IP Library Granted Patent US 10,844,008
Granted Patent B2
US 10,844,008 · App. 16/205,637 · Granted Nov 24, 2020

Compounds, pharmaceutical composition and their use in treating neurodegenerative diseases

Inventors: Patricia Melnyk (Annoellin, FR); Patrick Vermersch (Marcq en Baroeul, FR); Pascal Carato (Ronchin, FR); Bénédicte Oxombre-Vanteghem (Arneke, FR); Héléne Zephir (Lille, FR); Marion Donnier-Marechal (St Jean de Moirans, FR)
Assignees: UNIVERSITE DE LILLE 2 DROIT ET SANTE; CENTRE HOSPITALIER REGIONAL ET UNIVERSITAIRE DE LILLE (CHRU)
C07C233/78A61K49/00C07C211/27C07C211/29C07C235/50C07C237/10C07C237/20C07C237/34C07C255/57C07C255/60C07C311/37C07D209/08C07D209/44
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Quick Facts
Patent No.
US 10,844,008
App. No.
16/205,637
Granted
Nov 24, 2020
Kind
B2
Abstract

The present invention is directed to novel compounds of Formula (I), pharmaceutically acceptable salts or solvates thereof, and their use.

Claims (32)

1. A compound of Formula I:

or a pharmaceutically acceptable salt or solvate thereof,

wherein

X 1 and X 5 are independently selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, cyano, nitro, di(C1-C4-alkyl)amino, —NHCOOR′, and —COOR′, wherein R′ is methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl or tert-butyl;

X 2 , X 3 , X 4 are independently selected from the group consisting of hydrogen, chloro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyano, nitro, di(C1-C4-alkyl)amino, —NHCOOR′, and —COOR′, wherein R′ is methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl or tert-butyl; with the proviso that at least one of X 1 , X 2 , X 3 , X 4 , X 5 is not hydrogen and that at least one of X 2 , X 3 , X 4 is not C1-C4-alkoxy;

L is —NHC(O) or —NHSO 2 ;

n is 1;

m is 2, 3, 4 or 5;

R 1 is alkyl, and

R 2 is 5- or 6-membered arylalkyl, 5- or 6-membered cycloalkylalkyl, wherein the cyclic moiety of said arylalkyl or cycloalkylalkyl is optionally substituted by one or more fluoro; or

R 1 and R 2 together with the nitrogen atom to which they are attached, form a isoindolinyl group optionally substituted by one or more substituents independently selected from C1-C2 alkyl and halogen.

2. The compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof, wherein

n is 1 and L is —NHC(O)—.

3. The compound according to claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is methyl.

4. The compound according to claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 2 is 5- or 6-membered aryl-C1-C2-alkyl.

5. The compound according to claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein m is 2, 3 or 4.

6. The compound according to claim 1 , having Formula III

or a pharmaceutically acceptable salt or solvate thereof,

wherein

X 1 , X 2 , X 3 , X 4 , X 5 , L, n and m are as defined in claim 1 ;

p is 1 or 2;

X 6 , X 7 , X 8 , X 9 , X 10 are independently selected from H and fluoro.

7. The compound according to claim 1 , having Formula V

8. The compound according to claim 1 selected from the group consisting of:

N-[3-(benzylmethylamino)propyl]-4-chlorobenzensulfonamide,

4-(benzylmethylamino)-N-(4-chlorophenyl)butanamide,

N-(4-chlorobenzyl)-3-(benzylmethylamino)propanamide,

N-(4-nitrobenzyl)-3-(benzylmethylamino)propanamide,

N-(4-cyanobenzyl)-3-(benzylmethylamino)propanamide,

N-(2,4-dichlorobenzyl)-3-(benzylmethylamino)propanamide, and

N-(3-chlorobenzyl)-3-(benzylmethylamino)propanamide.

9. A pharmaceutical composition comprising an effective amount of compound according to claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2020
From: MELNYK, PATRICIA; VERMERSCH, PATRICK; CARATO, PASCAL; OXOMBRE-VANTEGHEM, BENEDICTE; ZEPHIR, HELENE; DONNIER-MARECHAEL, MARION
To: UNIVERSITE DE LILLE 2 DROIT ET SANTE; CENTRE HOSPITALIER REGIONAL ET UNIVERSITAIRE DE LILLE (CHRU)
Reel/Frame 054093/0242 →
MERGER Recorded Oct 19, 2020
From: UNIVERSITE DE LILLE 2 DROIT ET SANTE
To: UNIVERSITE DE LILLE
Reel/Frame 054173/0798 →
Priority Claims (1)
EP 14305919 · Jun 16, 2014 · regional
Continuity (2)
Division 15317742
Related Publication 20190092721A1 · Mar 28, 2019