Hydroquinone compounds, preparation methods therefor, and use in anti-tumor or immunomodulation therapy

US11738000B2 · kind B2 · utility

Assignees

• BIOMEDICAL ANALYSIS CENTER, ACADEMY OF MILITARY MEDICAL SCIENCES · CN
• INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY, ACADEMY OF MILITARY MEDICAL SCIENCES · CN

Inventors

• Xuemin Zhang · Shanghai, CN
• Xinhua He · Zionsville, US
• Tao Zhou · Daguantang, CN
• Zhenggang Liu · Beijing, CN
• Tao Li · San Diego, US

Key dates

• Filing date: Aug 7, 2020
• Grant date: Aug 29, 2023
• Expiry date: Mar 19, 2041

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D265/30
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Disclosed are hydroquinone compounds, preparation methods therefor, and uses thereof in anti-tumor or immunomodulation. The structural formula of the hydroquinone compounds are shown by formula I, wherein X is C═O or CH2; Y is NH, O or absent; R is: a substituted or unsubstituted alkyl group having at least one carbon atom, a substituted or unsubstituted cycloalkyl group having at least three carbon atoms, a substituted or unsubstituted alkenyl group or alkynyl group having at least two carbon atoms; and a substituted or unsubstituted aryl group or heteroaryl group containing at least four carbon atoms. The compounds provided slowly release 2-tert-butyl-4-methoxyphenol in vivo and maintain stable plasma concentration of 2-tert-butyl-4-methoxyphenol (T1/2=12-24 h). The compounds provided by the present invention protect the phenolic hydroxyl group of 2-tert-butyl-4-methoxyphenol, avoids environmental oxidation and increase the environmental stability of drugs containing the compounds.