# US 11,110,093 B2 · Sustained release small molecule drug formulation

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- Number: US 11,110,093 B2
- Document ID: US11110093B2
- Status: Granted
- Kind: B2
- Application number: 16/511,210
- Filed: 2019-07-15
- Published: 2020-02-13
- Granted: 2021-09-07
- Earliest claimed: 2005-09-30
- Assignees: Indivior UK Limited
- Applicants: Indivior UK Limited
- Inventors: Andrew S. Luk; Gunjan H. Junnarkar; Guohua Chen
- Web page: https://patentgrep.com/patent/US11110093B2

## CPC

- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- 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 9/0024: {Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L)}
- A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)}
- A61K 9/1617: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/1647: {Polyesters, e.g. poly(lactide-co-glycolide)}
- A61K 31/341: not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- 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 51/1213: {Semi-solid forms, gels, hydrogels, ointments, fats and waxes that are solid at room temperature}
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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

An injectable depot formulation includes a biocompatible polymer, an organic solvent combined with the biocompatible polymer to form a viscous gel, and a small molecule drug incorporated in the viscous gel such that the formulation exhibits an in vivo release profile having a Cmax to Cmin ratio of less than 200 and a lag time less than 0.2.

## Claims

### Claim 1

An injectable pharmaceutical composition comprising from about 10 wt % to about 30 wt % of risperidone base suspended in a gel comprising: (i) from about 40 wt % to about 60 wt % of a copolymer of lactic acid and glycolic acid, wherein the lactic acid to glycolic acid monomer ratio is from about 100:0 to about 60:40, and wherein the copolymer has a number average molecular weight from about 5,000 Daltons to about 30,000 Daltons, and (ii) benzyl benzoate, benzyl alcohol, ethyl benzoate, triacetin, N-methyl-2-pyrrolidone, or a combination of two or more thereof.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the gel consists of (i) and (ii).

### Claim 3

An injectable pharmaceutical composition comprising from about 1 wt % to about 50 wt % of risperidone base suspended in a gel comprising: (i) from about 5 wt % to about 80 wt % of a copolymer of lactic acid and glycolic acid, and (ii) benzyl benzoate, benzyl alcohol, ethyl benzoate, triacetin, N-methyl-2-pyrrolidone, or a combination of two or more thereof.

### Claim 4 (depends on 3)

The composition of claim 3, comprising from about 5 wt % to about 40 wt % of risperidone base.

### Claim 5 (depends on 4)

The composition of claim 4, comprising from about 5 wt % to about 30 wt % of risperidone base.

### Claim 6 (depends on 5)

The composition of claim 5, comprising from about 10 wt % to about 30 wt % of risperidone base.

### Claim 7 (depends on 3)

The composition of claim 3, wherein the gel comprises: (i) from about 20 wt % to about 70 wt % of a copolymer of lactic acid and glycolic acid, and (ii) benzyl benzoate, benzyl alcohol, ethyl benzoate, triacetin, N-methyl-2-pyrrolidone, or a combination of two or more thereof.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the gel comprises: (i) from about 40 wt % to about 60 wt % of a copolymer of lactic acid and glycolic acid, and (ii) benzyl benzoate, benzyl alcohol, ethyl benzoate, triacetin, N-methyl-2-pyrrolidone, or a combination of two or more thereof.

### Claim 9 (depends on 3)

The composition of claim 3, wherein the lactic acid to glycolic acid monomer ratio in the copolymer is from about 100:0 to 60:40.

### Claim 10 (depends on 9)

The composition of claim 9, wherein the lactic acid to glycolic acid monomer ratio in the copolymer is from about 100:0 to 75:25.

### Claim 11 (depends on 3)

The composition of claim 3, wherein the copolymer has a number average molecular weight from about 1,000 Daltons to about 120,000 Daltons.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the copolymer has a number average molecular weight from about 5,000 Daltons to about 30,000 Daltons.

### Claim 13 (depends on 3)

The composition of claim 3, wherein the gel consists of (i) and (ii).

### Claim 14

An injectable pharmaceutical composition comprising risperidone base suspended in a gel comprising: (i) a copolymer of lactic acid and glycolic acid, and (ii) benzyl benzoate, benzyl alcohol, ethyl benzoate, triacetin, N-methyl-2-pyrrolidone, or a combination of two or more thereof.

### Claim 15 (depends on 1)

A method of administering risperidone base to a subject in need thereof, the method comprising subcutaneously injecting the composition of claim 1 into the subject once per month.

### Claim 16 (depends on 3)

A method of administering risperidone base to a subject in need thereof, the method comprising subcutaneously injecting the composition of claim 3 into the subject once per month.

### Claim 17 (depends on 14)

A method of administering risperidone base to a subject in need thereof, the method comprising subcutaneously injecting the composition of claim 14 into the subject once per month.

### Claim 18 (depends on 1)

A syringe comprising the composition of claim 1.

### Claim 19 (depends on 3)

A syringe comprising the composition of claim 3.

### Claim 20 (depends on 14)

A syringe comprising the composition of claim 14.