# US 12,595,259 B2 · Aminopyridine compound

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- Number: US 12,595,259 B2
- Document ID: US12595259B2
- Status: Granted
- Kind: B2
- Application number: 18/000,684
- Filed: 2021-06-17
- Published: 2023-06-08
- Granted: 2026-04-07
- Earliest claimed: 2020-06-17
- Assignees: Zhuhai United Laboratories Co., Ltd.
- Applicants: Zhuhai United Laboratories Co., Ltd.
- Inventors: Peng Li; Chong Su; Xiaolin Li; Zhi Luo; Haiying He; Guoping Hu; Jian Li; Shuhui Chen
- Web page: https://patentgrep.com/patent/US12595259B2

## CPC

- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- A61K 31/136: having the amino group directly attached to the aromatic ring, e.g. benzeneamine
- A61P 27/00: Drugs for disorders of the senses
- A61P 27/04: Artificial tears; Irrigation solutions
- C07D 213/00: Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- 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

## Abstract

An aminopyridine compound that may be used as an aldehyde trapping agent, and specifically disclosed is a compound represented by formula (I) and a pharmaceutically acceptable salt thereof.

## Claims

### Claim 1

A compound represented by formula (I) or a pharmaceutically acceptable salt thereof,
wherein,
L is selected from —O— and —(CR4R5)n—;
R1 is selected from —C1-6 alkyl- and —C3-5 cycloalkyl-, and the —C1-6 alkyl- and —C3-5 cycloalkyl- are optionally substituted by 1, 2 or 3 Ra;
ring A is selected from phenyl, pyridyl and 5-membered heteroaryl, and the phenyl, pyridyl and 5-membered heteroaryl are optionally substituted by 1, 2 or 3 R3;
and when ring A is selected from phenyl and pyridyl, R2 is selected from —C5-6 alkyl- and —C3-5 cycloalkyl-, and the —C5-6 alkyl- and —C3-5 cycloalkyl- are optionally substituted by 1, 2 or 3 Rb;
when ring A is selected from 5-membered heteroaryl, R2 is selected from —C1-6 alkyl- and —C3-5 cycloalkyl-, and the —C1-6 alkyl- and —C3-5 cycloalkyl- are optionally substituted by 1, 2 or 3 Rc;
R3 is selected from H, F, Cl, Br, I and CH3;
R4 and R5 are each independently selected from H and CH3;
n is selected from 0, 1 and 2;
Ra, Rb and Rc are each independently selected from F, Cl, Br and I;
the “5-membered heteroaryl” comprises 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from —O—, —NH—, —S— and N, respectively.

### Claim 2 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein R1 is selected from CH2, C(CH3)2, C(CH2CH3)2, cyclopropyl and cyclobutyl, and the CH2, C(CH3)2, C(CH2CH3)2, cyclopropyl and cyclobutyl are optionally substituted by 1, 2 or 3 Ra;
or, L is selected from a single bond, —O—, CH2 and —CH2CH2—.

### Claim 3 (depends on 2)

The compound or the pharmaceutically acceptable salt thereof according to claim 2, wherein R1 is selected from C(CH3)2, C(CH2CH3)2, cyclopropyl and cyclobutyl.

### Claim 4 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein when ring A is selected from phenyl and pyridyl, R2 is selected from C(CH2CH3)2, cyclopropyl and cyclobutyl;
when ring A is selected from 5-membered heteroaryl, R2 is selected from C(CH3)2, C(CH2CH3)2, cyclopropyl and cyclobutyl.

### Claim 5 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein ring A is selected from phenyl, pyridyl, pyrrolyl, furyl, thienyl, oxazolyl and thiazolyl, and the phenyl, pyridyl, pyrrolyl, furyl, thienyl, oxazolyl and thiazolyl are optionally substituted by 1, 2 or 3 R3.

### Claim 6 (depends on 5)

The compound or the pharmaceutically acceptable salt thereof according to claim 5, wherein ring A is selected from

### Claim 7 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein the structural unit
is selected from

### Claim 8 (depends on 7)

The compound or the pharmaceutically acceptable salt thereof according to claim 7, wherein the structural unit
is selected from

### Claim 9 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, selecting from,
wherein,
T1, T3 and T4 are each independently selected from N and CR3;
T2, T5 and T6 are selected from CR3;
T7 is selected from N and CR3;
T8 is selected from O and S;
R3 is selected from H, F, Cl, Br, I and CH3;
R1, R2 and L are as defined in claim 1.

### Claim 10

A compound represented by the following formula or a pharmaceutically acceptable salt thereof, wherein the compound is selected from any one of the following compounds:

### Claim 11 (depends on 1)

A method for treating diseases related to an aldehyde trapping agent in a subject in need thereof, comprising: administering an effective amount of the compound or the pharmaceutically acceptable salt thereof according to claim 1 to the subject, wherein, the diseases related to the aldehyde trapping agent is xerophthalmia.

### Claim 12 (depends on 10)

A method for treating diseases related to an aldehyde trapping agent in a subject in need thereof, comprising: administering an effective amount of the compound or the pharmaceutically acceptable salt thereof according to claim 10 to the subject, wherein, the diseases related to the aldehyde trapping agent is xerophthalmia.

### Claim 13 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein ring A is selected from 5-membered heteroaryl and 5-membered heteroaryl are optionally substituted by 1, 2 or 3 R3, R2 is selected from —C1-6 alkyl- and —C3-5 cycloalkyl-, and the —C1-6 alkyl- and —C3-5 cycloalkyl- are optionally substituted by 1, 2 or 3 Rc.

### Claim 14 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein ring A is selected from pyrrolyl, furyl, thienyl, oxazolyl and thiazolyl, and the pyrrolyl, furyl, thienyl, oxazolyl and thiazolyl are optionally substituted by 1, 2 or 3 R3.

### Claim 15 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein ring A is selected from

### Claim 16 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein the structural unit
is selected from

### Claim 17 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein the structural unit
is selected from

### Claim 18 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, selecting from,
wherein,
T7 is selected from N and CR3;
T8 is selected from O and S;
R3 is selected from H, F, Cl, Br, I and CH3;
R1, R2 and L are as defined in claim 1.