# US 11,992,470 B2 · Stable aqueous capsaicin injectable formulations and medical uses thereof

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- Number: US 11,992,470 B2
- Document ID: US11992470B2
- Status: Granted
- Kind: B2
- Application number: 17/701,160
- Filed: 2022-03-22
- Published: 2022-07-07
- Granted: 2024-05-28
- Earliest claimed: 2016-11-02
- Assignees: Centrexion Therapeutics Corporation
- Applicants: Centrexion Therapeutics Corporation
- Inventors: Drazen Ostovic; Gary Fred Musso
- Web page: https://patentgrep.com/patent/US11992470B2

## CPC

- A61K 31/165: having aromatic rings, e.g. colchicine, atenolol, progabide
- 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 31/05: Phenols {(cannabinoids A61K31/658)}
- A61K 31/167: having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- 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 47/547: {Chelates, e.g. Gd-DOTA or Zinc-amino acid chelates; Chelate-forming compounds, e.g. DOTA or ethylenediamine being covalently linked or complexed to the pharmacologically- or therapeutically-active agent}
- A61K 47/55: the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 29/02: without antiinflammatory effect
- 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 provides stable, aqueous capsaicin injectable formulations, a unit dose containing such injectable formulations, medical kits, and methods for using such injectable formulations and unit doses to treat patients suffering from pain, such as osteoarthritic knee pain. The stable, aqueous capsaicin injectable formulations may contain, for example, capsaicin, a solubilizing agent (e.g., a polyethylene glycol ester of a (C15-C25) hydroxyalkanoic acid), an antioxidant, and water.

## Claims

### Claim 1

An aqueous, capsaicin injectable formulation, comprising
a. 0.04% (w/w) to 0.06% (w/w) of capsaicin;
b. 0.5% (w/w) to 1.5% (w/w) of a solubilizing agent, wherein the solubilizing agent comprises
and polyethylene glycol;
c. 0.005% (w/w) to 0.015% (w/w) of an antioxidant;
d. 0.2% (w/w) to 1% (w/w) of an alkali metal acetate;
e. 0.01% (w/w) to 0.05% (w/w) of a chelating agent;
f. 0.3% (w/w) to 0.9% (w/w) of a tonicity modifier;
g. at least 96% (w/w) water; and
having a pH of 5.5;
wherein the formulation does not contain of any phospholipid, polysaccharide, protein polymer, cellulose, sorbitan ester, histidine, or polyvinylpyrrolidone polymer.

### Claim 2 (depends on 1)

The formulation of claim 1, wherein the solubilizing agent comprises (a) from 68% (w/w) to 72% (w/w) of a mixture of
and (b) from 28% (w/w) to 32% (w/w) polyethylene glycol.

### Claim 3 (depends on 1)

The formulation of claim 1, wherein any polyethylene glycol or polyethylene glycolyl each independently have a weight-average molecular weight in the range of 300 g/mol to 900 g/mol.

### Claim 4 (depends on 1)

The formulation of claim 1, wherein any polyethylene glycol or polyethylene glycolyl each independently have a weight-average molecular weight in the range of 600 g/mol to 750 g/mol.

### Claim 5 (depends on 2)

The formulation of claim 2, wherein any polyethylene glycol or polyethylene glycolyl each independently have a weight-average molecular weight in the range of 600 g/mol to 750 g/mol.

### Claim 6 (depends on 1)

The formulation of claim 1, wherein any polyethylene glycol or polyethylene glycolyl each independently have a weight-average molecular weight of about 660 g/mol.

### Claim 7 (depends on 2)

The formulation of claim 2, wherein any polyethylene glycol or polyethylene glycolyl each independently have a weight-average molecular weight of about 660 g/mol.

### Claim 8 (depends on 1)

The formulation of claim 1, wherein the formulation has an osmolality in the range of from about 240 mOsm/kg to about 340 mOsm/kg.

### Claim 9 (depends on 5)

The formulation of claim 5, wherein the formulation has an osmolality in the range of from about 240 mOsm/kg to about 340 mOsm/kg.

### Claim 10 (depends on 1)

The formulation of claim 1, wherein less than 0.5% of the capsaicin degrades upon storage of the formulation at 25° C. for 24 weeks.

### Claim 11 (depends on 2)

The formulation of claim 2, wherein less than 0.5% of the capsaicin degrades upon storage of the formulation at 25° C. for 24 weeks.

### Claim 12 (depends on 5)

The formulation of claim 5, wherein less than 0.5% of the capsaicin degrades upon storage of the formulation at 25° C. for 24 weeks.

### Claim 13 (depends on 9)

The formulation of claim 9, wherein less than 0.5% of the capsaicin degrades upon storage of the formulation at 25° C. for 24 weeks.

### Claim 14 (depends on 1)

The formulation of claim 1, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 6000 particles having an average diameter of ≥10 μm.

### Claim 15 (depends on 1)

The formulation of claim 1, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 3000 particles having an average diameter of ≥10 μm.

### Claim 16 (depends on 1)

The formulation of claim 1, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 1000 particles having an average diameter of ≥10 μm.

### Claim 17 (depends on 5)

The formulation of claim 5, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 1000 particles having an average diameter of ≥10 μm.

### Claim 18 (depends on 1)

The formulation of claim 1, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 500 particles having an average diameter of ≥10 μm.

### Claim 19 (depends on 5)

The formulation of claim 5, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 500 particles having an average diameter of ≥10 μm.

### Claim 20 (depends on 13)

The formulation of claim 13, wherein a 2 mL aliquot of the formulation that has been stored at 25° C. and 60% Relative Humidity for a duration of 3 months contains less than 500 particles having an average diameter of ≥10 μm.