Fatty acids as anti-inflammatory agents

Patent metadata

Field	Value
Publication number	US-9750725-B2
Application number	US-201514717954-A
Country	US
Kind code	B2
Filing date	May 20, 2015
Priority date	Jul 31, 2009
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

Compounds of formula I and their metabolites are potent mediators of an inflammatory response:

where a, b, c, d, e, f, V, W, X, Y, R a , R a′ , R b , R b′ , R c , and R c′ are defined herein. In particular, the compounds of the invention are candidate therapeutics for treating inflammatory conditions.

First claim

What is claimed is:

1. A pharmaceutical formulation comprising an effective amount of a fatty acid, wherein the fatty acid is:
13-oxo-(7Z,10Z,14A,16Z,19Z)docosa-7,10,14,16,19-pentaenoic acid,
17-oxo-(7Z,10Z,13Z,15A,19Z)-docosa-7,10,13,15,19-pentaenoic acid,
13-oxo-(4Z,7Z,10Z,14A,16Z,19Z)-docosa-4,7,10,14,16,19-hexaenoic acid, or
17-oxo-(4Z,7Z,10Z,13Z,15A,19Z)-docosa-4,7,10,13,15,19-hexaenoic acid,
where A indicates either E or Z configuration.

2. A method for treating pulmonary fibrosis or fibrosis of the liver comprising administering to a subject a pharmaceutical formulation comprising a fatty acid selected from the group consisting of:
13-oxo-(7Z,10Z,14A,16Z,19Z)docosa-7,10,14,16,19-pentaenoic acid,
17-oxo-(7Z,10Z,13Z,15A,19Z)-docosa-7,10,13,15,19-pentaenoic acid,
13-oxo-(4Z,7Z,10Z,14A,16Z,19Z)-docosa-4,7,10,14,16,19-hexaenoic acid,
17-oxo-(4Z,7Z,10Z,13Z,15A,19Z)-docosa-4,7,10,13,15,19-hexaenoic acid,
where A indicates either E or Z configuration; and
a pharmaceutically acceptable excipient, carrier, or diluent.

3. A method for treating pulmonary fibrosis or fibrosis of the liver comprising administering to a subject a fatty acid selected from the group consisting of:
13-oxo-(7Z,10Z,14A,16Z,19Z)docosa-7,10,14,16,19-pentaenoic acid,
17-oxo-(7Z,10Z,13Z,15A,19Z)-docosa-7,10,13,15,19-pentaenoic acid,
13-oxo-(4Z,7Z,10Z,14A,16Z,19Z)-docosa-4,7,10,14,16,19-hexaenoic acid, or
17-oxo-(4Z,7Z,10Z,13Z,15A,19Z)-docosa-4,7,10,13,15,19-hexaenoic acid,
where A indicates either E or Z configuration.

4. A method for treating an inflammatory condition comprising administering to a subject the pharmaceutical formulation of claim 1 .

5. The method according to claim 4 , wherein the inflammatory condition is organ preservation for transplantation, osteoarthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, hypertension, allograft rejection, pelvic inflammatory disease, ulcerative colitis, Crohn's disease, allergic inflammation in the lung, cachexia, stroke, congestive heart failure, pulmonary fibrosis, hepatitis, glioblastoma, Guillain-Barre Syndrome, systemic lupus, erythematosus viral myocarditis, post-transplantation organ protection, acute pancreatitis, irritable bowel disease, general inflammation, autoimmune disease, autoinflammatory disease, arterial stenosis, organ transplant rejection, burns, chronic lung injury and respiratory distress, insulin-dependent diabetes, non-insulin dependent diabetes, hypertension, obesity, arthritis, neurodegenerative disorders, lupus, Lyme's disease, gout, sepsis, hyperthermia, ulcers, enterocolitis, osteoporosis, viral or bacterial infections, cytomegalovirus, periodontal disease, glomerulonephritis, sarcoidosis, lung disease, lung inflammation, fibrosis of the lung, asthma, acquired respiratory distress syndrome, tobacco induced lung disease, granuloma formation, fibrosis of the liver, graft vs. host disease, postsurgical inflammation, coronary and peripheral vessel restenosis following angioplasty, stent placement or bypass graft, coronary artery bypass graft (CABG), acute and chronic leukemia, B lymphocyte leukemia, neoplastic diseases, arteriosclerosis, atherosclerosis, myocardial inflammation, psoriasis, immunodeficiency, disseminated intravascular coagulation, systemic sclerosis, amyotrophic lateral sclerosis, multiple sclerosis, Parkinson's disease, Alzheimer's disease, encephalomyelitis, edema, inflammatory bowel disease, hyper IgE syndrome, cancer metastasis or growth, adoptive immune therapy, reperfusion syndrome, radiation burns, alopecia areta, ischemia, myocardial infarction, arterial stenosis, rheumatoid arthritis, coronary restenosis, neurocognitive decline, or insulin resistance.

Assignees

• Univ Of Pittsburgh—Of The Commonwealth System Of Higher Education

Inventors

• Freeman Bruce A
• Schopfer Francisco J

Classifications

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P35/02

  specific for leukemia · CPC title

• A61P37/04

  Immunostimulants · CPC title

• A61P35/04

  specific for metastasis · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title