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(12) Patent Application Publication (10) Pub. No.: US 2003/0054021 A1 Dalko Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2003/0054021 A1 Dalko Et Al US 20030054021A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2003/0054021 A1 Dalko et al. (43) Pub. Date: Mar. 20, 2003 (54) 7-OXO-DHEACOMPOUNDS FOR TREATING (30) Foreign Application Priority Data KERATINOUS CONDITIONS/AFFLICTIONS Jun. 14, 2001 (FR)............................................ 01/07804 (76) Inventors: Maria Dalko, Gif Sur Yvette (FR); Publication Classification Alexandre Cavezza, Tremblay-En-France (FR); Elisabeth (51) Int. Cl." ....................... A61K 31/695; A61K 31/66; Picard-Lesboueyries, Velizy (FR); A61K 31/58; A61K 31/56; Beatrice Renault, Saint Maurice (FR); A61K 7/OO Veronique Burnier, Paris (FR) (52) U.S. Cl. ............................ 424/401; 514/63; 514/172; 514/176; 514/177; 514/143 Correspondence Address: (57) ABSTRACT Norman H. Stepno, Esquire BURNS, DOANE, SWECKER & MATHIS, 7-Oxo-DHEA derivatives, various of which are themselves L.L.P. novel compounds, are well Suited for cosmetically/therapeu P.O. Box 1404 tically treating adverse conditions/afflictions of a keratinous Alexandria, VA 22313-1404 (US) Substrate/material, notably of human skin, hair, eyelashes and nails, to improve the appearance thereof, in particular to prevent or treat Signs of aging of the Skin and/or a dull (21) Appl. No.: 10/170,679 complexion and/or skin or hair pigmentation disorders and/ or dryneSS of the skin and/or hyperSeborrhoea and/or hyper Seborrhoea-related imperfections and/or Sensitive skin and/ (22) Filed: Jun. 14, 2002 or dandruff and/or natural hair loSS and/or baldness. US 2003/0054021 A1 Mar. 20, 2003 7-OXO-DHEACOMPOUNDS FOR TREATING KERATINOUS CONDITIONS/AFFLICTIONS (I) Me O CROSS-REFERENCE TO PRIORITY APPLICATION Me 0001. This application claims priority under 35 U.S.C. S 119 of FR-01/07804, filed Jun. 14, 2001, hereby expressly incorporated by reference. R No O BACKGROUND OF THE INVENTION 0010. Among these compounds, 3 B-acetoxy-7-oxo 0002) 1. Technical Field of the Invention DHEA or A5-androstene-3,3-acetoxy-7,17-dione is already 0003. The present invention relates to novel 7-oxo known and has been described as being effective in modu DHEA derivatives, to a process for Synthesizing Such novel lating the immune system (U.S. Pat. Nos. 5,292,730, 5,585, compounds and to cosmetic/therapeutic compositions com 371 and 5,641,766), treating Alzheimer's disease (U.S. Pat. prising Same. No. 5,707,983), treating HIV syndrome (U.S. Pat. No. 5,885,977) and for promoting weight loss (U.S. Pat. Nos. 0004. The present invention also relates to cosmetic 5,296,481 and 5,807,848). applications of at least one 7-oxo-DHEA derivative to 0011 WO-99/25333 also indicates the administration, improve the appearance of keratin materials and Substrates, especially topically, of 3,3-acetoxy-7-oxo-DHEA in the pro Such as the skin, the hair, the eyelashes and the nails, in phylactic and curative treatment of lupus erythematosus, particular to prevent or treat adverse signs of aging of the which is a disorder of the immune system that is liable to skin and/or a dull complexion and/or skin or hair pigmen affect Several organs and that is manifested in the skin by tation disorders and/or dryness of the skin and/or hyperse transverse redness of the face and/or by Squamous erythemal borrhoea and/or hyperSeborrhoea-related imperfections and/ plaques disseminated over the body. or Sensitive Skin and/or dandruff and/or natural hair loSS 0012 U.S. Pat. No. 5,424,463 especially describes and/or baldness. 7-keto-DHEA (or A5-androstene-3B-ol-7,17-dione) and 0005. This invention also relates to a cosmetic regime/ derivatives thereof wherein one or more of the hydroxyl or regimen for treating keratinous Substrates/materials by topi keto Substituents is a group convertible thereto by hydroly cal application thereon of a composition containing at least Sis. Hydrolyzable groups include hydroxyl groups esterified one 7-oxo-DHEA derivative, formulated into a physiologi with an acid selected from the group consisting of (i) a cally acceptable medium therefor. normal, branched, Saturated or unsaturated C-C aliphatic acid, (ii) a C7-C aromatic acid, (iii) a C- or more dicar 0006 2. Description of the Prior Art boxylic acid, for which only one carbonyl group is esterified with the 3-hydroxy group of the Steroid, (iv) an inorganic 0007 DHEA, or dehydroepiandrosterone, is a natural acid such as Sulfuric acid and phosphoric acid. U.S. Pat. No. Steroid produced essentially by the adrenal glands. EXOg 5,424,463 describes the 7-keto- and hydrolyzable deriva enous DHEA, administered topically or orally, is recognized tives thereof as being effective for promoting weight loSS. for its capacity to promote epidermal keratinization (JP-07, 0013 In addition, the following derivatives are also 196,467) and to treat dry skin by increasing the endogenous described as being effective for promoting weight loSS production and Secretion of Sebum and thus by reinforcing (Steroids, 1998, 63(3), pp. 158-165): 3 B-O-acetyl-7-oxo the skin's barrier effect (U.S. Pat. No. 4,496.556). U.S. Pat. dehydroepiandrosterone (or 3,3-acetyl-7-oxo-DHEA); No. 5,843,932 has also described the administration of 3|8-O-propionyl-7-oxo-dehydroepiandrosterone (or 3 B-pro DHEA to remedy dermal atrophy by inhibiting the loss of pionyl-7-oxo-DHEA); 3.3-O-butanoyl-7-oxo-dehydroepi collagen and of connective tissue. Too, the assignee hereof androsterone (or 3,3-butanoyl-7-oxo-DHEA); 3 B-O-isobu has demonstrated the capacity of DHEA to combat the tanoyl-7-oxo-dehydroepiandrosterone; 3 B-O-heptanoyl-7- weathered appearance of the skin (FR-00/00349), to modify OXO-dehydroepiandrosterone; 3f6-O-dodecanoyl-7-oxo skin and hair pigmentation (FR-99/12773) and to combat dehydroepiandrosterone; 3f6-O-palmitoyl-7-oxo epidermal atrophy (FR-00/06154). These properties of dehydroepiandrosterone; 3f6-O-stearoyl-7-oxo DHEA make it a candidate of choice as an anti-aging active dehydroepiandrosterone; 3.3-O-hemisuccinate-7-oxo agent. dehydroepiandrosterone. 0008. However, DHEA has hormonal effects that may 0014) Among the 7-oxo-DHEA derivatives of formula (I) prove difficult as regards the administration of Same. There that are described in the prior art are the following deriva need Still exists to provide DHEA analogs with properties as tives: advantageous as DHEA itself, but without eliciting any 0.015 (1) The derivative of formula (I) in which R is hormonal effects. a 2-tetrahydropyran group (RN 102 890-86-8). 0009. It was first considered by applicants that the 7-oxo 0016 (2) The compound of formula (I) in which R DHEA derivatives of general formula (I) below could satisfy is a CHOCO group, described as Suppressing the this need: transactivation of the androgenic receptor induced US 2003/0054021 A1 Mar. 20, 2003 by an androstenediol in human prostate cancer cells and/or Sulfate and/or phosphate and/or aryl and/or hetero (Proc. Natl. Acad. Sci. USA, 1999, 96(20), pp. cycle, Said heterocycle advantageously being an indole, a 11173-11177). pyrimidine, a piperidine, a morpholine, a pyran, a furan, a piperazine or a pyridine, an alkylcarbonyl radical, with the 0017 (3) Derivatives of formula (I) in which R is an exception of the CH-CO-radical, the C-C alkyl moiety of O=P(OH)OCOCH group or a group which is Saturated or unsaturated, linear or branched, or cyclic, and optionally Substituted with one or more Substitu CO2H ents selected from among -OR" and/or - SR" and/or -COOR" and/or -NR'R' and/or halogen and/or sulfate and/or phosphate and/or aryl and/or heterocycle, Said het erocycle advantageously being an indole, a pyrimidine, a piperidine, a morpholine, a pyran, a furan, a piperazine or a pyridine, an arylcarbonyl radical, preferably a phenylcarbo nyl radical, or an arylalkylcarbonyl radical, preferably a benzylcarbonyl radical, optionally Substituted with one or more of the Substituents -OR" and/or -SR' and/or COOR and/or -NR'R' and/or halogen and/or aryl and/or hetero cycle; a group O=P(OH)OR'; a group (O)SOR"; a trialkyl 0018) described in U.S. Pat. No. 5,837,269 as silyl radical (SiR') in which the 3 groups R' may be identical agents for increasing the immune response to a or different; an alkyloxycarbonyl group (R'OCO); an alky Vaccine. laminocarbonyl group (R'NHCO); wherein R' is a hydrogen 0.019 (4) The derivative of formula (I) in which R is atom, a Saturated or unsaturated, linear or branched, or a group molPhCO, described in an epoxidation cyclic C-C and preferably C-C alkyl radical, which may process for the synthesis of steroids (J. Chem. Soc. optionally contain one or more hetero atoms, optionally Perkin Trans. I, 1975 (4), pp. 323-6). functionalized with one or more of the groups -OR", -COOR", halogen, -NR"R", or with an aryl group, pref 0020 (5) Derivatives of formula (I) in which R is an erably a phenyl group, optionally functionalized with one or NaSOH group or an SOH group, noted in Endo more of the groups -OR", -COOR", halogen or crinol. Exp., 1971, 5(4), pp. 205-210, which -NR"R", and preferably wherein R' is a hydrogen atom, a describes the properties of these derivatives when methyl, an ethyl, a butyl, a propyl or an isopropyl radical; they are subjected to various hydrolysis conditions. and R" is a hydrogen atom or a Saturated or unsaturated, linear or branched or cyclic alkyl radical, preferably C-C, 0021 (6) The derivative of formula (I) in which R is preferably R" is a hydrogen atom, a methyl, an ethyl, abutyl, a tEuSi(Me) group, described in a steroid prepara a propyl or an isopropyl radical; with the proviso that, in tion process (Heterocycles, 1994, 38(5), pp.
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