# US 10,308,616 B2 · Trifluoroacetyl hydrazide compounds and methods of preparation and uses thereof

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- Number: US 10,308,616 B2
- Document ID: US10308616B2
- Status: Granted
- Kind: B2
- Application number: 15/731,538
- Filed: 2015-08-11
- Published: 2018-12-06
- Granted: 2019-06-04
- Earliest claimed: 2014-12-31
- Applicants: Guangzhou Magpie Pharmaceuticals Co., Ltd.
- Inventors: Yuqiang Wang; Haiyun Chen; Zaijun Zhang; Gaoxiao Zhang; Pei Yu; Yewei Sun; Luchen Shan; Liang Tao
- Web page: https://patentgrep.com/patent/US10308616B2

## CPC

- C07D 241/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A61K 31/4965: Non-condensed pyrazines
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C07C 241/00: Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to trifluoroacetyl hydrazide compounds and methods of preparation and uses thereof. The compounds have a structure of the following formula: The compounds showed multifunctional mechanisms, including inhibition of glutamate excitotoxicity, activation of MEF2 transcriptional activity, clearance of free radicals, and promotion of nerve differentiation, and has a better protective effect on cells especially nerve cells. The compound can be used to prepare prophylactic or therapeutic medicaments with cytoprotective effects, for the prevention or treatment of diseases related to glutamate receptor activation, MEF2 disorders or excessive free radicals generation. The diseases include, for example, neurodegenerative diseases such as Alzheimer's disease, Parkinson and stroke, and the free radicals related diseases such as heart disease, myocardial ischemia, diabetes and other cardiovascular and cerebrovascular diseases.

## Claims

### Claim 1

A trifluoroacetyl hydrazide compound of the following formula I:
wherein:
R1, R2 and R3 are each independently hydrogen or alkyl group, but cannot be hydrogen at the same time;
X and Y are both N.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the alkyl group is a lower alkyl group.

### Claim 3 (depends on 2)

The compound of claim 2, wherein R1, R2 and R3 are methyl, and thus the compound has a structure of formula II,

### Claim 4 (depends on 1)

A method of preparation of the compound of claim 1, the method comprising: 3,5,6-trimethyl-2-pyrazinecarboxaldehyde is condensed with 2,4-dimethylphenylhydrazide hydrochloride to give an intermediate of phenylhydrazone, which is then reacted with trifluoroacetic anhydride to give final product.