# US 10,479,767 B2 · Substituted heteroaryl compound, composition containing same, and application thereof

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- Number: US 10,479,767 B2
- Document ID: US10479767B2
- Status: Granted
- Kind: B2
- Application number: 16/079,880
- Filed: 2016-12-13
- Published: 2019-03-28
- Granted: 2019-11-19
- Earliest claimed: 2016-02-28
- Assignees: Shenzhen TargetRx, Inc.
- Applicants: Shenzhen TargetRx, Inc.
- Inventors: Yihan Wang; Xingye Ren
- Web page: https://patentgrep.com/patent/US10479767B2

## CPC

- C07D 217/26: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- A61K 31/438: The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
- A61P 7/06: Antianaemics
- C07B 59/002: {Heterocyclic compounds}
- 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

Provided in the present invention are a substituted heteroaryl compound, a composition containing same, and an application thereof, the present invention disclosing a heteroaryl compound of the formula (I), or a crystalline form, a pharmaceutically acceptable salt, a prodrug, a stereoisomer, a hydrate, or a solvent compound thereof. The substituted heteroaryl compound and the composition containing same set forth in the present invention can be used for regulating hypoxia inducible factor (HIF) and/or endogenous erythropoietin (EPO), simultaneously having better pharmacokinetic parameter characteristics and being able to improve the drug concentration of the compound in animal bodies, in order to improve the curative effect and safety of the drug.

## Claims

### Claim 1

A substituted heteroaryl compound, which is a heteroaryl compound represented by Formula (I), or a pharmaceutically acceptable salt thereof,
wherein R1, R2, R9, R10, R11, R12, and R13 are each independently hydrogen, or deuterium; and
R3, R4, R5, R6, R7, and R8 are each hydrogen;
provided that at least one of R1, R2, R9, R10, R11, R12, and R13 is deuterium.

### Claim 2 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R9, R10, R11, R12, and R13 are each independently hydrogen.

### Claim 3 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are deuterium.

### Claim 4 (depends on 2)

The compound according to claim 2 or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are deuterium.

### Claim 5 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of the following compounds:

### Claim 6 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is:

### Claim 7 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is:

### Claim 8 (depends on 1)

A pharmaceutical composition, characterized in that it comprises a pharmaceutically acceptable carrier and the compound according to claim 1 or a pharmaceutically acceptable salt thereof.