IP Library Granted Patent US 9,187,593
Granted Patent B2
US 9,187,593 · App. 12/527,377 · Granted Nov 17, 2015

Low burst polymers and methods to produce polymer

Inventors: Eric Dadey (Furlong, PA); John Middleton (Birmingham, AL); Richard L. Norton (Ft. Collins, CO)
Assignee: Tolmar Therapeutics, Inc.
C08G63/08C08G63/90A61K9/0024
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Quick Facts
Patent No.
US 9,187,593
App. No.
12/527,377
Granted
Nov 17, 2015
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 (11)

1. A biocompatible, biodegradable, non-hydrolyzed PLG low-burst copolymer material for a controlled release formulation having a weight average molecular weight of about 10 kilodaltons to about 23 kilodaltons and a ploydisperity index of about 1.4-2.0 which does not inclue a linear copolymer fraction characterized by a weight average molecular weight of about 4 kDa to about 10 kDa and a polydispersity index of about 1.4 to 2.5, and which PLG low burst copolymer material is produced by removing from a linear starting PLG copolymer material the linear copolymer fraction by a process of dissolving the starting PLG copolymer material in an organic solvent to provide a solution precipitating the low-burst copolymer material from the solution by contacting the solution with a non-solvent that is an organic liquid, and collecting the PLG low-burst copolymer material, the starting PLG copolymer material being produced by ring opening polymerization of cyclic dimer esters of lactide and glycolide or by condensation of lactic acid and glycolic acid and the stating PLG copolymer material being produced without hyrolysis of a higher molecular weight PLG copolymer material.

2. The PLG low-burst copolymer material of claim 1 wherein the content of unreacted lactide and glycolide is less than about 1.0 weight % and 0.1 weight % respectively.

3. The PLG low-burst copolymer material of claim 1 wherein the removed copolymer fraction is about 2% to about 20%, about 3% to about 15%, or about 5% to about 10% by weight of the sum of the weights of the removed copolymer fraction and the PLG low-burst copolymer material.

4. The low-burst copolymer material of claim 1 wherein the starting PLG copolymer material is prepared by a ring-opening polymerization reaction of lactide and glycolide.

5. The low-burst copolymer material of claim 4 wherein the ring-opening polymerization reaction is catalyzed by a tin salt.

6. The low-burst copolymer material of claim 1 wherein the organic solvent and the organic non-solvent are miscible.

7. The low-burst copolymer material of claim 6 wherein the organic solvent is dichloromethane or chloroform and the organic non-solvent is methanol or ethanol.

8. The low-burst copolymer material of claim 1 comprising copolymer molecular chains wherein a predominant proportion of the molecular chains comprise predominantly lactate or lactide residues in at least one end domain of each molecular chain and predominantly glycolate or glycolide resides in an internal domain of each molecular chain.

9. The low-burst copolymer material of claim 1 , wherein the copolymer material has a weight average molecular weight of about 10 kilodaltons to about 21 kilodaltons.

10. The low-burst copolymer material of claim 1 , wherein the copolymer material has a weight average molecular weight of about 10 kilodaltons to about 19 kilodaltons.

11. The low-burst copolymer material of claim 1 , wherein the copolymer comprises terminal carboxyl groups that are capped as esters.

Assignments (3)
MERGER Recorded Feb 23, 2023
From: TOLMAR THERAPEUTICS INC.
To: TOLMAR INC.
Reel/Frame 062785/0849 →
SECURITY INTEREST Recorded Oct 2, 2017
From: TOLMAR THERAPEUTICS, INC.; TOLMAR, INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 043756/0502 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2010
From: DADEY, ERIC; MIDDLETON, JOHN; NORTON, RICHARD L.
To: TOLMAR THERAPEUTICS INC.
Reel/Frame 024519/0712 →
Continuity (2)
Provisional Application 60901435 · Feb 15, 2007
Related Publication 20100292195A1 · Nov 18, 2010