Lipophenol compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-10011620-B2
Application number	US-201515303797-A
Country	US
Kind code	B2
Filing date	Apr 24, 2015
Priority date	Apr 24, 2014
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

The present invention relates to a compound of formula (I) wherein: i is 0 or 1; j is 0 or 1; k is 0 or 1; R 1 and R 2 are in particular H, (C 1 -C 12 )alkyl, or a group of formula C(O)R; R is a, linear or branched, alkyl radical, comprising at least 19 carbon atoms; R 3 is H and k=0 when j=1; or, when j=0, R 3 is —C(O)R or -L-C(O)R; L, U and L″ are linkers; wherein, when j=0, at least one of the groups R 1 ; R 2 and R 3 comprises a radical R.

First claim

The invention claimed is:

1. A compound having the following formula (I-2):

wherein:
k is 0 or 1;
R 1 is (C 1 -C 12 )alkyl
R 3 is a group of formula —C(O)R or -L-C(O)R, R being a, linear or branched, alkyl radical, optionally interrupted by one or several double bonds, comprising at least 19 carbon atoms, and wherein one or several hydrogen atoms may be replaced by deuterium atoms;
L is a linker having one of the following formulae (L1) or (L2):

L″ is a linker chosen from the group consisting of: (C 6 -C 10 )arylene, (C 1 -C 12 )alkylene, (C 1 -C 12 )alkylene-(C 6 -C 10 )arylene, (C 6 -C 10 )arylene-(C 1 -C 12 )alkylene, —CH═CH—(C 6 -C 10 )arylene and (C 1 -C 12 )alkylene-CH═CH—(C 6 -C 10 )arylene radicals;

or its pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.

2. The compound of claim 1 , having the following formula (I-2-1):

wherein Alk is a (C 1 -C 12 )alkyl group, and R is as defined in claim 1 , or its pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.

3. A compound having the following formula (I-3):

wherein:
A 1 is an alkylene radical comprising from 3 to 6 carbon atoms;
X 1 is a radical —C(O)—or an alkylene radical comprising from 1 to 6 carbon atoms;
X 2 is a radical —C(O)—or an alkylene radical comprising from 1 to 6 carbon atoms;
R is a, linear or branched, alkyl radical, possibly interrupted by one or several double bonds, comprising at least 19 carbon atoms, and wherein one or several hydrogen atoms may be replaced by deuterium atoms; and
R 1 is chosen from the group consisting of: H, (C 1 -C 12 )alkyl, (C 3 -C 6 )cycloalkyl, and (C 6 -C 10 )aryl radicals; or R 1 may form a heterocycloalkyl radical with the oxygen atom bearing it; or R 1 is a group of formula C(O)R, R being as defined above;

or its pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.

4. A compound having the following formula (I-4):

wherein R is a linear or branched, alkyl radical, possibly interrupted by one or several double bonds, comprising at least 19 carbon atoms, and wherein one or several hydrogen atoms may be replaced by deuterium atoms,
and R 1 is an alkyl group comprising from 1 to 12 carbon atoms,

or its pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.

5. The compound of claim 1 , wherein R 1 is a (C 1 -C 6 )alkyl group.

6. The compound of claim 1 , wherein R is a linear or branched alkyl group, optionally interrupted by one or several double bonds, comprising from 19 to 23 carbon atoms.

7. The compound of claim 1 , wherein R is a linear or branched alkyl group, optionally interrupted by one or several double bonds, comprising from 19 to 23 carbon atoms, and wherein one or several hydrogen atoms are replaced by deuterium atoms.

8. The compound of claim 1 , wherein R is a linear or branched alkyl group, interrupted by at least one double bond, comprising from 19 to 21 carbon atoms.

9. The compound of claim 1 , wherein R is the following radical:

10. The compound of claim 1 , wherein R is the following radical:

11. A pharmaceutical composition comprising the compound according to claim 1 , in association with a pharmaceutically acceptable vehicle.

12. The compound of claim 4 , wherein R 1 is a (C 1 -C 6 )alkyl group.

13. The compound of claim 4 , wherein R is a linear or branched alkyl group, optionally interrupted by one or several double bonds, comprising from 19 to 23 carbon atoms.

14. The compound of claim 4 , wherein R is a linear or branched alkyl group, interrupted by at least one double bond, comprising from 19 to 21 carbon atoms.

15. The compound of claim 1 , having the following formula:

16. A pharmaceutical composition comprising the compound according to claim 4 , in association with a pharmaceutically acceptable vehicle.

Assignees

• Inst Nat Sante Rech Med
• Ct Hospitalier Universitaire Montpellier
• Univ Dauvergne
• Univ Montpellier

Inventors

• Brabet Philippe
• Cia David
• Guillou Laurent
• Hamel Christian
• Vigor Claire
• Durand Thierry
• Crauste Céline
• Vercauteren Joseph

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• C07F9/106

  Adducts, complexes, salts of phosphatides · CPC title

• A61P3/00

  Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) · CPC title