IP Library Granted Patent US 9,913,909
Granted Patent B2
US 9,913,909 · App. 15/269,806 · Granted Mar 13, 2018

Compositions of a polyorthoester and an aprotic solvent

Inventors: Thomas B. Ottoboni (Belmont, CA); Lee Ann Lynn Schillinger (San Bruno, CA)
Assignee: Heron Therapeutics, Inc.
A61K47/34A61K31/439A61K47/10A61K47/20A61K47/22
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Quick Facts
Patent No.
US 9,913,909
App. No.
15/269,806
Granted
Mar 13, 2018
Kind
B2
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.

Claims (44)

1. A method of administering a therapeutically active agent to a subject in need thereof, comprising:

dispensing and administering to the subject a delivery system, wherein the delivery system comprises:

a polyorthoester of Formula III;

where

A is R 1 or R 3 ,

R* is C1-4 alkyl,

n ranges from 5 to 1000,

R 1 is:

p and q are integers that vary from between about 1 to 20 and the average number of p or the average of the sum of p and q is between 1 and 7;

R 3 and R 6 are each independently:

x is an integer of 1-4;

R 5 is H or methyl, and

the fraction of A units that are of formula R 1 is between 10-25 mole percent;

an aprotic solvent in which the polyorthoester is miscible to form a single phase, wherein the aprotic solvent is selected from dimethyl sulfoxide, dimethyl acetamide, and N-methyl pyrrolidone; and

a local amide- or anilide-type anesthetic dispersed or solubilized in the single phase,

wherein the aprotic solvent is present in amounts ranging from about 10-25% by weight of the delivery system and the polyorthoester of formula III is present in amounts ranging from about 45-80% by weight of the delivery system.

2. A method of treating pain in a subject in need thereof, comprising:

dispensing and administering to the subject a composition comprised of a therapeutically effective amount of a delivery system, wherein the delivery system comprises:

a polyorthoester of Formula III;

where

A is R 1 or R 3 ,

R* is C1-4 alkyl,

n ranges from 5 to 1000,

R 1 is:

p and q are integers that vary from between about 1 to 20 and the average number of p or the average of the sum of p and q is between 1 and 7;

R 3 and R 6 are each independently:

x is an integer of 1-4;

R 5 is H or methyl, and

the fraction of A units that are of formula R 1 is between 10-25 mole percent;

an aprotic solvent in which the polyorthoester is miscible to form a single phase, wherein the aprotic solvent is selected from dimethyl sulfoxide, dimethyl acetamide, and N-methyl pyrrolidone; and

a local amide- or anilide-type anesthetic dispersed or solubilized in the single phase.

3. The method of claim 2 , wherein the method reduces or prevents pain in the subject.

4. The method of claim 2 , wherein the administering comprises administering the composition locally.

5. The method of claim 4 , wherein the administering comprises administering the composition intrathecally, at a nerve, into the epidural space, or to a surgical wound.

6. The method of claim 2 , wherein the administering comprises administering the composition regionally.

7. The method of claim 6 , wherein the administering comprises administering the composition as a nerve block or as a sensory block.

8. The method of claim 2 , wherein the active agent is selected from the group consisting of bupivacaine, ropivacaine, levobupivacaine, dibucaine, mepivacaine, procaine, lidocaine, and tetracaine.

9. The method of claim 2 , wherein the therapeutically active agent is bupivacaine.

10. The method of claim 2 , wherein the therapeutically active agent is ropivacaine.

11. The method of claim 2 , wherein the delivery system has a viscosity of less than about 10,000 cP at 37° C.

12. The method of claim 2 , wherein the aprotic solvent is dimethyl sulfoxide.

13. The method of claim 1 , wherein the method comprises dispensing the delivery system from a tube.

14. The method of claim 1 , wherein the method comprises administering to the subject the delivery system in an amount effective to prevent or reduce pain.

15. The method of 1 , wherein the aprotic solvent is dimethyl sulfoxide.

Assignments (2)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Aug 9, 2023
From: HERON THERAPEUTICS, INC.
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 064546/0453 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2018
From: OTTOBONI, THOMAS B.; SCHILLINGER, LEE ANN LYNN
To: HERON THERAPEUTICS, INC.
Reel/Frame 044813/0984 →
Continuity (4)
Continuation 14213658 · Mar 14, 2014
Provisional Application 61902018 · Nov 8, 2013
Provisional Application 61789469 · Mar 15, 2013
Related Publication 20170100483A1 · Apr 13, 2017