# US 9,750,736 B2 · Oxycodone formulations

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- Number: US 9,750,736 B2
- Document ID: US9750736B2
- Status: Granted
- Kind: B2
- Application number: 14/843,376
- Filed: 2015-09-02
- Published: 2016-02-04
- Granted: 2017-09-05
- Earliest claimed: 2001-05-02
- Assignees: Purdue Pharma L.P.
- Applicants: Purdue Pharma L.P.
- Inventors: Benjamin Oshlack; Curtis Wright; Derek Prater
- Web page: https://patentgrep.com/patent/US9750736B2

## CPC

- A61K 31/485: Morphinan derivatives, e.g. morphine, codeine
- A61K 9/0004: {Osmotic delivery systems; Sustained release driven by osmosis, thermal energy or gas}
- A61K 9/1617: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/1635: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/2027: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/2031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers}
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 9/2086: {Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat (active cores with a complete drug-free outer coat A61K9/28)}
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61K 9/2018: {Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates}
- 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 invention is directed to sustained release formulations containing oxycodone or a pharmaceutically acceptable salt thereof which provide a mean C24/Cmax oxycodone ratio of 0.6 to 1.0 or 0.7 to 1 after oral administration at steady state to patients and methods thereof.

## Claims

### Claim 1

A sustained-release oral dosage form comprising:
a plurality of units containing one or more active agents and one or more excipients, wherein
one of the active agents is oxycodone or a pharmaceutically acceptable salt thereof,
the excipients comprise a sustained release material comprising ethylcellulose, a methacrylic acid copolymer or a mixture thereof,
the amount of the oxycodone or pharmaceutically acceptable salt thereof in the dosage form is from about 10 mg to about 320 mg,
the dosage form provides a mean C24/Cmax oxycodone ratio of from 0.6 to 1.0 and a mean Tmax of oxycodone of about 6.5 to about 17 hours after steady state oral administration with food to humans,
the dosage form is a capsule, and
a diameter of each unit is from about 0.1 mm to about 5 mm.

### Claim 2 (depends on 1)

The dosage form of claim 1, wherein the excipients are selected from the group consisting of (i) the sustained release material; (ii) cellulose ethers, (iii) hydroxyalkylcelluloses; (iv) plasticizers; (v) talc; and (vi) antioxidants.

### Claim 3 (depends on 1)

The dosage form of claim 1, wherein the dosage form provides a mean C24/Cmax oxycodone ratio of about 0.7 to 0.99 after administration with food at steady state to said humans.

### Claim 4 (depends on 3)

The dosage form of claim 3, wherein the dosage form provides a mean C24/Cmax oxycodone ratio of 0.7 to 0.95 after administration with food at steady state to said humans.

### Claim 5 (depends on 1)

The dosage form of claim 1, wherein the dosage form provides a mean Tmax of oxycodone at about 8 to about 16 hours after administration with food at steady state to said humans.

### Claim 6

A sustained-release oral dosage form comprising a plurality of units comprising:
oxycodone or a pharmaceutically acceptable salt thereof,
a sustained release material comprising ethylcellulose, a methacrylic acid copolymer, a hydroxyalkylcellulose, or mixtures thereof, and
plasticizers,
the dosage form providing a mean C24/Cmax oxycodone ratio of 0.6 to 1.0 and a mean Tmax of oxycodone of about 6.5 to about 17 hours after steady state oral administration to humans,
wherein the amount of the oxycodone or pharmaceutically acceptable salt thereof in the dosage form is from about 10 mg to about 320 mg,
the dosage form is a capsule, and
a diameter of each unit is from about 0.1 mm to about 5 mm.

### Claim 7 (depends on 6)

The dosage form of claim 6, providing a mean Tmax of oxycodone at about 8 to about 16 hours after administration at steady state to said humans.

### Claim 8 (depends on 6)

The dosage form of claim 6, providing a mean Tmax of oxycodone at about 10 to about 16 hours after administration at steady state to said humans.

### Claim 9 (depends on 6)

The dosage form of claim 6, wherein plasticizers comprise diethyl phthalate.

### Claim 10 (depends on 6)

The dosage form of claim 6, providing a mean Tmax of oxycodone at about 12 to about 16 hours after administration at steady state to said humans.

### Claim 11 (depends on 6)

The dosage form of claim 6, providing an analgesic effect for about 24 hours.

### Claim 12 (depends on 6)

The dosage form of claim 6, providing a mean C24/Cmax oxycodone ratio of 0.7 to 0.99 after administration at steady state to said humans.

### Claim 13 (depends on 6)

The dosage form of claim 6, providing a mean C24/Cmax oxycodone ratio of 0.8 to 0.95 after administration at steady state to said humans.

### Claim 14 (depends on 6)

The dosage form of claim 6, providing an in-vitro release rate of oxycodone, when measured by the USP Basket Method at 100 rpm in 900 ml aqueous buffer at a pH of between 1.6 and 7.2 at 37° C., such that from 0% to about 40% of the oxycodone is released at 1 hour, from about 8% to about 70% of the oxycodone is released at 4 hours, from about 20% to about 80% of the oxycodone is released at 8 hours, from about 30% to about 95% of the oxycodone is released at 12 hours, from about 35% to about 95% of the oxycodone is released at 18 hours, and greater than about 50% of the oxycodone is released at 24 hours.

### Claim 15 (depends on 6)

The dosage form of claim 6, wherein said oxycodone is coated with said sustained release material and plasticizers.

### Claim 16

A sustained-release oral dosage form comprising:
a plurality of units comprising oxycodone or a pharmaceutically acceptable salt thereof, a methacrylic acid copolymer and polyethylene glycol,
wherein the amount of the oxycodone or pharmaceutically acceptable salt thereof in the dosage form is from about 10 mg to about 320 mg,
the dosage form provides a mean C24/Cmax oxycodone ratio of 0.6 to 1.0 and a mean Tmax of oxycodone of about 6.5 to about 17 hours after steady state oral administration with food to humans,
the dosage form is a capsule, and
a diameter of each unit is from about 0.1 mm to about 5 mm.

### Claim 17 (depends on 16)

The dosage form of claim 16, wherein the amount of the oxycodone or pharmaceutically acceptable salt thereof in the dosage form is from about 10 mg to about 160 mg.

### Claim 18 (depends on 16)

The dosage form of claim 16, wherein the pharmaceutically acceptable salt of oxycodone is oxycodone hydrochloride.

### Claim 19 (depends on 16)

The dosage form of claim 16, wherein the dosage form provides a mean Tmax of oxycodone at about 8 to about 16 hours after administration with food at steady state to said humans.

### Claim 20 (depends on 16)

The dosage form of claim 16, wherein the dosage form provides a mean Tmax of oxycodone at about 10 to about 16 hours after administration with food at steady state to said humans.

### Claim 21 (depends on 16)

The dosage form of claim 16, wherein the dosage form provides an analgesic effect for about 24 hours.

### Claim 22 (depends on 16)

The dosage form of claim 16, wherein the dosage form provides a mean C24/Cmax oxycodone ratio of about 0.7 to 0.99 after administration with food at steady state to said humans.

### Claim 23 (depends on 16)

The dosage form of claim 16, wherein the dosage form provides a mean C24/Cmax oxycodone ratio of 0.7 to 0.95 after administration with food at steady state to said humans.

### Claim 24 (depends on 16)

The dosage form of claim 16, wherein the dosage form provides an in-vitro release rate of oxycodone, when measured by the USP Basket Method at 100 rpm in 900 ml aqueous buffer at a pH of between 1.6 and 7.2 at 37 ° C., such that from 0% to about 40% of the oxycodone is released at 1 hour, from about 8% to about 70% of the oxycodone is released at 4 hours, from about 20% to about 80% of the oxycodone is released at 8 hours, from about 30% to about 95% of the oxycodone is released at 12 hours, from about 35% to about 95% of the oxycodone is released at 18 hours, and greater than about 50% of the oxycodone is released at 24 hours.

### Claim 25 (depends on 16)

The dosage form of claim 16, wherein the units comprise talc.

### Claim 26 (depends on 1)

The dosage form of claim 1, wherein the dosage form provides an in-vitro release rate of oxycodone, when measured by the USP Basket Method at 100 rpm in 900 ml aqueous buffer at a pH of between 1.6 and 7.2 at 37 ° C., such that from 0% to about 40% of the oxycodone is released at 1 hour, from about 8% to about 70% of the oxycodone is released at 4 hours, from about 20% to about 80% of the oxycodone is released at 8 hours, from about 30% to about 95% of the oxycodone is released at 12 hours, from about 35% to about 95% at of the oxycodone is released at 18 hours, and greater than about 50% of the oxycodone is released at 24 hours.