Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1997-02-18
2001-02-06
Cook, Rebecca (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S627000, C514S629000, C514S549000, C514S551000, C514S880000
Reexamination Certificate
active
06184252
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Technical Field of the Invention
The present invention relates to novel cosmetic and/or pharmaceutical compositions for topical application to the hair and/or scalp of mammalian subjects, comprising an effective amount of at least one 2-amino-1,3-alkanediol, or derivative thereof, and to the use of such novel compositions for inducing and/or stimulating hair growth and/or retarding hair loss.
2. Description of the Prior Art
In human subjects, hair growth and its renewal are principally determined by the activity of the hair follicles. This activity is cyclical and essentially entails three phases, namely, the anagenic phase, the catagenic phase and the telogenic phase.
The active anagenic phase, or growth phase, which lasts for several years and during which the hair grows longer, is followed by a very short and transitory catagenic phase, which lasts a few weeks, and then by a resting or quiescent phase, designated the telogenic phase, which lasts a few months.
At the end of the rest period, the hair falls out and another cycle begins anew. The head of hair is thus constantly renewed and, of the approximately 150,000 hairs on a human head, at any given instant approximately 10% are at rest and will therefore be replaced in a few months.
In a significant number of cases, early hair loss occurs in genetically predisposed subjects and it affects men in particular. It is more particularly androgenetic or androgenic alopecia or, alternatively, androgeno-genetic alopecia.
This alopecia is essentially due to a disturbance in hair renewal which results, at first, in an acceleration in the frequency of the cycles at the expense of the quality of the hair and then of its amount. A progressive thinning of the head of hair occurs by regression of the so-called “terminal” hairs to the downy stage. Certain regions are preferentially affected, in particular the temple or frontal areas in men and, in women, a diffuse alopecia of the vertex is observed.
Compositions that eliminate or reduce the effects of alopecia and, in particular, that induce or stimulate hair growth or decrease hair loss have long been considered desiderata in the cosmetic and pharmaceutical industries.
In this regard, a large number of very diverse active compounds or substances have already been suggested for such purposes, for example vitamins, such as vitamin E, amino acids, such as serine or methionine, vasodilators, such as acetylcholine and derivatives thereof, female hormones, such as estradiol, keratolytic agents, such as salicylic acid, or chemical compounds, such as 2,4-diamino-6-piperidinopyrimidine 3-oxide or “Minoxidil,” described in U.S. Pat. No. 4,596,812 or, alternatively, its many derivatives, such as those described in EP-353,123, EP-356,271, EP-408,442, EP-522,964, EP-420,707, EP-459,890 and EP-519,819.
Also exemplary thereof are 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine and derivatives thereof, which are described, more particularly, in U.S. Pat. No. 4,139,619.
Nonetheless, considerable research and development is continuing in this art in quest of yet other such valuable active agents.
Minoxidil, while it remains the reference compound in the field, exhibits not insignificant side effects which complicate the use thereof.
SUMMARY OF THE INVENTION
Accordingly, a major object of the present invention is the provision of compounds of the 2-amino-1,3-alkanediol type for efficaciously inducing/stimulating hair growth and/or decreasing hair loss, without exhibiting the disadvantages and drawbacks to date characterizing the state of this art.
DETAILED DESCRIPTION OF BEST MODE AND SPECIFIC/PREFERRED EMBODIMENTS OF THE INVENTION
More particularly according to the present invention, the 2-amino-1,3-alkanediol type compounds or derivatives thereof constitute active agents emanating from tissues which are known to the art by the very general term of “sphingolipids.”
Among these sphingolipids, N-acylated derivatives based on sphinganine [(2S,3R)-2-amino-1,3-octadecanediol] are ceramides mostly present in the hair, whereas the analogous derivatives based on sphingenine [(2S,3R,4E)-2-amino-4-octadecene-1,3-diol), other ceramides, constitute a fraction of the lipids mostly present in the stratum corneum of the skin.
The ceramides are formulated into cosmetics in the natural or synthetic state, for example, to reinforce the barrier effect of the stratum corneum in order to reduce water loss and thus dryness of the skin (GB-2,178,312, GE-2,213,723, EP-227,994, EP-282,616 and EP-556,957).
They are also formulated into cosmetic compositions for their properties which confer a better elasticity on the skin (EP-500,437) or into compositions for hair use in order to reinforce the hair and/or to repair the damage caused by the continual attacks to which the latter is subjected.
Hitherto, to the knowledge of the assignee hereof, it has never been described nor even suggested that 2-amino-1,3-alkanediols or derivatives thereof exert an effect or influence on cell proliferation and still less on keratinocyte proliferation.
It is on the basis of this new property of these aminodiols that it has unexpectedly been shown that these compounds also exert an effect on the survival of the hair follicle.
Thus, by increasing the survival time of the hair follicle, the anagenic phase of the hair cycle is lengthened, which has the effect of delaying hair loss.
Among the sphingolipids, compounds based on sphingenine induce apoptosis, directly or through a series of events involving cellular proteins. This phenomenon, which results in cell death, transposed to the hair cycle, elicits a halt in the growth of the follicle and in hair loss.
The synthesis of compounds based on sphingenine results from several distinct mechanisms. Exemplary are the activation of cellular sphingomyelinase by &agr;-type tumor necrosis factor (TNF-&agr;), by vitamin D, by interleukin-1, by the FAS antigen or ionizing radiation. It is also known that compounds based on sphingenine can also be generated by activation of acyl-CoA: sphinganine (sphingosine) N-acyltransferase (EC 2.3.1.24).
Thus, it has now unexpectedly been determined that the compounds of formula (I) can interfere both during the synthesis of the compounds based on sphingenine and during the events induced by these compounds. The consequence of this is to prevent the apoptosis induced by the compounds based on sphingenine and also to stimulate cell growth and viability.
In chemotherapeutic anticancer treatments, the use of anticancer agents causes cell death in the hair follicle, resulting in hair loss. This induced alopecia is generally transitory, but can sometimes be permanent (A. M. Hussein,
South Med. J.,
1993, 86, 489-496). This side effect causes some patients to refuse this type of therapy (K. O. Baxley et al.,
Cancer Nurs.,
1984, 7, 499-503).
Doxorubicin, for example, induces such a hair loss. It is known that doxorubicin activates ceramide synthase, an enzyme whose activation results in an increase in the intracellular level of compounds based on sphingenine which themselves induce the phenomenon of apoptosis and of cell death.
It has now been determined that the compounds of formula (I) below counteract the harmful side effects of anticancer agents, such as, for example, doxorubicin, by increasing the cell viability of the keratinocytes of the hair follicles.
The present invention features the formulation, into cosmetic/pharmaceutical compositions, as active agents promoting hair survival and/or growth, of at least one compound having the general formula (I):
in which R
1
is a saturated or unsaturated, optionally hydroxylated, linear or branched hydrocarbon radical having from 4 to 28 carbon atoms; R
2
is a hydrogen atom or the radical:
wherein R
3
is a saturated or unsaturated, optionally hydroxylated, linear or branched hydrocarbon radical having from 1 to 29 carbon atoms, with the proviso that the hydroxyl group thereof may be esterified by a saturated or unsaturated, linear or branched acyl radical having from 2
Bernard Bruno
Fagot Dominique
Gaillard Olivier
Philippe Michel
Burns Doane Swecker & Mathis L.L.P.
Cook Rebecca
Societe L'Oreal S.A.
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