# US 11,077,077 B1 · Therapeutic compounds, formulations, and uses thereof

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- Number: US 11,077,077 B1
- Document ID: US11077077B1
- Status: Granted
- Kind: B1
- Application number: 17/203,639
- Filed: 2021-03-16
- Published: 2021-07-29
- Granted: 2021-08-03
- Earliest claimed: 2020-01-24
- Assignees: Tvardi Therapeutics, Inc.
- Applicants: Tvardi Therapeutics, Inc.
- Inventors: Imran Alibhai; Sofia De Achaval; Beverly C. Langevin; Tian Zhou
- Web page: https://patentgrep.com/patent/US11077077B1

## CPC

- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 31/18: Sulfonamides (compounds containing a para-N-benzene-sulfonyl-N- group A61K31/63)
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/1635: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/4825: {Proteins, e.g. gelatin (gelatin capsule shells with substantial amounts of other macromolecular substances A61K9/4816)}
- A61K 9/4858: {Organic compounds}
- A61K 9/4866: {Organic macromolecular compounds}
- A61K 9/4875: {Compounds of unknown constitution, e.g. material from plants or animals (oils, fats, waxes, shellac A61K9/4858)}
- A61K 9/5138: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- 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 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Provided herein are compositions, formulations, and (e.g., oral) dosage forms comprising a compound of Formula (I). In specific instances, such compositions comprise an emulsifier, a solubilizer, a polyethylene glycol, a surfactant, and an antioxidant. In some instances, such compositions are useful for the treatment of fibrosis, cancer, and/or chronic inflammation.

## Claims

### Claim 1

A pharmaceutical composition comprising:
a. at least 50 mg of a compound of Formula (I):
b. a glyceride emulsifier present in the composition in a weight ratio of compound of Formula (I) to emulsifier of about 1:1;
c. a solubilizer present in the composition in a weight ratio of compound of Formula (I) to solubilizer of about 1:3, wherein the solubilizer is polyoxyl castor oil;
d. a polyethylene glycol (PEG) present in the composition in a weight ratio of compound of Formula (I) to polyethylene glycol of about 1:4;
e. a surfactant present in the composition in a weight ratio of compound of Formula (I) to surfactant of about 1:2, wherein the surfactant is polysorbate; and
f. an antioxidant present in the composition in a weight ratio of compound of Formula (I) to antioxidant of about 20:1.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1, wherein the polyoxyl castor oil is PEG-40 hydrogenated castor oil.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1, wherein the PEG has an average molecular weight of about 200 to about 1000 Da.

### Claim 4 (depends on 1)

The pharmaceutical composition of claim 1, wherein the polysorbate is polysorbate 20.

### Claim 5 (depends on 1)

The pharmaceutical composition of claim 1, wherein the antioxidant is citric acid.

### Claim 6 (depends on 1)

The pharmaceutical composition of claim 1, wherein at least 50 mg of the glyceride emulsifier, at least 150 mg of the solubilizer, at least 200 mg PEG, at least 100 mg of surfactant, and at least 2.5 mg of the antioxidant are present in the pharmaceutical composition.

### Claim 7 (depends on 1)

An oral dosage form comprising the pharmaceutical composition of claim 1 contained within a capsule.

### Claim 8 (depends on 7)

A method of treating cancer in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 9 (depends on 8)

The method of claim 8, wherein the cancer is head and neck cancer, lung cancer, liver cancer, breast cancer, ovarian cancer, colon cancer, multiple myeloma, prostate cancer, cervical cancer, brain cancer, pancreatic cancer, myelodysplastic syndrome, leukemia, lymphoma, neuroblastoma, kidney cancer, or metastatic melanoma.

### Claim 10 (depends on 8)

The method of claim 8, wherein the cancer is head and neck cancer, lung cancer, liver cancer, breast cancer, ovarian cancer, colon cancer, multiple myeloma, leukemia, or pancreatic cancer.

### Claim 11 (depends on 7)

A method of treating fibrosis in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 12 (depends on 11)

The method of claim 11, wherein the fibrosis is associated with pulmonary fibrosis, intestine fibrosis, pancreatic fibrosis, joint fibrosis, liver fibrosis, retroperitoneal fibrosis, myelofibrosis, dermal fibrosis, non-alcoholic fatty liver disease, steatohepatitis, or systemic sclerosis.

### Claim 13 (depends on 11)

The method of claim 11, wherein the fibrosis is associated with pulmonary fibrosis, non-alcoholic fatty liver disease, steatohepatitis, or systemic sclerosis.

### Claim 14 (depends on 7)

A method of treating chronic inflammation in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 15 (depends on 7)

A method of treating chemotherapy-induced peripheral neuropathy in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 16 (depends on 7)

A method of treating diabetic neuropathy in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 17 (depends on 7)

A method of treating familial amyloid polyneuropathy in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 18 (depends on 7)

A method of treating cachexia in an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.

### Claim 19 (depends on 7)

A method of treating anaphylaxis an individual in need thereof, the method comprising administering to the individual the oral dosage form of claim 7.