# US 2014/0155441 A1 · Cosmetic Use of Substituted Amino Heterocylic Carbamoyl Analogs and Related Compounds

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- Number: US 2014/0155441 A1
- Document ID: US20140155441A1
- Status: Published application
- Kind: A1
- Application number: 14/174,455
- Filed: 2014-02-06
- Published: 2014-06-05
- Earliest claimed: 2011-08-25
- Assignees: Avon Products, Inc.
- Applicants: Avon Products, Inc.
- Inventors: John W. Lyga
- Web page: https://patentgrep.com/patent/US20140155441A1

## CPC

- C07D 263/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A61K 8/49: containing heterocyclic compounds
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/02: for chemically bleaching or whitening the skin
- A61Q 19/06: for countering cellulitis
- A61Q 19/08: Anti-ageing preparations
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## 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

### Claim at position 1

-18. (canceled)

### Claim 19

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 of formula I:
where:
X is selected from O, S, or NRN; and
R1 and R3 are independently a group of the form —[C(Ra)2]m-G-[C(Ra)2]n—Ra, where G is selected from a bond (i.e. absent), O, S, or NRN, and “m” and “n” are independently selected, at each occurrence, from an integer from 0 (zero) to 6;
R2 and R4 are independently selected from the group consisting of Ra, C1-6 alkyl, alkenyl, alkynyl, and aryl, each of which may be optionally substituted with one or more groups Ra;
L is selected from a CO, CO2, SO, SO2, PO3, or a bond (i.e. absent);
wherein Ra is independently, at each occurrence, selected from hydrogen, halogen (F, Cl, Br, or I); —OH; —NH2; —NRNRN; —SH; —CN; oxo; —CHO; —CO2H; —O—(C═O)—H; —O—(C═O)—C1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NRNRN; —O—C1-10 alkyl; —O—Ar; —S—C1-10 alkyl; —S—Ar; —Ar; —C1-10 alkyl; —NRN—CHO; —NRN—(C═O)—C1-10 alkyl; —C1-10 alkyl-O—C1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO2—RN; or nitro;
wherein RN is independently selected, at each occurrence, from hydrogen or a C1-16 hydrocarbon radical, optionally substituted with halogen (F, Cl, Br, or I); —OH; —NH2; —NR*R*; —SH; —CN; oxo; —CHO; —CO2H; —O—(C═O)—H; —O—(C═O)—C1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR*R*; —O—C1-10 alkyl; —O—Ar; S—C1-10 alkyl; —S—Ar; —Ar; —C1-10 alkyl; —NR*—CHO; —NR*—(C═O)—C1-10 alkyl; C1-10 alkyl-O—C1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO2—R*; or nitro; wherein R* is independently hydrogen or a C1-16 hydrocarbon radical;
where any two adjacent groups RN may together form a 5 or 6 membered ring;
or a cosmetically acceptable salt thereof;
and wherein said compound comprises from about 0.00001% to about 0.5% by weight of the composition.

### Claim 20 (depends on 1, 19)

The method according to claim 19, wherein said compound has the structure:
where, R2, Ra, and RN are as defined in claim 1; and
R1 and R3 are independently a group of the form —(CH2)m-G-(CH2)n—CH3, where G is selected from O, S, or NRN, and “m” and “n” are independently selected, at each occurrence, from an integer from 1 to 6;
R5-R9 are independently selected from the group consisting of Ra, C1-6 alkyl, alkenyl, alkynyl, and aryl, each of which could be optionally further substituted with one or more groups Ra;
or a cosmetically acceptable salt thereof.

### Claim 21 (depends on 1, 20)

The method according to claim 20, wherein said compound has the structure:
where, R1-R9, Ra, and RN are as defined in claim 1; and
“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.

### Claim 22 (depends on 21)

The method according to claim 21, wherein said compound has the structure:
or a cosmetically acceptable salt thereof.

### Claim 23 (depends on 21)

The method according to claim 21, wherein said compound has the structure:
or a cosmetically acceptable salt thereof.

### Claim 24 (depends on 19)

The method according to claim 19, 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.

### Claim 25 (depends on 24)

The method according to claim 24, 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.

### Claim 26 (depends on 25)

The method according to claim 25, 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.

### Claim 27 (depends on 26)

The method according to claim 26, 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.

### Claim 28

A cosmetic composition for improving the aesthetic appearance of human skin comprising a cosmetically acceptable vehicle, one or more skin active agents or cosmetic excipients, and an effective amount of a collagen-stimulating compound of formula I:
where:
X is selected from O, S, or NRN; and
R1 and R3 are independently a group of the form —[C(Ra)2]m-G-[C(Ra)2]n—Ra, where G is selected from a bond (i.e. absent), O, S, or NRN, and “m” and “n” are independently selected, at each occurrence, from an integer from 0 (zero) to 6;
R2 and R4 are independently selected from the group consisting of Ra, C1-6 alkyl, alkenyl, alkynyl, and aryl, each of which may be optionally substituted with one or more groups Ra;
L is selected from a CO, CO2, SO, SO2, PO3, or a bond (i.e. absent);
wherein Ra is independently, at each occurrence, selected from hydrogen, halogen (F, Cl, Br, or I); —OH; —NH2; —NRNRN; —SH; —CN; oxo; —CHO; —CO2H; —O—(C═O)—H; —O—(C═O)—C1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NRNRN; —O—C1-10 alkyl; —O—Ar; —S—C1-10 alkyl; —S—Ar; —Ar; —C1-10 alkyl; —NRN—CHO; —NRN—(C═O)—C1-10 alkyl; —C1-10 alkyl-O—C1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO2—RN; or nitro;
wherein RN is independently selected, at each occurrence, from hydrogen or a C1-16 hydrocarbon radical, optionally substituted with halogen (F, Cl, Br, or I); —OH; —NH2; —NR*R*; —SH; —CN; oxo; —CHO; —CO2H; —O—(C═O)—H; —O—(C═O)—C1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR*R*; —O—C1-10 alkyl; —O—Ar; —S—C1-10 alkyl; —S—Ar; —Ar; —C1-10 alkyl; —NR*—CHO; —NR*—(C═O)—C1-10 alkyl; —C1-10 alkyl-O—C1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO2—R*; or nitro; wherein R* is independently hydrogen or a C1-16 hydrocarbon radical;
where any two adjacent groups RN may together form a 5 or 6 membered ring;
or a cosmetically acceptable salt thereof;
and wherein said compound comprises from about 0.00001% to about 0.5% by weight of the composition.

### Claim 29 (depends on 10, 28)

The cosmetic composition according to claim 28, wherein said compound has the structure:
where, R2, Ra, and RN are as defined in claim 10; and
R1 and R3 are independently a group of the form —(CH2)2-G-(CH2)n—CH3, where G is selected from O, S, or NRN, and “m” and “n” are independently selected, at each occurrence, from an integer from 1 to 6;
R5-R9 are independently selected from the group consisting of Ra, C1-6 alkyl, alkenyl, alkynyl, and aryl, each of which could be optionally further substituted with one or more groups Ra;
or a cosmetically acceptable salt thereof.

### Claim 30 (depends on 10, 29)

The cosmetic composition according to claim 29, wherein said compound has the structure:
where, R1-R9, Ra, and RN are as defined in claim 10; and
“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.

### Claim 31 (depends on 30)

The cosmetic composition according to claim 30, wherein said compound has the structure:
or a cosmetically acceptable salt thereof.

### Claim 32 (depends on 30)

The cosmetic composition according to claim 30, wherein said compound has the structure:
or a cosmetically acceptable salt thereof.

### Claim 33 (depends on 28)

The cosmetic composition according to claim 28, wherein said vehicle is in the form of water-in-oil or oil-in water emulsion.

### Claim 34 (depends on 28)

The cosmetic composition according to claim 28, comprising a polydiorganosiloxane-polyoxyalkylene block copolymer.

### Claim 35 (depends on 28)

The cosmetic composition according to claim 28, comprising an emulsifier selected from the group consisting of dimethicone PEG 10/15 crosspolymer, dimethicone copolyol, cetyl dimethicone copolyol, PEG-15 lauryl dimethicone crosspolymer, laurylmethicone crosspolymer, cyclomethicone and dimethicone copolyol, dimethicone copolyol (and) caprylic/capric triglycerides, polyglyceryl-4 isostearate (and) cetyl dimethicone copolyol (and) hexyl laurate, dimethicone copolyol (and) cyclopentasiloxane, and mixtures thereof.

### Claim 36 (depends on 28)

The cosmetic composition according to claim 28, comprising a compound selected from the group consisting of acrylates/C10-30 alkyl acrylate crosspolymer, cetyl ethylhexanoate, C12-15 alkyl benzoate, isopropyl isostearate, diisopropyl dimer dillinoleate, methyl gluceth-20, acrylates/acrylamide copolymer/mineral oil, DMDM hydantoin/iodopropynylbutylcarbonate, and mixtures thereof.

### Claim 37 (depends on 28)

The cosmetic composition according to claim 28, comprising a filler selected from the group consisting of silica, treated silica, talc, zinc stearate, mica, kaolin, Nylon powders, polyethylene powder, Teflon™, starch, boron nitride, copolymer microspheres, silicone resin microbeads, and mixtures thereof.