Benzo lipoxin analogues

• US 7,683,193 B2
• Filed: 04/04/2006
• Issued: 03/23/2010
• Est. Priority Date: 09/10/2003
• 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:
  US11/398,481
• Publication Number:
  US 20060270734A1
• Time in Patent Office: 1,449 Days
• Field of Search: None
• US Class Current: 554/61
• CPC Class Codes: A61J 1/14 Details; Accessories therefor A61J7/00 takes precedence; openers B65D, B67B7/00
• CPC Class Codes: A61K 31/216 of acids having aromatic rings, e.g. benactizyne, clofibrate
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 47/02 Inorganic compounds
• 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 9/0019 Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner non-active ingredients are additionally classified in A61K47/00
• CPC Class Codes: A61K 9/0031 Rectum, anus
• CPC Class Codes: A61K 9/0048 Eye, e.g. artificial tears
• CPC Class Codes: A61K 9/0053 Mouth and digestive tract, i.e. intraoral and peroral administration rectal administration A61K9/0031
• CPC Class Codes: A61K 9/0078 for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
• 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 35/02 specific for leukemia
• CPC Class Codes: A61P 37/04 Immunostimulants
• CPC Class Codes: C07C 69/618 having unsaturation outside the six-membered aromatic ring
• CPC Class Codes: C07C 69/732 of unsaturated hydroxy carboxylic acids

Abstract

Benzolipoxin analogs, methods of their preparation and pharmaceutical compositions containing the compounds are provided. The compounds and compositions are useful in methods for treatment of various diseases, including, inflammation, autoimmune disease and abnormal cell proliferation.

Claims

1. A compound represented by one of the following structural formulae:

2. The compound of claim 1, wherein the compound is represented by one of the following structural formulae, or a pharmaceutically acceptable salt thereof:

3. The compound of claim 2, wherein W is alkyl.

4. The compound of claim 2, wherein W is aryloxy.

5. The compound of claim 2, wherein A is hydroxy or alkoxy.

6. The compound of claim 2, wherein R^a, R^b, and R^c are each hydrogen.

7. The compound of claim 6, wherein the compound is represented by structural formula

8. The compound of claim 7, wherein W is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, halo, hydroxy, alkoxy, or aryloxy.

9. The compound of claim 7, wherein W is alkyl.

10. The compound of claim 7, wherein W is aryloxy.

11. The compound of claim 7, wherein A is hydroxy or alkoxy.

12. A method of ameliorating or treating a disease or condition associated with inflammation or an autoimmune disease, the method comprising administering to a subject a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof.

13. The method of claim 12, wherein the disease or condition associated with inflammation is neutrophil-mediated inflammation or neutrophil-mediated damage.

14. The method of claim 12, wherein the disease is arthritis, asthma, psoriasis, inflammatory bowel disease, systemic lupus erythematosus, systemic dermatomyositis, inflammatory ophthalmic disease, multiple sclerosis, vasculitis, idiopathic nephrotic syndrome or graft versus host disease.

15. An article of manufacture, comprising packaging material, a compound of claim 1 or a pharmaceutically acceptable salt thereof contained within the packaging material, and a label that indicates that the compound or pharmaceutically acceptable salt thereof is used for treatment or amelioration of one or more symptoms associated with inflammation, neutrophil-mediated inflammation, or autoimmune disease.

16. The article of manufacture of claim 15, wherein the label indicates that the compound or pharmaceutically acceptable salt thereof is used for treatment or amelioration of one or more symptoms associated with inflammation, wherein the inflammation is neutrophil-mediated inflammation or neutrophil-mediated damage.