Cosmetic and pharmaceutical compositions comprising compounds that display retinoid like activities
View Patent ↗This invention relates to novel compounds that display retinoid like activities, including HB-EGF (Heparin Binding Epidermal Growth Factor) release from keratinocytes, cell proliferation, and epidermal thickening without the irritation potentials, such as release of interleukin 8 and inhibition of terminal differentiation of keratinocytes. This invention also relates to the use of such a compound for both external and non-external applications.
1. A compound of Formula (I)
wherein
R 1 is COOR 10 ;
Z is selected from a bond, and O—C 1-4 alkyl;
R 2 is hydrogen;
R 3 is hydroxyl;
X is selected from the group consisting of —CH═CH— and —N═N—;
R 4 is selected from the group consisting of hydroxy and —NR 15 R 16 ;
R 5 is selected from the group consisting of hydrogen and —NR 15 R 16 ;
R 6 is hydrogen;
R 7 is hydrogen;
R 8 is selected from the group consisting of hydrogen, and halo;
R 9 is selected hydroxy;
R 10 is hydrogen;
R 15 and R 16 are each independently hydrogen; or
a pharmaceutically acceptable or a cosmetically acceptable salt thereof.
2. The compound of claim 1 , wherein R 5 is hydrogen.
3. A compound selected from the group consisting of
4. A cosmetic or pharmaceutical composition comprising at least one compound as claimed in claim 1 .
5. A composition according to claim 4 , wherein said composition comprises from 0.001% to 10% by weight of a compound as claimed in claim 1 .
6. A process for preparing a composition according to claim 4 , wherein the compound of Formula (I) is intimately mixed with the other constituents of the composition.
7. The compound as claimed in claim 1 for treating acne.
8. The compound as claimed in claim 1 for treating skin atrophy.
9. The compound as claimed in claim 1 for treating photo-aging.
10. The compound as claimed in claim 1 for treating the skin in need of reducing the appearance of wrinkles, fine lines, stretch marks, or cellulite.
11. A compound of the formula
wherein
R 1 is COOH;
Z is oxygen;
R2, R3, R4, R5, R6, R7, R8 and R9 are each independently H; and
X is —CH═CH—; or
a pharmaceutically acceptable or a cosmetically acceptable salt thereof.