Patent Search
 
Hair Loss Patent

Compositions for slowing down hair loss and for inducing and stimulating its growth, based on 24-diamino-pyrimidine 3-oxide derivatives, and new 24-diaminopyrimidine 3-oxide derivatives

Hair loss abstract


Composition for slowing down hair loss and inducing and stimulating its growth, comprising a compound of the following formula: ##STR1## wherein R.sub.1 and R.sub.3 denote H; R.sub.2 and R.sub.4 denote H or an alkyl; R.sub.5 denotes H, an alkyl, an alkenyl, a cycloalkyl, an aryl, an arylalkyl, a hydroxyalkyl or an aminoalkyl; X denotes H, halogen, alkyl, nitro, benzoyloxy or --NHR.sub.6 where R.sub.6 denotes H, acyl or alkyl; Z denotes sulfur or oxygen, with the proviso that Z denotes sulfur when X denotes H or R.sub.5 denotes aryl; Y denotes oxygen or OSO.sub.3 ; as well as its physiologically acceptable salts.

Hair loss claims


We claim:

1. A composition for slowing down hair loss and for inducing and stimulating its growth, which comprises, in a physiologically acceptable medium, between 0.1 and 10% by weight relative to the total weight of the composition of at least one compound corresponding to the following formula: ##STR42## in which: R.sub.1 and R.sub.3 denote a hydrogen atom;

R.sub.2 and R.sub.4, which are identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group;

R.sub.5 denotes a hydrogen atom, a C.sub.1 -C.sub.12 alkyl radical, a C.sub.3 -C.sub.12 alkenyl radical, a C.sub.3 -C.sub.8 cycloalkyl radical, an aryl radical, an arylalkyl radical or a hydroxyalkyl or aminoalkyl radical in which the alkyl radical has 1 to 6 carbon atoms;

X denotes a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl radical, a nitro group, a benzoyloxy group or a group --NHR.sub.6 in which R.sub.6 denotes a hydrogen atom, an acyl radical or a C.sub.1 -C.sub.6 alkyl radical;

Z denotes sulfur or oxygen, with the proviso that Z denotes sulfur when X denotes hydrogen or when R.sub.5 denotes an aryl radical;

Y denotes oxygen or OSO.sub.3 ; as well as its addition salts with physiologically acceptable acids.

2. The composition as claimed in claim 1, wherein, in formula (I), the C.sub.1 -C.sub.6 alkyl radicals are methyl, ethyl, propyl, n-butyl, n-pentyl or n-hexyl; the C.sub.1 -C.sub.12 alkyl radicals are methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, 2-ethylhexyl, octyl, decyl or are dodecyl; the C.sub.3 -C.sub.12 alkenyl groups are allyl, butenyl, hexenyl, decenyl or dodecenyl; the aryl radicals are phenyl or benzyl; and the halogen atoms are chlorine, bromine, fluorine or iodine.

3. The composition as claimed in claim 1, wherein in the compound of formula (I) Z denotes sulfur; X denotes chlorine or nitro; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 denote hydrogen and R.sub.5 denotes methyl, ethyl, n-butyl, phenyl, 2-hydroxyethyl or 2-aminoethyl.

4. The composition as claimed in claim 1, wherein the compound of formula (I) is 2,4-diamino-5-chloro-6-n-butyloxypyrimidine 3-oxide or 2,4-diamino-5-nitro- 6 -n-butyloxypyrimidine 3 -oxide.

5. The pharmaceutical or cosmetic composition, intended to be used in topical application, which comprises, in a physiologically acceptable medium, at least one compound as defined in claim 1.

6. The composition as claimed in claim 5, in the form of an anhydrous or aqueous, ointment, tincture, cream, pomade, powder, patch, impregnated pad, solution, emulsion, vesicular dispersion, lotion, gel, spray or suspension.

7. The composition defined in claim 5, in the form of a lotion, gel, soap, shampoo, aerosol or foam, at a concentration of between 0.01 and 5% by weight.

8. The composition as claimed in claim 5, further comprising antiseborrheic agents.

9. The composition as claimed in claim 5, further comprising agents for further improving the activity of the compounds of formula (I) for slowing down hair loss and for inducing and stimulating its growth.

10. The composition as claimed in claim 9, wherein the agents are nicotinic acid esters, steroidal or nonsteroidal antiinflammatory agents, retinoids, antibacterial agents, calcium antagonistic agents, hormones, antiandrogenic agents or hydroxyl radical scavengers.

11. The composition as claimed in claim 9, further comprising diazoxide, spiroxasone, the phospholipids, linoleic or linolenic acids, salicylic acid or its derivatives, the hydroxycarboxylic or ketocarboxylic acids, their esters, the lactones their corresponding salts, anthralin, the carotenoids, 5,8,11,14-eicosatetraynoic or 5,8,11-eicosatriynoic acids, their esters or amides.

12. The composition as claimed in claim 5, further comprising nonionic or amphoteric surface-active agents.

13. The composition as claimed in claim 5, wherein the physiologically acceptable medium consists of water, a mixture of water and one or more organic solvent(s) or of a mixture of organic solvents, the organic solvents being pharmaceutically or cosmetically acceptable.

14. The composition as claimed in claim 13, wherein the solvents are C.sub.1 -C.sub.4 lower alcohols, alkylene glycols or mono- and dialkylene glycol alkyl ethers.

15. The composition as claimed in claim 5, wherein the physiologically acceptable medium is thickened by means of thickening and/or gelling agents and contains preserving agents, stabilizing agents, pH regulating agents, agents for modifying osmotic pressure, emulsifying agents, UV-A or UV-B filters or antioxidant agents.

16. Compounds of formula: ##STR43## in which: R.sub.1 and R.sub.3 denote a hydrogen atom;

R.sub.2 and R.sub.4, which are identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group;

R.sub.5 denotes a hydrogen atom, a C.sub.1 -C.sub.12 alkyl radical, a C.sub.3 -C.sub.12 alkenyl radical, a C.sub.3 -C.sub.8 cycloalkyl radical, an aryl radical, an arylalkyl radical or a hydroxyalkyl or aminoalkyl radical in which the alkyl radical has 1 to 6 carbon atoms;

X denotes a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl radical, a nitro group, a benzoyloxy group or a group --NHR.sub.6 in which R.sub.6 denotes a hydrogen atom, an acyl radical or a C.sub.1 -C.sub.6 alkyl radical;

Z denotes sulfur or oxygen; with the proviso that Z denotes sulfur when X denotes hydrogen or when R.sub.5 denotes an aryl radical;

Y denotes oxygen or OSO.sub.3 ;

and the addition salts with cosmetically and pharmaceutically acceptable acids; with the exception of the compounds 2,4-diamino-6-hydroxy-5-bromopyrimidine 3-oxide and 2,4-diamino-6-thiophenylpyrimidine 3-oxide and their addition salts with acids.

Hair loss description

The present invention relates to new compositions for slowing down hair loss and for inducing and stimulating its growth, based on 2,4-diaminopyrimidine 3-oxide derivatives, as well as to the new compounds used in these compositions.

2,4-Diamino-6-piperidinopyrimidine 3-oxide or minoxidil is already known in the state of the art for its antihypertensive qualities but also for its use in the treatment of hair loss, of pelade, of desquamative dermatitis and of alopecia.

The Applicant has discovered new compositions for the treatment and prevention of hair loss, used particularly in topical application, containing a particular family of 6-alkoxy- or 6-thioalkyl-2,4-diaminopyrimidine 3-oxide compounds which can be substituted at position 5.

The compounds retained by the Applicant are, surprisingly, very effective for hair regrowth and particularly for inducing and stimulating its growth. Additionally, they have a remarkable solubility in the media normally used in cosmetics or pharmaceuticals.

The subject of the invention is thus new compositions intended for the treatment and prevention of hair loss which contain particular 6-alkoxy- or 6-thioalkyl-2,4-diaminopyrimidine 3-oxide compounds, optionally substituted at position 5.

Another subject of the invention is new compounds used in these compositions.

Another subject of the invention is the use of these particular compounds for the preparation of a medicament intended for the therapeutic treatment of hair loss.

Other subjects will become apparent in the course of the description and examples which follow.

The compositions in accordance with the invention essentially comprise, in a physiologically acceptable medium, at least one compound corresponding to the formula (I): ##STR2## in which: R.sub.1 and R.sub.3 denote a hydrogen atom;

R.sub.2 and R.sub.4, which are identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group;

R.sub.5 denotes a hydrogen atom, a C.sub.1 -C.sub.12 alkyl radical, a C.sub.3 -C.sub.12 alkenyl radical, a C.sub.3 -C.sub.8 cycloalkyl radical, an aryl radical, an arylalkyl radical or a hydroxyalkyl or aminoalkyl radical in which the alkyl radical has 1 to 6 carbon atoms;

X denotes a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl radical, a nitro group, a benzoyloxy group or a group --NHR.sub.6 in which R.sub.6 denotes a hydrogen atom, an acyl radical or a C.sub.1 -C.sub.6 alkyl radical;

Z denotes sulfur or oxygen, with the proviso that Z denotes sulfur when X denotes hydrogen or when R.sub.5 denotes an aryl radical;

Y denotes oxygen or OSO.sub.3 ;

as well as its addition salts with physiologically acceptable acids.

The halogen atoms in the structure of formula (I) are preferably chlorine, bromine, fluorine or iodine.

The C.sub.1 -C.sub.6 alkyl radicals are preferably chosen from methyl, ethyl, propyl, n-butyl, n-pentyl and n-hexyl.

The C.sub.1 -C.sub.12 alkyl radicals are preferably chosen from methyl, ethyl, propyl, 2-ethylhexyl, decyl, octyl and dodecyl.

The C.sub.3 -C.sub.12 alkenyl groups are preferably chosen from allyl, n-butenyl, hexenyl and dodecenyl.

The aryl or aralkyl radicals are preferably chosen from phenyl, benzyl and tolyl.

The compounds of formula (I) according to the invention can be converted into their addition salts with pharmaceutically or cosmetically acceptable acids such as the salts of sulfuric, hydrochloric, hydrobromic, phosphoric, acetic, benzoic, salicylic, glycolic, succinic, tartaric, nicotinic, maleic, pamoic, methanesulfonic, picric and lactic acids, etc.

The compounds of general formula (I) are novel with the exception of the compound 2,4-diamino-6-hydroxy-5-bromopyrimidine 3-oxide described in the document W. L. F. Armarego and P. Waring, Aust. J. Chem., 1981, 34 (9), 1921-33 and the compound 2,4-diamino-6-thiophenylpyrimidine 3-oxide described in the document W. B. Cowden and N. W. Jacobsen, Aust. J. Chem., 1979, 32 (9), 2049-57.

The compounds in accordance with the present invention can be obtained from compounds derived from 2,4-diaminopyrimidine 3-oxide, of formula: ##STR3## in which: R.sub.1 and R.sub.3 denote a hydrogen and R.sub.2 and R.sub.4 denote a hydrogen or a C.sub.1 -C.sub.4 alkyl radical and X' denotes a hydrogen or a C.sub.1 -C.sub.6 alkyl radical or a group --NHR.sub.6 where R.sub.6 denotes an alkyl radical or a C.sub.1 -C.sub.6 acyl radical.

The particular starting compounds of the following formula (IIA): ##STR4## are obtained by cyclization of guanidine (1) with an alkyl cyanoacetate of the formula (2), followed by a halogenation at position 6 of the 2,4-diaminopyrimidine derivative of formula (3) obtained. An oxidation at position 3 of the pyrimidine ring is then carried out, preferably in a polar protic solvent in the presence of a percarboxylic acid R'CO.sub.3 H where R' denotes an alkyl or aryl radical. This process can be represented by the following scheme: ##STR5##

The particular starting compounds of the following formula (IIB ): ##STR6## with R.sub.3 =H and different from R.sub.4, can be obtained in a first step by cyclization of guanidine with diethyl malonate, optionally monosubstituted at the alpha-position, followed by a chlorination reaction of the pyrimidine derivative thus obtained. The amine NHR.sub.3 R.sub.4 is then introduced by nucleophilic aromatic substitution on the pyrimidine ring of the product obtained and then an oxidation at position 3 is carried out, according to the principle described previously. This process can be represented by the following scheme: ##STR7##

The particular starting compounds of formula (IIC): ##STR8## in which R.sub.1 denotes hydrogen and R.sub.2 denotes alkyl, are obtained by oxidation, by means of a peracid, of the pyrimidine derivative of formula: ##STR9## where R" denotes an aryl or an alkyl radical, followed by a nucleophilic aromatic substitution, of the group --SO.sub.2 R" obtained, by the amine NHR.sub.1 R.sub.2 on the pyrimidine range. An oxidation at position 3 of the pyrimidine range is then carried out under the same conditions as previously.

The particular starting compounds of the following formula: ##STR10## in which R.sub.1 and R.sub.3 denote hydrogen and R.sub.2 and R.sub.4 denote alkyl, can be obtained according to the following reaction scheme: ##STR11##

Starting from the compound of formula (8), two equivalents of the amine NHR.sub.3 R.sub.4 are introduced into the pyrimidine ring and then, after separating on silica gel the products (9) and (9') formed, the second amine NHR.sub.1 R.sub.2 is introduced.

An oxidation at position 3 of the pyrimidine ring is then carried out as previously.

The particular compounds of the present invention of the following formula: ##STR12## where R.sub.1, R.sub.2, R.sub.3, R.sub.4, Z and R.sub.5 have the same meanings indicated above in the general formula (I), and X denotes hydrogen, a C.sub.1 -C.sub.6 alkyl radical or a group --NHR.sub.6 where R.sub.6 denotes a C.sub.1 -C.sub.6 alkyl radical or an acyl radical, can be obtained by reacting the compounds of formula (II), either with an alkoxide W.sup.+ OR.sub.5.sup.- in the corresponding alcohol R.sub.5 OH, where W denotes an alkali metal such as sodium, potassium or lithium, or with a thiolate W.sup.+ SR.sub.5.sup.- in the presence of a solvent such as dimethylformamide.

This process can be represented by the following reaction scheme: ##STR13##

The particular compounds of the invention of the following formula: ##STR14## where R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and Z have the same meanings indicated above and X denotes a halogen atom, can be obtained by reacting a compound of formula (II) in which X' denotes hydrogen with a halogenating agent. In the case where X denotes chlorine, iodine or bromine, an N-halosuccinimide of formula (III): ##STR15## for example, is used in the presence of an alcohol such as methanol.

The chlorine atom at position 6 of the pyrimidine ring is then substituted by the group --ZR.sub.5 according to the process described above in Scheme A.

The process can be represented by the following scheme: ##STR16##

The particular compounds of the invention of the following formula ##STR17## can be obtained from the compounds of formula (IA) where X denotes hydrogen. An electrophilic aromatic substitution reaction is carried out using a nitrating agent, such as nitric acid, in the presence of concentrated sulfuric acid.

This process can be represented by the following reaction scheme: ##STR18##

The particular compounds of the invention of the following formula: ##STR19## can be obtained from the compounds of formula (IC) by catalytic reduction. Palladium on charcoal under a hydrogen atmosphere is used in particular.

This process can be represented by the following scheme: ##STR20##

The particular compounds of the invention of the following formula: ##STR21## can be obtained by the action of dibenzoyl peroxide in acetic acid medium on a compound of formula (IA), in which X' denotes hydrogen, according to the following reaction scheme: ##STR22##

The particular compounds of the invention of general formula (I) in which Y denotes an oxygen atom can be converted into their O-sulfate homologs of formula (IF) defined below by chemical sulfating according to the conventional methods described in the literature (J. Med. Chem., 1983, 26, pages 1791-1793).

The sulfur trioxide-pyridine, sulfur trioxidetriethylamine or sulfur trioxide-ethyldiisopropylamine complexes are used as sulfating reagent.

The solvents used are preferably dimethylformamide, chloroform or acetonitrile or their binary mixtures.

The temperature is of the order of 0.degree. to 25.degree. C. and the reaction time varies from 1 to 24 hours. ##STR23##

Among the compounds of the invention of general formula (I) in which Z denotes oxygen, the particularly preferred compounds are those for which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 denote hydrogen, X denotes chlorine or the nitro group and R.sub.5 denotes n-butyl.

Among the compounds of the invention of formula (I) in which Z denotes sulfur, the particularly preferred compounds are those for which X denotes chlorine or the nitro group, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 denote a hydrogen atom and R.sub.5 denotes methyl, ethyl, n-butyl, 2-hydroxyethyl, 2-aminoethyl or phenyl.

The compositions in accordance with the present invention, which contain, in a physiologically acceptable medium, at least one compound corresponding to the formula (I) or one of its addition salts with physiologically acceptable acids, can be applied in the cosmetics or pharmaceutical field, particularly in topical application. They are intended for the treatment and the prevention of hair loss, and particularly of pelade and alopecia as well as of desquamative dermatitis, and the stimulation of hair regrowth.

These compositions can contain, as physiologically acceptable medium, any medium suitable for topical application, either in cosmetics or in pharmaceuticals, and which is compatible with the active substance.

The compounds in accordance with the invention can be found in this medium contained either in the dissolved state or in the dispersed state, in particular in the micronized form.

The compositions intended to be used as pharmaceuticals are present in the form of an ointment, tincture, cream, pomade, powder, patch, impregnated pad, solution, emulsion or vesicular dispersion, lotion, gel, spray or suspension. They can be either anhydrous or aqueous according to the clinical indication.

The compounds according to the invention are present in these pharmaceutical compositions at concentrations of between 0.1 and 10% by weight, and in particular of between 0.2 and 5% by weight.

The cosmetic compositions are particularly intended to be used in the form of a lotion, gel, soap, shampoo, aerosol or foam and contain, in a cosmetically acceptable carrier, at least one compound of formula (I) or one of its addition salts with acids.

The concentration of these compounds of formula (I) in these compositions is, preferably, of between 0.01 and 5% by weight and in particular between 0.05 and 3% by weight.

The compositions in accordance with the invention can contain various additives normally used in cosmetics or in pharmaceuticals and, in particular, active substances, for example hydrating agents, such as thiamorpholine and its derivatives or urea; antiseborrheic agents such as S-carboxymethylcysteine, S-benzylcysteamine and their derivatives; and thioxolone.

The compounds in accordance with the invention can be combined with compounds which further improve their activity towards the regrowth and/or slowing down of hair loss, such as the following compounds:

nicotinic acid esters, more particularly C.sub.1 -C.sub.6 alkyl nicotinates and particularly methyl nicotinate or benzyl nicotinate;

steroidal and nonsteroidal anti-inflammatory agents well known in the state of the art and in particular hydrocortisone, its salts and its derivatives, and niflumic acid;

retinoids and more particularly all-trans-retinoic acid, also called tretinoin, isotretinoin, retinol or vitamin A and its derivatives, such as the acetate, the palmitate or the propionate, motretinide, etretinate or zinc all-trans-retinoate;

antibacterial agents chosen more particularly from the macrolides, the pyranosides and the tetracyclines and particularly erythromycin;

calcium antagonist agents, such as, more particularly, cinnarizine and diltiazem;

hormones, such as estriol or analogs or thyroxine and its salts;

antiandrogenic agents, such as oxendolone, spironolactone or diethylstilbestrol;

OH radical scavengers, such as dimethyl sulfoxide.

It is also possible to combine with the compounds of the invention, optionally mixed with others, compounds such as diazoxide, corresponding to 3-methyl-7-chloro-[2H]-1,2,4-benzothiadiazine 1,1-dioxide; spiroxasone or 7-(acetylthio)-4',5'-dihydrospiro[androst-4-ene-17,2'-(3'H)furan]-3-one; p hospholipids, such as lecithin; linoleic and linolenic acids; salicylic acid and its derivatives described in French Patent 2,581,542, and more particularly the salicylic acid derivatives which carry an alkanoyl group having 2 to 12 carbon atoms at position 5 of the benzene ring; hydroxycarboxylic or ketocarboxylic acids and their esters, lactones and their corresponding salts; anthralin or 1,8,9-trihydroxyanthracene, the carotenoids, 5,8,11,14-eicosatetraynoic or 5,8,11-eicosatriynoic acid, their esters and amides.

The compounds in accordance with the invention can also be combined with surface-active agents, particularly those chosen from the nonionic and amphoteric surface-active agents.

Among the nonionic surfactants, there are to be mentioned the polyhydroxypropyl ethers described particularly in the French Patents Nos. 1,477,048; 2,091,516; 2,169,787; 2,328,763; 2,574,786; the oxyethylenated (C.sub.8 -C.sub.9)-alkylphenols containing 1 to 100 mol of ethylene oxide and preferably 5 to 35 mol of ethylene oxide; the alkylpolyglycosides of formula:

in which n varies from 8 to 15 inclusive and x from 1 to 10 inclusive.

Among the amphoteric surface-active agents, there are to be mentioned more particularly the amphocarboxyglycinates and the amphocarboxypropionates defined in the CTFA dictionary, 3rd edition, 1982, and sold, particularly, under the name Miranol.RTM. by the Miranol Company.

The compounds according to the invention can be introduced into carriers which further improve the activity as regards regrowth while, at the same time, having advantageous properties at the cosmetic level, such as volatile ternary mixtures of alkyl ethers of alkylene glycols, in particular C.sub.1 -C.sub.4 alkyl ethers of C.sub.1 -C.sub.4 alkylene glycols or dialkylene glycols, preferably C.sub.1 -C.sub.4 dialkylene glycols, ethyl alcohol and water, the glycol solvent more particularly denoting ethylene glycol monoethyl ether, propylene glycol monomethyl ether or diethylene glycol monomethyl ether.

The compounds in accordance with the invention can also be introduced into gelled or thickened carriers, such as essentially aqueous carriers gelled with heterobiopolysaccharides, such as xanthan gum, scleroglucans or cellulose derivatives, aqueous-alcoholic carriers gelled with polyhydroxyethyl acrylates or methacrylates, or essentially aqueous carriers thickened in particular with polyacrylic acids crosslinked by a polyfunctional agent, such as the Carbopol products sold by the Goodrich Company.

These compositions can also contain preserving agents, stabilizing agents, pH regulating agents, agents for modifying osmetic pressure, emulsifying agents, UVA and UVB filters and antioxidant agents, such as .alpha.-tocopherol, butylhydroxyanisole or butylhydroxytoluene.

The physiologically acceptable medium can consist of water or a mixture of water and a solvent or a mixture of solvents, the solvents being chosen from the organic solvents acceptable at the cosmetic or pharmaceutical level and chosen more particularly from the lower, C.sub.1 -C.sub.4 alcohols, such as ethyl alcohol, isopropyl alcohol or tert-butyl alcohol, the alkylene glycols or the alkyl ethers of alkylene glycol and of dialkylene glycol, such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether or diethylene glycol monomethyl ether. The solvents, when they are present, are present in proportions of between 1 and 80% by weight in relation to the total weight of the composition.

The thickening agents are preferably present in proportions of between 0.1 and 5% by weight and in particular between 0.4 and 3% by weight in relation to the total weight of the composition.

Another subject of the invention is a process for cosmetic treatment of hair or of the scalp, consisting in applying to them at least one composition such as is defined above, with the aim of improving the attractiveness of the hair.

Another subject of the invention consists in the use of the composition containing the compounds of formula (I) defined above for the preparation of a medicament which has the effect of inducing or stimulating hair growth and of slowing down its loss.

The treatment principally consists in applying the composition such as is defined above to the alopecic areas of the scalp of an individual.

The preferred method of application consists in applying 1 to 2 g of the composition to the alopecic area, at a frequency of one to two applications per day, for 1 to 7 days per week for a period of 1 to 6 months.

The compositions can particularly be used in the treatment of pelade, hair loss and desquamative dermatitis.

The following examples are intended to illustrate the invention without having any limiting character.


Photodynamic therapy for the treatment of hair loss
Nutrient composition for preventing hair loss
Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins

7090691 Photodynamic therapy for the treatment of hair loss
7041636 Composition for counteracting hair loss
6762193 Method of treating hair loss
6680344 Method of treating hair loss using diphenylmethane derivatives
6653317 Pyrimidine 3-oxide compounds for inducing/stimulating hair growth and/or retarding hair loss
6646005 Method of treating hair loss using sulfonyl thyromimetic compounds
6541507 Indolecarboxylic compounds for inducing/stimulating hair growth and/or retarding hair loss
6525094 Method of treating hair loss using diphenylether derivatives
6511659 Pyrimidine 3-oxide compounds for inducing/stimulating hair growth and/or retarding hair loss
6468972 Method to promote, stimulate and/or delay hair loss by a brady kinin antagonist
6458835 Method of inhibiting or treating chemotherapy-induced hair loss
6447762 Hair lotion useful for treatment of hair loss and stimulating hair growth
6420352 Hair loss prevention
6358541 Topical preparation for the treatment of hair loss
6344448 Composition for the treatment of hair loss
6299893 Method to reduce hair loss and stimulate hair regrowth
6291532 Use of N-aryl-2-hydroxyalkylamides for stimulating or inducing hair growth and/or arresting hair loss
6291468 Pyrimidine 3-oxide compounds for inducing/stimulating hair growth and/or retarding hair loss
5470876 Topical sod for treating hair loss
5466694 Compositions for slowing down hair loss and for inducing and stimulating its growth, based on 24-diamino-pyrimidine 3-oxide derivatives, and new 24-diaminopyrimidine 3-oxide derivatives
5438058 Composition intended to be used for retarding hair loss and for inducing and stimulating hair growth, containing 2-alkyl-4-aminopyrimidine (or 24-dialkylpyrimidine) 3-oxide derivatives and new compounds derived from 2-alkyl-4-aminopyrimidine 3-oxide
5431881 Treatment of hair loss and dermatological problems
5376373 Method of inhibiting radiation induced weight and hair loss
5328914 Use of pyrimidine 3-oxide derivatives for slowing down hair loss and topical compositions used
5215760 Saturated solution of purified sodium chloride in purified aloe vera for inducing and stimulating hair growth and for decreasing hair loss

  Copyright © 2006 - 2015 Patent Information Search