Process for preparing covalently bound-heparin containing polyurethane-peo-heparin coating compositions
AssigneeMeadox Medicals, Inc.
InventorBirendra K. Patnaik
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Abstract
A bio-active coating composition is described which is the reaction product of two different reactions. The first reaction includes reacting a bio-compatible polymer backbone having .alpha.,.beta.-unsaturated carbonyl functionality with a hydrophilic spacer having at least one reactive functional group at its first and second ends. In this reaction, one of the reactive functional groups of the spacer reacts with a .beta.-carbon of the carbonyl functionality to bond the spacer to the polymer backbone. The second reaction includes reacting a bio-active agent with a remaining unreacted reactive functional group of the spacer in the presence of an optional catalyst to covalently bind the bio-active agent to the spacer.
Claims44
A bio-active coating comprising the reaction product of:
- a) a first reaction that includes reacting a bio-compatible polymer backbone having .alpha.,.beta.-unsaturated carbonyl functionality with a hydrophilic spacer having at least one reactive functional group at its first and second ends, wherein one of said reactive functional groups reacts with a .beta.-carbon of said unsaturated carbonyl functionality to bond said spacer to said polymer backbone;
- and
- b) a second reaction that includes reacting a bio-active agent with a remaining unreacted reactive functional group of said spacer to covalently bind said bio-active agent to said spacer.
A coating composition including a polymeric structure defined by a bio-compatible polymeric backbone having .alpha.,.beta.-unsaturated carbonyl functionality and at least one pendant moiety bonded to a .beta.-carbon of said unsaturated carbonyl functionality, said pendant moiety selected from the group consisting of:
- NH--R.sup.1 --NH--R.sup.2,
- wherein R.sup.1 is a hydrophilic spacer group selected from the group consisting of aliphatic hydrocarbons, poly(oxy olfins), hydrophilic polyethers, hydrophilic polyethylenes, modified polyolefins, aliphatic polyesters, polyamines, polysiloxanes, polysilazanes, hydrophilic acrylates, hydrophilic methacrylates, polyamino acids, and linear polysaccharides;
- and R.sup.2 is a bio-active agent selected from the group consisting of antithrombogenic agents, antibiotics, antibacterial agents, antiviral agents, their pharmaceutical salts and mixtures thereof.
A method for preparing a bio-active polymer coating having a bio-active group covalently bonded through a hydrophilic spacer group to a polymer backbone comprising:
- a) providing a polymer backbone having .alpha.,.beta.-unsaturated carbonyl functionality therewithin;
- b) reacting a .beta.-carbon of said unsaturated carbonyl functionality with said hydrophilic spacer having at least one reactive functional group at its first and second ends to attach said hydrophilic spacer as a pendant group off said backbone;
- and
- d) further reacting said pendant group with a bio-active agent to covalently bond said bio-active agent to said pendant group.
A polymer-bound bio-active composition represented by the structure:
- ##STR8## wherein P is a biocompatible polymer backbone having a .beta.-carbonyl derived from an .alpha.,.beta.-unsaturated carbonyl functionality therewithin;
- R.sup.1 is a hydrophilic spacer group having at least one reactive functional group at its first and second ends and is further selected from the group consisting of aliphatic hydrocarbons, poly(oxy olefins) hydrophilic polyethers, hydrophilic polyethylenes, modified polyolefins, aliphatic polyesters, polyamines, polysiloxanes, polysilazanes, hydrophilic acrylates, hydrophilic methacrylates, polyamino acids, and linear polysaccharides;
- and R.sup.2 is a bio-active agent selected from the group consisting of antithrombogenic agents, antibiotics, antibacterial agents, antiviral agents, their pharmaceutical salts and mixtures thereof.
A bio-active coating composition comprising a polymer backbone having at least one pendant moiety bonded to a .beta.-carbon of an .alpha.,.beta.-unsaturated functionality, said composition prepared by the process of:
- a) reacting a poly(diol) with methylene diisocyanate to form a NCO-terminated prepolymer;
- b) reacting a compound having an .alpha.,.beta.-unsaturated carbonyl functionality with said NCO terminated prepolymer to form said polymer backbone;
- c) reacting said polymer backbone with a hydrophilic spacer group having at least one reactive functionality at its first and second ends;
- and
- d) reacting a bio-active agent with an unreacted end of said hydrophilic spacer to convalently bond said bio-active agent to said polymer backbone via said hydrophilic spacer.
Dependencies are inferred from the claim text.