ANTI-INFLAMMATORY ACTIONS OF NEUROPROTECTIN D1/PROTECTIN D1 AND IT'S NATURAL STEREOISOMERS

• US 20090156673A1
• Filed: 10/03/2006
• Published: 06/18/2009
• Est. Priority Date: 10/03/2005
• Status: Active Grant

• Current Assignee: Brigham and Women's Hospital Incorporated, University of Southern California
• Original Assignee: The Brigham and Women's Hospital Incorporated Corporate Sponsored Research and Licensing
• Inventors: Serhan, Charles N., Petasis, Nicos A., Levy, Bruce D.
• Granted Patent: US 8,273,792 B2
• Time in Patent Office: Days
• US Class Current: 514/549
• CPC Class Codes: A61K 31/202 having three or more double bonds, e.g. linolenic eicosanoids, e.g. leukotrienes A61K31/557
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: C07C 59/42 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 69/732 of unsaturated hydroxy carboxylic acids

Abstract

(Neuro)protectin D1 (1OR,17S-dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid) and 15,16-dehydro-PD1 and their derivatives are useful in the treatment of airway inflammation, especially asthma.

Claims

1. A compound of formula (II):

wherein R is a hydrogen atom, an alkyl group, or a pharmaceutically acceptable salt; and

P₁ and P₂ are each, individually, a hydrogen atom or a protecting group, provided when P₁ and P₂ are both hydrogen atoms, then R is other than a hydrogen atom.

2. The compound of claim 1, wherein the compound is purified.

5. A composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

6. The composition of claim 5, wherein the compound is purified.

9. A method to treat airway inflammation comprising administration of a therapeutically acceptable amount of a compound of claim 1

11. The method of claim 9, wherein said airway inflammation is asthma.

36. A method to treat airway inflammation comprising administration of a therapeutically acceptable amount of a composition of claim 5.

3-4. -4. (canceled)

7-8. -8. (canceled)

10. (canceled)

12-16. -16. (canceled)

17. A compound of formula (IX):

wherein R is a hydrogen atom, an alkyl group, or a pharmaceutically acceptable salt; and

P₁ and P₂ are each, individually, a hydrogen atom or a protecting group.

18. The compound of claim 17, wherein when P₁ and P₂ are both hydrogen atoms, then R is other than a hydrogen atom.

20. The compound of claim 17, wherein P₁ and P₂ are each hydrogen atoms and R is a hydrogen atom.

21. A composition comprising a compound of claim 17 and a pharmaceutically acceptable carrier.

29. A method to treat airway inflammation comprising administration of a therapeutically acceptable amount of a compound of claim 17.

30. The method of claim 29, wherein P₁ and P₂ are each hydrogen atoms and R is a hydrogen atom.

31. The method of claim 29, wherein said airway inflammation is asthma.

32. The method of claim 29, wherein when P₁ and P₂ are both hydrogen atoms, then R is other than a hydrogen atom.

33. A method to treat airway inflammation comprising administration of a therapeutically acceptable amount of a composition of claim 21.

34. The method of claim 33, wherein P₁ and P₂ are each hydrogen atoms and R is a hydrogen atom.

35. The method of claim 33, wherein said airway inflammation is asthma.

37. The method of claim 33, wherein P₁ and P₂ are each hydrogen atoms and R is a hydrogen atom.

38. The method of claim 33, wherein said airway inflammation is asthma.

19. (canceled)

22-28. -28. (canceled)