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Phosphoryl choline coating compositions

a technology of phosphoryl choline and composition, applied in the direction of drug composition, prosthesis, extracellular fluid disorder, etc., can solve the problem that diverse compositions have been used with limited success

Inactive Publication Date: 2005-09-22
ABBOTT CARDIOVASCULAR
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0017] The biocompatible polymer described herein can be used alone or in combination with one or more polymers and/or biobeneficial materials, and optionally a bioactive agent. Representative biobeneficial materials include non-fouling materials such as PEG and polyalkene oxides and anti-thrombogenic materials such as heparin. Representative bioactive agents include, but are not limited to, proteins, peptides, anti-inflammatory agents, antivirals, anticancer drugs, anticoagulant agents, free radical scavengers, steroidal anti-inflammatory agents, antibiotics, nitri

Problems solved by technology

A continuing challenge in the art of implantable stents is to provide a coating that possesses good biobeneficial properties, which refer to good biocompatibilities in both the acute and chronic timeframes.
To provide for a coating that is biologically benign, various compositions have been used with limited success.

Method used

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  • Phosphoryl choline coating compositions
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Examples

Experimental program
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Effect test

example 1

P(MPC-PEGA-BMA) Copolymer

[0054] The components, 2-methacryloyloxyethyl phosphorylcholine (MPC) butylmethacrylate (BMA), poly(ethylene glycol)acrylate (PEGA) (Mn=350 Da) and AIBN (α,α′-azobutyronitrile) were dissolved in ethanol at a molar ratio of (15:10:74:1). The reactants were maintained at 62° C. for 24 h. The polymer was purified, by a double precipitation in methanol, to yield a white powder.

[0055] A first composition was prepared by mixing the following components: [0056] (a) about 2 mass % poly(butyl methacrylate) (PBMA); [0057] (b) dissolved in a mixture of acetone and cyclohexanone (30% and 70% respectively).

[0058] The first composition was applied onto the surface of a bare 12 mm VISION stent (available from Guidant Corporation) by spraying and dried to form a stent coating. A spray coater was used, having a 0.014 fan nozzle maintained at ambient temperature with a feed pressure of about 0.2 atm (about 3 psi) and an atomization pressure of about 1.3 atm (about 20 psi)....

example 2

Hydroxyl Functional Caprolactone

[0069] A 100 g 1,4-hexanediol was dissolved in 1.4 L of a mixture of acetonitrile and water (7:3 by volume). A mixture of 45.4 g of sodium bromate and 16.5 g of ammonium cerium (IV) nitrate was slowly added. The reaction was maintained under reflux conditions for 90 min. Once acetonitrile was removed by rotary evaporation, the solution was diluted with 800 mL of water and continuously extracted with chloroform for 72 h. The organic solution was dried over magnesium sulfate. Finally chloroform was evaporated from the organic solution to yield 99.5 g of a colorless oil (4-hydroxycyclohexanone).

[0070] 130 g of benzyl chloride were slowly added to a solution of 60 g of 4-hydroxycyclohexanone in 400 mL of triethylamine. The solution was left to react at 25 ° C. for 2 h. After removal of the solvent, the product was purified by column chromatography to yield 100 g of a white powder 4-benzylestercyclohexanone.

[0071] To a solution of 20 g 3-chloroperoxyben...

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Abstract

A polymer comprising phospholipid moieties and a biocompatible polymer backbone, a composition comprising the polymer and optionally a bioactive agent, an implantable devices such as a DES comprising thereon a coating comprising the polymer and optionally a bioactive agent, and a method of using the device for the treatment of a disorder in a human being are provided.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] This invention generally relates to a composition comprising at least a hospholipid such as phosphoryl choline that is useful for coating an implantable device such as a drug eluting stent. [0003] 2. Description of the Background [0004] Implanted stents have been used to carry medicinal agents, such as thrombolytic agents. U.S. Pat. No. 5,163,952 to Froix discloses a thermal-memoried expanding plastic stent device formulated to carry a medicinal agent in the material of the stent itself. Pinchuk, in U.S. Pat. No. 5,092,877, discloses a stent of a polymeric material which may have a coating associated with the delivery of drugs. Other patents which are directed to devices of the class utilizing bio-degradable or bio-absorbable polymers include Tang et al., U.S. Pat. No. 4,916,193, and MacGregor, U.S. Pat. No. 4,994,071. [0005] A patent to Sahatjian, U.S. Pat. No. 5,304,121, discloses a coating applied to a stent cons...

Claims

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Application Information

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IPC IPC(8): A61L27/34A61L31/10C08G63/91
CPCA61L27/34A61L31/10C08L33/14A61P1/16A61P13/02A61P35/00A61P7/02A61P7/04A61P9/10A61P9/14A61L31/148A61L31/16A61L33/0011A61L33/08A61L2300/42A61L2300/40A61L2300/604A61L2300/606A61L2400/18
Inventor GLAUSER, THIERRYPACETTI, STEPHEN DIRKHOSSAINY, SYED F.A.DING, NI
Owner ABBOTT CARDIOVASCULAR
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