# US 11,304,968 B2 · Pharmaceutical compositions comprising a hydroxyethylquercetin glucuronide

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,304,968 B2
- Document ID: US11304968B2
- Status: Granted
- Kind: B2
- Application number: 16/563,620
- Filed: 2019-09-06
- Published: 2020-05-21
- Granted: 2022-04-19
- Earliest claimed: 2018-11-16
- Assignees: Janssen Pharmaceutica NV
- Applicants: Janssen Pharmaceutica NV
- Inventors: Thomas M. DiMauro
- Web page: https://patentgrep.com/patent/US11304968B2

## CPC

- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 47/02: Inorganic compounds
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/186: {Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide}
- A61K 47/38: Cellulose; Derivatives thereof
- A61K 47/42: Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein (oligopeptides having up to five amino acids {A61K47/183}; polyamino acids A61K47/34)
- A61K 47/46: Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
- A61P 25/24: Antidepressants
- A61K 9/4866: {Organic macromolecular compounds}
- 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

Disclosed herein are hydroxyethylquercetin glycosides, including compounds of Structural Formulas I, II, III and IV. The compounds disclosed are useful for inhibiting norepinephrine metabolism and treating antenatal and postnatal depression in subjects in need thereof.

## Claims

### Claim 1

A pharmaceutical composition comprising from about 5% to about 95% weight/weight of a hydroxyethylquercetin-O-glucuronide, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1, wherein the composition is formulated for oral administration.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1, further comprising a second acid.

### Claim 4 (depends on 3)

The pharmaceutical composition of claim 3, wherein the second acid is citric acid or hydrochloric acid or a combination thereof.

### Claim 5 (depends on 1)

The pharmaceutical composition of claim 1, wherein the hydroxyethylquercetin-O-glucuronide is a hydroxyethylquercetin-3-O-glucuronide.

### Claim 6

A pharmaceutical composition comprising from about 5% to about 95% weight/weight of a hydroxyethylquercetin-5-O-glucuronide, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

### Claim 7

A pharmaceutical composition comprising from about 5% to about 95% weight/weight of a hydroxyethylquercetin-3′-O-glucuronide, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

### Claim 8

A pharmaceutical composition comprising from about 5% to about 95% weight/weight of a hydroxyethylquercetin-4′-O-glucuronide, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

### Claim 9

A pharmaceutical composition comprising from about 5% to about 95% weight/weight of a monohydroxyethylquercetin-O-glucuronide, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

### Claim 10 (depends on 9)

The pharmaceutical composition of claim 9, wherein the monohydroxyethylquercetin-O-glucuronide is a mono-3′-O-hydroxyethyl quercetin-O-glucuronide.

### Claim 11

A pharmaceutical composition comprising a mono-4′-O-hydroxyethylquercetin-O-glucuronide, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

### Claim 12 (depends on 1)

A method of inhibiting norepinephrine metabolism in a subject in need thereof, comprising:
administering to the subject an effective amount of the pharmaceutical composition of claim 1.

### Claim 13 (depends on 12)

The method of claim 12, wherein the administering is orally administering.

### Claim 14 (depends on 12)

The method of claim 12, further comprising administering an acidifier.

### Claim 15 (depends on 14)

The method of claim 14, wherein the acidifier is betaine, or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 14)

The method of claim 14, wherein the acidifier is acidic liquid media.

### Claim 17 (depends on 16)

The method of claim 16, wherein the acidic liquid media has a pH of less than about 3.

### Claim 18 (depends on 17)

The method of claim 17, wherein the acidic liquid media comprises citric acid, acetic acid, or hydrochloric acid, or a combination of any of the foregoing.

### Claim 19 (depends on 16)

The method of claim 16, wherein the acidic liquid media comprises vinegar or a citrus juice, or a combination of the foregoing.