IP Library Granted Patent US 9,592,186
Granted Patent B2
US 9,592,186 · App. 14/409,607 · Granted Mar 14, 2017

Topical compositions and methods for skin lightening

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Quick Facts
Patent No.
US 9,592,186
App. No.
14/409,607
Granted
Mar 14, 2017
Kind
B2
Abstract

Embodiments of the invention are generally directed to compositions useful for reducing pigmentation in the skin. The composition may further include other depigmenting agents such as nicotinamide and its melanasome transfer-inhibiting derivatives, 3,3′-thiodipropanoic acid and its tyrosinase-inhibiting derivatives, or resorcinol and its tyrosinase-inhibiting derivatives, in a topically acceptable vehicle.

Claims (12)

1. A method for reducing pigmentation of human skin comprising topically applying to an area of the skin in need thereof a composition comprising, in a topically acceptable vehicle, an effective amount of a compound having the structure of formula (I):

wherein, R N are independently selected at each occurrence from hydrogen or C 1- C 12 hydrocarbons, optionally containing from 1-8 heteroatoms selected from halogen, O, N, and S and combinations thereof; and wherein two groups R N on the same nitrogen atom may together form a three- to six-membered ring;

R a is independently selected from hydrogen, —F; —Cl; —Br; —I; —OH, —OR*; —NH 2 ; —NHR*; —N(R*) 2 ; —N(R*) 3 + ; —N(R*)—OH; —N(→O)(R*) 2 ; —O—N(R*) 2 ; —N(R*)—O—R*; —N(R*)—N(R*) 2 ; —C═N—R*; —N═C(R*) 2 ; —C═N—N(R*) 2 ; —C(═NR*)—N(R*) 2 ; —SH; —SR*; —CN; —NC; —(C═O)—R*; —CHO; —CO 2 H; —CO 2 − ; —CO 2 R*; —(C═O)—S—R*; —O—(C═O)—H; —O—(C═O)—R*; —S—(C═O)—R*; —(C═O)—NH 2 ; —(C═O)—N(R*) 2 ; —(C═O)—NHNH 2 ; —O—(C═O)—NHNH 2 ; —(C═S)—NH 2 ; —(C═S)—N(R*) 2 ; —N(R*)—CHO; —N(R*)—(C═O)—R*; —(C═NR)—O—R*; —O—(C═NR*)—R*, —SCN; —NCS; —NSO; —SSR*; —N(R*)—C(═O)—N(R*) 2 ; —N(R*)—C(═S)—N(R*) 2 ; —SO 2 —R*; —O—S(═O) 2 —R*; —S(═O) 2 —OR*; —N(R*)—SO 2 —R*; —SO 2 —N(R*) 2 ; —O—SO 3 − ; —O—S(═O) 2 —OR*; —O—S(═O)—OR*; —O—S(═O)—R*; —S(═O)—OR*; —S(═O)—R*; —NO; —NO 2 ; —NO 3 ; —O—NO; —O—NO 2 ; —N 3 ; —N 2 —R*; —N(C 2 H 4 ); —Si(R*) 3 ; —CF 3 ; —O—CF 3 ; —PR* 2 ; —O—P(=O)(OR*) 2 ; —P(=O)(OR*) 2 ; C 1 -C 8 perfluoroalkyl; an aliphatic C 1 -C 8 hydrocarbon radical; a C 1 -C 8 aromatic hydrocarbon radical; or a C 1 -C 8 heteroaryl radical;

X 1 and X 2 are independently selected from oxygen, sulfur, or NR N ;

R* is independently at each occurrence hydrogen or a straight chained, branched, or cyclic C 1 -C 20 hydrocarbon radical, optionally substituted with one or more groups R a or with 1-6 heteroatoms selected from nitrogen, oxygen, sulfur, or halogen and combinations thereof;

ring “A” is a five or six-membered optionally aromatic ring, z 1 is —C—, —N—, —NL 1 -, or —CL 1 -;

and z 2 -z 6 are independently selected from —N—, —NH—, —NR—, —O—, —S—, —CH—, —CR—, —CR*—, and in the case where ring “A” is a five membered ring, z 4 is a bond (i.e., it is absent); where L 1 is group —V—(CH 2 ) r —(CH═CH) s —X b —(CH 2 ) y —(CH═CH) z —X c —, where X a , X b , and X c are independently a bond (i.e., absent), —O—, —S—, —NH—, —NR*— and “r,” “s,” “y,” and “z” are independently at each occurrence integers from 0-2;

Ω is selected from H, R*, OH, OR*, or NR N R N , wherein R N and R* are as defined above;

and n and m are independently integers from 0-6;

and topically acceptable salts thereof, for a time sufficient to reduce the pigmentation of said human skin.

2. The method of claim 1 , wherein the compound has the structure of formula (II):

3. The method according to claim 1 , wherein said composition is applied at least once daily for a period of at least four weeks.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Jan 28, 2026
From: NATURA &CO LUXEMBOURG HOLDINGS S.À R.L., AS A SECURED PARTY; NATURA &CO UK HOLDINGS LIMITED, AS A SECURED PARTY
To: AVON PRODUCTS, INC.
Reel/Frame 074508/0281 →
SECURITY INTEREST Recorded Apr 29, 2024
From: AVON PRODUCTS, INC.; MI HOLDINGS, INC.; AVON INTERNATIONAL OPERATIONS, INC.; AVON CAPITAL CORPORATION; AVON COSMETICS LIMITED; AVON BEAUTY LIMITED
To: NATURA &CO HOLDING S.A., AS SECURED PARTY; NATURA &CO LUXEMBOURG HOLDINGS S.À R.L., AS A SECURED PARTY; NATURA COSMÉTICOS S.A., AS A SECURED PARTY
Reel/Frame 067249/0491 →
SECURITY INTEREST Recorded Aug 11, 2023
From: AVON PRODUCTS, INC.
To: NATURA &CO LUXEMBOURG HOLDINGS S.À R.L., AS A SECURED PARTY; NATURA &CO UK HOLDINGS LIMITED, AS A SECURED PARTY
Reel/Frame 064566/0872 →
SECURITY INTEREST Recorded Nov 14, 2019
From: AVON PRODUCTS, INC.
To: CITIBANK, N.A., LONDON BRANCH
Reel/Frame 051032/0210 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2014
From: HU, HONG; YIM, SUNGHAN; SANTHANAM, UMA; LYGA, JOHN W.
To: AVON PRODUCTS, INC.
Reel/Frame 034555/0550 →