Sinomenine derivatives, synthetic methods and uses thereof

US8557837B2 · kind B2 · utility

Assignees

• SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES · CN
• Shanghai Institutes for Biological Sciences Chinese Academy of Sciences · CN

Inventors

• Zhujun Yao · Shanghai, CN
• Bing Sun · Shanghai, CN
• Yangtong LOU · Shanghai, CN
• Zhenyu Yang · Shanghai, CN
• Aizhong Chen · Shanghai, CN
• Zhao Ma · Xi'an, CN

Key dates

• Filing date: Feb 9, 2011
• Grant date: Oct 15, 2013
• Expiry date: Feb 9, 2031

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02A50/30
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The invention relates to sinomenine derivatives, methods for their synthesis and their applications. The sinomenine derivatives include oxidation derivatives, and C-10 substituted sinomenine derivatives. Based on the readily oxidizable phenol group on sinomenine structure, using oxidation, oxidative dearomatization, or conjugated addition aromatization, one can introduce C-10 substitutions to synthesize the sinomenine derivatives. The sinomenine derivatives of the invention have the following structures:Using in vitro TNF-α inhibition assay, the activities of the synthetic compounds are assessed. Results from these assays shown that most compounds have anti-inflammatory effects, and some compounds have better activities than that of sinomenine. These compounds may be used in treating immune diseases such as rheumatoid arthritis (RA).