# US 11,993,598 B2 · Compounds for inhibiting EGFR kinase, preparation methods and uses thereof

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- Number: US 11,993,598 B2
- Document ID: US11993598B2
- Status: Granted
- Kind: B2
- Application number: 17/200,856
- Filed: 2021-03-14
- Published: 2021-07-29
- Granted: 2024-05-28
- Earliest claimed: 2019-07-04
- Assignees: Wigen Biomedicine Technology (Shanghai) Co., Ltd.
- Applicants: Wigen Biomedicine Technology (Shanghai) Co., Ltd.
- Inventors: Yuli Xie; Gang Cao; Houxing Fan
- Web page: https://patentgrep.com/patent/US11993598B2

## CPC

- C07D 471/06: Peri-condensed systems
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. The compounds can selectively inhibit the activity of epidermal growth factor receptor (EGFR) mutants, and shows good inhibitory effect towards mutant EGFR and anti-proliferative activity against cancer cells. Thus they can be used for treating tumors and related diseases.

## Claims

### Claim 1

A compound of general formula (I) or a pharmaceutically acceptable salt thereof:
wherein:
X is selected from the group consisting of N and CH;
R1 is selected from the group consisting of hydrogen, halogen, C1-6 alkyl, C3-6 cycloalkyl, —C(O)OR8 and CN;
R2 is selected from the group consisting of C1-6 alkyl, C3-6 cycloalkyl and C1-6 haloalkyl;
R3 is selected from the group consisting of —NR9(CH2)2NR9′R9″ and
R4 is
R5, R6, and R7 are independently selected from the group consisting of hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy and CN;
R8 is selected from the group consisting of hydrogen, C1-6 alkyl and C1-6 haloalkyl;
R9 is selected from the group consisting of hydrogen, C1-6 alkyl and C1-6 haloalkyl;
R9′ and R9″ are independently selected from the group consisting of hydrogen, C1-6 alkyl and C1-6 haloalkyl, or R9′ and R9″ together with the nitrogen connected thereto form a heterocycle, the heterocycle is unsubstituted or optionally substituted with 1-3 groups selected from the group consisting of halogen, C1-6 alkyl and C1-6 haloalkyl,
R10 is selected from the group consisting of hydrogen, halogen, C1-6 alkyl and —CH2NR12′R12″;
R11 is selected from the group consisting of hydrogen, halogen and C1-6 alkyl; and
R12 and R12′ are independently selected from the group consisting of hydrogen, C1-6 alkyl and C1-6 haloalkyl, or R12′ and R12″ together with the nitrogen connected thereto form a heterocycle, the heterocycle is unsubstituted or optionally substituted with 1-3 groups selected from the group consisting of halogen, C1-6 alkyl and C1-6 haloalkyl.

### Claim 2 (depends on 1)

The compound of general formula (I) or a pharmaceutically acceptable salt thereof according to claim 1, wherein:
R1 is selected from the group consisting of hydrogen, halogen, C1-6 alkyl, —C(O)OR8 and CN; and
R5, R6 and R7 are independently selected from the group consisting of hydrogen and halogen.

### Claim 3 (depends on 2)

The compound of general formula (I) or a pharmaceutically acceptable salt thereof according to claim 2, wherein the compound is: