Biaromatic propynyl compounds, pharmaceutical and cosmetic compositions containing same, and uses thereof

Patent metadata

Field	Value
Publication number	US-10995052-B2
Application number	US-201716075592-A
Country	US
Kind code	B2
Filing date	Feb 3, 2017
Priority date	Feb 3, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

Compounds of general formula (I) are described. Also described, is the use of such compounds in pharmaceutical compositions for use in human or veterinary medicine (dermatological, rheumatic, respiratory, cardiovascular and ophthalmologic disorders, in particular), or in cosmetic compositions.

First claim

The invention claimed is:

1. A compound having the structure of formula (I) below:

in which:
Ar is a radical selected from the group of radicals of formula (a) or (b) below:

wherein R 5 is OH;

R 1 is: (i) a hydrogen atom,
(ii) a —CH 3 radical,
(ii) a —CH 2 —O—R 6 radical,
(iv) an —O—R 6 radical,
(v) a —CO—R 7 radical, or
(vi) an —S(O) t R 9 radical;

R 2 and R 3 , together with the carbon atoms to which they are attached, form a 5- or 6-membered ring optionally substituted by methyl groups and includes only carbon atoms;
R 4 is a halogen atom or an —OR 6 radical;
R 6 is a hydrogen atom, a lower alkyl radical, a linear or branched alkyl radical having 1 to 20 carbon atoms, or a —CO—R 9 radical;

R 7 is a hydrogen atom, a lower alkyl radical, a radical of formula:

or
an —OR 8 radical;
R 8 is a hydrogen atom, a linear or branched alkyl radical having 1 to 20 carbon atoms, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, a sugar residue, an amino acid, or a peptide residue;
R 9 represents a lower alkyl radical, or a linear or branched alkyl radical having 1 to 20 carbon atoms;
each of R′ and R″ is a hydrogen atom, a lower alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl radical, an amino acid, a peptide residue, or a sugar residue; or R′ and R″, together with the nitrogen atom to which they are attached, form a heterocycle; and
t is 0, 1 or 2,
or a salt, or an optical or geometric isomer thereof.

2. The compound according to claim 1 , wherein the compound is an alkali metal or alkaline earth metal salt, a zinc salt, or an organic amine salt.

3. The compound according to claim 1 , wherein the lower alkyl radicals are selected from the group consisting of methyl, ethyl, isopropyl, butyl, tert-butyl, and hexyl radicals.

4. The compound according to claim 1 , wherein the linear or branched alkyl radicals having 1 to 20 carbon atoms are selected from the group consisting of methyl, ethyl, propyl, cyclopropyl, cyclobutyl, and cyclopentyl radicals.

5. The compound according to claim 1 , wherein the monohydroxyalkyl radicals are selected from the group consisting of 2-hydroxyethyl, 2-hydroxypropyl, and 3-hydroxypropyl radicals.

6. The compound according to claim 1 , wherein the polyhydroxyalkyl radicals are selected from the group consisting of 2,3-dihydroxypropyl, 2,3,4-trihydroxybutyl, 2,3,4,5-tetrahydroxypentyl radicals, and a pentaerythritol residue.

7. The compound according to claim 1 , wherein the aryl radical is a phenyl radical optionally substituted with at least one halogen atom, hydroxyl, or nitro.

8. The compound according to claim 1 , wherein the aralkyl radicals are selected from the group consisting of benzyl or phenethyl radicals optionally substituted by at least one halogen atom, hydroxyl, or nitro.

9. The compound according to claim 1 , wherein the alkenyl radicals are selected from the group consisting of radicals containing 2 to 5 carbon atoms and having one or more double bonds.

10. The compound according to claim 1 , wherein the sugar residues are selected from the group consisting of glucose, galactose, mannose, and glucuronic acid residues.

11. The compound according to claim 1 , wherein the amino acid residues are selected from the group consisting of residues deriving from lysine, glycine, and aspartic acid.

12. The compound according to claim 1 , wherein the peptide residues are selected from the group consisting of dipeptide and tripeptide residues.

13. The compound according to claim 1 , wherein the heterocyclic radicals are selected from the group consisting of piperidino, morpholino, pyrrolidino, and piperazino radicals, optionally substituted in position 4 by a C1-C6 alkyl or mono- or polyhydroxyalkyl radical.

14. The compound according to claim 1 , wherein the halogen atoms are selected from the group consisting of fluorine, chlorine, and bromine.

15. The compound according to claim 1 , wherein the compound is an alkali metal salt, an alkaline earth metal salt, a zinc salt, or an organic amine salt of compound 1 or 2:

16. The compound according to claim 1 , wherein R 4 is an —OR 6 radical, R 1 is a —CO—R 7 radical, and R 7 is an —OR 8 radical.

17. The compound according to claim 1 , wherein the compound is added to a medicament.

18. The compound according to claim 9 , wherein the alkenyl radical is an allyl radical.

19. A pharmaceutical or cosmetic composition comprising an effective amount of the compound of claim 1 .

Assignees

• Galderma Res & Dev

Inventors

• Portal Thibaud

Classifications

• C07D213/80

  in position 3 · CPC title

• C07C65/19 Primary

  having unsaturation outside the aromatic ring · CPC title

• C07C63/66

  Polycyclic acids with unsaturation outside the aromatic rings · CPC title

• A61Q19/08

  Anti-ageing preparations · CPC title

• A61P17/10

  Anti-acne agents · CPC title