Trihydroxy polyunsaturated eicosanoid derivatives

• US 7,582,785 B2
• Filed: 03/29/2005
• Issued: 09/01/2009
• Est. Priority Date: 04/01/2002
• Status: Expired due to Fees

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Petasis, Nicos A.
• Primary Examiner(s): Carr; Deborah D
• Application Number:
  US11/093,757
• Publication Number:
  US 20050228047A1
• Time in Patent Office: 1,617 Days
• Field of Search: None
• US Class Current: 554/224
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/02 Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
• CPC Class Codes: C07B 2200/05 Isotopically modified compounds, e.g. labelled
• CPC Class Codes: C07C 67/303 by hydrogenation of unsaturated carbon-to-carbon bonds
• 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 7/1892 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 having the formula 23,

2. A pharmaceutical composition, comprising a compound according to claim 1;

and a pharmaceutically acceptable carrier.

3. A compound having a formula 39 or a formula 41,

4. A pharmaceutical composition, comprising a compound according to claim 3;

and a pharmaceutically acceptable carrier.

5. A compound having a formula 40 or a formula 42,

6. A pharmaceutical composition, comprising a compound according to claim 5;

and a pharmaceutically acceptable carrier.

7. A compound selected from a group consisting of compounds having the general formulas 29 or 43-47:

8. A compound having the general formula 3:

14. A pharmaceutical composition comprising an effective amount of a compound according to claim 8;

and a pharmaceutically acceptable carrier.

9. A compound having the general formula 29:

15. A pharmaceutical composition comprising an effective amount of a compound according to claim 9;

and a pharmaceutically acceptable carrier.

10. A compound having the general formula 44:

16. A pharmaceutical composition comprising an effective amount of a compound according to claim 10;

and a pharmaceutically acceptable carrier.

11. A compound having the general formula 46

17. A pharmaceutical composition comprising an effective amount of a compound according to claim 11;

and a pharmaceutically acceptable carrier.

12. A compound of the general formula 25

13. The compound according to claim 12, wherein Y is propylene and Z is methylene.

18. A pharmaceutical composition comprising an effective amount of a compound according to claim 12;

and a pharmaceutically acceptable carrier.