Linear polyesteramides from aminophenolic esters
AssigneeTYRX, Inc.
InventorsArthur Schwartz, Satish Pulapura, Sarita Nethula, Archana Rajaram, Arikha Moses
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Abstract
The present invention is directed to linear, biodegradable polyesteramide (PEA) polymers synthesized with repeating units derived from aminophenol esters and diacids. These PEAs have a monomer repeat represented by as well as a variety of uses to coat, form or comprise medical devices, combination medical devices and pharmaceutical compositions, including sustained release formulations.
Claims33
A synthetic polymer comprising monomer units represented by the formula:
- wherein
- R is —(CR3R4)a— or —CR3═CR4—;
- R1 is hydrogen;
- saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms;
- or —(R5)qO((CR3R4)rO)s—R6;
- each R2 is independently a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, divalent alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms;
- —(R5)qO((CR3R4)rO)s(R5)q—;
- or —(R5)qCO2((CR3R4)rO)sCO(R5)q—;
- R3 and R4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,
- R5 is independently linear or branched lower alkylene or lower alkenylene;
- R6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;
- the aromatic ring has from zero to four Z1 substituents, each of which is independently selected from the group consisting of halide, lower alkyl, alkoxy, nitro, alkyl ether, a protected hydroxyl group, a protected amino group and a protected carboxylic acid group;
- Y is
- a is 0 to 10;
- each q is independently 1 to 4;
- each r is independently 1 to 4;
- and
- each s is independently 1 to 5000.
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A method of synthesizing a strictly alternating (ab)n PEA polymer comprising:
- (a) reacting about two molar equivalents of an aminophenol with about one molar equivalent of a first diacid in the presence of a first coupling agent for a time and under conditions to preferentially form amide bonds, and thereby produce an aminophenol-diacid-aminophenol trimer;
- (b) optionally recovering said trimer;
- (c) reacting about one equivalent of said trimer with about one equivalent of a second diacid in the presence of a second coupling agent for a time and under conditions to form said strictly alternating (ab)n PEA polymer.
Dependencies are inferred from the claim text.