Derivatized polyurethane compositions which exhibit enhanced stability in biological systems and methods of making the same
AssigneeThe Children's Hospital of Philadelphia
InventorsRobert J. Levy, Ivan Alferiev
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Abstract
The invention relates to methods of making polyurethane derivatives which can be readily further derivatized using stabilizing agents such as anti-calcification agents, anti-thrombogenesis agents, and chemical and mechanical degradation-inhibiting agents. The invention also includes methods of making polyurethane derivatives so further derivatized and to polyurethanes derivatives made using such methods.
Claims53
A polyurethane composition, comprising a polyurethane having a geminal bisphosphonate substituent pendant therefrom.
A method of making a geminal bisphosphonate-derivatized polyurethane, the method comprising
- grafting a 1,ω-dibromoalkyl compound with a urethane amino moiety of a polyurethane to form an ω-bromoalkyl-substituted polyurethane and
- grafting a geminal bisphosphonate thiol with the ω-bromoalkyl-substituted polyurethane to form the geminal bisphosphonate-derivatized polyurethane.
A method of making a geminal bisphosphonate-derivatized polyurethane, the method comprising
- grafting a ω-bromocarboxylic acid with a urethane amino moiety of a polyurethane to form an ω-carboxyalkyl-substituted polyurethane and
- grafting a geminal bisphosphonate amine with the ω-carboxyalkyl-substituted polyurethane to form the geminal bisphosphonate-derivatized polyurethane.
A method of making a gerninal bisphosphonate-derivatized polyurethane, the method comprising
- grafting a 1,ω-dibromoalkyl compound with a urethane amino moiety of a polyurethane to form an ω-bromoalkyl-substituted polyurethane;
- contacting the ω-bromoalkyl-substituted polyurethane with an ωthiocarboxylic acid to form an ω-carboxyl-thioalkyl-substituted polyurethane;
- and
- grafting a geminal bisphosphonate amine with the ω-carboxyl-thioalkyl-substituted polyurethane to form the geminal bisphosphonate-derivatized polyurethane.
A method of making a geminal bisphosphonate-derivatized polyurethane, the method comprising
- grafting a bromo-epoxyalkyl compound with a urethane amino moiety of a polyurethane to form an bromo-epoxyalkyl-substituted polyurethane and
- grafting a geminal bisphosphonate thiol with the bromo-epoxyalkyl-substituted polyurethane to form the geiinal bisphosphonate-derivatized polyurethane.
A method of preparing a polyurethane derivative, the method comprising contacting a polyurethane with a bi-functional linker reagent in the presence of an aprotic solvent and a strong base to form an activated polyurethane derivative, wherein the bi-functional linker reagent has a bromine substituent and a second functional group.
Dependencies are inferred from the claim text.