# US 11,433,051 B2 · ST-246 (tecovirimat monohydrate) suspension formulations

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- Number: US 11,433,051 B2
- Document ID: US11433051B2
- Status: Granted
- Kind: B2
- Application number: 16/071,119
- Filed: 2017-02-15
- Published: 2021-07-15
- Granted: 2022-09-06
- Earliest claimed: 2016-02-16
- Assignees: Siga Technologies, Inc.
- Applicants: Siga Technologies, Inc.
- Inventors: Shanthakumar R. Tyavanagimatt; Kris Holt; Ying Tan; Melialani A. C. L. S. Anderson; Dennis E. Hruby
- Web page: https://patentgrep.com/patent/US11433051B2

## CPC

- A61K 31/403: condensed with carbocyclic rings, e.g. carbazole
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/0095: {Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches (A61K9/0007 takes precedence; eatable gels or foams A61K9/0056; oral mucosa adhesive forms A61K9/006)}
- A61K 9/143: {with inorganic compounds}
- A61K 9/146: {with organic macromolecular compounds}
- A61K 9/16: Agglomerates; Granulates; Microbeadlets {; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction (A61K9/20 takes precedence if the final form is a tablet; microspheres with drug-free outer coating, microcapsules A61K9/50; mixture of different granules, microcapsules, (coated) microparticles A61K9/5084; nanoparticles A61K9/51)}
- 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 47/34: 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 47/38: Cellulose; Derivatives thereof
- A61P 31/12: Antivirals
- A61P 31/20: for DNA viruses
- 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 is directed to a dry suspension for reconstitution containing Tecovirimat (ST-246) powder and simethicone. The dry suspension is dispersed in water to provide an aqueous pharmaceutical suspension formulation for oral administration for treating orthopoxvirus infections and/or eczema vaccinatum. The suspension formulation exhibits excellent stability and good dissolution and has an improved taste and texture.

## Claims

### Claim 1

A dry suspension comprising polymorph Form I of 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2-(1H)-yl)-benzamide (Tecovirimat (ST-246)) and simethicone.

### Claim 2 (depends on 1)

A dry suspension according to claim 1 further comprising at least one suspending agent.

### Claim 3 (depends on 2)

A dry suspension according to claim 2 wherein the suspending agent is methylcellulose or hydroxypropyl cellulose.

### Claim 4 (depends on 3)

A dry suspension according to claim 3 wherein the methylcellulose is methylcellulose 400 Cps; or wherein the methylcellulose is 15 Cps.

### Claim 5 (depends on 2)

A dry suspension according to claim 2 comprising methylcellulose and hydroxypropyl cellulose.

### Claim 6 (depends on 1)

A dry suspension according to claim 1 further comprising one or more of a lubricant, an excipient, an antifoaming agent, a sweetener, and/or a flavoring.

### Claim 7 (depends on 6)

A dry suspension according to claim 6 wherein the lubricant is magnesium stearate and/or wherein the excipient is lactose monohydrate.

### Claim 8 (depends on 1)

A dry suspension according to claim 1 wherein the ST-246 is micronized; or wherein the ST-246 is granulated.

### Claim 9 (depends on 1)

A dry suspension according to claim 1 wherein the simethicone is granular form; or wherein the simethicone is in liquid form and adsorbed on lactose monohydrate.

### Claim 10 (depends on 1)

A dry suspension according to claim 1 comprising one or more of 10 to 70 wt % of ST-246; 0.2 to 6.0 wt % simethicone; 1 to 5 wt % methylcellulose; 1.0 to 30 wt % hydroxypropylcellulose; 0.1 to 1.0 wt % of lubricant; 10 to 20 wt % of excipient; 1.0 to 3.0 wt % of sweetener; and/or 0.1 to 1.0 wt % of flavoring.

### Claim 11 (depends on 1)

A dry suspension according to claim 1 wherein the particle size of ST-246 is 0.5 to 10 μm.

### Claim 12 (depends on 1)

An aqueous pharmaceutical suspension formulation comprising a dry suspension according to claim 1 and water; wherein the aqueous pharmaceutical suspension formulation optionally further comprises a pharmaceutically acceptable ingredient.

### Claim 13 (depends on 12)

A formulation according to claim 12 wherein the pharmaceutically acceptable ingredient is selected from the group consisting of carrier, excipient, diluent, additive, filler, lubricant and binder.

### Claim 14 (depends on 12)

A formulation according to claim 12 having a pH between 4 and 7.

### Claim 15 (depends on 12)

A method of treating orthopoxvirus infections and/or eczema vaccinatum comprising oral administration to a subject in need thereof a formulation according to claim 12.

### Claim 16 (depends on 15)

The method of claim 15, wherein the subject is administered 400 mg to 2000 mg daily of ST-246.

### Claim 17 (depends on 1)

A process of making the dry suspension according to claim 1 comprising mixing ST-246 with simethicone and optionally at least one suspending agent, at least one lubricant, at least one excipient, at least one further anti-foaming agent, at least one sweetener and/or at least one flavoring.

### Claim 18 (depends on 17)

A process according to claim 17 wherein the mixing is carried out using geometric mixing.

### Claim 19 (depends on 12)

A method of making the formulation according to claim 12 comprising dispersing the dry suspension in water; wherein the water optionally contains a suspending agent.