# US 12,595,236 B2 · Pyrimidine-2,4-diamine compound and preparation method and application thereof

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- Number: US 12,595,236 B2
- Document ID: US12595236B2
- Status: Granted
- Kind: B2
- Application number: 17/915,121
- Filed: 2022-01-21
- Published: 2023-05-18
- Granted: 2026-04-07
- Earliest claimed: 2021-01-29
- Assignees: Anhui Medical University
- Applicants: Anhui Medical University
- Inventors: Xinhua Liu; Xing Chen; Jingbo Shi; Mingming Liu; Yaoyao Yan; Zhaoyan Zhang; Famin Zhang
- Web page: https://patentgrep.com/patent/US12595236B2

## CPC

- C07D 239/48: Two nitrogen atoms
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- Y02P 20/584: Recycling of catalysts
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A pyrimidine-2,4-diamine compound and a preparation method and application thereof are provided. The pyrimidine-2,4-diamine compound of the present disclosure can be used in the research of biological or pharmacological phenomena and cathepsin C-involved signal pathway transduction and the evaluation of novel cathepsin C inhibitors. The pyrimidine-2,4-diamine compound is subjected to the screening of anti-cathepsin C activity in vitro and in vivo and proved to have strong inhibitory activity on cathepsin C. The pyrimidine-2,4-diamine compound is subjected to the screening of anti-NSP activity in vivo and proved to have strong inhibitory activity on NSP. The pyrimidine-2,4-diamine compound is subjected to the screening of anti-inflammatory activity in vivo and proved to have an effective therapeutic effect on inflammatory disease models. Meanwhile, the pyrimidine-2,4-diamine compound shows low toxicity and exhibits good application prospect.

## Claims

### Claim 1

A method for regulating a catalytic activity of cathepsin in a subject in need thereof, comprising administering to the subject an effective amount of a pyrimidine-2,4-diamine compound as shown in Formula II:
wherein, R1 is selected from the group consisting of phenyl and substituted phenyl: R2* is one selected from the group consisting of pyridyl, pyrimidinyl, and pyridazinyl; R3 is one selected from the group consisting of N-methylpiperazine, N-ethylpiperazine, N-propylpiperazine, N-cyclopropylpiperazine, N-butylpiperazine, and piperazine; R4 is one selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, and methoxy.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the cathepsin is cathepsin C.