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US 8,273,828 B2Granted
Methods for introducing reactive secondary amines pendant to polymers backbones that are useful for diazeniumdiolation
AssigneeMedtronic Vascular, Inc.
InventorsMingfei Chen, Peiwen Cheng, Kishore Udipi
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Abstract
Biocompatible polymers having polymer backbones with at least one secondary amine suitable for diazeniumdiolation are disclosed. Specifically, methods for providing secondary amines-containing polymers using epoxide-opening reactions are provided. More specifically, nitric oxide-releasing medical devices made using these polymers are disclosed.
Claims14
A method of providing a polymer, the method comprising:
- (a) providing a polymer having epoxide pendant groups;
- (b) reacting said polymer with an amine compound having the general formula R2—NH2;
- wherein the molar ratio of amine compound to epoxide groups of the epoxide-containing polymer is at least 39:1 and no greater than 48:1;
- wherein R2 is selected from the group consisting of C1 to C20 straight chain alkyls, C3 to C8 cycloalkyls, C2 to C20 alkenyls, C2 to C20 alkynyls, C2 to C14 heteroatom substituted alkyls, C2 to C14 heteroatom substituted cycloalkyls, C1 to C10 multiple amine containing-hydrocarbons, C4 to C10 substituted aryls and C4 to C10 substituted heteroatom substituted heteroaryls, under conditions wherein a secondary amine is formed;
- and
- (c) reacting said secondary amine with NO under pressure to form a diazeniumdiolate thereof.
3 more elements
A method of providing a nitric oxide (NO)-donating polymer, the method comprising:
- (a) providing a polymer having epoxide pendant groups;
- (b) reacting said epoxide pendant groups on said polymer with a primary amine under conditions effective to ring open the epoxide and form side chains comprising secondary amine groups;
- wherein the molar ratio of the primary amine compound to epoxide groups of the epoxide-containing polymer is at least 39:1 and no greater than 48:1;
- and
- (c) reacting said secondary amine groups with NO under pressure to form a diazeniumdiolate thereof, thereby forming an NO-donating polymer;
- wherein said primary amine is of the formula R2—NH2 , wherein R2 is selected from the group consisting of C1 to C20 straight chain alkyls, C3 to C8 cycloalkyls, C2 to C20 alkenyls, C2 to C20 alkynyls, C2 to C14 heteroatom substituted alkyls, C2to C14 heteroatom substituted cycloalkyls, C1 to C10 multiple amine containing-hydrocarbons, C4 to C10 substituted aryls and C4 to C10 substituted heteroatom substituted heteroaryls.
3 more elements
Dependencies are inferred from the claim text.