Compounds for treating skin conditions

Details Compounds for treating skin conditions Compounds for treating skin conditions

2000-05-08

2001-12-25

Spivack, Phyllis G. (Department: 1614)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S637000

Reexamination Certificate

active

06333356

ABSTRACT:

BACKGROUND OF THE INVENTION
I. Field of Invention
The present invention relates to a new class of compounds for use as active principals for topical treatment of skin conditions, to compositions containing these compounds and to methods of treating skin conditions using these compounds and compositions. Compounds of the class include those of Formula (I):
wherein, R
4
is (CR
5
R
6
—CR
7
R
8
—X
1
)
n
—CR
9
R
10
R
11
; n is an integer from 1 to 18; R
1
, R
2
, R
3
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
and R
11
, are independently hydrogen or non-hydrogen substituents, with preferred non-hydrogen substituents including alkyls, alkenyls, oxa-alkyls, aralkyls and aryls; and X, X
1
, Y and Z are independently, O, NH or S, with preferred compounds including those in which X, X
1
, Y and Z are each oxygen and R
1
, R
2
, R
3
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
and R
11
are each hydrogen.
II. Description of the Prior Art
Dermal use of alpha hydroxyacids having an all carbon backbone is described in U.S. Pat. No. 5,091,171. Cosmetic compositions using 2-hydroxyalkenoic acid are disclosed, for example, in U.S. Pat. No. 5,108,751. Such compounds must have an unsubstituted alpha hydoxy group on a carbon backbone and are purportedly used in impart beneficial effects to the skin. However, the trend is away from the use of such alpha hydroxyacids since they necessitate low operational pH ranges that for the most common forms, i.e. glycolic and lactic acids, are known to cause skin irritation.
Topical formulations comprising straight, all carbon backbone, dicarboxylic acids have been proposed as replacements for alpha hydroxyacids. For example, U.S. Pat. Nos. 4,292,326, 4,386,104 and 5,385,943 describe the use of dicarboxylic acids having 7 to 13 carbon atoms for various skin indications. Similarly, U.S. Pat. No. 4,885,282 states that a 4 to 18 carbon dicarboxylic acid compound is useful for the treatment of skin disorders.
The problem with the use of these dicarboxylic acids is their inherent insolubility in aqueous solutions. Such solutions make up the majority of cosmetic delivery systems. Also, dicarboxylic acids that have all carbon backbones are solid at ambient temperatures, extremely difficult to work with and, if a solution is achieved, the result is an aesthetically unpleasant mixture unsuitable for cosmetic use.
Therefore, there is a need for a compound or class of compounds that can be used as mild, exfoliating actives for topical treatment of skin.
There is also a need for a mild, exfoliating topical composition that contains a water soluble compound that can be manufactured into an aesthetically acceptable cosmetic or dermatologic products.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a water soluble compound or class of such compounds that can be manufactured into an aesthetically acceptable, mild, exfoliating composition for topical use.
It is another object of the present invention to provide topical compositions with such water soluble compounds that have multiple skin care benefits.
It is a further object of the present invention to provide a new, dermatologic and cosmetic use for oxa acids.
These and other objects will become evident from the following disclosure.
DETAILED DESCRIPTION OF THE INVENTION
The basic compound of this invention is a compound of the following Formula (I):
wherein, R
4
is (CR
5
R
6
—CR
7
R
8
—X
1
)
n
—CR
9
R
10
R
11
; n is an integer from 1 to 18; R
1
, R
2
, R
3
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
and R
11
are independently hydrogen or non-hydrogen substituents.
X, X
1
, Y and Z are independently, O, NH, or S. Preferred are those compounds in which X, X
1
, Y and Z are all oxygen. Most preferred are those compounds in which X, X
1
, Y and Z are each oxygen, and R
1
, R
2
, R
3
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
and R
11
, are each hydrogen.
The preferred non-hydrogen substituents include alkyls alkenyls, oxa-alkyls, aralkyls and aryls. Examples of non-hydrogen substituents include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, heptyl, octyl, nonyl, dodecanyl, methoxy, ethoxy, propoxy, butoxy, cyclohexenyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, cyclobutyl and cyclohexanyl.
Exemplary compounds of Formula (I) include 3,6-dioxaheptanioic acid (CH
3
—O—CH
2
—CH
2
—O—CH
2
—COOH); 7,7-dimethyl-3,6-dioxaheptanoic acid ((CH3)
2
CH—O—CH
2
—CH
2
—O—CH
2
—COOH); 3,6-dioxanheptanoic acid ethyl ester (CH
3
—O—CH
2
—CH
2
—O—CH
2
—COOC
2
—CONH
2
); 3,6-dioxanheptanoic acid dodecyl ester (CH
3
—O—CH
2
—CH
2
—O—CH
2
—COOC
12
H
25
); 2-phenyl-3,6-dioxaheptanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH(Phe)—COOH); 2-benzyl-3,6-dioxaheptanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH(CH
2
Phe)—COOH); 2-methyl-3,6-dioxaheptanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH(CH
3
)—COOH); 3-amino-6-oxaheptanoic acid (CH
3
—O—CH
2
—CH
2
—NH—CH
2
—COOH); 3,6,9-trioxadecanoic acid (CH
3
—O—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 2-phenyl-3,6,9-trioxadecanoic acid (CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH(Phe)—COOH); 2-benxyl-3,6,9-trioxadecanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
)—CH(CH
2
-Phe)—COOH); 2-decyl-3,6,9-trioxadecanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH(C
10
H
21
)—COOH); 3,6,9,12-tetraoxatridecanoic acid (Ch
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 3,6,9,12,15-pentaoxahexadecanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 2-methyl-3,6,9,-trioxadecanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH(CH
3
)—COOH); 10,10-dimethyl-3,6,9-trioxadecanoic acid ((CH
3
)
2
CH—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 2-ethyl-3,6,9,12-tetraoxatridecanoic acid (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH(C
2
H
5
)—COOH); 10-phenyl-3,6,9-trioxadecanoic acid (Phe-CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 3,6,9-trioxadecanoic acid ethyl ester (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOC
2
H
5
); 3,6,9-triaminodecanoic acid (CH
3
—NH—CH
2
—CH
2
—NH—CH
2
—CH
2
—NH—CH
2
—COOH); 3,6,9,12-tetraaminotridecanoic acid (CH
3
—NH—CH
2
—CH
2
—NH—CH
2
—CH
2
—NH—CH
2
—CH
2
—NH—CH
2
—COOH); 9-amino-3,6-dioxadecanoic acid (CH
3
—NH—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 6,9-diamino-3-oxadecanoic acid (CH
3
—NH—CH
2
—CH
2
—NH—CH
2
—CH
2
—O—CH
2
—COOH); 3,6,9-trithiodecanoic acid (CH
3
—S—CH
2
—CH
2
—S—CH
2
—CH
2
—S—CH
2
—COOH); 9,12-dithio-3,6-dioxatridecanoic acid (CH
3
—S—CH
2
—CH
2
—S—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOH); 9-amino-3,6-dioxadecanoic acid monoamide (CH
3
—NH—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CONH
2
); 3,6,9-trioxadecanoic acid monoamide (CH
3
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CONH
2
); 10,10-dimethyl-3,6,9-trioxadecanoic acid amide ((CH
3
)
2
CH—O—CH
2
—O—CH
2
—O—CH
2
—CONH
2
); 10,10-dimethyl-3,6,9-trioxadecanoic acid heptadecanyl ester ((CH
3
)
2
CH—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOC
2
H
5
); 10,10-dimethyl-3,6,9-trioxadecanoic acid heptadecanyl ester ((CH
3
)
2
CH—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—COOC
17
H
35
); and 10,10-dimethyl-3,6,9-trioxadecanoic acid ((CH
3
)
2
CH—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH(CH
3
)—COOH).
Compounds of Formula (I) are described as intermediates useful in the making of curing agents and hardeners for epoxy resins in U.S. Pat. Nos. 5,017,675 and 5,319,004, both assigned to Hoechst AG. German Published Application No. DE-A-2936123 describes the preparation of such epoxy resin intermediate compounds. Such compounds are also commercially available from Hoechst AG.
Compounds of Formula I can also be prepared from commercially available polamines, polyols and polythiols by routine chemical reactions well known to those skilled in the art such as amidation, catalytic oxidation, esterification and other well known organic chemistry synthetic protocols, as described in organic chemistry textbooks including March,
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure,
3rd ed., John Wiley Interscience (1985) and Carey et al.
Advanced Organic Chemistry,
3rd ed., Parts A and B, Plenum Press, N. Y. (1990).
The oxa acid compounds useful in the topical compositions of this invention can also be in the form of derivative

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