Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-10-31
2002-04-09
Raymond, Richard (Department: 1624)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C514S544000, C514S549000, C514S568000, C514S622000, C514S700000, C514S708000, C514S710000, C514S731000
Reexamination Certificate
active
06368608
ABSTRACT:
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to novel polyaromatic propynyl compounds and to pharmaceutical/cosmetic compositions comprised thereof; the subject 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 can also be formulated into cosmetic compositions for body and hair care.
Briefly, the polyaromatic propynyl compounds according to this invention have the following structural formula (I):
in which X is one of the radicals:
wherein R
10
and R
11
are as defined below; Ar is a radical selected from among those of the following formulae (a)-(e):
wherein R
5
and R
6
are as defined below; R
1
is (i) a hydrogen atom, (ii) a radical —CH
3
, (iii) a radical —CH
2
—O—R
6
, (iv) a radical —O—R
6
, (v) a radical —CO—R
7
, or (vi) a radical —S(O)
t
R
9
wherein R
6
, R
7
, R
9
and t are as defined below; R
2
and R
3
, which may be identical or different, 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
may together form, with the carbon atoms from which they depend, a 5-or 6-membered ring optionally substituted by methyl groups and/or optionally interrupted by an oxygen or sulfur atom; 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; R
5
has the definition of R
4
, with the proviso that R
4
and R
5
may be identical or different; R
6
is a hydrogen atom, a lower alkyl radical or a radical —CO—R
9
wherein R
9
is as defined below and further wherein the radicals R
6
may be identical or different; R
7
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
8
wherein R
8
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
9
is a lower alkyl radical; R
10
is a hydrogen atom, a lower alkyl radical, or a radical —OR
6
; R
11
is a radical —OR
6
; 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; t is an integer equal to 0, 1 or 2; and with the further proviso that the radicals R
10
and R
11
may together form a single oxo group of the formula ═O.
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: 4703110 (1987-10-01), Shudo
patent: 5223518 (1993-06-01), Dinerstein et al.
patent: 5248825 (1993-09-01), Dinerstein et al.
patent: 0170105 (1986-02-01), None
patent: 0401517 (1990-12-01), None
patent: 0476645 (1992-03-01), None
patent: 0476658 (1992-03-01), None
patent: 0514264 (1992-11-01), None
patent: 9220643 (1992-11-01), None
Chemical Abstracts CA97:215237w (1982).
Chemical Abstracts CA98:178949c (1982).
Chemical Letters, vol. 10:1551-1557 (1982).
Burns Doane Swecker & Mathis L.L.P.
Centre International de Recherche Dermatologiques Galderma (C.I.
Raymond Richard
LandOfFree
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