# US 2014/0193365 A1 · Biodegradable Drug Delivery Composition

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- Number: US 2014/0193365 A1
- Document ID: US20140193365A1
- Status: Published application
- Kind: A1
- Application number: 14/102,453
- Filed: 2013-12-10
- Published: 2014-07-10
- Earliest claimed: 2010-11-24
- Assignees: Durect Corporation
- Applicants: Durect Corporation
- Inventors: William W. van Osdol; Su Il Yum; Felix Theeuwes; Michael Sekar; John W. Gibson; Keith E. Branham; Huey-Ching Su
- Web page: https://patentgrep.com/patent/US20140193365A1

## CPC

- A61K 38/212: {IFN-alpha}
- 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)}
- A61K 31/7052: having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K 38/26: Glucagons
- A61K 38/27: Growth hormone [GH], i.e. somatotropin
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- 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)
- A61K 47/52: the modifying agent being an inorganic compound, e.g. an inorganic ion that is complexed with the active ingredient
- A61K 47/541: {Organic ions forming an ion pair complex with the pharmacologically or therapeutically active agent}
- A61K 47/64: Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent (peptidic linkers A61K47/65)
- A61P 5/06: of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present disclosure provides a biodegradable drug delivery composition including a vehicle and an insoluble component comprising beneficial agent dispersed in the vehicle. Typically, the composition is not an emulsion, but has a low viscosity and further provides for minimized initial burst and sustained release of the beneficial agent over time. Also provided, are kits including the biodegradable drug delivery composition or components thereof, as well as methods of making and using the biodegradable drug delivery composition.

## Claims

### Claim at position 1

-22. (canceled)

### Claim 23

A composition comprising:
a vehicle comprising:
sucrose acetate isobutyrate,
a biodegradable polymer present in an amount of from about 5% to about 40% by weight of the vehicle, the biodegradable polymer having a weight average molecular weight ranging from 2000 Daltons to 10,000 Daltons, and
a hydrophobic solvent present in an amount of from about 60% to about 95% by weight of the vehicle; and
a complex dispersed in the vehicle, the complex having a solubility of less than 1 mg/mL in the vehicle at 25° C.,
wherein the complex comprises:
a protein, peptide, nucleic acid, or low molecular weight compound, the low molecular weight compound having a molecular weight of less than or equal to about 800 Daltons, and
a counterion of the protein, peptide, nucleic acid, or low molecular weight compound,
wherein the composition has a zero shear viscosity less than 1,200 centipoise at 25° C., and
wherein the composition is not an emulsion.

### Claim 24 (depends on 23)

The composition of claim 23, wherein the composition is not a gel.

### Claim 25 (depends on 23)

The composition of claim 23, wherein the composition has a G″/G′ ratio of greater than or equal to 10.

### Claim 26 (depends on 23)

The composition of claim 23, wherein the biodegradable polymer comprises at least one member selected from poly-lactide, poly-glycolide, poly-caprolactone, and copolymers and terpolymers thereof.

### Claim 27 (depends on 23)

The composition of claim 23, wherein the biodegradable polymer comprises at least one of polylactic acid and poly(lactic acid-co-glycolic acid).

### Claim 28 (depends on 23)

The composition of claim 23, wherein the hydrophobic solvent comprises at least one member selected from benzyl alcohol, methyl benzoate, ethyl benzoate, n-propyl benzoate, isopropyl benzoate, butyl benzoate, isobutyl benzoate, sec-butyl benzoate, tert-butyl benzoate, isoamyl benzoate, and benzyl benzoate.

### Claim 29 (depends on 23)

The composition of claim 23, wherein the hydrophobic solvent comprises benzyl benzoate.

### Claim 30 (depends on 23)

The composition of claim 23, wherein the vehicle further comprises benzyl alcohol.

### Claim 31 (depends on 23)

The composition of claim 23, wherein the vehicle further comprises ethanol.

### Claim 32 (depends on 23)

The composition of claim 23, wherein the counterion comprises a divalent metal, and wherein the complex further comprises one of a polymeric cationic complexing agent and a polymeric anionic complexing agent.

### Claim 33 (depends on 23)

The composition of claim 23, wherein the counterion comprises at least one member selected from protamine, poly-lysine, poly-arginine, polymyxin, carboxy-methyl-cellulose (CMC), poly-adenosine, and poly-thymine.

### Claim 34 (depends on 23)

The composition of claim 23, wherein the counterion comprises protamine.

### Claim 35 (depends on 23)

The composition of claim 23, wherein the counterion comprises a divalent metal or salt thereof.

### Claim 36 (depends on 23)

The composition of claim 23, wherein the counterion is selected from Zn2+, Mg2+, and Ca2+.

### Claim 37 (depends on 36)

The composition of claim 36, wherein the complex further comprises protamine.

### Claim 38 (depends on 23)

The composition of claim 23, wherein the counterion comprises protamine, wherein the molar ratio of the protein, peptide, nucleic acid, or low molecular weight compound and protamine is approximately 1:0.1 to 0.5.

### Claim 39 (depends on 23)

The composition of claim 23, wherein the counterion comprises zinc and protamine, wherein the molar ratio of the protein, peptide, nucleic acid, or low molecular weight compound, zinc, and protamine is approximately 1:0.4 to 2:0.1 to 0.5.

### Claim 40 (depends on 23)

The composition of claim 23, wherein the complex comprises the protein, peptide, or nucleic acid.

### Claim 41 (depends on 23)

The composition of claim 23, wherein the composition has a viscosity at 25° C. that varies less than 7% when measured at a shear rate ranging from 7 sec−1 to 500 sec−1.

### Claim 42 (depends on 23)

The composition of claim 23, wherein the complex comprises a charge-neutralized complex.