IP Library Granted Patent US 10,179,761
Granted Patent B2
US 10,179,761 · App. 15/317,742 · Granted Jan 15, 2019

Compounds, pharmaceutical composition and their use in treating neurodegenerative diseases

Inventors: Patricia Melnyk (Annoeullin, FR); Patrick Vermersch (Marcq En Baroeul, FR); Pascal Carato (Ronchin, FR); Bénédicte Oxombre-Vanteghem (Arneke, FR); Hélène 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 10,179,761
App. No.
15/317,742
Granted
Jan 15, 2019
Kind
B2
Abstract

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

Claims (40)

1. A compound of Formula I:

or a pharmaceutically acceptable salt or solvate thereof,

wherein:

X 1 , X 2 , X 3 , X 4 , X 5 are hydrogen and X 3 is n-propyl, n-butyl, nitro or dialkylamino, or

X 2 , X 3 , X 4 , X 5 are hydrogen and X 1 is fluoro, iodo, C1-C4-alkyl, C1-C2-haloalkyl, cyano, nitro, or dialkylamino, or

X 1 , X 3 , X 4 , X 5 are hydrogen and X 2 is C1-C4-aklyl, C1-C2-haloalkyl, cyano, nitro, or

X 3 , X 4 , and X 5 are hydrogen and X 1 and X 2 are independently selected from the group consisting of chloro, C1-C4-alkyl, C1-C2-haloalkyl, cyano, nitro, and dialkylamino, or

X 2 , X 4 , and X 5 are hydrogen and X 1 and X 3 are independently selected from the group consisting of chloro, C1-C4-alkyl, C1C2-haloalkyl, cyano, nitro, and dialkylamino, or

X 1 , X 4 , and X 5 are hydrogen and X 2 and X 3 are independently selected from the group consisting of chloro, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, cyano, nitro, and dialkylamino, or

X 1 , X 3 , and X 5 are hydrogen and X 2 and X 4 are independently selected from the group consisting of chloro, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, cyano, nitro, and dialkylamino;

L is —C(O)NH—;

n is 0, or 1;

m is 1, 2, 3, 4 or 5;

R 1 is methyl, 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 substituents independently selected from halogen.

2. The compound according to claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein n is 0.

3. 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.

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

5. The compound according to claim 1 , having Formula II

or a pharmaceutically acceptable salt or solvate thereof,

wherein:

X 3 , m, R 1 , and R 2 are as defined in claim 1 , with the proviso that X 3 is not hydrogen.

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 halogen.

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

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

N-[3-(benzylmethylamino)propyl]-4-propylbenzamide;

N-[3-(benzylmethylamino)propyl]-4-butylbenzamide;

N-[3-(benzylmethylamino)propyl]-2,3-dichlorobenzamide;

N-[3-(benzylmethylamino)propyl]-2,4-dichlorobenzamide;

N-[3-(benzylmethylamino)propyl]-3,4-dichlorobenzamide;

N-[3-(benzylmethylamino)propyl]-3,5-dichlorobenzamide;

N-[3-(benzylmethylamino)propyl]-4-nitrobenzamide;

N-(2-(benzyl(methyl)amino)ethyl)-2,4-dichlorobenzamide; and

N-(2-(benzyl(methyl)amino)ethyl)-4-nitrobenzamide.

9. A pharmaceutical composition comprising an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof and at least one pharmaceutically acceptable carrier, diluent, excipient and/or adjuvant.

Assignments (2)
MERGER Recorded Oct 19, 2020
From: UNIVERSITE DE LILLE 2 DROIT ET SANTE
To: UNIVERSITE DE LILLE
Reel/Frame 054173/0798 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2017
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 042565/0057 →
Priority Claims (1)
EP 14305919 · Jun 16, 2014 · regional
Continuity (1)
Related Publication 20170107174A1 · Apr 20, 2017