Anti-inflammatory nitro-and thia-fatty acids

Inactive Publication Date: 2005-08-11
FERRANTE ANTONIO +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0047] Synthesis of hydroxy and hydroperoxy products of compound 6b was based on Scheme 8. Pure compound 17 was obtained in the yield of 32%. Compound 16 was relatively unstable, but

Problems solved by technology

Although EFAs play important roles in the biological process of the mammalian body, they are not widely used as therapeutics due to their limited availability in vivo.

Method used

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  • Anti-inflammatory nitro-and thia-fatty acids
  • Anti-inflammatory nitro-and thia-fatty acids
  • Anti-inflammatory nitro-and thia-fatty acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0054] Octadecan-1-ol (1a) was obtained from Aldrich Chemical Co. Arachidonyl alcohol (1b), linolenyl alcohol (1c), gamma linolenyl alcohol (1d) and docosahexaenyl alcohol 1e were purchased from Nu-Chek Prep. Inc. (Elysian, Minn., USA).

1-Bromooctadecane (2a); Typical Procedure

[0055] Octadecan-1-ol (1a) (520 mg, 1.92 mmol) and Ph3P (550 mg, 2.10 mmol) were dissolved in CH2Cl2 (25 mL). The mixture was cooled in an ice bath and CBr4 (630 mg, 1.90 mmol) was added with stirring. The mixture was allowed to warm to r.t. and was stirred overnight, then it was concentrated under a stream of N2 and the residue was subjected to flash column chromatography on silica, eluting with hexane, to afford 1-bromooctadecane (2a) (605 mg, 96%) as a waxy solid; mp 26-28° C.

[0056] IR (KBr): v 2920 (s), 2848 (s), 1468 (s), 1378 (w), 1254 (w), 1144 (m), 720 (m), 638 (s) cm1.

[0057]1H NMR (CDCl3, 300 MHz): δ=0.87 (t, 3H, J=6.7 Hz, C18-H3), 1.25-1.32 [m, 30H, (C3-17)-H2)], 1.82-1.85 (m, 2H, C2-H2), 3.40 (t,...

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Abstract

The present invention relates to compounds of the general formula: NO2-A-B wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 carbon atoms and B is (CH2)n(COOH)m in which n is an integer from 0 to 2 and m is an integer from 0 to 2; or of general formula (I), wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH2)j(COOH)k in which j is an integer from 1 to 3 and k is 0 or 1; and the derivatives thereof in which the hydrocarbon chain includes one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy. These compounds have biological activity, e.g. as anti-infective or anti-inflammatory agents.

Description

FIELD OF THE INVENTION [0001] The present invention relates to compounds which include a carbon chain of 14 to 26 carbon atoms and a nitro or sulphur group. In a particular embodiment the invention relates to nitro analogues of polyunsaturated fatty acids. The present invention further relates to the use of these compounds in methods of treatment. BACKGROUND OF THE INVENTION [0002] Fatty acids are one of the most extensively studied classes of compounds due to their important role in biological systems(1,2). Hundreds of different fatty acids exist in nature. They consist of saturated, monounsaturated and polyunsaturated fatty acids, having chain lengths from 4 to 22 carbon atoms. Polyunsaturated fatty acids (PUFAs) contain 16 to 22 carbon atoms with two or more methylene-interrupted double bonds. The PUFA, arachidonic acid, contains 20 carbons and four methylene-interrupted cis-double bonds commencing six carbons from the terminal methyl group, which therefore leads to an abbreviate...

Claims

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Application Information

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IPC IPC(8): A61K8/30A61K8/36A61K8/40A61K8/46A61K31/04A61K31/10A61K31/19A61K31/20A61K31/202A61K31/21A61K31/335A61P1/04A61P1/18A61P3/10A61P9/00A61P9/10A61P11/00A61P11/02A61P11/06A61P17/00A61P17/06A61P25/00A61P29/00A61P31/00A61P33/06A61P35/00A61P37/02A61P37/06A61P37/08A61P39/06A61P43/00C07C17/16C07C45/30C07C205/02C07C205/03C07C205/14C07C205/15C07C205/50C07C205/51C07C317/44C07C321/14C07C321/18C07C323/52C07C409/40
CPCA61K31/19A61K31/20C07C409/40C07C323/52C07C317/44C07C205/51C07C205/50C07C205/15C07C205/14C07C205/03C07C205/02C07C45/30C07C17/16A61K31/202A61K31/21A61K31/335A61K45/06C07C19/075C07C21/14C07C47/02C07C47/21A61K2300/00A61P1/04A61P1/18A61P11/00A61P11/02A61P11/06A61P17/00A61P17/06A61P25/00A61P29/00A61P3/10A61P31/00A61P33/00A61P33/06A61P35/00A61P37/02A61P37/06A61P37/08A61P39/06A61P43/00A61P9/00A61P9/10Y02A50/30
Inventor FERRANTE, ANTONIOEASTON, CHRISTOPHER J.XIA, LING
Owner FERRANTE ANTONIO
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