IP Library Granted Patent US 9,056,842
Granted Patent B2
US 9,056,842 · App. 14/174,455 · Granted Jun 16, 2015

Cosmetic use of substituted amino heterocylic carbamoyl analogs and related compounds

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Quick Facts
Patent No.
US 9,056,842
App. No.
14/174,455
Granted
Jun 16, 2015
Kind
B2
Abstract

Cosmetic compositions comprising substituted amino heterocyclic carbamoyl analogs and methods of using such compositions to impart anti-aging benefits to the skin are disclosed. The substituted amino heterocyclic carbamoyl analogs are believed to have modulatory activity against one or more biochemical pathways implicated in skin aging.

Claims (47)

1. A method for improving the aesthetic appearance of human skin comprising topically applying to an area of the skin in need thereof, a composition comprising a cosmetically acceptable vehicle and an effective amount of a collagen-stimulating compound having the structure:

where:

X is selected from O, S, or NR N ; and

R 2 is selected from the group consisting of hydrogen and C 1-6 alkyl;

R 4 is selected from hydrogen, C 1-6 alkyl, or a group:

wherein R 5 -R 9 are independently selected from the group consisting of hydrogen; F, Cl, Br, I; —OH; —NH 2 ; —NR N R N ; —SH; —CN; oxo; —CHO; —CO 2 H; —O—(C═O)—H; —O—(C═O)—C 1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C 1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR N R N ; —O—C 1-10 alkyl; —O—Ar; —S—C 1-10 alkyl; —S—Ar; —Ar; —C 1-10 alkyl; —NR N —CHO; —NR N —(C═O)—C 1-10 alkyl; —C 1-10 alkyl-O—C 1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO 2 —R N ; nitro; and C 1-6 alkyl, alkenyl, alkynyl, and aryl, wherein each of said C 1-6 alkyl, alkenyl, alkynyl, and aryl could be optionally further substituted with one or more groups R a ;

wherein R a is independently, at each occurrence, selected from hydrogen, halogen (F, Cl, Br, or I); —OH; —NH 2 ; —NR N R N ; —SH; —CN; oxo; —CHO; —CO 2 H; —O—(C═O)—H; —O—(C═O)—C 1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C 1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR N R N ; —O—C 1-10 alkyl; —O—Ar; —S—C 1-10 alkyl; —S—Ar; —Ar; —C 1-10 alkyl; —NR N —CHO; —NR N —(C═O)—C 1-10 alkyl; —C 1-10 alkyl-O—C 1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO 2 —R N ; or nitro;

wherein R N is independently selected, at each occurrence, from hydrogen or a C 1-16 hydrocarbon radical, optionally substituted with halogen (F, Cl, Br, or I); —OH; —NH 2 ; —NR*R*; —SH; —CN; oxo; —CHO; —CO 2 H; —O—(C═O)—H; —O—(C═O)—C 1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C 1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR*R*; —O—C 1-10 alkyl; —O—Ar; —S—C 1-10 alkyl; —S—Ar; —Ar; —C 1-10 alkyl; —NR*—CHO; —NR*—(C═O)—C 1-10 alkyl; —C 1-10 alkyl-O—C 1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO 2 —R*; or nitro; wherein R* is independently hydrogen or a C 1-16 hydrocarbon radical;

where any two adjacent groups R N may together form a 5 or 6 membered ring;

“m” is independently selected, at each occurrence, from an integer from 1 to 6, and “n” is independently selected, at each occurrence, from an integer from 0 to 4;

or a cosmetically acceptable salt thereof;

and wherein said compound comprises from about 0.00001% to about 0.5% by weight of the composition.

2. The method according to claim 1 , wherein R 4 is:

where,

X is selected from O or S; and R 2 is H

or a cosmetically acceptable salt thereof.

3. The method according to claim 2 , wherein said compound has the structure:

or a cosmetically acceptable salt thereof.

4. The method according to claim 3 , wherein said compound has the structure:

or a cosmetically acceptable salt thereof.

5. The method according to claim 3 , wherein said compound has the structure:

or a cosmetically acceptable salt thereof.

6. The method according to claim 1 , wherein said aesthetic improvement of said skin is selected from the group consisting of:

(a) treatment, reduction, and/or prevention of fine lines or wrinkles;

(b) reduction of skin pore size;

(c) improvement in skin thickness, plumpness, and/or tautness;

(d) improvement in skin smoothness, suppleness and/or softness;

(e) improvement in skin tone, radiance, and/or clarity;

(f) improvement in procollagen and/or collagen production;

(g) improvement in maintenance and remodeling of elastin;

(h) improvement in skin texture and/or promotion of retexturization;

(i) improvement in skin barrier repair and/or function;

(j) improvement in appearance of skin contours;

(k) restoration of skin luster and/or brightness;

(l) replenishment of essential nutrients and/or constituents in the skin;

(m) decreased by aging and/or menopause;

(n) improvement in skin moisturization;

(o) increase in skin elasticity and/or resiliency;

(p) treatment, reduction, and/or prevention of skin sagging;

(q) improvement in skin firmness;

(r) reduction of pigment spots and/or mottled skin;

(s) improving the appearance of acne scars or marks;

(t) improving the appearance of stretch marks; and/or

(u) improvement in the appearance of cellulite.

7. The method according to claim 6 , wherein said aesthetic improvement of said skin is the treatment, reduction, and/or prevention of: fine lines and/or wrinkles, skin sagging, or loss of elasticity.

8. The method according to claim 7 , wherein said aesthetic improvement of said skin is the treatment of wrinkles and/or fine lines on the skin, and wherein said method comprises topically applying an effective amount of a collagen-stimulating compound of formula I or a cosmetically acceptable salt thereof in a cosmetically acceptable vehicle to affected skin of an individual in need thereof, for a time sufficient to reduce the severity of said wrinkles or fine lines.

9. The method according to claim 8 , wherein said collagen-stimulating compound of formula I or a cosmetically acceptable salt thereof is applied to said skin at least once daily for a period of at least four weeks.

Assignments (3)
SECURITY INTEREST Recorded Nov 14, 2019
From: AVON PRODUCTS, INC.
To: CITIBANK, N.A., LONDON BRANCH
Reel/Frame 051032/0210 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Aug 15, 2016
From: CITIBANK, N.A.
To: AVON PRODUCTS, INC.
Reel/Frame 039690/0331 →
SECURITY INTEREST Recorded Jun 12, 2015
From: AVON PRODUCTS, INC.
To: CITIBANK, N.A.
Reel/Frame 035899/0776 →