Viscous terpolymers as drug delivery platform

• US 9,090,737 B2
• Filed: 11/12/2008
• Issued: 07/28/2015
• Est. Priority Date: 11/13/2007
• Status: Active Grant

• Current Assignee: Brookwood Pharmaceuticals Inc (Surmodics Incorporated)
• Original Assignee: Surmodics Incorporated
• Inventors: Markland, Peter, Bowman, Howard
• Primary Examiner(s): Kwon, Brian-Yong
• Assistant Examiner(s): BECKHARDT, LYNDSEY MARIE
• Application Number:
  US12/269,135
• Publication Number:
  US 20090124535A1
• Time in Patent Office: 2,449 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 31/7088 Compounds having three or more nucleosides or nucleotides
• CPC Class Codes: A61K 47/02 Inorganic compounds
• CPC Class Codes: A61K 47/10 Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 47/36 Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
• CPC Class Codes: A61K 9/0019 Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner non-active ingredients are additionally classified in A61K47/00
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 23/00 Anaesthetics
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C08G 2261/126 block
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids

Abstract

Disclosed are terpolymer compositions of lactide, glycolide, and caprolactone and methods of making such polymers with an initiator. Methods of using the terpolymers as a drug delivery platform are also disclosed.

Claims

1. A terpolymer composition, comprising:

a terpolymer of lactide, glycolide, and caprolactone residues, wherein the terpolymer comprises an end group that is a residue of an initiator, wherein the initiator is selected from the group consisting of oleyl alcohol and 1-dodecanol; and

wherein the amount of lactide residue in the terpolymer is from 10 to 31 mole percent, the amount of glycolide in the terpolymer is from 10 to 40 percent, and the amount of caprolactone is at least 49 mole percent;

wherein the terpolymer has a Mw equal to or less than 11,000 Daltons wherein the terpolymer exhibits a steady-state viscosity of less than or equal to 1720 poise when measured at room temperature.

2. The composition of claim 1, wherein the amount of lactide residue in the terpolymer is 16 mole percent, the amount of glycolide residue is 26 mole percent, and the amount of caprolactone residue is 58 mole percent.

3. The composition of claim 1, wherein the terpolymer has a Tg of less than 20°

C.

4. The composition of claim 1, further comprising a bioactive agent.

5. The composition of claim 4, wherein the bioactive agent comprises a drug, a peptide, a protein, an antibody or fragment thereof, a nucleic acid, or imaging agent.

6. The composition of claim 1, further comprising a plasticizer.

7. The composition of claim 1, further comprising an agent, surfactant, excipient, or additive.

8. The composition of claim 1, further comprising an aqueous diluent.