IP Library Granted Patent US 11,717,572
Granted Patent B2
US 11,717,572 · App. 17/477,361 · Granted Aug 8, 2023

Low-burst polymers and methods to produce polymer

Inventors: Eric Dadey (Sevierville, TN); John Middleton (Fort Collins, CO); Richard L. Norton (Fort Collins, CO)
Assignee: Tolmar, Inc.
A61K47/34A61K9/0024A61K38/08A61K38/12C08G63/08C08G63/90
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Quick Facts
Patent No.
US 11,717,572
App. No.
17/477,361
Granted
Aug 8, 2023
Kind
B2
Abstract

A PLG copolymer material, termed a PLG(p) copolymer material, adapted for use in a controlled release formulation for a bioactive material is provided, wherein the formulation exhibits a reduced “initial burst” effect when introduced into the tissue of a patient in need thereof. A method of preparation of the PLG copolymer material is also provided, as are methods of use.

Claims (32)

1. A controlled release formulation, comprising:

an organic solvent;

a peptide bioactive agent useful for modulating LHRH levels; and

a biocompatible, biodegradable, linear poly(DL-lactide-co-glycolide) (PLG) copolymer comprising a weight average molecular weight of about 10 kilodaltons to about 50 kilodaltons and a polydispersity index of about 1.4 to about 2.0;

wherein:

a low-molecular weight copolymer fraction having a weight average molecular weight of about 10 kilodaltons or less and comprising unreacted, residual lactide and glycolide monomers has been removed from the PLG copolymer; and

the controlled release formulation is formulated to release the peptide bioactive agent for a period of 30 days to 6 months.

2. The controlled release formulation of claim 1 , wherein the peptide bioactive agent is leuprolide or an analog thereof.

3. The controlled release formulation of claim 1 , wherein the PLG copolymer comprises less than about 1.0 weight % residual lactide monomer.

4. The controlled release formulation of claim 1 , wherein the PLG copolymer comprises about 0.5 weight % or less residual lactide monomer and about 0.1 weight or less residual glycolide monomer.

5. The controlled release formulation of claim 1 , wherein the PLG copolymer is not a product of hydrolysis of a higher molecular weight copolymer.

6. The controlled release formulation of claim 1 , wherein the PLG copolymer was prepared by a ring-opening polymerization reaction of lactide and glycolide.

7. The controlled release formulation of claim 1 , wherein the organic solvent is selected from the group consisting of N-methylpyrrolidone, N,N-dimethylacetamide, dimethylsulfoxide, and combinations thereof.

8. The controlled release formulation of claim 7 , wherein the organic solvent is N-methylpyrrolidone.

9. The controlled release formulation of claim 1 , wherein the PLG copolymer is 85/15 poly(DL-lactide-co-glycolide).

10. The controlled release formulation of claim 1 , wherein the PLG copolymer comprises a terminal ester group and a terminal hydroxyl group.

11. A method of modulating LHRH levels in a patient, comprising administering to the patient a therapeutically effective amount of a controlled release formulation, comprising:

an organic solvent;

a peptide bioactive agent; and

a biocompatible, biodegradable, linear poly(DL-lactide-co-glycolide) (PLG) copolymer comprising a weight average molecular weight of about 10 kilodaltons to about 50 kilodaltons and a polydispersity index of about 1.4 to about 2.0,

wherein:

a low-molecular weight copolymer fraction having a weight average molecular weight of about 10 kilodaltons or less and comprising unreacted, residual lactide and glycolide monomers has been removed from the PLG copolymer; and

the controlled release formulation forms an in situ solid or semi-solid depot with the body of the patient that provides for the controlled release of the peptide bioactive agent for a period of 30 days to 6 months.

12. The method of claim 11 , wherein the administration of the controlled release formulation suppresses testosterone biosynthesis in the patient.

13. The method of claim 11 , wherein the patient has prostate cancer.

14. The method of claim 11 , wherein the peptide bioactive agent is leuprolide or an analog thereof.

15. The method of claim 11 , wherein the PLG copolymer comprises about 1.0 weight % or less residual lactide monomer and/or about 0.1 weight % or less residual glycolide monomer.

16. The method of claim 11 , wherein the linear PLG copolymer is not a product of hydrolysis of a higher molecular weight copolymer.

17. The method of claim 11 , wherein the linear PLG copolymer was prepared by a ring-opening polymerization reaction of lactide and glycolide.

18. The method of claim 11 , wherein the organic solvent is selected from the group consisting of N-methylpyrrolidone, N,N-dimethylacetamide, dimethylsulfoxide, and combinations thereof.

19. The method of claim 11 , wherein the linear PLG copolymer is 85/15 poly(DL-lactide-co-glycolide).

20. The method of claim 11 , wherein the linear PLG copolymer comprises a terminal ester group and a terminal hydroxyl group.

Assignments (3)
MERGER Recorded Feb 23, 2023
From: TOLMAR THERAPEUTICS INC.
To: TOLMAR INC.
Reel/Frame 062785/0849 →
SECURITY INTEREST Recorded Aug 9, 2022
From: TOLMAR THERAPEUTICS, INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 060762/0256 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2021
From: DADEY, ERIC; MIDDLETON, JOHN; NORTON, RICHARD L.
To: TOLMAR THERAPEUTICS INC.
Reel/Frame 058407/0355 →
Continuity (8)
Continuation 16242316 · Jan 8, 2019
Continuation 15950024 · Apr 10, 2018
Continuation 15490615 · Apr 18, 2017
Continuation 15384117 · Dec 19, 2016
Continuation 14924243 · Oct 27, 2015
Division 12527377
Provisional Application 60901435 · Feb 15, 2007
Related Publication 20220202941A1 · Jun 30, 2022