Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-07-23
2001-02-27
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S233500, C514S253030, C514S311000, C514S314000, C514S320000, C514S422000, C514S432000, C514S443000, C544S151000, C544S376000, C546S165000, C546S173000, C546S196000, C549S023000, C549S053000, C549S058000, C549S400000, C549S403000, C549S404000, C549S405000, C549S406000, C548S525000
Reexamination Certificate
active
06194450
ABSTRACT:
BACKGROUND OF THE INVENTION
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel polyaromatic heterocyclic compounds and to pharmaceutical/cosmetic compositions comprised thereof; the subject compounds are especially useful in human or veterinary medicine, or alternatively in cosmetic compositions.
This invention also relates to unique intermediates for the synthesis of the subject novel polyaromatic heterocyclic compounds.
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.
Too, the compounds according to the invention can be formulated into cosmetic compositions for body and hair care.
Briefly, the polyaromatic heterocyclic compounds according to the invention have the following structural formula (I):
in which Z is a divalent radical selected from among —O—, —S— or —Nr′—; Ar is either a radical having the following structural formula (II):
or a radical having the following structural formula (III):
wherein m is equal to 0 or 1; R
1
is (i) a hydrogen atom, (ii) the —CH
3
radical, (iii) a radical —(CH
2
)
p
—O—R
12
, (iv) a radical —OR
12
, (v) a radical:
or (vi) a radical —S(O)
t
R
14
, wherein R
12
, R
13
, R
14
, p and t are as defined below; R
2
is a hydrogen atom, a halogen atom, a lower alkyl radical or a radical —OR
12
, wherein R
12
is as defined below; R
3
and R
4
, which may be identical or different, are each a halogen atom, a hydrogen atom, a lower alkyl radical or a radical OR
12
, wherein R
12
is as defined below; R
5
is a halogen atom, a hydrogen atom, a lower alkyl radical or a radical —OR
15
, wherein R
15
is as defined below; R
6
, R
7
, R
8
and R
9
, which may be identical or different, are each a hydrogen atom, a halogen atom, an alkyl radical, a cycloalkyl radical, a radical —(Z
1
)
n
—(CH
2
)
q
—CO—R
13
, or a radical —Z
2
—R
12
, with the proviso that at least two of the radicals R
6
, R
7
, R
8
and R
9
are other than a hydrogen atom and further wherein Z
1
, Z
2
, R
12
, R
13
, n and g are as defined below; R
10
and R
11
are lower alkyl radicals; Y is a divalent radical selected from among —C(R
11
)
2
—, —O—, —S—, —Nr′—, —CH(OH)—, —CO—, —SO— and —SO
2
—, wherein R
11
is as defined above and r is as defined below, with the proviso that R
1
, R
2
, R
3
, R
4
and R
5
cannot simultaneously each be a hydrogen atom; R
12
is a hydrogen atom, a lower alkyl radical, an aryl radical, an aralkyl radical, a polyhydroxyalkyl radical, a polyether radical or a lower acyl radical; R
13
is (a) a hydrogen atom, (b) a radical:
wherein r and r are as defined below, or (c) a radical —OR
14
wherein R
14
is as defined below; R
14
is a hydrogen atom, an alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, or a sugar or amino acid residue; R
15
is a hydrogen atom, a lower alkyl radical, an aryl radical, an aralkyl radical or a polyether radical; r and r′, which may be identical or different, are each a hydrogen atom, a lower alkyl radical, an optionally substituted aryl radical, or an amino acid or sugar residue, with the proviso that r and r′ may together form, with the nitrogen atom from which they depend, a heterocycle; Z
1
is O, S or Nr′; Z
2
is O or S, n is equal to 0 or 1; p is equal to 0, 1, 2 or 3; g is an integer ranging from 0 to 10;
t
is equal to 0, 1, 2 or 3; and the optical and geometric isomers and salts thereof.
When the compounds according to the invention are in the form of salts, by addition of a base thereto, these are preferably salts of an alkali or alkaline earth metal, or, alternatively, of zinc or of an organic amine.
When the subject compounds are in the form of salts, by addition of an acid thereto, these are pharmaceutically or cosmetically acceptable salts prepared by addition of an inorganic or organic acid thereto, in particular hydrochloric acid, sulfuric acid, acetic acid, citric acid, fumaric acid, hemisuccinic acid, maleic acid and mandelic acid.
Preferably, R
1
and R
2
are not simultaneously either a hydrogen atom or a hydrogen atom and a halogen atom, respectively.
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Charpentier Bruno
Diaz Philippe
Nedoncelle Philippe
Burns Doane Swecker & Mathis L.L.P.
Centre International de Recherches Dermatologiques Galderma
Coleman Brenda
Shah Mukund J.
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