Vinyl substituted fatty acids

Patent metadata

Field	Value
Publication number	US-9790167-B2
Application number	US-201213611112-A
Country	US
Kind code	B2
Filing date	Sep 12, 2012
Priority date	May 1, 2008
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

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.

First claim

What is claimed is:

1. A pharmaceutical composition comprising an unsaturated or polyunsaturated fatty acid having an aliphatic chain comprised of an odd number of carbons; and one or more electron withdrawing groups selected from the group consisting of an aldehyde (—COH), acyl (—COR), carbonyl (—CO), cyano (—CN), sulfoxide (—SOR), sulfonyl (—SO 2 R), and sulfonic acid (—SO 3 H), wherein R is a hydrogen, methyl or C 2 -C 6 alkyl, associated with at least one carbon-carbon double bond, or a pharmaceutically acceptable salt or prodrug thereof, and a pharmaceutical acceptable carrier or excipient.

2. The pharmaceutical composition of claim 1 , wherein the aliphatic chain of the unsaturated or polyunsaturated fatty acid comprises 5 to 23 carbons.

3. The pharmaceutical composition of claim 1 , wherein the unsaturated or polyunsaturated fatty acid comprises an aliphatic chain having 5, 7, 9, 11, 13, 15, 17, 19, 21 or 23 carbons.

4. The pharmaceutical composition of claim 1 , wherein the unsaturated or polyunsaturated fatty acid prodrug is selected from the group consisting of a cholesterol ester, a glycolipid, a glycerolipid, and a phospholipid.

5. The pharmaceutical composition of claim 1 , wherein the one or more electron withdrawing group is positioned on a sp 2 carbon of a carbon-carbon double bond of the unsaturated or polyunsaturated fatty acid.

6. The pharmaceutical composition of claim 1 , wherein the one or more electron withdrawing group is positioned on a beta carbon of a carbon-carbon double bond of the non-naturally occurring, unsaturated or polyunsaturated fatty acid.

7. The pharmaceutical composition of claim 1 , wherein the one or more electron withdrawing group is positioned on a gamma carbon of a carbon-carbon double bond of the non-naturally occurring, unsaturated or polyunsaturated fatty acid.

8. The pharmaceutical composition of claim 1 , wherein a carbon-carbon double bond associated with the one or more electron withdrawing group is in cis configuration.

9. The pharmaceutical composition of claim 1 , wherein a carbon-carbon double bond associated with the one or more electron withdrawing group is in trans configuration.

10. The pharmaceutical composition of claim 1 , wherein the one or more electron withdrawing group is in an absolute stereochemistry of R at an sp 3 chiral/stereogenic center.

11. The pharmaceutical composition of claim 1 , wherein the one or more electron withdrawing group is in an absolute stereochemistry of S at an sp 3 chiral/stereogenic center.

12. The pharmaceutical composition of claim 1 , wherein a carbon-carbon double bond occurs at any carbon of the aliphatic chain of the non-naturally occurring, unsaturated or polyunsaturated fatty acid.

13. The pharmaceutical composition of claim 1 , wherein the unsaturated or polyunsaturated fatty acid is a fatty acid with two or more conjugated carbon-carbon double bonds.

14. The pharmaceutical composition of claim 13 , wherein at least one of the one or more electron withdrawing group is at any carbon in the two or more conjugated carbon-carbon double bonds.

15. The pharmaceutical composition of claim 1 , wherein at least one of the one or more electron withdrawing group is positioned at C-9, C-10, C-12, C-13 or a combination thereof.

16. The pharmaceutical composition of claim 1 , further comprising one or more of diluents, fillers, disintegrants, binders, lubricants, surfactants, hydrophobic vehicles, water soluble vehicles, emulsifiers, buffers, humectants, moisturizers, solubilizers, antioxidants, preservatives or combinations thereof.

17. The pharmaceutical composition of claim 1 , wherein the pharmaceutically acceptable carrier or excipient is formulated as a solid solution, powder, fluid emulsion, fluid suspension, semi-solid or dry powder.

18. The pharmaceutical composition of claim 1 , wherein the unsaturated or polyunsaturated fatty acid is selected from the group consisting of ω-2, ω-3, ω-4, ω-5, ω-6, ω-7, ω-8, and ω-9 fatty acids.

19. The pharmaceutical composition of claim 1 , wherein the unsaturated or polyunsaturated fatty acid is selected from the group consisting of (E)-10-acetylheptadec-9-enoic acid, (E)-9-acetylheptadec-9-enoic acid, (E)-11-acetyloctahepta-9-enoic acid, (E)-8-acetylheptadec-9-enoic acid, (E)-10-methylsulfonylnonadec-9-enoic acid, (E)-9-methylsulfonylnonadec-9-enoic acid, (E)-11-methylsulfonylnonadec-9-enoic acid, (E)-8-methylsulfonylnonadec-9-enoic acid, (E)-10-acetylnonadec-10,13-ienoic acid, (E)-9-acetylnonadec-9,12-enoic acid, (E)-11-acetylnonadec-10,13-ienoic acid, (E)-8-acetylnonadec-9,12-enoic acid, (E)-10-methylsulfonylpentadec-9,11-ienoic acid, (E)-9-methylsulfonylpentadec-8,9-ienoic acid, (E)-11-methylsulfonylpentadec-9,10-ienoic acid, (E)-8-methylsulfonylpentadec-8,9-ienoic acid, (Z)-10-acetylheptadec-9-enoic acid, (Z)-9-acetylheptadec-9-enoic acid, (Z)-11-acetyloctahepta-9-enoic acid, (Z)-8-acetylheptadec-9-enoic acid, (Z)-10-methylsulfonylnonadec-9-enoic acid, (Z)-9-methylsulfonylnonadec-9-enoic acid, (Z)-11-methylsulfonylnonadec-9-enoic acid, (Z)-8-methylsulfonylnonadec-9-enoic acid, (Z)-10-acetylnonadec-10,13-ienoic acid, (Z)-9-acetylnonadec-9,12-enoic acid, (Z)-11-acetylnonadec-10,13-ienoic acid, (Z)-8-acetylnonadec-9,12-enoic acid, (Z)-10-methylsulfonylpentadec-9,11-ienoic acid, (Z)-9-methylsulfonylpentadec-8,9-ienoic acid, (Z)-11-methylsulfonylpentadec-9,10-ienoic acid, and (Z)-8-methylsulfonylpentadec-8,9-ienoic acid or a pharmaceutically acceptable salt or prodrug thereof.

Assignees

• Freeman Bruce A
• Branchaud Bruce
• Complexa Inc
• Univ Pittsburgh Commonwealth Sys Higher Education

Inventors

• Freeman Bruce A
• Branchaud Bruce

Classifications

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• A61P7/00

  Drugs for disorders of the blood or the extracellular fluid · CPC title

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · CPC title

• A61P35/02

  specific for leukemia · CPC title