Polymers containing poly(ester amides) and agents for use with medical articles and methods of fabricating the same
a technology of polyester amide and polymer, which is applied in the field of polyester amide and agent for use with medical articles, can solve the problems of insufficient hardness of currently available polyester amide, insufficient mechanical properties of polyester amide for many stent applications, and the possibility of binding of molecules from the polymeric carrier to the agen
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example 1
[0105] The PEA of formula (XVII) can be prepared according to the following procedure:
Method of preparing of L-Leucine-ε-L-Lysine Benzyl Ester-2TosOH
[0106] L-leucine-ε-L-lysine HCl (New England Peptide, Inc.) (73.86 gm, 0.25 mole), p-toluenesulfonic acid (152.15 gm, 0.80 mole), benzyl alcohol (100.9 ml, 0.97 mole), and 200 ml of benzene is added to a 1 liter reaction flask equipped with a mechanical stirrer, Dean Stark trap, thermometer and argon inlet. The mixture is heated to 80° C. for 8 hours, and condensate is collected in the Dean Stark trap. The mixture is transferred to a 2 liter flask, and 1 liter of ethyl acetate is added to the mixture with stirring. The mixture is stored overnight at 4° C., and L-Leucine-ε-L-Lysine Benzyl Ester-2TosOH and is isolated by filtration.
Method of preparing co-poly-{[N,N′-sebacoyl-bis-(L-leucine)-1,6-hexylene diester]-[N,N′-sebacoyl-L-leucine-L-lysine mPEG amide]}
[0107] Dry triethylamine (61.6 ml, 0.44 mole) is added to a mixture of di-p-tol...
example 2
[0109] The copolymer represented by formula (XII) can be prepared in a manner analogous to the method used to prepare the copolymer represented by formula (XVII) by replacing the L-leucine-ε-L-lysine-HCl with L-lysine HCl. While not intending to be bound by any theory or mechanism of action, a proposed reaction mechanism for the preparation of the PEA of formula (XII) according to one embodiment of the present invention is illustrated in FIG. 2.
example 3
[0110] The PEA of formula (XV) can be prepared according to the following procedure:
Method of preparing co-poly-{[N,N′-sebacoyl-bis-(L-leucine)-1,4-butylene diester]-[N,N′-sebacoyl-L-lysine-4-carboxy-TEMPO anhydride]}
[0111] Dry triethylamine (61.6 ml, 0.44 mole) is added to a mixture of a di-p-toluenesulfonic acid salt of bis-(L-leucine)-1,4-butylene diester (118.82 gm, 0.18 mole), a di-p-toluenesulfonic acid salt of L-lysine benzyl ester (11.603 gm, 0.02 mole), and di-p-nitrophenyl sebacinate (88.88 gm, 0.2 mole) in dry DMAC (110 ml). The mixture is stirred and heated at 80° C. for 12 hours, cooled to room temperature, diluted with ethanol (300 ml), and poured into water (1 liter). The polymer is separated, washed with water, and dried under vacuum. A free carboxyl group can be generated by hydrogenolysis over a palladium catalyst. Ethanol (1200 ml) is combined with the polymer (100 gm) and a palladium on carbon catalyst in a 2 liter flask (Aldrich). Hydrogen is bubbled and stirre...
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