Curcumin Derivatives

• US 20100087527A1
• Filed: 09/30/2009
• Published: 04/08/2010
• Est. Priority Date: 04/17/2007
• Status: Active Grant

• Current Assignee: DePuy Synthes Products LLC (Johnson & Johnson)
• Original Assignee: Codman & Shurtleff Incorporated (Johnson & Johnson)
• Inventors: DiMauro, Thomas M.
• Granted Patent: US 8,383,865 B2
• Time in Patent Office: Days
• US Class Current: 514/551
• CPC Class Codes: A61K 31/047 having two or more hydroxy groups, e.g. sorbitol
• CPC Class Codes: A61K 31/05 Phenols cannabinoids A61K31/658
• CPC Class Codes: A61K 31/09 having two or more such linkages
• CPC Class Codes: A61K 31/12 Ketones
• CPC Class Codes: A61K 31/222 with compounds having aromatic groups, e.g. dipivefrine, ibopamine
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/0043 Nose
• CPC Class Codes: A61K 9/06 Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels composition of ointments, creams or gels A61K47/00
• CPC Class Codes: A61K 9/1075 Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers A61K9/0026 takes precedence
• CPC Class Codes: A61K 9/127 Liposomes
• CPC Class Codes: A61K 9/7023 Transdermal patches and similar drug-containing composite devices, e.g. cataplasms galenical aspects of iontophoretic devices A61K9/0009; microneedle arrays A61K9/0021; buccal patches A61K9/006
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07C 229/12 to carbon atoms of acyclic carbon skeletons
• CPC Class Codes: C07C 229/34 the carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 39/21 with at least one hydroxy group on a non-condensed ring
• CPC Class Codes: C07C 43/23 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 51/235 : of —CHO groups or primary alcohol groups
• CPC Class Codes: C07C 51/265 : having alkyl side chains which are oxidised to carboxyl groups
• CPC Class Codes: C07C 63/16 : 1,2 - Benzenedicarboxylic acid
• CPC Class Codes: C07D 207/08 : with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 295/15 : to an acyclic saturated chain

Abstract

The present invention is directed to a compound represented by Structural Formula (I):

or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (I) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (I) and its therapeutic use.

Claims

1. A compound represented by the following structural formula:

2. The compound of claim 1, wherein the compound is represented by the following structural formula:

3. The compound of claim 2, wherein R₂ and R₃ are the same;

and m and p are the same.

4. The compound of claim 3, wherein R₁ is —

OH or —

O—

(C₁-C₆)alkyl.

5. The compound of claim 4, wherein P is selected from the group consisting of —

C(O)—

(CH₂)_1-3—

N(R₅)(R₆),

6. The compound of claim 5, wherein the compound is represented by a structural formula selected from:

7. The compound of claim 6, wherein R₁ is —

OH or —

OMe.

8. The compound of claim 7, wherein m and p are an integer from 1 to 3.

9. The compound of claim 8, wherein the compound is represented by a structural formula selected from the following:

10. The compound of claim 9, wherein each R₂ and R₃ are independently —

OH or —

OMe.

11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by the following structural formula:

12-20. -20. (canceled)

21. A method of treating a subject with a disorder selected from Alzheimer'"'"'s disease, cancer, diabetes, arthritis and sclerosis comprising administering to the subject an effective amount of a compound represented by the following structural formula:

22. The method of claim 21, wherein the compound is represented by the following structural formula:

23. The method of claim 22, wherein R₂ and R₃ are the same;

and m and p are the same.

24. The method of claim 23, wherein R₁ is —

OH or —

O—

(C₁-C₆)alkyl.

25. The method of claim 24, wherein P is selected from the group consisting of —

C(O)—

(CH₂)_1-3—

N(R₅)(R₆),

31. The method of claim 21, wherein the disorder is Alzheimer'"'"'s disease.

32. The method of claim 21, wherein the disorder is cancer.

33. The method of claim 21, wherein the disorder is arthritis.

34. The method of claim 21, wherein the disorder is sclerosis.

26-30. -30. (canceled)