Phenyl C-glucoside derivative containing deoxyglucose structure, preparation method and use thereof

US9505734B2 · kind B2 · utility

Assignee

• Tianjin Institute of Pharmaceutical Research Co., Ltd. · CN

Inventors

• Guilong Zhao · Tianjin, CN
• Yuli Wang · Tianjin, CN
• Bingni Liu · Tianjin, CN
• Yafei Xie · Tianjin, CN
• Yuqiang Liu · Beijing, CN
• Peng Liu · Tianjin, CN
• Jiang Wu · Longbeilingcun, CN
• Jiajia Hou · Tianjin, CN
• Wei Wei · Lo Wu, CN
• Wen Du · Hunan, CN
• Weiren Xu · Tianjin, CN
• Lida Tang · Tianjin, CN
• Meixiang Zou · Tianjin, CN

Key dates

• Filing date: Dec 5, 2013
• Grant date: Nov 29, 2016
• Expiry date: Dec 5, 2033

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/10
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicaments for treating diabetes, wherein substituents R1-R7 are as defined in the specification. The present invention also provides a method for synthesizing the phenyl C-glucoside derivative containing a deoxyglucose structure and an intermediate product. The method has advantages of being simple to manage and of low cost, which is suitable for large-scale industrial production. The present invention further provides a cocrystal of (1S)-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1,6-dideoxy-D-glucose and L-proline, and preparation method and uses thereof.