Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1998-12-07
2001-09-18
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C424S062000, C424S070100, C424S070600, C514S252010, C514S649000, C514S776000, C514S880000
Reexamination Certificate
active
06291532
ABSTRACT:
The present invention relates to the use as active principle, in a physiologically acceptable medium, in a cosmetic composition or for the preparation of a pharmaceutical composition, of an effective amount of at least one specific compound from the family of the N-aryl-2-hydroxyalkylamides, intended to induce and/or stimulate hair growth and/or to slow down hair loss.
In man, hair growth and its renewal are mainly determined by the activity of the hair follicles. Their activity is cyclical and essentially comprises three phases, namely the anagen phase, the catagen phase and the telogen phase.
The active anagen phase or growth phase, which lasts several years and during which the hair lengthens, is succeeded by a very short and transitory catagen phase, which lasts a few weeks, and then by a resting phase, also known as the telogen phase, which lasts a few months.
At the end of the period of rest, the hairs fall out and another cycle commences. The head of hair is thus constantly renewed and at any moment, out of the approximately 150,000 hairs which a head of hair comprises, approximately 10% of them are at rest and will thus be replaced in a few months.
However, various causes can result in a significant, temporary or permanent, hair loss. Alopecia is essentially due to a disturbance of hair renewal which results, firstly, in an acceleration in the frequency of the cycles at the expense of the quality of the hair and then of its amount. A gradual thinning of the head of hair takes place by regression of the so-called “terminal” hairs at the downy stage. Areas are preferentially affected, in particular the temples or the front of the head in men, and, in women, a diffuse alopecia of the vertex is observed.
The term alopecia covers a whole family of conditions of the hair follicle having, as final consequence, partial or general permanent hair loss. In a significant number of cases, early hair loss takes place in genetically predisposed subjects and it effects men in particular. It relates more particularly to androgenetic or androgenic or even androgeno-genetic alopecia.
There has been a search for many years, in the cosmetic or pharmaceutical industry, for substances which make it possible to eliminate or reduce alopecia and in particular to induce or stimulate hair growth or to decrease hair loss.
From this viewpoint, a large number of very diverse active compounds have certainly already been provided, such as, for example, 2,4-diamino-6-piperidinopyrimidine 3-oxide or “Minoxidil”, disclosed in Patents U.S. Pat. No. 4,139,619 and U.S. Pat. No. 4,596,812, or its numerous derivatives, such as those disclosed, for example, in Patent Applications EP 0,353,123, EP 0,356,271, EP 0,408,442, EP 0,522,964, EP 0,420,707, EP 0,459,890 and EP 0,519,819.
It remains generally the case that it would be advantageous and useful to be able to have available active compounds other than those already known which are potentially more active and/or less toxic.
This aim and others are achieved by the present invention which relates to the use as active principle, in a physiologically acceptable medium, in a cosmetic composition or for the preparation of a pharmaceutical composition, of an effective amount of at least one compound corresponding to the general formula (I):
in which
R
1
is a cyano group, a halogen atom or an alkyl group, having from 1 to 4 carbon atoms, substituted by at least one halogen atom;
R
2
is a cyano group or a halogen atom;
R
3
is an alkyl group, having 1 or 2 carbon atoms, optionally substituted by at least one halogen atom;
R
4
is a hydrogen atom or an alkyl group, having from 1 to 4 carbon atoms, substituted by at least one halogen atom, or an aryl group, optionally substituted by one or more halogen atoms or by one or more hydroxyl, carboxyl, nitro, cyano, linear or branched alkyl, having 1 to 4 carbon atoms, linear or branched alkoxy, having 1 to 4 carbon atoms, linear or branched alkanoyl, having 1 to 4 carbon atoms, or perfluoroalkyl groups;
or of at least one of its isomers, of at least one of its acylated forms or alternatively of at least one of its salts;
this compound or the pharmaceutical composition being intended to induce and/or stimulate hair growth and/or to slow down hair loss.
These compounds exhibit notable activities which justify their use as active principle for inducing and/or stimulating hair growth and/or slowing down hair loss.
This is because they are excellent openers of potassium channels, the main property of Minoxidil, the only compound recognized to date as effective in the treatment of hair loss
They are also excellent receptorial antagonists of androgens, androgens being responsible for a particularly widespread form of alopecia, androgen-dependent alopecia.
To the knowledge of the Applicant Company, provision has never been made in the prior art for the use of such compounds possessing mixed activity, openers of potassium channels/antiandrogens, for controlling hair loss.
According to a specific embodiment of the invention, R
1
. can be a chlorine, bromine or fluorine atom, preferably a chlorine atom.
According to another embodiment of the invention, R
1
, can be an alkyl group, having from 1 to 4 carbon atoms, substituted by at least one chlorine, bromine or fluorine atom. R
1
, is preferably an alkyl group, having from 1 to 4 carbon atoms, substituted by at least one fluorine atom, more preferably R
1
, is a perhalogenated alkyl radical, having from 1 to 4 carbon atoms, more preferably still R
1
, is a perhalogenated methyl radical and more preferably still R
1
, is a perfluorinated methyl radical.
When R
2
is a halogen atom, R
2
can be a chlorine, bromine or fluorine atom; R
2
is preferably a chlorine atom.
R
3
is preferably a methyl radical or a perfluorinated methyl radical.
When R
4
is an alkyl group, having from 1 to 4 carbon atoms, substituted by at least one halogen atom, such as chlorine, bromine or fluorine, the halogen atom is preferably a fluorine atom.
R
4
is preferably a perhalogenated alkyl radical having from 1 to 4 carbon atoms and, more preferably still, R
4
is a perhalogenated methyl radical, preferably a perfluorinated methyl radical.
When R4 is an aryl group, it is preferably a phenyl radical.
R
3
and R
4
preferably have a different meaning.
The compound used according to the invention is preferably chosen from N-(4-cyano-3-(trifluoromethyl)phenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, N-(3-chloro-4-cyanophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, N-(3,4-dichlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-phenylpropionamide and N-(3,4-dicyanophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide.
These compounds can be used alone or as a mixture.
The effective amount of compound to be used corresponds, of course, to the amount necessary in order to obtain the desired result. A person skilled in the art is thus in a position to evaluate this effective amount, which depends on the nature of the compound used and on the person thus treated. To give an order of magnitude, according to the invention, in a cosmetic composition, the compound can be present at a concentration of between 10
−6
% and 5%, by weight with respect to the total weight of the composition, and preferably of between 10
−3
% and 1%. In the preparation of a pharmaceutical composition, the compound can be used at a concentration of between 10
−5
% and 10%, by weight with respect to the total weight of the composition, and preferably of between 10
−2
% and 2%.
The pharmaceutical composition according to the invention can be administered parenterally, enterally or topically. The pharmaceutical composition is preferably administered topically
The physiologically acceptable medium in which the active principle is used according to the invention can be anhydrous or aqueous. Anhydrous medium is understood to mean a solvent medium containing less than 1% of water. This medium can be composed of a solvent or of a mixture of solvents chose
Breton Lionel
Galey Jean-Baptiste
Burns Doane Swecker & Mathis L.L.P.
L'Oreal
Page Thurman K.
Tran S.
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