Compositions of a polyorthoester and an aprotic solvent

Inventors

Ottoboni, Thomas B. • Girotti, Lee Ann Lynn

Assignees

Heron Therapeutics LLC

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Publication Number

US-12318376-B2

Patent

Publication Date

2025-06-03

Expiration Date


Abstract

Delivery systems and compositions comprised of a biodegradable polyorthoester polymer, an aprotic solvent, and a drug are described. The solvent is selected to modulate release of drug from the composition, where, in some embodiments, the solvent is rapidly released after administration and provides a corresponding rapid rate of drug release. Alternatively, in other embodiments, the solvent is slowly released from the composition after its administration, and provides a correspondingly slow rate of drug release.

Core Innovation

The invention relates to a delivery system that includes a biodegradable polyorthoester represented by Formula III and combined with an aprotic solvent in which the polyorthoester is miscible to form a single phase. A therapeutically active agent is dispersed or solubilized in the single phase, and the agent includes a local amide- or anilide-type anesthetic.

The polyorthoester is defined by specific structural and compositional constraints, including A-unit identity, ranges for p and q, an integer range for x, R5 as H or methyl, and a limitation on the fraction of A units that are of the formula R1 between 0 and 25 mole percent. The polyorthoester subunits include α-hydroxyacid-containing subunits, and increasing the mole fraction of α-hydroxyacid-containing subunits increases bioerodibility.

The disclosed approach uses solvent selection and solvent concentration to modulate solvent and drug release kinetics. The anesthetic is released over a period of between approximately 1 day and approximately 8 weeks, and the system is described in the context of hydrolysis to hydroxyacids that catalyze further polymer erosion.

Claims Coverage

The independent claim coverage centers on three inventive features: a polyorthoester defined by Formula III with specified structural and compositional constraints, an aprotic solvent miscible with the polyorthoester to form a single phase, and a local amide- or anilide-type anesthetic dispersed or solubilized in that phase with release over approximately 1 day to approximately 8 weeks.

Polyorthoester of formula III with A-unit limitation

A polyorthoester represented by Formula III, with A as R1 or R3, p and q integer ranges, x as an integer range, R5 as H or methyl, and the fraction of A units that are of the formula R1 between 0 and 25 mole percent.

Aprotic solvent miscible to form a single phase

An aprotic solvent in which the polyorthoester is miscible to form a single phase.

Dispersed or solubilized local amide- or anilide-type anesthetic with extended release

A local amide- or anilide-type anesthetic dispersed or solubilized in the single phase, wherein the anesthetic is released from the system over a period of between approximately 1 day and approximately 8 weeks.

Overall, the claim coverage centers on a polyorthoester/aprotic-solvent single phase that carries a local amide- or anilide-type anesthetic, with the polyorthoester defined by Formula III constraints and with anesthetic release over approximately 1 day to approximately 8 weeks.

Stated Advantages

Solvent selection and solvent concentration modulate solvent and drug release kinetics.

Increasing the mole fraction of α-hydroxy acid-containing subunits increases bioerodibility via hydrolysis to hydroxyacids that catalyze further polymer erosion.

The system provides release of a local amide- or anilide-type anesthetic over a period of between approximately 1 day and approximately 8 weeks.

Local pain reduction is supported by a porcine incisional pain model.

Measurable plasma levels for at least approximately 5 days are described to support in vivo release.

Documented Applications

Delivery of local amide- or anilide-type anesthetics.

Delivery of anti-emetic agents.

Delivery of semi-synthetic opioids.

Delivery of granisetron.

A local anesthesia delivery context supported by a porcine incisional pain model.

A delivery system configured for anesthetic release from the system, supporting in vivo release via measurable plasma levels for at least approximately 5 days.

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