Trihydroxy polyunsaturated eicosanoid derivatives

• US 8,481,772 B2
• Filed: 02/28/2012
• Issued: 07/09/2013
• Est. Priority Date: 04/01/2002
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Petasis, Nicos A.
• Primary Examiner(s): Carr, Deborah D
• Application Number:
  US13/407,346
• Publication Number:
  US 20120157700A1
• Time in Patent Office: 497 Days
• Field of Search: 554/224
• US Class Current: 554/224
• CPC Class Codes: C07B 2200/05 Isotopically modified compounds, e.g. labelled
• CPC Class Codes: C07C 69/732 of unsaturated hydroxy carboxylic acids
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 7/1892 by reactions not provided for in C07F7/1876 - C07F7/1888

Abstract

The invention features methods for the preparation of naturally occurring trihydroxy polyunsaturated eicosanoids and their structural analogs. The invention further provides new derivatives and analogs of trihydroxy polyunsaturated eicosanoids that can be prepared according to these methods. The invention also provides compositions and methods using trihydroxy polyunsaturated eicosanoid derivatives for the prevention, amelioration and treatment of a variety of diseases or conditions associated with inflammation or inflammatory response, autoimmune diseases, rheumatoid arthritis, cardiovascular diseases, or abnormal cell proliferation or cancer.

Claims

1. A compound of the general formula 25,

2. The compound of claim 1, wherein A is hydroxyl.

3. The compound of claim 1, wherein A is alkoxy.

4. The compound of claim 3, wherein the alkyl group of the alkoxy is a branched chain alkyl group.

5. The compound of claim 1, wherein Z is —

CH₂—

.

6. The compound of claim 1, wherein Y is —

CH₂CH₂CH₂—

.

7. The compound of claim 1, wherein A is hydroxyl;

Z is —

CH₂—

; and

Y is —

CH₂CH₂CH₂—

.

8. The compound of claim 2, wherein A is alkoxy;

Z is —

CH₂—

; and

Y is —

CH₂CH₂CH₂—

.

9. The compound of claim 8, wherein the alkyl group of the alkoxy is a branched chain alkyl group.

10. A compound of the general formula 29,

11. The compound of claim 10, wherein A is hydroxyl.

12. The compound of claim 10, wherein A is alkoxy.

13. The compound of claim 12, wherein the alkyl group of the alkoxy is a branched chain alkyl group.