Heteroethylene compounds and pharmaceutical and cosmetic...

Details Heteroethylene compounds and pharmaceutical and cosmetic... Heteroethylene compounds and pharmaceutical and cosmetic...

2000-02-07

2002-09-03

Dees, Jose′ G. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Sulfur, selenium or tellurium compound

C514S430000, C514S432000, C514S438000, C514S443000, C514S449000, C514S451000, C514S453000, C514S456000, C514S461000, C514S468000, C514S469000, C514S708000, C514S709000, C514S710000, C514S712000, C514S713000, C514S715000, C514S717000, C514S718000, C514S719000, C514S720000, C514S724000, C514S730000, C514S738000, C514S739000, C514S824000, C514S825000, C514S859000, C514S861000, C514S863000, C514S864000, C514S866000, C514S880000, C514S886000, C514S887000, C514S902000, C514S909000, C514S912000, C549S015000, C549S

Reexamination Certificate

active

06444709

ABSTRACT:

This application is a 371 of PCT/FR99/00727, filed Mar. 29, 1999.
The invention relates, as novel and useful industrial products, to heteroethynylenic compounds. It also relates to the use of these novel compounds in pharmaceutical compositions intended for a 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 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. They moreover 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) a —CH
3
radical
(ii) a radical —CH
2
—O—R
5
(iii) a radical —COR
6
 R
5
and R
6
having the meanings given below,
X represents: O, Se, S(O)n, n being 0, 1 or 2,
Y represents a divalent radical which has the formula:
 R
7
, R
8
, R
9
and R
10
having the meanings given below,
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,
given that R
2
and R
3
independently, which may be identical or different, can represent:
a) a hydrogen atom,
b) a radical chosen from the following radicals
methyl,
tert-butyl,
1-methylcyclohexyl,
1-adamantyl,
c) a radical —OR
11
d) a polyether radical
e) a halogen atom
 R
11
having the meaning given below,
it being understood that at least one of the substituents R
2
and R
3
represents (b),
R
4
represents a hydrogen atom, a lower alkyl radical, a radical OR
12
, a polyether radical, a radical COR
13
or a halogen atom,
 R
12
and R
13
having the meanings given below,
R′
4
represents a hydrogen atom or a halogen atom,
R
5
represents a hydrogen atom or a lower alkyl radical,
R
6
represents:
(i) a hydrogen atom
(ii) a lower alkyl radical
(iii) a radical OR
14
R
14
having the meaning given below
(iv) a radical of formula
 R′ and R″ having the meanings given below,
R
7
, R
8
, R
9
and R
10
, which may be identical or different, represent a hydrogen atom, a lower alkyl radical or an aryl radical,
R
11
and R
12
, which may be identical or different, represent a hydrogen atom, a lower alkyl radical, an optionally substituted aryl radical, an optionally substituted aralkyl radical, a monohydroxyalkyl or polyhydroxyalkyl radical or a lower acyl radical,
R
13
represents a lower alkyl radical, a radical OR
15
or a radical
 R
15
, R′ and R″ having the meanings given below,
R
14
and R
15
, which may be identical or different, represent a hydrogen atom, a lower alkyl radical, an aryl radical, an optionally substituted aralkyl radical, a monohydroxyalkyl radical or a polyhydroxyalkyl radical,
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 residue, or alternatively, taken together with the nitrogen atom, form a heterocycle.
The invention is also directed towards the salts of the compounds of formula (I) when R
1
represents a carboxylic acid function and the geometrical and optical isomers of the 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 metal or alkaline earth metal, or alternatively of zinc or of an organic amine.
The term “lower alkyl radical” means a radical containing from 1 to 6 carbon atoms, and preferably methyl, ethyl, isopropyl, butyl and tert-butyl radicals.
The term “monohydroxyalkyl radical” should be understood as meaning a radical containing from 1 to 6 carbon atoms, in particular a 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl radical.
The term “polyhydroxyalkyl radical” should be understood as meaning a radical containing from 2 to 6 carbon atoms and from 2 to 5 hydroxyl groups, such as 2,3-dihydroxypropyl, 2,3,4-trihydroxybutyl or 2,3,4,5-tetrahydroxypentyl radicals or a pentaerythritol residue.
The term “optionally substituted aryl radical” should be understood as meaning a phenyl radical optionally substituted with at least one halogen atom, a hydroxyl or a nitro function.
The term “optionally substituted aralkyl radical” should be understood as meaning a benzyl or phenethyl radical optionally substituted with at least one halogen atom, a hydroxyl or a nitro function.
The term “lower acyl radical” should be understood as meaning a radical containing from 1 to 4 carbon atoms, in particular an acetyl or propionyl radical.
The term “amino acid residue” should be understood as meaning a residue derived, for example, from one of the 20 amino acids of L or D configuration which constitute mammalian proteins.
The term “heterocycle” preferably means 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.
The term “polyether radical” means a radical containing from 1 to 6 carbon atoms and from 1 to 3 oxygen or sulphur atoms, such as methoxymethyl ether, methoxyethoxymethyl ether or methylthiomethyl ether radicals.
The term “halogen atom” preferably means a fluorine, bromine or chlorine atom.
Among the compounds of formula (I) above which fall within the context of the present invention, mention may be made in particular of the following:
Ethyl 3-methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoate
3-Methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoic acid
Ethyl 3-methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoate
3-Methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoic acid
Ethyl 3-methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoate
3-Methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoic acid
Ethyl 3-methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoate
3-Methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoic acid
Ethyl 3-methyl-5-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoate
3-Methyl-5-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoic acid
Ethyl 3-methyl-5-(5,5,8,8-tetramethyl-4-propoxy-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoate
3-Methyl-5-(5,5,8,8-tetramethyl-4-propoxy-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)pent-2-en-4-ynoic acid
Ethyl 5-(4-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)-3-methylpent-2-en-4-ynoate
5-(4-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)-3-methylpent-2-en-4-ynoic acid
Ethyl 5-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)-3-methylpent-2-en-4-ynoate
5-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-ylselenyl)-3-phenylpent-2-en-4-ynoic acid
5-(4-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)-3-phenylpent-2-en-4-ynoic acid
Methyl 5-(4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)-3-phenylpent-2-en-4-ynoate
3-Propyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetra-hydronaphth

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