# US 2019/0169150 A1 · Compounds, compositions and methods for treating or preventing a symptom associated with gout or hyperuricemia

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- Number: US 2019/0169150 A1
- Document ID: US20190169150A1
- Status: Published application
- Kind: A1
- Application number: 16/268,367
- Filed: 2019-02-05
- Published: 2019-06-06
- Earliest claimed: 2016-07-18
- Assignees: Arthrosi Therapeutics, Inc.
- Applicants: Arthrosi Therapeutics, Inc.
- Inventors: Shunqi YAN; Li-Tain YEH; Robert ORR
- Web page: https://patentgrep.com/patent/US20190169150A1

## CPC

- C07D 307/80: Radicals substituted by oxygen atoms
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 19/06: Antigout agents, e.g. antihyperuricemic or uricosuric agents
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The inventive subject matter provides compounds, compositions and methods for lowering serum acid (sUA) for the treatment of gout, and having reduced liver toxicity, associated with CYP2C9 metabolic pathway.

## Claims

### Claim 1

A method of treating hyperuricemia or gout in a mammal, comprising administering to the mammal a therapeutically effective amount of a compound of Formula 1, or a pharmaceutically acceptable salt thereof:
wherein:
X is —OH, —F, or —Cl; and
R1, R2, R3, R4 and R5 are each independently selected from a group consisting of H, deuterium, and F;
wherein at least one of R1, R2, R3, R4, and R5 is deuterium.

### Claim 2 (depends on 1)

The method of claim 1, wherein X is —OH and R5 is H.

### Claim 3 (depends on 2)

The method of claim 2, wherein each of R1, R2, R3, and R4 is deuterium.

### Claim 4 (depends on 2)

The method of claim 2, wherein each of R1, R2, and R4 is deuterium and R3 is —F.

### Claim 5 (depends on 2)

The method of claim 2, wherein R1 and R3 are deuterium and R2 and R4 are H.

### Claim 6 (depends on 2)

The method of claim 2, wherein R1 and R3 are H and R2 and R4 are deuterium.

### Claim 7 (depends on 1)

The method of claim 1, wherein X is —F and R5 is H.

### Claim 8 (depends on 7)

The method of claim 7, wherein each of R1, R3, and R4 is H, and R2 is deuterium.

### Claim 9 (depends on 7)

The method of claim 7, wherein each of R1, R2, and R4 is H, and R3 is deuterium.

### Claim 10 (depends on 7)

The method of claim 7, wherein R1 and R3 are deuterium and R2 and R4 are H.

### Claim 11 (depends on 7)

The method of claim 7, wherein R1 and R3 are H and R2 and R4 are deuterium.

### Claim 12 (depends on 7)

The method of claim 7, wherein R1 and R4 are H and R2 and R3 are deuterium.

### Claim 13 (depends on 7)

The method of claim 7, wherein each of R1, R2, R3, and R4 is deuterium.

### Claim 14 (depends on 1)

The method of claim 1, wherein X is —Cl and R5 is H.

### Claim 15 (depends on 14)

The method of claim 14, wherein each of R1, R2, R3, and R4 is deuterium.

### Claim 16 (depends on 1)

The method of claim 1, wherein X is —F and R5 is —F.

### Claim 17 (depends on 16)

The method of claim 16, wherein each of R1, R2, R3, and R4 is deuterium.

### Claim 18 (depends on 1)

The method of claim 1, wherein the compound of Formula 1 is selected from:

### Claim 19 (depends on 1)

The method of claim 1, wherein the compound of Formula 1 is: