Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
1999-03-29
2003-10-14
Killos, Paul J. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C560S102000, C549S078000, C549S079000, C549S497000, C549S499000, C548S560000, C548S564000, C568S630000, C568S632000
Reexamination Certificate
active
06632963
ABSTRACT:
BACKGROUND OF THE INVENTION
Technical Field of the Invention
The present invention relates to novel biaromatic 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 have pronounced 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 (or other) conditions including an inflammatory and/or immunoallergic component, and dermal or epidermal proliferations, whether benign or malignant. The subject compounds can also be used for the treatment of degenerative diseases of connective tissue, to combat aging of the skin, whether photoinduced or chronological aging, and to treat cicatrization disorders. They are also useful for ophthalmological applications, especially for the treatment of corneopathies.
The compounds according to the invention can also be formulated into cosmetic compositions for body and hair hygiene.
Briefly, the bicyclic aromatic compounds according to this invention have the following structural formula (I):
in which R
1
is (i) the radical —CH
3
, (ii) a radical —CH
2
OR
2
, or (iii) a radical —CO—R
3
, wherein R
2
and R
3
are as defined below; Ar
1
is a radical selected from among those of the following formulae (a)-(c):
wherein R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
and R
11
are as defined below; Ar
2
is a radical selected from among those of the following formulae (d)-(h):
wherein R
12
and R
13
are as defined below; X is a radical selected from among those of the following formulae (i)-(l):
wherein R
14
, R
15
and Y are as defined below; R
2
is a hydrogen atom, a lower alkyl radical or a radical —CO—R
16
, wherein R
16
is as defined below; R
3
is a hydrogen atom, a lower alkyl radical, a radical of the formula:
wherein R′ and R″ are as defined below, or a radical —OR
17
, wherein R
17
is as defined below; R
4
is a hydrogen atom, a polyether radical, a lower alkyl radical, or a radical —OR
18
, wherein R
18
is as defined below; R
5
is a hydrogen atom, a lower alkyl radical, a polyether radical, or a radical —OR
19
, wherein R
19
is as defined below; R
6
is a tert-butyl radical; R
7
is a lower alkyl radical, a polyether radical, or a radical —OR
20
, wherein R
20
is as defined below, with the proviso that R
6
and R
7
may together form, with the carbon atoms from which they depend, a 6-membered ring optionally substituted with at least one methyl group and/or optionally interrupted by an oxygen or sulfur atom; R
8
is a tert-butyl, adamantyl, aryl or aralkyl radical; R
9
and R
10
together form, with the carbon atoms from which they depend, a 5- or 6-membered ring optionally substituted with at least one methyl group and/or optionally interrupted by an oxygen or sulfur atom; R
11
is a hydrogen atom, a lower alkyl radical having from 1 to 9 carbon atoms, a hydroxyl radical, an alkoxy radical, a polyether radical or a radical —OR
21
, wherein R
21
is as defined below; R
12
is a hydrogen atom, a hydroxyl radical, an alkoxy radical, a polyether radical or a radical —OR
22
, wherein R
22
is as defined below; R
13
is a hydrogen atom, a lower alkyl radical, or a radical —COR
23
, wherein R
23
is as defined below; R
14
and R
15
, which may be identical or different, are each a hydrogen atom, or a lower alkyl radical; Y is an oxygen atom or a CH
2
radical; R
16
is a lower alkyl radical; R
17
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; 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 residue, with the proviso that R′ and R″ may together form, with the nitrogen atom from which they depend, a nitrogenous heterocycle; R
18
, R
19
and R
20
, which may be identical or different, are each a hydrogen atom, a lower alkyl radical, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an aryl radical, an optionally substituted aralkyl radical or a radical —(CH
2
)
n
—R
24
, wherein n and R
24
are as defined below; R
21
and R
22
, which may be identical or different, are each an alkenyl radical, a mono- or polyhydroxyalkyl radical, an aryl radical, an optionally substituted aralkyl radical, or a radical —(CH
2
)
n
—R
24
, wherein n and R
24
are as defined below; R
23
is a lower alkyl radical; R
24
is a heterocycle, a monohydroxyalkyl radical, a thiol radical optionally substituted with a lower alkyl radical, an amino radical optionally substituted with at least one lower alkyl radical, a radical —COOR
25
, or a radical —CON(R
26
)R
27
, wherein R
25
, R
26
and R
27
are as defined below; R
25
is a hydrogen atom or a lower alkyl radical; R
26
and R
27
, which may be identical or different, are each a hydrogen atom, a lower alkyl radical, or an optionally substituted aryl radical, with the proviso that R
26
and R
27
may together form, with the nitrogen atom from which they depend, a nitrogenous heterocycle; n is an integer such that 2≦n≦9; with the further provisos that, when Ar
1
is the radical of formula (c) and X is a radical of formulae (i) or (j), then R
11
is the radical —OR
21
or a polyether radical, or when Ar
2
is the radical of formula (d), then R
12
is the radical —OR
22
or a polyether radical, and the compounds of formula (I) do not include those wherein R
11
is a methoxymethoxy radical in an ortho position relative to the substituent Ar
2
when Ar
1
is the radical of formula (c), X is the radical of formula (i), R
12
is hydrogen and R
1
is the radical —COR
3
wherein R
3
is the radical —OR
17
and R
17
is a hydrogen atom, and those wherein R
12
is a methoxymethoxy radical in an ortho- or para-position relative to the substituent Ar
1
when Ar
1
is the radical of formula (c), X is the radical of formula (i), R
11
is a methyl radical in an ortho-position relative to Ar
2
, and R
1
is the radical —COR
3
wherein R
3
is the radical —OR
17
and R
17
is a hydrogen atom.
This invention also features the salts of the compounds of formula (I) when R
1
represents a carboxylic acid function, and the geometrical and optical isomers of said compounds of formula (I).
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.
BRIEF DESCRIPTION OF THE DRAWINGS
The FIGURE of Drawing sets forth reaction schemes/mechanisms illustrating representative syntheses for the preparation of the bicyclic aromatic compounds according to the present invention.
DETAILED DESCRIPTION OF BEST MODE AND SPECIFIC/PREFERRED EMBODIMENTS OF THE INVENTION
More particularly according to the present invention, by the term “lower alkyl radical” is intended an alkyl radical having from 1 to 12, preferably from 1 to 9, carbon atoms, advantageously the methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, nonyl, decyl and dodecyl radicals.
By the expression “linear or branched alkyl radical having from 1 to 20 carbon atoms” are particularly intended the methyl, ethyl, propyl, isopropyl, tert-butyl, octyl and 2-ethylhexyl radicals.
By the term “alkoxy radical” is intended an alkoxy radical preferably having from 1 to 9 carbon atoms, in particular the methoxy, propyloxy, pentyloxy and heptyloxy radicals.
By the term “monohydroxyalkyl” or “polyhydroxyalkyl” radical is intended a radical having from 1 to 6 carbon atoms and from 1 to 5 hydroxyl groups. Among such monohydroxyalkyl radicals, preferred are those having 2 or 3 carbon atoms, in particular a 2-hydroxyethyl, 2-hydroxypropyl or 3-hyd
Galderma Research & Development S.N.C.
Killos Paul J.
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