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US6664406: Nervonic acid derivatives, their preparation and use

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Filing Information

Inventor(s) Keith Coupland · Yann Raoul ·
Assignee(s) Croda International PLC ·
Attorney/Agent(s) Stevens, Davis, Miller & Mosher, L.L.P. ·
Primary Examiner Deborah Carr ·
Application Number US10130672
Filing date 08/19/2002
PCT 371 date 08/19/2002
Issue date 12/16/2003
Predicted expiration date 08/19/2022
U.S. Classifications 554/225  · 514/838  · 554/168  · 514/558  · 514/560  · 514/825  · 554/159  · 514/861  · 514/885  · 514/886  · 514/912  · 514/894  · 554/227  ·
International Classifications --
Kind CodeB1
International Classifications 589159 · 589168 · 589227 · 514558 · 514828 · 514838 · 514861 · 514888 · 514884 · 514912 ·
Related U.S. Application DataThis application is a 371 of PCT/GB00/04453 filed Nov. 23, 2000.
PCT Application Number WO20PCTGB0004453 - 11/23/2000
PCT Publication Number WO200138288 - 05/31/2001
Foreign Priority GB9927629 - 11/24/1999 ·
29 Claims, No Drawings


Abstract

The present invention relates to a nervonic acid derivatives of formula (I) CH3—(CH2)7—CHCH—(CH2)13—C(O)—O—(CH2)3—OR  (I) wherein R is hydrogen (H) or a residue of a carboxylic acid; or a salt of the compound where R is H; or a bioprecursor, prodrug thereof. Those compounds wherein R is other than H have pharmacological activity, in particular anti-inflammatory and immunomodulatory effects. Those compounds wherein R is H can be used to prepare the pharmacologically active derivatives.

Independent Claims | See all claims (29)

  1. 1. A compound of formula (I): CH3—(CH2)7—CHCH—(CH2)13—C(O)—O—(CH2)3—OR  (I) wherein R is a compound selected from the group consisting of hydrogen (H) and a residue of a carboxylic acid; and salts of the compound where R is H; and bioprecursors, prodrugs and hydrates thereof.
  2. 6. A compound selected from the group consisting of: 1-(z-15-tetracosenoyloxy)-3-hydroxypropane; 1-(z-15-tetracosenoyloxy)-3-(z,z,z-6,9,12-octadecatrienoyloxy)propane (hereinafter referred to as NA:GLA); 1-(z-15-tetracosenoyloxy)-3-(z,-4,7,10,13,16,19-docosahexaenoyloxy)propane (hereinafter referred to as NA:DHA); and 1,3-di-(z-15-tetracosenoyloxy)propane (hereinafter referred to as NA:NA).

References Cited

U.S. Patent Documents

Document NumberAssigneesInventorsIssue/Pub Date
US5194448 Croda International PLC Coupland et al. Mar 1993

Foreign Patent Documents

Document NumberAssigneesInventorsIssue/Pub Date
WO199107955Jun 1991
WO199634846Nov 1996
WO20wo9634846*Nov 1996
* cited by examiner

Other Publications

European Search Report.
Great Britain Search Report.

Referenced By