Biomedical Analysis Center, Academy of Military Medical Sciences

Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences

Biomedical Anaylsis Center, Academy of Military Medical Sciences

Zhenggang Liu

Tao Li

Tao Zhou

Xinhua He

Xuemin Zhang

Shengming Wu

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&#x2550;O or CH; 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.

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

The present invention relates to a stable crystal form, i.e. form A, of 2-tert-butyl-4-methoxyphenol, and to a new preparation method for the 2-tert-butyl-4-methoxyphenol; and the use of the 2-tert-butyl-4-methoxyphenol and the stable crystal form thereof, i.e. form A, in preparing antitumor drugs or immunomodulator drugs. The stable crystal form, i.e. form A, as expressed by a powder X-ray diffraction pattern in an angle of 2&#x3b8;, using Cu-K&#x3b1; radiation, has at least 3 absorption peaks selected from the following positions: 6.27&#xb1;0.10, 6.94&#xb1;0.10, 12.27&#xb1;0.10, 13.36&#xb1;0.10, 14.01&#xb1;0.10, 14.79&#xb1;0.10, 15.31&#xb1;0.10, 17.05&#xb1;0.10, 18.30&#xb1;0.10, 19.00&#xb1;0.10, 20.47&#xb1;0.10, 20.98&#xb1;0.10, 22.37&#xb1;0.10, 23.68&#xb1;0.10, 24.55&#xb1;0.10, 25.37&#xb1;0.10, 30.83&#xb1;0.10, 33.12&#xb1;0.10, 40.50&#xb1;0.10, 42.81&#xb1;0.10.

Method for preparing 2-tert-butyl-4-methoxyphenol and new crystal form thereof

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&#x2550;O or CH; 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 (T&#xbd;=12&#x2dc;24 h). The compounds provided by the present invention protect the phenolic hydroxyl group of 2-tert-butyl-4-methoxyphenol, avoid environmental oxidation and increase the environmental stability of drugs containing the compounds.

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Beijing, China

Zhenggang Liu