# US 10,945,947 B2 · Formulations for intravenous administration

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- Number: US 10,945,947 B2
- Document ID: US10945947B2
- Status: Granted
- Kind: B2
- Application number: 16/701,729
- Filed: 2019-12-03
- Published: 2020-07-02
- Granted: 2021-03-16
- Earliest claimed: 2015-11-30
- Assignees: GlaxoSmithKline Intellectual Property (No. 2) Limited
- Applicants: Glaxosmithkline Intellectual Property (No.2) Limited
- Inventors: Rachel Apfelbaum; Andrew James Peat; Yoon Oh
- Web page: https://patentgrep.com/patent/US10945947B2

## CPC

- 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 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 9/19: lyophilised {, i.e. freeze-dried, solutions or dispersions (lyophilised products with subsequent particle size reduction A61K9/14; granules or pellets made by lyphilisation A61K9/1682; solid oral dosage forms made by lyophilisation A61K9/2095; lyophilisation additives A61K47/00)}
- A61K 31/4462: only substituted in position 3
- A61K 47/02: Inorganic compounds
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- 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 47/40: Cyclodextrins; Derivatives thereof
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 31/16: for influenza or rhinoviruses
- 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 invention relates to an improved formulation of danirixin in its hydrobromide salt form. This improved formulation can be an aqueous intravenous formulation containing danirixin or a lyophilized pharmaceutical solid composition containing danirixin to be reconstituted to provide a solution for intravenous administration.

## Claims

### Claim 1

A pharmaceutical composition comprising:
danirixin in its hydrobromide salt form; and one or more pharmaceutically acceptable excipients comprising: sulfobutyl ether-β-cyclodextrin, mannitol, and a citrate buffer.

### Claim 2 (depends on 1)

The pharmaceutical composition according to claim 1, wherein danirixin has the structure:

### Claim 3 (depends on 1)

The pharmaceutical composition according to claim 1, wherein danirixin has the structure:

### Claim 4 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the composition is an aqueous composition.

### Claim 5 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the composition is an aqueous composition suitable for intravenous administration.

### Claim 6 (depends on 3)

The pharmaceutical composition according to claim 3, wherein the composition has a pH that ranges from 3.5 to 4.5.

### Claim 7 (depends on 6)

The pharmaceutical composition according to claim 6, wherein the pH is about 4.

### Claim 8 (depends on 1)

A process for the preparation of the pharmaceutical composition according to claim 1 comprising mixing danirixin with the excipients.

### Claim 9 (depends on 6)

The pharmaceutical composition according to claim 6, which is freeze-dried to form a lyophilized powder.

### Claim 10 (depends on 1)

A method of treating an infectious disease comprising administering to a subject in need thereof the pharmaceutical composition according to claim 1.

### Claim 11 (depends on 10)

The method according to claim 10, wherein the infectious disease is a viral disease.

### Claim 12 (depends on 11)

The method according to claim 11 wherein the infectious disease is influenza or respiratory syncytial virus.

### Claim 13 (depends on 11)

The method according to claim 11, wherein the infectious disease is influenza.

### Claim 14 (depends on 1)

The pharmaceutical composition according to claim 1 having the formulation as shown in the table below:
COMPOSITION
Formula
Unit Formula,
(HBr lyophilized
(mg/mL)
Nominal Fill
formulation)
2 mg/mL
(mg/13 mL)
Danirixin, HBr. ACTIVE
2.46
mg*
31.98
mg
SUBSTANCE
B-CYCLODEXTRIN
40.0
mg
520.0
mg
SULFOBUTYLETHER
MANNITOL
50
mg
650.0
mg
CITRIC ACID
0.655
mg
8.515
mg
SODIUM CITRATE
0.555
mg
7.215
mg
SODIUM HYDROXIDE
QS
QS
HYDROCHLORIC
QS
QS
ACID
pH
3.9
—
QS refers to “quantity sufficient” to fill the vial to the nominal fill (or volume);
*indicates 2 mg/mL that has been adjusted for the salt factor of 1.228 = 2.46 mg/mL.