US 7,320,967 B2
Cosmetic composition, method of cosmetic treatment and preparation of a composition for promoting the growth and/or preventing or delaying the loss of hair
Jean-François Michelet, Creteil (France); Bruno Bernard, Neuilly sur Seine (France); Roger Rozot, Lagny/Marne (France); and Christophe Boulle, Lagny S/Marne (France)
Assigned to L'Oreal, Paris (France)
Filed on Apr. 23, 2003, as Appl. No. 10/420,831.
Claims priority of provisional application 60/425330, filed on Nov. 12, 2002.
Claims priority of provisional application 60/387420, filed on Jun. 11, 2002.
Claims priority of application No. 02 05067 (FR), filed on Apr. 23, 2002; and application No. 02 13461 (FR), filed on Oct. 28, 2002.
Prior Publication US 2004/0052760 A1, Mar. 18, 2004
Int. Cl. A61K 31/675 (2006.01); A61K 31/655 (2006.01); A61K 8/18 (2006.01); A01N 25/34 (2006.01); C12N 9/99 (2006.01)
U.S. Cl. 514—91  [514/157; 424/70.1; 424/408; 435/184] 52 Claims
 
1. A method for stimulating or inducing the growth and/or reducing the loss and/or increasing the density and/or reducing the heterogeneity of the diameter of keratinous fibers in a human being in need of same, said method comprising administering an effective amount at least one 15-hydroxyprostaglandin dehydrogenase (15-PGDH) inhibitor, or an effective amount of a composition comprising at least one 15-hydroxyprostaglandin dehydrogenase (15-PGDH) inhibitor and a cosmetically or pharmaceutically acceptable medium, to said human being, wherein said at least one 15-PGDH inhibitor is at least one tetrazole compound of formula (I) or (II):

OG Complex Work Unit Drawing
or an inorganic or organic salt thereof, in which:
each of R1 and R2 is independently hydrogen, halogen, OR5, SR5, NR5R′5, COOR5, COR5, CONR5R′5, CF3, CN, NR5COR′5, SO2R5, SO2NR5R′5, NR5SO2R′5, CSR5, OCOR5, COSR5, SCOR5, CSNR5R′5, NR5CONR′5R″5, NR5C(=NR′5)NR″5R′″5, NR5CSR′5, NR5CSNR′5R″5, a linear or branched C1-C20 alkyl radical, or a ring that is cyclopentyl, cyclohexyl, pyridine, piperidine, morpholine, pyrrole, furan, thiazole, phenyl or naphthyl, each R1 and R2 alkyl radical being saturated or unsaturated, each R1 and R2 alkyl radical and each R1 and R2 ring being optionally substituted with at least one substituent A1, where each of R5, R′5, R″5 and R′″5 independently is hydrogen, a linear or branched C1-C20 alkyl radical or a 4- to 7-atom hydrocarbon ring, each R5, R′5, R″5 and R′″5 hydrocarbon ring and each R5, R′5, R″5 and R′″5 alkyl radical being saturated or unsaturated and optionally substituted with at least one substituent A2;
R3 is hydrogen, OR6, SR6, NR6R′6, CF3, NR6COR′6, NR6SO2R′6, NR6CONR′6R″6, NR6CSR′6, NR6CSNR′6R″6, a linear or branched C1-C20 alkyl radical, or a ring that is cyclopentyl, cyclohexyl, phenyl or naphthyl, the R3 alkyl radical being saturated or unsaturated, the R3 alkyl radical or the R3 ring being optionally substituted with at least one substituent A3, with each of R6, R′6 and R″6 independently being hydrogen, a linear or branched C1-C20 alkyl radical, or a 4- to 7-atom hydrocarbon ring, each R6, R′6 and R″6 alkyl radical and each R6, R′6 and R″6 hydrocarbon ring being saturated or unsaturated and optionally substituted with at least one substituent A4;
R4 is hydrogen, COOR7, CONR7R′7, SO2R7, SO2NR7R′7, COR7, CSR7, COSR7, CSNR7R′7, a linear or branched C1-C20 alkyl radical, or a ring that is cyclopentyl, cyclohexyl, phenyl or naphthyl, the R4 alkyl radical being saturated or unsaturated, the R4 alkyl radical or the R4 ring being optionally substituted with at least one substituent A5; or R4 additionally represents, in the case of formula (II), halogen, OR7, SR7, NR7R′7, CF3, CN, NR7COR′7, NR7SO2R′7, OCOR7, SCOR7, NR7CONR′7R″7, NR7C(=NR′7)NR″7R′″7, NR7CSR′7 or NR7CSNR′7R″7, with R7, R′7, R″7 and R′″7 independently being hydrogen, a linear or branched C1-C20 alkyl radical, or a 4- to 7-atom hydrocarbon ring, each R7, R′7, R″7 and R′″7 alkyl radical and each R7, R′7, R″7 and R′″7 hydrocarbon ring being saturated or unsaturated and optionally substituted with at least one substituent A6;
each of A1 and A2 independently is halogen, a heterocycle having from 4 to 7 atoms and at least one hetero ring atom, OR8, SR8, NR8R′8, COOR8, CONR8R′8, CF3, CN, NR8COR′8, SO2R8, SO2NR8R′8, NR8SO2R′8, COR8, CSR8, OCOR8, COSR8, SCOR8, CSNR8R′8, NR8CONR′8R″8, NR8C(=NR′8)NR″8R′″8, NR8CSR′8, or NR8CSNR′8R″8;
each of A3 and A4 is independently halogen, R9, OR9, SR9, NR9R′9, COOR9, CONR9R′9, CF3, CN, NR9COR′9, SO2R9, SO2NR9R′9, NR9SO2R′9, CSR9, OCOR9, COSR9, SCOR9, CSNR9R′9, NR9CONR′9R″9, NR9C(=NR′9) NR″9R′″9, NR9CSR′9, or NR9CSNR′9R″9;
each of A5 and A6 is independently halogen, R10, OR10, SR10, NR10R′10, CF3, CN, NR10COR′10, SO2R10, SO2NR10R′10, NR10SO2R′10, CSR10, OCOR10, SCOR10, CSNR10R′10, NR10CONR′10R″10, NR10C(=NR′10)NR″10R′″10, NR10CSR′10, and NR10CSNR′10R″10; and
each of R8, R′8, R″8, R′″8, R9, R′9, R″9, R′″9, R10, R′10, R″10 and R′″10 independently is hydrogen, a saturated or unsaturated, linear or branched C1-C20 alkyl radical, a saturated or unsaturated 4- to 7-atom hydrocarbon ring, or a benzyl radical.