Heteroatom containing substituted fatty acids

• US 9,663,444 B2
• Filed: 03/11/2014
• Issued: 05/30/2017
• Est. Priority Date: 10/02/2009
• Status: Active Grant

• Current Assignee: Complexa, Inc.
• Original Assignee: Complexa, Inc.
• Inventors: Miller, Raymond A.
• Primary Examiner(s): Cutliff, Yate K
• Application Number:
  US14/205,081
• Publication Number:
  US 20140256814A1
• Time in Patent Office: 1,176 Days
• CPC Class Codes: A61K 31/201 having one or two double bonds, e.g. oleic, linoleic acids
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/14 for baldness or alopecia
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/06 Antigout agents, e.g. antihyperuricemic or uricosuric agents
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/16 Anti-Parkinson drugs
• CPC Class Codes: 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
• 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 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 35/04 specific for metastasis
• CPC Class Codes: A61P 37/02 : Immunomodulators
• CPC Class Codes: A61P 37/04 : Immunostimulants
• CPC Class Codes: A61P 7/10 : Antioedematous agents; Diuretics
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 : Antihypertensives
• CPC Class Codes: C07C 205/50 : having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 211/01 : having amino groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 317/02 : having sulfone or sulfoxide groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 323/52 : the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 57/52 : containing halogen
• CPC Class Codes: C07C 69/587 : Monocarboxylic acid esters having at least two carbon-to-carbon double bonds

Abstract

Activated fatty acids, pharmaceutical compositions including activated fatty acids, methods for using activated fatty acids to treat a variety of diseases, and methods for preparing activated fatty acids are provided herein.

Claims

1. An activated fatty acid comprising a hydrochloride salt of an unsaturated or polyunsaturated aliphatic chain having at least one electron withdrawing group positioned immediately adjacent to a carbon-carbon double bond wherein two or more carbon-carbon double bonds are conjugated;

wherein the at least one electron withdrawing group is selected from the group consisting of a vinyl group, an allylic group, or an allyl fluoride (—

CH═

CHCH₂F) group.

2. The activated fatty acid of claim 1, wherein the unsaturated or polyunsaturated aliphatic chain comprises from about 4 to about 25 carbons.

3. The activated fatty acid of claim 1, wherein the unsaturated or polyunsaturated aliphatic chain is selected from the group consisting of glycolipids, glycerolipids, phospholipids, and a cholesterol esters.

4. The activated fatty acid of claim 1, further comprising an additional electron withdrawing group selected from the group consisting of aldehyde (COH), acyl (—

COR), carbonyl (—

CO), carboxylic acid (—

COOH), ester (—

COOR), halides (—

Cl, —

F, —

Br, —

I), fluoromethyl (—

CF_n), allyl fluoride (—

CH═

CHCH₂F), cyano (—

CN), sulfoxide (—

SOR), sulfonyl (—

SO₂R), sulfonic acid (—

SO₃H), 1°

, 2°

, and 3°

ammonium (—

NR₃⁺), or nitro (—

NO₂), wherein R is selected from the group consisting of hydrogen, methyl, and C₂-C₆ alkyl.

5. The activated fatty acid of claim 1, further comprising an additional electron withdrawing group wherein the additional electron withdrawing group is a nitro (—

NO₂) group.

6. The activated fatty acid of claim 1, wherein the at least one electron withdrawing group is positioned on an alpha carbon of a carbon-carbon double bond of the unsaturated or polyunsaturated aliphatic chain.

7. The activated fatty acid of claim 1, wherein the at least one electron withdrawing group is positioned on a beta carbon of a carbon-carbon double bond of the unsaturated or polyunsaturated aliphatic chain.

8. The activated fatty acid of claim 1, wherein the at least one electron withdrawing group is positioned on a gamma carbon of a carbon-carbon double bond of the unsaturated or polyunsaturated aliphatic chain.

9. The activated fatty acid of claim 1, wherein a carbon-carbon double bond associated with the at least one electron withdrawing group is in a configuration selected from the group consisting of cis and trans.

10. The activated fatty acid of claim 1, wherein the unsaturated or polyunsaturated aliphatic chain comprises 18 carbons and the at least one electron withdrawing group is at a position selected from the group consisting of C-9, C-10, C-12, C-13, and a combination thereof.

11. The activated fatty acid of claim 1, further comprising one or more functional group other than an electron withdrawing group.