Back to results
US 9,428,482 B2Granted
Process for synthesis of polyphenols
AssigneeSphaera Pharma Pte. Ltd.
InventorsSundeep Dugar, Dinesh Mahajan, Peter Giannousis Pantelis, Vijay Singh, Kamal Kishore Kapoor
Life of this patent
Estimating the term…
Abstract
The present invention provides synthetic processes for preparing racemic and/or optically pure epicatechin, epigallocatechin and related polyphenols as such or as their variously functionalized derivatives. A principle objective of the disclosure is to provide a new and useful method of synthesis to obtain polyphenols in isomerically pure and/or racemic forms.
Claims20
A process for the preparation of compounds of Formula (I)
- or enantiomers, diastereomers or mixtures thereof, or pharmaceutically acceptable salts thereof, wherein;
- Y is selected from the group consisting of H and OR6;
- R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of H, acetyl, allyl, propargyl, benzyl, 2-fluoroethyl, 4-nitrobenzyl, 4-chlorobenzyl, 4-methoxybenzyl, 4-methoxybenzonitrile, cinnamyl, but-2-en-1-yl, 2-penten-1-yl, 1-trimethylsilyl-prop-1-yn-3-yl, 2-octyne-1-yl, 2-butyne-1-yl, 2-picolyl, 3-picolyl, 4-picolyl, quinolin-4-yl-methyl, oxiranylmethyl, fluoromethyl, nitromethyl, methoxycarbonylmethyl, methoxymethyl, 1-phenylethanone-2-yl, 2-butanone-1-yl, chloromethyl, phenyl sulfonylmethyl, 1-bromo-prop-1-en-3-yl, t-butyl, methyl, ethyl, trimethylsilyl, and t-butyldiphenylsilylethyl;
- said process comprising the steps of:
- i. protecting the hydroxyl groups of a compound of Formula (II) with one or more protecting groups, to give a compound of Formula (III)
- ii. treating said compound of Formula (III) with a reducing agent to produce a compound selected from the group of Formula (IV), Formula (V) and Formula (VI), wherein X is selected from halide, acetate, trifloroacetate, methanesulfonate, and hydroxyl;
- and
- iii. treating a compound selected from the group of Formula (IV), Formula (V) and Formula (VI) with a reducing agent to produce a compound of Formula (I).
5 more elements
A compound of Formula (IV) or Formula (V)
- wherein:
- Y is selected from the group consisting of H and OR6R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of H, benzyl, acetyl, Si(CH3)3, and allyl, provided that at least one of R1, R2, R3, R4, R5 and R6 is benzyl.
Dependencies are inferred from the claim text.