Key intermediate for the preparation of Stilbenes, solid forms of Pterostilbene, and methods for making the same

US8524782B2 · kind B2 · utility

Assignee

• LAURUS LABS LIMITED · IN

Inventors

• Gottumukkala V. Subbaraju · Darsi, IN
• Masna Mahesh · Hyderabad, IN
• Hindupur R. Mohan · Hyderabad, IN
• Thatipally Suresh · Hyderabad, IN
• Igor Ivanisevic · West Lafayette, US
• Mark Andres · West Lafayette, US
• Kyle Stephens · West Lafayette, US

Key dates

• Filing date: Jan 21, 2011
• Grant date: Sep 3, 2013
• Expiry date: Sep 23, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D309/12
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a scalable process for the preparation of stilbenes by (i) condensing 3,5-dialkylbenzyl phosphonates with 4′-O-tetrahydropyranyl benzaldehyde to get 3,5-alkyl-4′-O-tetrahydropyranyl Stilbene and (ii) deprotecting the obtained 3,5-Dialkyl-4′-O-tetrahydropyranylstilbene to yield stilbenes. The present invention also provides a novel intermediate 3,5-Dialkyl-4′-O-tetrahydropyranyl stilbene, which is a key intermediate for the synthesis of stilbenes such as Pterostilbene and Resveratrol. The present invention also provides characteristics of various solid forms of Pterostilbene, methods for their preparation, as well as dosage forms containing the same for administration to or consumption by humans.