Vinyl substituted fatty acids

Inactive Publication Date: 2009-12-31
COMPLEXA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013]Various embodiments of the invention are directed to compounds including a non-naturally occurring, unsaturated or polyunsaturated fatty acid having one or more electron withdrawing group associated with at least one carbon-carbon double bond or a pharmaceutically acceptable salt thereof. In some embodiments, the non-naturally occurring, unsaturated or polyunsaturated fatty acid may include an aliphatic chain having an odd numbe

Problems solved by technology

To date, a gap in the clinical detection and structural characterization of nitrated fatty acids has limited defining NO2-FA derivatives as biologically-relevant lipid signaling mediators that converge .NO and oxygenated lipid signaling pathways.

Method used

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  • Vinyl substituted fatty acids
  • Vinyl substituted fatty acids
  • Vinyl substituted fatty acids

Examples

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example 1

Preparation of (E)-9-nitro-octadec-9-enoic acid

[0123]Commercially available 9-bromononanol was oxidized using Jones' reagent, chromium trioxide (CrO3) in concentrated sulfuric acid (H2SO4), 67%, to form a carboxylic acid protected as an allyl ester (92% yield) and was nitrated using the Kornblum method, silver nitrate (AgNO2) in diethyl ether (Et2O), to form 9-nitro-nonanoic acid, allyl ester, in an overall yield of 42%. Nitroaldol condensation was then carried out by combining this intermediate with commercially available nonyl aldehyde in the presence of a catalytic amount of (10 mol %) of DBU to produce β-hydroxynitro (81% yield) as a 1:1 mixture of diastereomers. The β-hydroxynitro ester intermediate was acetylated in acetic anhydride with a catalytic amount of β-toluenesulfonic acid to produce a β-acetoxynitro ester intermediate in high yield, and the nitroalkene was generated by from the β-acetoxynitro ester intermediate by base-induced elimination with azeotropic removal of w...

example 2

Production of (Z)-isomers

[0124](Z)-9-nitro-octadec-9-enoic was formed from the (E)-9-nitro-octadec-9-enoic acid using the Ono method as described in Ono, N, et al. J. Chem. Soc., Chem. Commun. 1987, 1551-1551 and Sharpless et al., Am. Chem. Soc. 1973, 95, 2697-2699, both of which are hereby incorporated by reference in their entireties, at about 80% to about 90% yield.

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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.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a non-provisional application claiming priority to U.S. Provisional Patent Application No. 61 / 049,649 filed May 1, 2008 which is herein incorporated by reference in its entirety.GOVERNMENT INTERESTS[0002]Not applicablePARTIES TO A JOINT RESEARCH AGREEMENT[0003]Not applicableINCORPORATION BY REFERENCE OF MATERIAL SUBMITTED ON A COMPACT DISC[0004]Not applicableBACKGROUND[0005]1. Field of Invention[0006]Not applicable[0007]2. Description of Related Art[0008]Nitric oxide (NO) is an endogenously generated, lipophilic signaling molecule that has been implicated in the maintenance of vascular homeostasis, modulation of oxygen radical reactions, inflammatory cell function, post-translational protein modification and regulation of gene expression. In addition, nitric oxide-derived species display separate and unique pharmacological properties, specifically can mediate oxidation and nitration of biomolecules such as, for example...

Claims

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Application Information

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IPC IPC(8): A61K31/202C07C57/03C07H15/02C07F9/08A61K31/20A61P11/00
CPCC07C205/50A61P1/00A61P1/02A61P1/04A61P1/16A61P11/00A61P11/06A61P13/00A61P13/12A61P15/00A61P17/00A61P17/02A61P17/06A61P17/14A61P19/00A61P19/02A61P19/04A61P19/06A61P19/10A61P21/04A61P25/00A61P25/16A61P25/28A61P29/00A61P3/04A61P31/00A61P31/04A61P31/12A61P35/00A61P35/02A61P35/04A61P37/00A61P37/06A61P7/00A61P7/02A61P9/00A61P9/10A61P9/12
InventorFREEMAN, BRUCE A.BRANCHAUD, BRUCE
OwnerCOMPLEXA