# US 9,750,725 B2 · Fatty acids as anti-inflammatory agents

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- Number: US 9,750,725 B2
- Document ID: US9750725B2
- Status: Granted
- Kind: B2
- Application number: 14/717,954
- Filed: 2015-05-20
- Published: 2015-10-29
- Granted: 2017-09-05
- Earliest claimed: 2009-07-31
- Assignees: University of Pittsburgh—Of the Commonwealth System of Higher Education
- Applicants: University of Pittsburgh—Of the Commonwealth System of Higher Education
- Inventors: Bruce A. Freeman; Francisco J. Schopfer
- Web page: https://patentgrep.com/patent/US9750725B2

## CPC

- A61K 31/426: 1,3-Thiazoles
- A61K 31/12: Ketones
- A61K 31/231: having one or two double bonds
- A61K 31/232: having three or more double bonds, e.g. etretinate
- A61K 31/4166: having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
- A61K 31/4192: 1,2,3-Triazoles
- A61K 31/421: 1,3-Oxazoles, e.g. pemoline, trimethadione
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/02: Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 1/18: for pancreatic disorders, e.g. pancreatic enzymes
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/50: for increasing or potentiating the activity of insulin
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 7/10: Antioedematous agents; Diuretics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 13/12: of the kidneys
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/06: Antipsoriatics
- A61P 17/14: for baldness or alopecia
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/06: Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 19/10: for osteoporosis
- A61P 21/02: Muscle relaxants, e.g. for tetanus or cramps
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/04: Antibacterial agents
- A61P 31/12: Antivirals
- A61P 31/18: for HIV
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 35/04: specific for metastasis
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/04: Immunostimulants
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## 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, Ra, Ra′, Rb, Rb′, Rc, and Rc′ are defined herein. In particular, the compounds of the invention are candidate therapeutics for treating inflammatory conditions.

## Claims

### Claim 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.

### Claim 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.

### Claim 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.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 4)

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.