IP Library Granted Patent US 10,098,957
Granted Patent B2
US 10,098,957 · App. 15/644,715 · Granted Oct 16, 2018

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 10,098,957
App. No.
15/644,715
Granted
Oct 16, 2018
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 (39)

1. A method for reducing pain, comprising:

administering to a wound a composition comprised of a delivery system that is in the form of a semi-solid polymer formulation comprising a polyorthoester, 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 polyorthoester is represented by 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 and/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

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

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

5. The method of claim 1 , wherein said administering comprises administering a composition wherein the delivery system is a sustained-release delivery system.

6. The method of claim 1 , wherein the delivery system further comprises a polar aprotic solvent and a triglyceride viscosity reducing agent.

7. The method of claim 6 , wherein the triglyceride viscosity reducing agent is selected from the group consisting of triacetin and tributyrin.

8. The method of claim 6 , wherein the polar aprotic solvent is selected from dimethyl sulfoxide, N-methyl pyrrolidone and dimethyl acetamide.

9. The method of claim 6 , wherein bupivacaine and meloxicam are soluble in the triglyceride viscosity reducing agent, the polar aprotic solvent, or a mixture thereof.

10. The method of claim 6 , wherein bupivacaine is present in the composition at between about 0.01 wt % and about 7.5 wt % of the composition.

11. The method of claim 6 , wherein the meloxicam is present in the composition at between about 0.005 wt % to 0.25 wt % of the composition.

12. The method of claim 6 , 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 %.

13. The method of claim 12 , wherein the delivery system further comprises 0.01 wt % to 0.3 wt % maleic acid.

14. The method of claim 12 , wherein the polyorthoester has a weight average molecular weight between about 2,500 Daltons and about 10,000 Daltons.

15. The method of claim 12 , wherein the delivery system has a viscosity less than 10000 mPa-s when measured at 37° C. using a viscometer.

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

17. The method of claim 1 , wherein the administering to a wound is via instillation to the wound.

18. The method of claim 1 , wherein the administering to a wound is via instillation to an open wound as part of a surgical procedure.

19. The method of claim 1 , wherein the composition is administered to a surgical wound.

20. The method of claim 1 , wherein the pain is post-operative pain.

21. The method of claim 1 , wherein the administering produces pain relief for a time period of about 3 days to about 5 days following administration.

22. The method of claim 1 , wherein the administering to a wound is via instillation to an open wound as part of a surgical procedure and wherein the administering produces pain relief for a time period of about 3 days.

23. The method of claim 1 , wherein the administering to a wound is via instillation to an open wound as part of a surgical procedure and wherein the administering produces pain relief for a time period of at least about 3 days.

24. The method of claim 1 , wherein the composition forms an implant or depot in situ.

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 Sep 30, 2017
From: OTTOBONI, THOMAS B.; GIROTTI, LEE ANN LYNN
To: HERON THERAPEUTICS, INC.
Reel/Frame 043748/0043 →
Continuity (7)
Continuation 15331767 · Oct 21, 2016
Continuation In Part 15260820 · Sep 9, 2016
Continuation 14691464 · Apr 20, 2015
Provisional Application 62131797 · Mar 11, 2015
Provisional Application 61996788 · May 14, 2014
Provisional Application 61982314 · Apr 21, 2014
Related Publication 20170304455A1 · Oct 26, 2017
Cited By (1)
US 12,514,756