IP Library Granted Patent US 10,011,620
Granted Patent B2
US 10,011,620 · App. 15/303,797 · Granted Jul 3, 2018

Lipophenol compounds and uses thereof

Inventors: Philippe Brabet (Montpellier, FR); David Cia (Clermont-ferrand, FR); Laurent Guillou (Montpellier, FR); Christian Hamel (Montpellier, FR); Claire Vigor (Montpellier, FR); Thierry Durand (Montpellier, FR); Céline Crauste (Montpellier, FR); Joseph Vercauteren (Montpellier, FR)
Assignees: INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER; UNIVERSITE D'AUVERGNE; UNIVERSITE DE MONTPELLIER
C07F9/10C07B59/001C07B59/004C07C69/017C07C69/587C07F9/106C07B2200/05
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Quick Facts
Patent No.
US 10,011,620
App. No.
15/303,797
Granted
Jul 3, 2018
Kind
B2
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.

Claims (34)

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.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME PREVIOUSLY RECORDED AT REEL: 057442 FRAME: 0626. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Nov 15, 2021
From: INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER; UNIVERSITÉ CLERMONT AUVERGNE; UNIVERSITE DE MONTPELLIER
To: INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); UNIVERSITE DE MONTPELLIER; UNIVERSITÉ CLERMONT AUVERGNE; CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)
Reel/Frame 058122/0289 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2021
From: INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER; UNIVERSITÉ CLERMONT AUVERGNE; UNIVERSITE DE MONTPELLIER
To: INSTITUT NATIONAL DE RECHERCHE POUR L'AGRICULTURE, L'ALIMENTATION ET L'ENVIRONNEMENT; UNIVERSITE DE MONTPELLIER; UNIVERSITÉ CLERMONT AUVERGNE; CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)
Reel/Frame 057442/0626 →
MERGER Recorded Sep 7, 2021
From: UNIVERSITE D'AUVERGNE
To: UNIVERSITÉ CLERMONT AUVERGNE
Reel/Frame 057424/0407 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 13, 2016
From: BRABET, PHILIPPE; CIA, DAVID; GUILLOU, LAURENT; HAMEL, CHRISTIAN; VIGOR, CLAIRE; DURAND, THIERRY; CRAUSTE, CELINE; VERCAUTEREN, JOSEPH
To: UNIVERSITE D'AUVERGNE; UNIVERSITE DE MONTPELLIER; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER
Reel/Frame 040006/0758 →
Priority Claims (1)
EP 14305607 · Apr 24, 2014 · regional
Continuity (1)
Related Publication 20170037067A1 · Feb 9, 2017