Aromatic polyenic compounds and pharmaceutical/cosmetic...

Details Aromatic polyenic compounds and pharmaceutical/cosmetic... Aromatic polyenic compounds and pharmaceutical/cosmetic...

2000-01-05

2002-12-31

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S047000, C424S443000, C424S450000, C424S451000, C424S464000, C424S489000, C424S701000, C514S844000, C514S846000, C514S944000, C560S062000, C560S100000, C560S104000, C560S106000, C560S112000, C560S113000, C562S490000, C562S495000, C564S180000, C564S182000, C568S308000, C568S328000, C568S425000, C568S444000, C568S626000, C568S716000, C568S763000, C568S764000, C568S780000, C585S534000

Reissue Patent

active

RE037947

ABSTRACT:

BACKGROUND OF THE INVENTION
Technical Field of the Invention
The present invention relates to novel aromatic polyenic compounds and to pharmaceutical/cosmetic compositions comprised thereof; the subject compounds are especially useful in humans or veterinary medicine, or, alternatively, in cosmetic compositions.
SUMMARY OF THE INVENTION
The compounds according to the invention display a pronounced activity in the fields of cell differentiation and proliferation, and are particularly useful in the topical and systemic treatment of dermatological conditions associated with a keratinization disorder, dermatological (or other) conditions including an inflammatory and/or immunoallergic component, and dermal or epidermal proliferations, whether benign or malignant. The subject compounds can, in addition, be used for the treatment of the degenerative diseases of the connective tissue, for combating aging of the skin, whether photoinduced or chronologic, and for treating cicatrization or healing disorders. They are also useful for ophthalmological applications, especially for the treatment of corneopathies.
The compounds according of this invention are also useful for the treatment of osteoporosis or for the treatment of viral diseases, as well as for the treatment of any disease state associated with hypervitaminosis A. Generally, they are useful for the treatment of any disease or condition associated with a modification in the expression of receptors belonging to the superfamily of steroid and thyroid hormone receptors.
Too, the compounds according to this invention can also be formulated into cosmetic compositions for body and hair care/hygiene.
Briefly, the aromatic polyenic compounds according to the invention have the following structural formula (I):
in which R
1
is a —CH
3
radical, a radical —CH
2
—O—R
9
, a radical —CH
2
—O—CO—R
10
, or a radical —CO—R
11
, wherein R
9
, R
10
and R
11
are as defined below; R
2
is a hydrogen atom or a lower alkyl radical; R
3
is a hydrogen atom or a lower alkyl radical; R
4
is a hydrogen atom; R
5
is a hydrogen atom or a lower alkyl radical; R
6
is a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, a radical —O—CH
2
—O—CH
2
—CH
2
—O—CH
3
or a radical —O—R
13
, wherein R
13
is as defined below; R
7
and R
8
independently are each (i) a hydrogen atom, (ii) a linear or branched alkyl radical having from 1 to 20 carbon atoms, (iii) a cycloaliphatic radical, (iv) a radical —O—CH
2
—O—CH
2
—CH
2
—O—CH
3
, (v) a radical —O—R
13
, or (vi) a radical —S(O)
n
R
13
, wherein R
13
and n are as defined below, with the proviso that R
4
and R
6
may together form, with the carbon atoms from which they depend and with the adjacent benzene ring, a naphthalene ring, and at least one of R
7
and R
8
has the above definition (ii) or (iii); R
9
is a hydrogen atom or a lower alkyl radical; R
10
is a lower alkyl radical R
11
is (a) a hydrogen atom, (b) a lower alkyl radical, (c) a radical of formula:
in which R′ and R″ independently are each a hydrogen atom, a lower alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl radical, or an amino acid residue or peptide residue or sugar residue, with the proviso that R′ and R″ may together form, with the nitrogen atom from which they depend, a nitrogen-containing heterocycle, or (d) a radical —OR
12
, wherein R
12
is a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, or a sugar residue, or an amino acid residue or peptide residue; R
13
is a hydrogen atom or a linear or branched alkyl radical having from 1 to 20 carbon atoms; and n is an integer equal to 0, 1 or 2.
This invention also features the salts of the compounds of formula (I) in the event that the radical R
1
represents a carboxylic acid function, or when R
7
and/or R
8
represents a sulfonic acid function, as well as the optical (chiral) and geometric isomers thereof. When the compounds according to the invention exist in the form of salts, they are preferably alkali metal salts or alkaline earth metal salts, or, alternatively, zinc salts or salts of an organic amine.


REFERENCES:
patent: 3882157 (1975-05-01), Henrick
patent: 4193931 (1980-03-01), Loeliger
patent: 4201727 (1980-05-01), Chan et al.
patent: 0486885 (1992-05-01), None
patent: 2390428 (1978-12-01), None
Patel et al., Journal of Organic Chemistry, vol. 43, No. 26, pp. 5018-5020, Dec. 1978.*
Skin Pharmacol.,3, pp. 256-267 (1990).
Anal. Biochem.,192, pp. 232-236 (1991).

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