Stilbene compounds comprising an adamantyl group,...

Details Stilbene compounds comprising an adamantyl group,... Stilbene compounds comprising an adamantyl group,...

1997-12-31

2001-04-10

Fan, Jane (Department: 1612)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Radical -xh acid, or anhydride, acid halide or salt thereof...

C546S316000, C546S318000, C546S323000, C546S326000, C560S102000, C562S492000, C514S350000, C514S351000, C514S532000, C514S569000, C424S060000

Reexamination Certificate

active

06214878

ABSTRACT:

BACKGROUND OF THE INVENTION
Technical Field of the Invention
The invention relates to stilbene compounds containing an adamantyl group which are novel and useful industrial products. The invention also relates to the use of these novel compounds in pharmaceutical compositions intended for use in human or veterinary medicine, or alternatively, in cosmetic compositions.
SUMMARY OF THE INVENTION
The compounds according to the present invention have pronounced activity in the fields of cell proliferation and differentiation, and find application more particularly in the topical and systemic treatment of dermatological complaints associated with a keratinization disorder, dermatological (or other) complaints with an inflammatory and/or immunoallergic component, and dermal or epidermal proliferations, whether benign or malignant. These compounds can also be used in the treatment of degenerative diseases of connective tissue, to combat aging of the skin, both light-induced and chronological aging, and to treat cicatrization disorders. They also find application in the ophthalmic field, in particular, in the treatment of corneopathies.
The compounds according to the present invention can also be used in cosmetic compositions for body and hair hygiene.
The compounds according to the invention can be represented by the general formula (I) below:
wherein:
R
1
represents
(i) the —CH
3
radical,
(ii) the radical —CH
2
—O—R
6
,
(iii) the radical —O—R
6
, or
(iv) the radical —CO—R
7
,
wherein the radicals R
6
and R
7
have the meanings given below,
Ar represents a radical of formulae (a) to (f) below:
 wherein R
8
and R
9
have the meanings given below,
R
2
and R
3
, which may be identical or different, independently represent a hydrogen atom or a lower alkyl radical,
R
4
represents the radical —(X)
m
—(CH
2
)
n
—Y—(CH
2
)
p
—R
10
,
wherein the values m, n and p and the radicals X, Y and R
10
having the meanings given below,
R
5
represents a hydrogen or halogen atom, a lower alkyl radical or a radical —O—R
6
,
R
6
represents a hydrogen atom, a lower alkyl radical or a radical —CO—R
11
,
R
7
represents a hydrogen atom, a lower alkyl radical, a radical —OR
12
or a radical
 wherein R′ and R″, which may be identical or different, independently represent 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, or alternatively, taken together, form a heterocycle, it being understood that, in all of the text hereinabove:
m is an integer ranging from 0 to 1,
n is an integer ranging from 1 to 6, inclusive,
p is an integer ranging from 1 to 6, inclusive,
X represents O or S(O)
q
,
Y represents O, S(O)
q
or N—R
9
,
q is an integer ranging from 0 to 2, inclusive,
R
8
represents a hydrogen or halogen atom, a lower alkyl radical or a radical —O—R
6
,
R
9
represents a hydrogen atom, a lower alkyl radical or a radical —CO—R
11
,
R
10
represents a mono- or polyhydroxyalkyl radical wherein the hydroxyls are optionally protected in the form of methoxy, ethoxy, acetoxy or acetonide, a radical —CO—R
7
or an optionally substituted aryl or aralkyl radical,
R
11
represents a lower alkyl radical,
R
12
represents a hydrogen atom, an alkyl radical, an alkenyl radical, a mono- or polyhydroxyalkyl radical in which the hydroxyls are optionally protected in the form of methoxy, ethoxy, acetoxy or acetonide, an optionally substituted aryl or aralkyl radical, a sugar residue or an amino acid or peptide residue, and the optical and geometrical isomers of the compounds of formula (I), as well as the salts thereof.


REFERENCES:
patent: 5124473 (1992-06-01), Shroot et al.
patent: 5436369 (1995-07-01), Bronson et al.
patent: 5547893 (1996-08-01), Charpentier
patent: 0776881 (1997-06-01), None
patent: 0776885 (1997-06-01), None
patent: WO 97/13505 (1997-04-01), None
patent: WO 98/01132 (1998-01-01), None
Journal of Medicinal Chemistry, vol. 38, No. 26, Dec. 22, 1995, Washington D. C.; pp. 4993-5006, XP002026831, B. Charpentier et al.
Cancer Res. (1997), 75(21) 4931-4939, XP002062312, Shi-Yong Sun et al.

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