Propynyl or dienyl biaromatic compounds

Details Propynyl or dienyl biaromatic compounds Propynyl or dienyl biaromatic compounds

1999-12-17

2001-11-06

Lambkin, Deborah C. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S456000, C549S023000, C549S028000, C549S398000, C549S399000

Reexamination Certificate

active

06313162

ABSTRACT:

The invention relates to propynyl or dienyl biaromatic compounds as novel and useful industrial products. It 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.
The compounds according to the invention have pronounced activity in the fields of cell differentiation and cell proliferation, and find applications more particularly in the topical and systemic treatment of dermatological complaints associated with a disorder of keratinization, dermatological (or other) complaints with an inflammatory and/or immunoallergic component, and dermal or epidermal proliferations, these being either benign or malignant. These compounds may also be used in the treatment of degenerative diseases of connective tissue, for combating either light-induced or chronological ageing of the skin, and for treating disorders of cicatrization. They moreover find an application in the ophthalmological field, in particular in the treatment of corneopathies.
The compounds according to the invention may also be used in cosmetic compositions for body and hair hygiene.
The compounds according to the invention may be represented by the general formula (I) below:
in which:
R
1
represents
(i) the —CH
3
radical
(ii) the radical —CH
2
—O—R
6
(iii) the radical —O—R
6
(iv) the radical —CO—R
7
R
6
and R
7
having the meanings given below,
Ar represents a radical chosen from the radicals of formulae (a)-(e) below:
 R
5
and R
6
having the meanings given below,
X represents a radical of formula:
 R
8
R
9
having the meanings given below,
R
2
and R
3
, which may be identical or different, represent
(i) a hydrogen atom,
(ii) a linear or branched alkyl radical having from 1 to 20 carbon atoms,
(iii) a radical —OR
6
,
(iv) a radical —SR
6
,
R
6
having the meaning given below,
it being understood that R
2
and R
3
, taken together, may 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,
and it being understood that R
2
and R
3
cannot simultaneously have the meanings (i), (iii) and (iv) mentioned above,
R
4
and R
5
, 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
6
,
it being understood that when R
4
is a hydroxyl radical, then R
2
and R
3
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,
R
6
represents a hydrogen atom, a lower alkyl radical or a radical —COR
10
R
10
having the meaning given below,
R
7
represents:
(a) a hydrogen atom
(b) a lower alkyl radical
(c) a radical of formula:
 R′ and R″ having the meaning given below,
(d) a radical —OR
11
,
(e) a radical —NHOR
6
,
R
11
having the meaning given below,
R
8
and R
9
, taken separately, either simultaneously have the same meaning: a hydrogen atom or a radical —OR
10
, or one of them represents a hydrogen atom and the other represents a lower alkyl radical, or, taken together, form a ring —Y—(CH
2
)
n
—Y—, with Y representing an oxygen or sulphur atom and with n equal to 2 or 3,
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, 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 sugar residue, or alternatively, taken together, form a heterocycle.
The invention is also directed towards compounds which are intermediates in the synthesis of the compounds of general formula (I), of general formula (II)
in which R
1
and Ar have the same meanings as for the general formula (I) and R′
2
and R′
4
, which may be identical or different, represent a linear or branched alkyl radical having from 1 to 20 carbon atoms.
The invention is also directed towards the salts of the compounds of formulae (I) and (II) when R
1
represents a carboxylic acid function, and the geometrical and optical isomers of the said compounds of formulae (I) and (II).
When the compounds according to the invention are in the form of salts, they are preferably salts of an alkali metal or alkaline earth metal, or alternatively of zinc or of an organic amine.
According to the present invention, the expression lower alkyl radical is understood to refer to a 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.
The expression linear alkyl radical having from 1 to 20 carbon atoms is understood to refer in particular to the methyl, ethyl, propyl, pentyl, hexyl, octyl, decyl, dodecyl, hexadecyl and octadecyl radicals.
The expression branched alkyl radical having from 1 to 20 carbon atoms is understood to refer in particular to the 2-ethylhexyl, 2-methylbutyl, 2-methylpentyl, 1-methylhexyl and 3-methylheptyl radicals.
Among the monohydroxyalkyl radicals, a radical having 2 or 3 carbon atoms, in particular a 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl radical, is preferred.
Among the polyhydroxyalkyl radicals, a radical having from 3 to 6 carbon atoms and from 2 to 5 hydroxyl groups, such as the 2,3-dihydroxypropyl, 2,3,4-trihydroxybutyl and 2,3,4,5-tetrahydroxypentyl radicals or the pentaerythritol residue, is preferred.
Among the aryl radicals, a phenyl radical optionally substituted with at least one halogen atom, a hydroxyl or a nitro function, is preferred.
Among the aralkyl radicals, the benzyl or phenethyl radical optionally substituted with at least one halogen atom, a hydroxyl or a nitro function, is preferred.
Among the alkenyl radicals, a radical containing from 2 to 5 carbon atoms and having one or more ethylenic unsaturations, in particular such as the allyl radical, is preferred.
The term sugar residue is understood to refer to a residue derived in particular from glucose, galactose or mannose, or alternatively from glucuronic acid.
The term amino acid residue is understood to refer in particular to a residue derived from lysine, glycine or aspartic acid, and the term peptide residue is understood to refer more particularly to a dipeptide or tripeptide residue resulting from the combination of amino acids.
Lastly, the term heterocycle is understood to refer preferably to a piperidino, morpholino, pyrrolidino or piperazino radical, optionally substituted in position 4 with a C
1
-C
6
alkyl or mono- or polyhydroxyalkyl radical as defined above.
When the radicals R
4
and R
5
represent a halogen atom, this is preferably a fluorine, bromine or chlorine atom.
Among the compounds of formula (I) above which fall within the scope of the present invention, mention may be made in particular of the following compounds:
4-[3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-propynyl]benzoic acid.
2-Hydroxy-4-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-propynyl]benzoic acid.
4-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid.
Methyl 2-hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate.
2-Hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid.
2-Hydroxy-4-[3-(3-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid.
2-Hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzenemethanol.
Diethanolamine 2-hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate.
Lithium 2-hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8

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