# US 11,439,591 B2 · Moxifloxacin and triamcinolone compositions and associated methods

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- Number: US 11,439,591 B2
- Document ID: US11439591B2
- Status: Granted
- Kind: B2
- Application number: 17/686,368
- Filed: 2022-03-03
- Published: 2022-06-16
- Granted: 2022-09-13
- Earliest claimed: 2020-08-26
- Assignees: Somerset Therapeutics, LLC
- Applicants: Somerset Therapeutics, LLC
- Inventors: Mandar V. Shah; Ilango Subramanian; Veerappan Subramanian; Aman Trehan
- Web page: https://patentgrep.com/patent/US11439591B2

## CPC

- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 31/4709: Non-condensed quinolines and containing further heterocyclic rings
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 47/183: {Amino acids, e.g. glycine, EDTA or aspartame}
- 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 47/36: Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K 47/38: Cellulose; Derivatives thereof
- A61P 27/02: Ophthalmic agents
- A61P 31/04: Antibacterial agents
- 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

Provided here are new ophthalmologically suitable pharmaceutical compositions comprising an effective amount of a moxifloxacin compound and an effective amount of a triamcinolone compound. In aspects, the compositions are stable suspensions, which maintain physical stability and chemical stability for extended periods of time (e.g., exhibiting no sustained flocculation, coagulation, or clumping after several months of storage under typical storage conditions). In aspects, the compositions are suspensions that include a suspension component comprising one or more suspension agents. In aspects, the suspension component includes an ionic suspension agent. In aspects, the composition also or alternatively comprises a non-ionic surfactant, non-ionic suspension agent, or both, or an agent that provides both functions. Further described are related compositions and methods of making and using such compositions, e.g., in the treatment of eye infections.

## Claims

### Claim 1

An ophthalmologically suitable pharmaceutical composition in the form of a suspension comprising: (a) an effective amount of at least one ionic suspension agent, wherein the at least one ionic suspension agent is at least mostly composed of a hyaluronic acid component; (b) an effective amount of at least one non-ionic suspension agent; and (c) at least two pharmaceutical ingredients comprising (1) moxifloxacin or a pharmaceutically acceptable salt thereof in a range of about 0.01% to about 0.5% by weight, and (2) triamcinolone or a pharmaceutically acceptable salt thereof in a range of about 0.1% to about 5% by weight, wherein the composition does not comprise hydroxypropyl methylcellulose.

### Claim 2 (depends on 1)

The composition of claim 1, wherein at least one ionic suspension agent in the composition is not a solubilizing agent.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the composition comprises only a single ionic suspension agent.

### Claim 4 (depends on 1)

The composition of claim 1, wherein at least one non-ionic suspension agent is also a non-ionic surfactant.

### Claim 5 (depends on 4)

The composition of claim 4, wherein the non-ionic surfactant comprises an effective amount of a polysorbate, a polyoxyl-ethylated castor oil, or a combination thereof.

### Claim 6 (depends on 5)

The composition of claim 5, wherein the non-ionic surfactant comprises an effective amount of polysorbate 80.

### Claim 7 (depends on 6)

The composition of claim 6, wherein polysorbate 80 is present in the composition in a concentration of about 5 mg/mL to about 15 mg/mL.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the ratio of moxifloxacin or pharmaceutically acceptable salt thereof to the combination of the at least one ionic suspension agent and the at least one non-ionic suspension agent is about 1:10 to about 1:32.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the ratio of the at least one ionic suspension agent to the at least one non-ionic suspension agent is about 1:8 to about 4:1.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the composition comprises a pharmaceutically acceptable chelating agent in a concentration of about 0.1 mg/mL to about 0.5 mg/mL.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the chelating agent is disodium edetate.

### Claim 12 (depends on 10)

The composition of claim 10, wherein the pharmaceutically acceptable chelating agent is a chelating agent which results in a significantly similar or improved stability of the moxifloxacin or pharmaceutically acceptable salt thereof and triamcinolone or pharmaceutically acceptable salt thereof as compared to disodium edetate in a concentration of about 0.1 mg/mL to about 0.5 mg/mL.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the composition comprises hyaluronic acid in a concentration of about 2 mg/mL to about 20 mg/mL.

### Claim 14 (depends on 1)

The composition of claim 1, wherein the average molecular weight of most of the hyaluronic acid in the composition is about 360 kDa to about 1200 kDa.

### Claim 15 (depends on 13)

The composition of claim 13, wherein the composition further comprises chondroitin sulfate in a concentration of about 5 mg/mL to about 50 mg/mL.

### Claim 16 (depends on 1)

The composition of claim 1, wherein (a) the concentration of moxifloxacin or pharmaceutically acceptable salt thereof is about 0.1% by weight, (b) the concentration of triamcinolone or pharmaceutically acceptable salt thereof is about 1.5% by weight, or (c) the concentration of moxifloxacin or pharmaceutically acceptable salt thereof is about 0.1% by weight and the concentration of triamcinolone or pharmaceutically acceptable salt thereof is about 1.5% by weight.

### Claim 17 (depends on 1)

The composition of claim 1, wherein the osmolality of the composition is about 200 mOsm/kg to about 350 mOsm/kg.

### Claim 18 (depends on 1)

The composition of claim 1, wherein the composition comprises an effective amount of a polyoxyl-ethylated castor oil solubilizing agent.

### Claim 19 (depends on 18)

The composition of claim 18, wherein the polyoxyl-ethylated castor oil is present in an amount of about 0.1% to about 1% by weight.

### Claim 20 (depends on 1)

The composition of claim 1, wherein the composition is formulated for injection and contained in an injection delivery device, a device adapted for injection delivery, or is packaged with an injection delivery device.

### Claim 21 (depends on 20)

The composition of claim 20, wherein the composition is free of an effective amount of any non-ionic polyoxyethylene-polyoxypropylene block copolymer having the following chemical structure —HO—(CH2-CH2-O)x-(C3H6-O)y-(CH2-CH2-O)x-H, wherein x is an integer having a value of at least 8 and y is an integer having a value of at least 38.

### Claim 22 (depends on 20)

The composition of claim 20, wherein the composition is free of an effective amount of any non-ionic polyoxyethylene-polyoxypropylene block copolymer.

### Claim 23 (depends on 1)

The composition of claim 1, wherein the composition is free of an effective amount of any non-ionic polyoxyethylene-polyoxypropylene block copolymer having the following chemical structure —HO—(CH2-CH2-O)x-(C3H6-O)y-(CH2-CH2-O)x-H, wherein x is an integer having a value of at least 8 and y is an integer having a value of at least 38.

### Claim 24 (depends on 1)

The composition of claim 1, wherein the composition is free of an effective amount of any non-ionic polyoxyethylene-polyoxypropylene block copolymer.

### Claim 25 (depends on 1)

The composition of claim 1, wherein the moxifloxacin or pharmaceutically acceptable salt thereof and the triamcinolone or pharmaceutically acceptable salt thereof in the composition do not exhibit significant sustained flocculation, clumping, or coagulation after more than three months of storage at 25° C. and 60% relative humidity or at 40° C. and 75% relative humidity.

### Claim 26

An ophthalmologically suitable pharmaceutical composition in the form of a suspension comprising: (a) an effective amount of at least one ionic suspension agent wherein the at least one ionic suspension agent is at least mostly composed of a hyaluronic acid component; (b) an effective amount of at least one non-ionic suspension agent; and (c) at least two pharmaceutical ingredients comprising (1) an effective amount of moxifloxacin or a pharmaceutically acceptable salt thereof, and (2) an effective amount of triamcinolone or a pharmaceutically acceptable salt thereof, wherein the composition does not comprise any block copolymer of poly (ethylene oxide) and poly (propylene oxide).

### Claim 27 (depends on 26)

The composition of claim 26, wherein the composition comprises only a single ionic suspension agent.

### Claim 28 (depends on 27)

The composition of claim 27, wherein at least one non-ionic suspension agent is also a non-ionic surfactant.

### Claim 29 (depends on 28)

The composition of claim 28, wherein the non-ionic surfactant comprises an effective amount of a polysorbate, a polyoxyl-ethylated castor oil, or a combination thereof.

### Claim 30 (depends on 26)

The composition of claim 26, wherein the ratio of moxifloxacin or pharmaceutically acceptable salt thereof to the combination of the at least one ionic suspension agent and the at least one non-ionic suspension agent is about 1:10 to about 1:32 and the ratio of the ionic suspension agent to the non-ionic suspension agent is about 1:8 to about 4:1.

### Claim 31 (depends on 26)

The composition of claim 26, wherein the composition comprises hyaluronic acid in a concentration of about 2 mg/mL to about 20 mg/mL.

### Claim 32 (depends on 26)

The composition of claim 26, wherein the average molecular weight of most of the hyaluronic acid in the composition is about 360 kDa to about 1200 kDa.

### Claim 33 (depends on 26)

The composition of claim 26, wherein the osmolality of the composition is about 200 mOsm/kg to about 350 mOsm/kg.