Bi-aromatic compounds, compositions containing them and uses

Details Bi-aromatic compounds, compositions containing them and uses Bi-aromatic compounds, compositions containing them and uses

1999-01-08

2001-12-04

Killos, Paul J. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S009000, C560S010000, C560S075000, C564S162000, C564S168000, C564S173000, C564S174000, C514S532000, C514S613000, C549S483000, C549S064000, C546S314000

Reexamination Certificate

active

06326510

ABSTRACT:

FIELD OF THE INVENTION
The invention relates, as novel and useful industrial products, to biaromatic compounds. 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.
BRIEF DESCRIPTION OF THE INVENTION
The compounds according to the invention have pronounced activity in the fields of cell differentiation and proliferation, and find applications 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 they are benign or malignant. These compounds can also be used in the treatment of degenerative diseases of connective tissue, to combat ageing of the skin, whether this is light-induced or chronological ageing, and to treat cicatrization disorders. Elsewhere, these compounds find an application in the ophthalmological field, in particular in the treatment of corneopathies.
The compounds according to the 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:
in which:
R
1
represents
(i)
the radical
—CH
3
(ii)
the radical
—CH
2
—O—R
5
(iii)
the radical
—O—R
5
(iv)
the radical
—CO—R
6
R
5
and R
6
having the meanings given below,
Y represents a radical chosen from the radicals of formulae (a) to (c) below:
R
7
and n having the meanings given below,
Ar represents a radical chosen from the radicals of formulae (d) to (g) below:
R
8
having the meaning given below,
X represents a radical chosen from the radicals of formulae (h) to (p) below, which can be read from left to right or vice-versa,
it being understood that when X represents the radical of formula (n), then Y cannot represent the radical of formula (a),
R
7
and R
9
having the meanings given below,
R
2
and R
3
, which may be identical or different, represent an atom or a radical chosen from:
(i)
a hydrogen atom,
(ii)
a linear or branched alkyl
radical having from 1 to 20 carbon atoms,
(iii)
a radical -OR
5
,
(iv)
a radical -SR
5
,
R
5
having the meaning given below,
with the condition that at least one of the radicals R
2
and R
3
represents a radical having the meaning (ii),
it being understood that R
2
and R
3
, taken together, can form, with the adjacent aromatic ring, a 5- or 6-membered ring optionally substituted with methyl groups and/or optionally interrupted by an oxygen or sulphur atom,
with the condition that R
2
and R
3
, taken together, form, with the adjacent aromatic ring, a 5- or 6-membered ring optionally substituted with methyl groups and/or optionally interrupted by an oxygen or sulphur atom, when X represents the radical of formula (m) or (i), Y represents the radical of formula (a) with n=0, Ar represents the radical of formula (d), R
1
represents the radical —CO—R
6
with R
6
= —O—R
11
and R
8
and R
9
represent hydrogen,
R
4
and R
8
, which may be identical or different, represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms or a radical —OR
5
,
R
5
, which may be identical or different, represents a hydrogen atom, a lower alkyl radical or a radical —COR
10
,
 R
10
having the meaning given below,
R
6
represents an atom or a radical chosen from:
 (a) a hydrogen atom,
 (b) a lower alkyl radical,
 (c) a radical of formula:
R′ and R″ having the meanings given below,
 (d) a radical —OR
11
R
11
having the meaning given below, R
7
, R′
7
and R
9
, which may be identical or different, represent a hydrogen atom or a lower alkyl radical,
n is equal to 0, 1 or 2,
R
10
represents a lower alkyl radical,
R
11
represents 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, 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,
and the optical and geometrical isomers of the said compounds of formula (I), as well as the salts thereof.


REFERENCES:
patent: 5128470 (1992-07-01), Klaus et al.
patent: 0 617 020 (1994-09-01), None
patent: 2 735 371 (1996-12-01), None
patent: 92 06948 (1992-04-01), None
Chemical Abstracts, vol. 85, No. 1, Jul. 5, 1976, Columbus, Ohio, US: Abstract No. 5395, Harita, Kozaburo et al, “Aromatic carboxylic acid amines”, XP002044627.

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