SYNTHESIS OF OLIGOMERIC EPICATECHIN AND CATECHIN-DERIVED PROCYANIDINS

Title:

SYNTHESIS OF OLIGOMERIC EPICATECHIN AND CATECHIN-DERIVED PROCYANIDINS

Document Type and Number:

WIPO Patent Application WO2004030440

Kind Code:

A3

Abstract:

Various processes are disclosed for preparing procyanidin oligomers having (4,8)interflavan linkages. In an improved process, a tetra-O-protected-epicatechin or -catechin monomer or oligomer is coupled with a protected, C-4 alkoxy-activated-epicatechin or -catechin monomer in the presence of an acidic clay instead of a Lewis acid. In a second process, a 5,7,3',4'-tetra-O-protected or preferably penta-O-protected-epicatechin or -catechin monomer or oligomer is reacted with a tetra-O-protected or preferably penta-O-protected-epicatechin or -catechin monomer having a thio activating group at the C-4 position; the coupling is carried out in the presence of silver tetrafluoroborate. In third process, two molecules of a penta-O-protected-epicatechin or -catechin monomer activated with a 2(benzothiazolyl)thio group at the C-4 position are self-condensed in the presence of silver tetrafluoroborate. An improved two-step process for preparing a C-4 alkoxy activated tetra-O-benzyl-protected, 8-bromo-blocked-epicatechin or -catechin monomer is also provided. The use of naturally-derived and synthetically-prepared procyanidin (4beta,8)4-pentamers to treat cancer is also disclosed.

More Like This:

WO/2023/161247	SALICYLIC ACID COMPOSITIONS AND USES THEREOF
WO/2013/184837	METHODS OF TREATING OVERWEIGHT AND OBESITY
JPH0717854	ANTI-OSTEOPATHIC AGENT

Inventors:

KOZIKOWSKI ALAN P (US)
TUCKMANTEL WERNER (US)
ROMANCZYK LEO J JR (US)
MA XINGQUAN (US)

Application Number:

PCT/US2003/031375

Publication Date:

June 10, 2004

Filing Date:

October 02, 2003

Export Citation:

Click for automatic bibliography generation Help

Assignee:

MARS INC (US)
KOZIKOWSKI ALAN P (US)
TUCKMANTEL WERNER (US)
ROMANCZYK LEO J JR (US)
MA XINGQUAN (US)

International Classes:

A61K31/335; A61K31/352; A61K31/353; A61K31/7048; A61P35/00; C07D311/60; C07D311/62; C07D311/74; C07D313/00; C07D417/12; C07D417/14; (IPC1-7): A61K31/335; C07D311/60; C07D313/00

Foreign References:

US20030114691A1	2003-06-19
US6420572B1	2002-07-16

Other References: