Hair growth promoter

Abstract

The present invention relates to an agent for promoting the growth of hair and decreasing hair fall-out containing compounds of formulas (I), (II) and/or (III) a method for reducing the loss of hair and for promoting the growth of hair by using this agent and to the use of the compounds of formulas (I), (II) and/or (III) for promoting hair growth and/or reducing androgenic loss of hair.

1 . An agent for promoting the growth of hair and/or decreasing hair fallout, wherein at least one of the compounds of formula (I), (II) and/or (III) or their physiologically tolerated salts,  
       
         
           
           
               
               
           
         
       
       is contained, in which the groups A, B, Y, Z and R1 to R8 independently of one another have the following meaning: 
 A and B independently of one another represent a CH group or a nitrogen atom, at least one of the two groups A and B representing a CH group,  
 Y represents —O—, —(CH 2 ) n —, —NH—CH 2 —, —CH 2 —NH—, —NH—CH 2 —, —N═N—, —CH═CH—, —CH 2 —O—, O—CH 2 —, —N═CH—, —CH═N, —(CH 2 —CH 2 —O) m — or —(O—CH 2 —CH 2 ) m —, with m and n equal to a whole number from 1 to 4,  
 Z represents —NH—CH 2 —, —CH 2 —CH 2 —, —CH═CH— or —CH 2 —NH—,  
 R1 is —H, —OH or a C 1  to C 4  hydroxyalkyl group,  
 R2 is H, cyclopropyl or a C 1  to C 4  alkyl group,  
 R3 is a C 1  to C 2  hydroxyalkyl group, —CH 2 —X or —CHX 2  (with X=F, Cl, Br or I), —COCH 3 , —CF 3 , —CH 3  or  
                     (in which R is NO 2 , SO 2 CH 3 , CF 3 , CHF 2 , F, Cl),    
 R4, R5, R6 independently of one another are —NO 2 , —CF 3 , —CHF 2 , —F, —Cl, —Br or —H,  
 R7 is OH, —OSO 3 H, —O—(C 1  to C 4  alkyl) or —OCOCH 3 ,  
 R8 is a C 1  to C 6  alkyl group, a C 1  to C 6  hydroxyalkyl group, a C 2  to C 6  hydroxy-alkenyl group, an aryl group, a heteroaryl group or a C 2  to C 6  alkenyl carboxylic acid group.  
 
     
     
         2 . The agent of  claim 1 , wherein the compound of formula (1), in which Z is —NH—CH 2 —, —CH 2 —CH 2 —, —CH═CH— or —CH 2 —NH—, R1 is —OH, —CH 2 OH or —CH 2 CH 2 OH, R2 is —H, CH 3 , or —C 2 H 5 ; R3 is  
       
         
           
           
               
               
           
         
         C 1  to C 2  hydroxyalkyl group, —CH 2 —X (with X=F, Cl Br or I), —CF 3 , or —CH 3  and R4, R5, R6 independently of one another are —NO 2 , —CHF 2 , —CH 2 F, —F, —Cl, —Br or —H.  
       
     
     
         3 . The agent of  claim 1 , wherein the compound of formula (II) is selected from compounds of formula (II) in which A represents —CH— or —N, Y represents —N═N—, —(CH 2 ) n —, —CH═CH, —CH—N— or —N═CH— and R8 a C 1  to C 6  alkyl group, a C 1  to C 6  hydroxyalkyl group, a phenyl group, a benzyl group or a pyridyl group.  
     
     
         4 . The agent of  claim 1 , wherein the compound of formula (III) is selected from compounds of formula (III) in which A is —CH— and B is —CH— or —N—, Y is —N═N—, —(CH 2 ) n —, —CH═CH—, —CH═N— or N═CH—, R7 is —OH, —OSO 3 H or —O—(C 1  to C 4  alkyl) and R8 is a C, to C 6  alkyl group, a C 1  to C 6  hydroxyalkyl group, a phenyl group, a benzyl group or a pyridyl group.  
     
     
         5 . The agent of one of the  claims 1  to  4 , wherein the compound of formula (I), (II) and/or (III) is selected from 1-(N-(2′-nitro-4′-trifluoromethyl-phenyl)-amino)-3-chloro-2-hydroxy-propane, 1-(N-(2′-nitro-4′-trifluoromethyl-phenyl)-amino)-2-hydroxy-2-trifluoromethylethane, 1-(N-(2′-nitro-4′-trifluoromethyl-phenyl)-amino)-2,3′-dihydroxy-propane, 1-(2′-nitro-4′-trifluoromethyl-phenyl))-3,4-dihydroxy-1-butene, 2,6-diamino-3-((pyridine-3-yl)-azo)-pyridine and 2,6-diamino-3-((pyridine-3-yl)-azo-)-pyridine-1-oxide or combinations of these compounds.  
     
     
         6 . The agent of  claim 5 , wherein the compound of formula (I), (II) and/or (III) is selected from 1-(N-(2′-nitro-4′-trifluoromethyl-phenyl)-amino)-2,3-propylene glycol and 2,6-diamino-3-((pyridine-3-yl)-azo)-pyridine as well as from the combination of these compounds.  
     
     
         7 . The agent of one of the  claims 1  to  6 , wherein the compound of formulas (I) and/or (II) are contained in a total amount of 0.001 to 10 percent by weight.  
     
     
         8 . The agent of one of the  claims 1  to  7 , present in the form of a sustained release preparation or a hair tonic.  
     
     
         9 . A hair treatment method for reducing the fall-out of hair and for promoting hair growth, wherein a sufficient amount of an agent of one of the  claims 1  to  8  is applied on the hair and the scalp, subsequently the scalp is massaged and the agent is left for at least 24 hours on the hair and the scalp.  
     
     
         10 . The use of compounds of formulas (I), (II) and/or (III) for promoting hair growth and/or for reducing the androgenic loss of hair.  
     
     
         11 . The use of one or more compounds of the group consisting of 1-(N-(2′-nitro-4′-trifluoromethyl-phenyl)-amino)-3-chloro-2-hydroxy-propane, 1-(N-(2′-nitro-4′-trifluoromethyl-phenyl)-amino)-2-hydroxy-2-trifluoromethylethane, 1-(N-(2′-nitro-4′-tri-fluoromethyl-phenyl)-amino)-2,3-propylene glycol, 1-(2′-nitro-4′-trifluoromethylphenyl)-3,4-dihydroxy-1-butene, 2,6-diamino-3-((pyridine-3-yl)-azo)-pyridine and 2,6-diamino-3-((pyridine-3-yl)-azo)-pyridine-1-oxide. Of these compounds, 1-(N-(2′-nitro-4′-tri-fluoromethyl-phenyl)-amino)-2,3-propylene glycol and 2,6-diamino-3-((pyridine-3-yl)-azo)-pyridine are particularly preferred for promoting hair growth and/or decreasing androgenic loss of hair.