containing phosphoryl choline groups can also reduce the adhesion or growth of microorganisms such as bacteria, yeast, algae and fungi, and in particular bacteria at a surface. This renders the use of compounds containing such groups advantageous in a variety of situations where the growth of such microorganisms is undesirable.
In U.S. Pat. No. 4,610,979 synthetic phospholipid analogs are described for use as pharmaceutically active ingredients for the treatment of asthma. Compositions containing the compounds are administered by enteral, oral, rectal and parenteral routes/though no specific details of any pharmaceutical compositions are given.
In "Platelet Activating Factor--INSERM Symposium No.23" eds Benveniste J and Arnoux B,(1983) pp49-56, Lee et al describe the preparation of an analog of platelet activating factor 1-O-octadecyl-2-deoxy-2-(2'-oxopropyl)rac-glycero-3-phosphorylcholine. An aqueous solution of the analog was administered intravenously to determine the bronchoconstriction properties of the compound.
The present invention relates to materials which comprise a surface having pendant groups of the formula (I) ##STR2## in which the groups --B-- are the same or diff

REFERENCES:
patent: 4610979 (1986-09-01), Lautenschlager et al.
patent: 5066745 (1991-11-01), Engelhardt et al.
Chemistry and Physics of Lipis 16 (1976) 107-114, A P J Mank et al.
Platelet Activating Factor--INSERM Symposium No. 23 eds Benvenieste J and Arnoux B, (1983) pp. 49-56, et al.

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