Bioaromatic amido compounds and pharmaceutical/cosmetic...

Details Bioaromatic amido compounds and pharmaceutical/cosmetic... Bioaromatic amido compounds and pharmaceutical/cosmetic...

1999-02-09

2001-01-09

Raymond, Richard L. (Department: 1611)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C514S535000, C514S563000, C514S617000, C514S621000, C514S622000

Reexamination Certificate

active

06171603

ABSTRACT:

BACKGROUND OF THE INVENTION
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel amide-derived biaromatic compounds and to pharmaceutical/cosmetic compositions comprised thereof; the subject amido compounds are especially useful in human or veterinary medicine, or alternatively in cosmetic compositions.
SUMMARY OF THE INVENTION
The compounds according to the invention display marked 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 conditions (and the like) 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 degeneration diseases of the connective tissue, for combating skin aging, whether photoinduced or chronologic, and for treating cicatrization disorders. They are also useful for ophthalmological applications, especially for the treatment of corneopathies.
The compounds according to this invention are also useful for the treatment of osteoporosis, and for the treatment of viral diseases, as well as for the treatment of any condition associated with hypervitaminose A. In general, they are useful for the treatment of any disease state which is associated with a modification of the expression of receptors belonging to the superfamily of steroid and thyroid hormone receptors.
Too, the compounds according to the invention can be formulated into cosmetic compositions for body and hair care.
Briefly, the biaromatic amido compounds according to the invention have the following structural formula (I):
in which Ar is a radical selected from among those of the following formulae (a)-(e):
in which R
5
and R
6
are as defined below; Z is —CO—NR
7
—; R
1
is (i) a —CH
3
radical, (ii) a radical —CH
2
—O—R
6
, (iii) a radical —O—R
6
, (iv) a radical —CO—R
8
or (v) a radical —S(O)
t
R
9
, wherein R
6
, R
8
, R
9
and t are as defined below; X and Y may be taken separately, in which event X is a hydrogen atom or a lower alkyl radical, and Y is a radical of the formula —(CH
2
)
n
—CH
3
or of the formula —(CH
2
)
n
—R
10
, or X and Y may be taken together, in which event X and Y together form, with the carbon atom from which they depend, a single radical containing a double bond, selected from among those of the formulae ═N—O—(CH
2
)
n
—R
10
, ═CH—(CH
2
)
m
—R
10
, ═N—O—(CH
2
)
2
—O—CH
2
—CH
3
, ═N—O—CH
2
—O—CH
2
—CH
2
—O—CH
3
, and ═CH—(CH
2
)
m
—CH
3
, wherein R
10
, m and n are as defined below; R
2
and R
3
, taken separately, are each a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, a radical —OR
6
or a radical —SR
6
, wherein R
6
is as defined below, with the proviso that R
2
and R
3
cannot simultaneously be a hydrogen atom, a radical —OR
6
or a radical —SR
6
, or R
2
and R
3
together form, with the adjacent aromatic ring from which they depend, a 5- or 6-membered ring optionally substituted by methyl radicals and/or optionally interrupted by an oxygen or sulfur atom or by an —SO— or —SO
2
— radical; R
4
is a hydrogen atom, a halogen atom, a lower alkyl radical or a radical —OR
6
, wherein R
6
is as defined below, with the proviso that R
5
has the same definition as R
4
; R
6
is a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms or a radical —CO—R
11
, wherein R
11
is as defined below; R
7
is a hydrogen atom or a lower alkyl radical; R
8
is (a) a hydrogen atom, (b) a lower alkyl radical, (c) a radical of the formula:
wherein R′ and R″ are as defined below, or (d) a radical —OR
12
, wherein R
12
is as defined below; R
9
and R
11
, which may be identical or different, are each a lower alkyl radical; R
10
is (i) a radical —OR
6
, (ii) a radical —CO—R
8
, (iii) a radical of the formula:
wherein R′ and R″ are as defined below, (iv) an optionally substituted aryl radical, (v) a heterocyclic radical, or (vi) a C
3
or C
6
cycloaliphatic radical; 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 or peptide residue; R′ and R″, which may be identical or different, are each a hydrogen atom, a lower alkyl radical, a mono or polyhydroxyalkyl radical, an optionally substituted aryl radical or an amino acid or peptide or sugar residue with the proviso that R′ and R″ may together form, with the nitrogen atom from which they depend, a heterocycle; m is an integer ranging from 1 to 20; n is an integer ranging from 2 to 20; and t 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 R
1
is a carboxylic acid functional group, as well as the optical and geometric isomers thereof. When the compounds according to the invention are in the form of salts, they are preferably salts of an alkali or alkaline earth metal, or alternatively, of zinc or of an organic amine.


REFERENCES:
patent: 0227431 (1987-07-01), None
patent: 0514264 (1992-11-01), None
patent: 0661260 (1995-07-01), None
patent: 92/06948 (1992-04-01), None

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