Vicinal primary diamines associated with metal and/or free radical chelation motifs, and active against carbonyl and oxidative stress, and use thereof

Patent metadata

Field	Value
Publication number	US-10464920-B2
Application number	US-201615742276-A
Country	US
Kind code	B2
Filing date	Jul 6, 2016
Priority date	Jul 6, 2015
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The invention relates to compounds of Formula I:

or the salts thereof, as well as the use thereof in the pharmaceutical, cosmetic or agrofood industry.

First claim

The invention claimed is:

1. Compound of Formula I:

and the salts thereof,
wherein
n is an integer from 1 to 6;
X is CO or CH 2 ;
Y is NR 1 R 2 or R 2 or

R 1 is H or alkyl or alkyl-aryl;
R 2 is Z-L-R 3 ;
Z is non-existent, CO or CH 2 ;
L is non-existent, CH═CH or (CH 2 ) m ;
m is an integer from 1 to 6;
R 3 is phenyl, substituted by at least one OH group and one or more substituents selected from OH, C1 to C4 alkoxy and C1 to C4 alkyl, or R 3 is N-pyridinonyl, substituted by at least one OH group and possibly by one or more substituents selected from OH, C1 to C4 alkoxy and C1 to C4 alkyl.

2. Compound or salt according to claim 1 , having Formula II

II.

3. Compound or salt according to claim 1 , having Formula III

4. Compound or salt according to claim 1 , having Formula IV

5. Compound or salt according to claim 1 , having Formula V

6. Compound or salt according to claim 4 , wherein Z-L-R 3 is selected from:

wherein R 5 , R 6 , R 9 , R 10 , R 11 , R 16 , R 17 and R 21 are selected, independently of one another, from OH, C1 to C4 alkoxy and C1 to C4 alkyl.

7. Compound or salt according to claim 1 , having Formula VI

8. Compound or salt according to claim 1 selected from:
(E)-4,5-diamino-1-(4-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)piperazin-1-yl)pentan-1-one,
(E)-N-(5,6-diaminohexyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide,
4,5-diamino-1-(4-(3,4,5-trihydroxybenzoyl)piperazin-1-yl)pentan-1-one,
N-(5,6-diaminohexyl)-3,4,5-trihydroxybenzamide,
N-(4,5-diaminopentyl)-3-(3-hydroxy-2-oxopyridin-1(2H)-yl)propanamide,
N-(5,6-diaminohexyl)-3-(3-hydroxy-2-oxopyridin-1(2H)-yl)propanamide,
4,5-diamino-N-(3-(3-hydroxy-2-oxopyridin-1(2H)-yl)propyl)pentanamide,
1-(2-(4-(4,5-diaminopentanoyl)piperazin-1-yl)-2-oxoethyl)-3-hydroxypyridin-2(1H)-one,
N-(4,5-diaminopentyl)-2-(3-hydroxy-2-methyl-4-oxopyridin-1(4H)-yl)acetamide,
N-(5,6-diaminohexyl)-2-(3-hydroxy-2-methyl-4-oxopyridin-1(4H)-yl)acetamide,
1-(2-(4-(4,5-diaminopentanoyl)piperazin-1-yl)-2-oxoethyl)-3-hydroxy-2-methylpyridin-4(1H)-one,
1-(3-(4-(4,5-diaminopentyl)piperazin-1-yl)propyl)-3-hydroxypyridin-2(1H)-one,
1-(3-((4,5-diaminopentyl)(methyl)amino)propyl)-3-hydroxypyridin-2(1H)-one, and
1-(5,6-diaminohexyl)-3-hydroxy-2-methylpyridin-4(1H)-one.

9. Pharmaceutical composition comprising at least one compound or one of the pharmaceutically acceptable salts thereof according to claim 1 and at least one pharmaceutically acceptable excipient.

10. Cosmetic composition comprising a compound according to claim 1 .

11. Agrofood composition comprising a compound according to claim 1 .

12. Compound or salt according to claim 5 , wherein Z-L-R 3 is selected from:

wherein R 5 , R 6 , R 9 , R 10 , R 11 , R 16 , R 17 and R 21 are selected, independently of one another, from OH, C1 to C4 alkoxy and C1 to C4 alkyl.

Assignees

• Univ Amiens Picardie Jules Verne
• Univ Centre Hospitalier
• Centre Nat Rech Scient
• Inst Nat Sante Rech Med
• Inserm Institute National De La Sante Et De La Rech Medicale
• Centre Hospitalier Univeritaire

Inventors

• Sasaki Nobumichi André
• Sonnet Pascal
• Boullier Agnès
• Lohou Elodie

Classifications

• C07D295/192

  from aromatic carboxylic acids · CPC title

• C07D213/69

  Two or more oxygen atoms · CPC title

• C07D295/185

  from aliphatic carboxylic acids · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• A61K8/4953

  containing pyrimidine ring derivatives, e.g. minoxidil · CPC title