Curcumin derivatives

Patent metadata

Field	Value
Publication number	US-9650404-B2
Application number	US-201113581020-A
Country	US
Kind code	B2
Filing date	Feb 25, 2011
Priority date	Feb 26, 2010
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

The invention relates to novel curcumin derivatives in which one or two of the phenolic groups have been modified.

First claim

The invention claimed is:

1. A curcumin derivative having the formula I:

wherein:
A is —CH 2 —CH 2 — or —CH═CH—;
R 1 represents L 1 m1 -Y 1 ;
R 2 represents L 2 m2 -Y 2 ;
L 1 and L 2 are

m1 and m2 are 1;
n1 is independently 0 or an integer from 1 to 50;
Y 1 and Y 2 independently represent a saccharide with 1 to 51 monosaccharide units; CH 2 —CH═CH 2 or CH 2 —C═CH;
R 3 independently represents a saturated, unbranched hydrocarbyl with 1 to 4 carbon atoms and n2 independently represents an integer from 5 and 50.

2. A curcumin derivative according to claim 1 , wherein L 1 is

and Y 1 is a saccharide.

3. A curcumin derivative according to claim 2 , wherein the saccharide is a monosaccharide.

4. A curcumin derivative according to claim 3 , wherein the monosaccharide is glucose or galactose.

5. A curcumin derivative according to claim 1 , wherein Y 1 or Y 2 is a saccharide.

6. A curcumin derivative according to claim 1 , wherein Y 1 or Y 2 is a disaccharide or a trisaccharide.

7. A curcumin derivative according to claim 1 , wherein the saccharide is a monosaccharide.

8. A curcumin derivative according to claim 1 , wherein the monosaccharide is glucose or galactose.

9. A method of treating Alzheimer's disease in a patient comprising administering to the patient in need thereof a therapeutically effective amount of a curcumin derivative having the formula I:

wherein:
A is —CH 2 —CH 2 — or —CH═CH—;
R 1 represents L 1 m1 -Y 1 ;
R 2 represents L 2 m2 -Y 2 ;
L 1 and L 2 are

m1 and m2 are 1;
n1 is independently 0 or an integer from 1 to 50;
Y 1 and Y 2 independently represent a saccharide with 1 to 51 monosaccharide units; CH 2 —CH═CH 2 or CH 2 —C═CH;
R 3 independently represents a saturated, unbranched hydrocarbyl with 1 to 4 carbon atoms; and n2 independently represents an integer from 5 and 50.

Assignees

• Raja Krishnaswami
• Alonso Alejandra
• Banerjee Probal
• Dolai Sukanta
• Corbo Christopher
• Averick Saadyah
• Mogha Amit
• Debnath Shawon
• Univ City New York Res Found

Inventors

• Raja Krishnaswami
• Alonso Alejandra
• Banerjee Probal
• Dolai Sukanta
• Corbo Christopher
• Averick Saadyah
• Mogha Amit
• Debnath Shawon

Classifications

• C07H7/06

  Heterocyclic radicals · CPC title

• C07D249/04

  1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles · CPC title

• C07C69/42

  Glutaric acid esters · CPC title

• C07C49/255

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• A61K31/7056

  containing five-membered rings with nitrogen as a ring hetero atom · CPC title