IP Library Granted Patent US 9,801,945
Granted Patent B2
US 9,801,945 · App. 15/331,767 · Granted Oct 31, 2017

Long-acting polymeric delivery systems

Inventors: Thomas B. Ottoboni (Belmont, CA); Lee Ann Lynn Girotti (San Bruno, CA)
Assignee: Heron Therapeutics, Inc.
A61K47/34A61K9/0019A61K9/0024A61K9/0085A61K9/127A61K9/14A61K31/00A61K31/196A61K31/445A61K31/5415A61K47/12A61K47/14A61K47/20A61K47/32
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Quick Facts
Patent No.
US 9,801,945
App. No.
15/331,767
Granted
Oct 31, 2017
Kind
B2
Abstract

Compositions comprised of a delivery vehicle or delivery system and an active agent dispersed within the delivery vehicle or system, wherein the delivery vehicle or system contains a polyorthoester polymer and a polar aprotic solvent. Also disclosed are low viscosity delivery systems for administration of active agents. The low viscosity delivery systems have a polyorthoester polymer, a polar aprotic solvent and a solvent containing a triglyceride viscosity reducing agent. Compositions described include an amide- or anilide-type local anesthetic of the “caine” classification, and a non-steroidal anti-inflammatory drug (NSAID), along with related methods, e.g., for treatment of post-operative pain or for prophylactic treatment of pain. The compositions are suitable for delivery via, e.g., direct application and instillation, intradermal injection, subcutaneous injection, and nerve block (perineural).

Claims (44)

1. A pharmaceutical composition, comprising: a delivery system, bupivacaine, and meloxicam, wherein bupivacaine and meloxicam are present in the composition at a ratio ranging from about 15:1 to 50:1, wherein meloxicam is present in the composition in an amount between about 0.005-0.75 wt %, and wherein the composition forms an implant or depot in situ.

2. The composition of claim 1 , wherein bupivacaine is present in the composition in an amount ranging from about 0.1 to 8.0 wt % and the meloxicam is present in the composition in an amount ranging from about 0.01-0.5 wt %.

3. The composition of claim 1 , wherein the delivery system is a sustained-release delivery system.

4. The composition of claim 1 , wherein the delivery system is aqueous based.

5. The composition of claim 3 , wherein the sustained-release delivery system is a semi-solid polymer formulation comprising a polymer.

6. The composition of claim 5 , wherein the polymer is a bioerodible or biodegradable polymer.

7. The composition of claim 5 , wherein the polymer formulation forms an implant or depot in situ.

8. The composition of claim 5 , wherein the polymer is a polyorthoester represented by the structure shown as Formula I:

where:

R* is a C 1-4 alkyl,

n is an integer ranging from 5 to 400, and

A is a diol; where A is R 1 or R 3 , where the fraction of A units that are of formula R 1 is between 0 and 25 mole percent, where

when A is R 3 , R 3 is

where x is 2; and

when A is R 1 , R 1 is

R 5 is H, and R 6 is

the sum of p and q is, on average, 2 and s is 2,

where the resulting component of the polyorthoester comprises the subunit

9. The composition of claim 8 , wherein the delivery system comprises the polyorthoester, a polar aprotic solvent and a triglyceride viscosity reducing agent.

10. The composition of claim 9 , wherein the triglyceride viscosity reducing agent is selected from the group consisting of triacetin and tributyrin.

11. The composition of claim 9 , wherein the polar aprotic solvent is selected from dimethyl sulfoxide, N-methyl pyrrolidone and dimethyl acetamide.

12. The composition of claim 9 , wherein bupivacaine and meloxicam are soluble in the triglyceride viscosity reducing agent, the polar aprotic solvent, or a mixture thereof.

13. The composition of claim 9 , wherein bupivacaine is present in the composition at between about 0.01 wt % and about 7.5 wt % of the composition.

14. The composition of claim 13 , wherein the meloxicam is present in the composition at between about 0.005 wt % to 0.25 wt % of the composition.

15. The composition of claim 9 , wherein the delivery system comprises:

40 wt % to 75 wt % of the polyorthoester;

5 wt % to 12 wt % dimethyl sulfoxide; and

20 wt % to 40 wt % triacetin;

and wherein bupivacaine is present in an amount of between about 1 wt % to 5 wt %.

16. The composition of claim 15 , wherein the delivery system further comprises 0.01 wt % to 0.3 wt % maleic acid.

17. The composition of claim 15 , wherein the polyorthoester has a weight average molecular weight between 2,500 daltons and 10,000 daltons.

18. The composition of claim 15 , wherein the delivery system has a viscosity less than 10000 mPa-s when measured at 37° C. using a viscometer.

19. The composition of claim 3 , wherein bupivacaine is released from the composition over a time period of about 1 day to about 5 days.

20. A method for producing analgesia or pain relief in a subject in need thereof, comprising: administering to the subject the composition according to claim 1 .

21. A method for managing pain in a subject in need thereof, comprising administering to the subject the composition according to claim 1 .

22. A method for prophylactic treatment of pain in a subject, comprising administering to the subject the composition according to claim 1 .

23. The method of claim 20 , wherein the administering is intramuscular, subcutaneous, perineural or to a wound.

24. The method of claim 20 , wherein the pain is acute pain or chronic pain.

25. The method of claim 20 , wherein the composition is administered to a surgical wound.

26. The method according to claim 20 , wherein the pain is postsurgical pain.

27. The method of claim 20 , wherein the composition produces pain relief for a time period of about 3 days to about 5 days following administration.

28. The method of claim 20 , wherein the composition is administered as a nerve block or as a peripheral nerve block.

29. The composition of claim 1 , wherein the meloxicam is present in the composition in an amount ranging from about 0.005-0.25 wt %.

30. The composition of claim 1 , wherein the meloxicam is present in the composition in an amount ranging from about 0.005-0.125 wt %.

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 Jan 5, 2017
From: OTTOBONI, THOMAS B.; GIROTTI, LEE ANN LYNN
To: HERON THERAPEUTICS, INC.
Reel/Frame 040867/0294 →
Continuity (6)
Continuation In Part 15260820 · Sep 9, 2016
Continuation 14691464 · Apr 20, 2015
Provisional Application 61982314 · Apr 21, 2014
Provisional Application 61996788 · May 14, 2014
Provisional Application 62131797 · Mar 11, 2015
Related Publication 20170035888A1 · Feb 9, 2017