Coating processes – With pretreatment of the base – Organic base
Patent
1993-04-30
1997-02-04
Caldarola, Glenn A.
Coating processes
With pretreatment of the base
Organic base
427301, 568 14, 564496, 564503, C07F 909
Patent
active
055995870
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a new process for the preparation of compounds useful in the production of biocompatible surfaces, certain new compounds produced by the process, and a process for treating a surface with such compounds.
The clinical use of blood contacting devices and prostheses is of major importance today in cardiovascular surgery and other fields of medicine. Heart valves and blood vessel prostheses, balloon pumps and catheters are being implanted in daily surgical practice in restoration and diagnosis of cardiovascular function. Artificial organs are routinely employed in blood detoxification by absorptive haemoperfusion and in oxygenation (membrane oxygenators and heart-lung devices). Considerable effort and capital is invested in Europe and the U.S.A. in the development and experimental evolution of an implantable artificial heart system.
The devices are generally constructed from polymeric materials and, when in use, blood-polymer contact occurs. This contact will cause a reaction in the recirculating blood, which, depending on the choice of material, the design parameters, the flow or the addition of the anticoagulants, may lead to protein deposition, adhesion and destruction of red blood cells (haemolysis), platelet (thrombocyte) adhesion and aggregation and blood coagulation leading to formation of a haemostatic plug (thrombus). The occurrence of thromboembolism in cardiovascular surgery continues to be a problem, notwithstanding routine treatment with anticoagulants. For these reasons the search for biocompatible non-thrombogenic materials has been an important research objective over the last two decades.
Synthetic polymers are also widely employed in sight correction devices, such as soft, rigid, gas permeable and hard contact lenses and intra-ocular lenses. However, it is now well recognised that the performance of commonly employed polymer compositions can be hindered by the adsorption of tear proteins (such as lysozyme) at polymer interfaces. A variety of problems can then result such as reduction in gas permeability of the lens, discomfort to the patient and loss of visual acuity. Complete rejection of the lens is not uncommon.
Protein absorption can also cause serious problems in separation apparatus and other devices which come into contact extra-corporeally or intra-corporeally with protein solutions including body fluids. For example, polymeric particles and separation membranes can become fouled or blocked by such adsorption despite selection of the materials and careful design of the apparatus.
Biocompatible materials are also therefore of particular use in the treatment of polymeric materials for use as contact lenses. Such treatments help to improve the comfort of the wearer and in particular help to prevent the build up of protein deposits.
Our earlier patent application, EP-A-157,469 discloses compounds which aim to mimic the interfacial characteristics of the outer cell surface of red blood cells and platelets, and in particular the lipid component of the biological membrane which is the simplest common factor of all these surfaces. That application discloses compounds which are derivatives or analogues of phosphatidylcholine or phosphatidyl ethanolamine that can be covalently linked to the surface which is to be rendered biocompatible so as to deposit a phosphatidylcholine or phosphatidyl ethanolamine type of residue on a surface. Such residues are commonly found in lipid membranes.
We have now devised a new and more convenient process, which may be used to obtain some of the compounds of EP-A-157,469 in surprisingly pure form. These compounds moreover, show surprisingly increased biocompatibility over that disclosed in EP-A-157,469. Moreover the process also allows the preparation of new compounds.
Accordingly the present invention provides a process for the preparation of a compound of formula (I) ##STR1## in which Z is hydrogen or --NHZ is an activated amine group capable of reacting with a surface, the groups R are the same or different and each is a straight or b
REFERENCES:
Biomaterials, Hayward et al Biomembranes as models for polymer surfaces 1986, vol. 7, Jul. pp. 252-258.
Umeda et al Makromol Chem, Rapid Commun Jul. 1982 vol. 3 pp. 457-459 Polymeric Phospholipid Analogues.
Kurioka J. Biochemistry, 1968, vol. 63, No. 5, pp. 678-679 Synthesis of p-Nitrophenyl phosphorylcholine etc.
Chesebro et al Biochemistry, vol. 11, No. 5, 1972, pp. 766-771 Affinity Labeling of a Phosphorylcholine.
Volanakis et al J. Immunological Methods, 23, (1978) 285-295 C-Reactive Protein: Purification by Affinity etc.
Oliveira et al J. of Immunology vol. 124, No. 3, Mar. 1980 1396-1402 Comparative Studies on the Binding Properties of Human and Rabbitt etc.
J. Biological Chemistry vol. 256, No. 2, Jan. 25, 969-975, 1981 Robey et al "Limulin: A C-reactive Protein from Limulus polyphemus".
FEBS Letters vol. 88 No. 2, Apr. 1978 pp. 172-175 Pontet et al One Step Preparation of Both Human C-Reactive Protein etc.
Immunobiol. vol. 163, pp. 36-47 (1982) Uhlenbruck et al Two Different Anti-Galactan Lectins in Eel Serum
Biochimie, 1979, 61, 1293-1299 Pontet et al Preparation et forme serique de la proteine etc.
Proc. Natl. Acad. Sci vol. 75 No. 9, pp. 4074-4077 Sep. 1978 Eibl Phospholipid synthesis: Oxazaphospholanes etc.
Pierce Immunotechnology Catalogue 1990, p. 35--Affinity Chromatography and Gel Permeation.
Bowers Roderick W. J.
Driver Michael J.
Jones Stephen A.
Russell Jeremy C.
Stratford Peter W.
Biocompatibles Limited
Caldarola Glenn A.
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