United States Patent 5,439,901
Schwen, et. al. Aug. 8, 1995
Inventors:
Schwen; Richard J. (Cincinnati, OH); Sine; Mark R. (Morrow, OH); Warren; Raphael (Amberly Village, OH).
Asignee:
The Procter & Gamble Company (Cincinnati, OH).
Appl. No:
096,081
Filed:
Jul. 23, 1993
Intl. Cl.: A61K 31/56; C07J 7/00
U.S. Cl.: 514/178; 552/511
Field of Search: 552/585, 511; 514/181, 178; 424/449
Abstract:
The present invention relates to the compound cyproterone thiopivalate (CTP) and compositions comprising CTP. The present invention further relates to methods of treating acne and/or sebaceous gland activity comprising topical application of CTP. The present invention additionally relates to methods of regulating hair growth comprising application of compositions comprising CTP.
5 Claims, No Drawings
References Cited:
U.S. Patent Documents
3,234,093 Feb, 1966 Wierchert et al. 167/74
4,014,909 Mar, 1977 Torossian et al. 260/397
4,098,803 Jul, 1978 Torossian et al. 260/397.45
4,098,804 July, 1978 Torossian et al. 260/397.45
4,177,268 Dec, 1979 Torossian et al. 424/243
4,269,778 May, 1981 Torossian et al. 260/397.45
4,361,559 Nov, 1982 Varma 424/243
4,861,765 Aug, 1989 Mituskuchi et al. 514/181
4,877,781 Oct, 1989 LaHaye et al. 514/179
5,021,408 Jun, 1991 Aubard et el. 514/179
Foreign Patent Documents
0163490 Dec, 1985 EP
4006165A1 Feb, 1990 DE
86/01402 Mar, 1986 WO
93/13122 May, 1992 WO
Other References
Bettendorf, G., “Effect of Cyproterone in Female Virilizing Syndromes”, Proceedings of 3rd Meeting of International Study Group on Steroid Hormones, vol. 3, pp. 267-276 (1968).
Bodor, N. “The Application of Soft Drug Approaches to the Design of Safer Corticosteroids”, Topical Corticosteroid Therapy: A Novel Approach to Safer Drugs, pp. 13-25 (1988).
Bodor, N. “Soft Drugs: Principles and Methods for the Design of Safe Drugs”, Medicinal Research Reviews, vol. 4, No. 4, pp. 449-469 (1984).
Bodor, N. and K. B. Sloan, “Soft Drugs V: Thiazolidine-Type Derivatives of Progesterone and Testosterone”, Journal of Pharmaceutical Sciences, vol. 71, No. 5, pp. 514-520 (May 1982).
Burton, J. L., U. Laschet and S. Shuster, “Reduction of Sebum Excretion in Man by the Antiandrogen, Cyproterone Acetate”, British Journal of Dermatology, vol. 89, pp. 487-490 (1973).
Chanoine, F. and J. L. Junien, “Comparative Pharmacokinetic Studies of Tixocortol Pivalate and Cortisol in the Rat”, J. Steroid Biochem, vol. 21, No. 4, pp. 453-459 (1984).
Cunliffe, W. J., S. SHuster and A. J. Cassels Smith, “The Effect of Topical Cyproterone Acetate on Sebum Secretion in Patients With Acne”, Br. J. Derm., vol. 81, No. 3, pp. 200-201 (1969).
Dawber, R. P. R., T. Sonnex and I. Ralfs, “Oral Anti-androgen Treatment of Common Baldness in Women”, B. J. Derm., Suppl. 22, vol. 107, p. 20 (1982).
Devlin, R. G., A. Dean, K. Kripalani, J. R. Taylor and A. A. Sugerman, “Percutaneous Absorption and Adrenal Suppressive Potency of Tipredane, A New Topical Corticosteroid”, J. Toxicol . . .–Cut, & Ocular Toxicol., vol. 5, No. 1, pp. 35-43 (1986).
Huber, J., R. Zeillinger, J. Spona, J. Schmidt, U. Tauber and W. Kuhnz, “Parenteral and Peroral Cyproterone Acetate (CPA) in Severe Hirsutism”, Proceedings of World Congress of Dermatology, Berlin, May 24-29, 1987.
Lan, S. J., L. M. Scanlan, S. H. Weinstein, R. K. Varma, B. M. Warrack, S. E. Unger, M. A. Porubcan and B. H. Migdalof, “Biotransformation of Tipredane, A Novel Topical Steroid, In Mouse, Rat, and Human Liver Homogenates”, Drug Metabolism and Disposition, vol. 17, No. 5, pp. 532-541, 1988.
Lan, S. J., L. M. Scanlan, J. Mitroka, S. H. Weinstein, B. N. Lutsky, C. A. Free, R. J. Wonjar, R. C. Millonig and B. H. Migdalof, “Rapid Metabolic Inactivation of Tipredane, A Structurally Novel Topical Steroid”, Journal of Steroid Biochemistry, vol. 31, No. 5, pp. 825-834 (1988).
Larochelle, P., P. Du Souich, E. Bolte, J. Lelorier and R. Goyer, “Tixocortol Pivalate, a Corticosteroid With No Systemic Glucocorticoid Effect After Oral, Intrarectal, and Intranasal Application”, Clin. Pharmacol. Ther., vol. 33, No. 3, pp. 343-350 (Mar. 1983).
Lutsky, B. N., R. C. Millonig, R. J. Wojnar, C. A. Free, R. G. Devlin, R. K. Varma and D. S. Karanewsky, “Androstene-17-thioketals”, Arzneim.-Forsch./Drug Res., vol. 36(II), No. 12, pp. 1787-1795 (1986).
Lyons, F. and S. Shuster, “Indirect Evidence That The Action of Cyproterone Acetate On The Skin is Due To A Metabolite”, Clinical Endocrinology, vol. 19, pp. 53-55 (1983).
Matias, J. and N. Orentreich, “The Effect of Androgens, Antiandrogens, and Vasodilating Agents on Hairloss in the Androchronogenetic Alopecia (AGA)–Mouse Model”, Proceedings of World Congress of Dermatology, Berlin, May 24-29, 1987.
Neumann, F., R. von Berswordt-Wallrabe, W. Elger, H. Steinbeck, J. D. Hahn and M. Kramer, “Aspects of Androgen-Dependent Events as Studied by Antiandrogens”, Recent Progress in Hormone Research, vol. 26, pp. 337-410 (1970).
Pye, R. J., J. L. Burton and J. I. Harris, “Effect of 1% Cyproterone Acetate in Cetomacrogol Cream BPC (Formula A) on Sebum Excretion Rate in Patients With Acne”, British Journal of Dermatology, vol. 95, No. 4, pp. 427-428 (Oct. 1976).
Vermorken, A. J. M., “Reversal of Androgenic Alopecia by Minoxidil: Lack of Effect of Simultaneously Administered Intermediate Doses of Cyproterone Acetate”, Acta Dermatovener, vol. 63, pp. 268-269 1982.
Voigt, W. and S. L. Hsia, “Further Studies on Testosterone 5().alpha. -Reductase of Human Skin”, The Journal of Biological Chemistry, vol. 218, No. 12, pp. 4280-4285 (Jun. 1973).
Wendt, H., S. H. Hasan, I. Heinze and U. Tauber, “Systemic Effects of Local Antiandrogen Therapy”, Arch Dermatol. Res., vol. 273, p. 171 (1982).
Wiechert, Neumann, “Cyproterone”, The Merck Index, 11th Edition, p. 435 1989.
Wojnar, R. J., R. K. Varma, C. A. Free, R. C. Millonig, D. Karanewsky and B. N. Lutsky, “Androstene-17-thioketals”, Arzneim.-Forsch./Drug. Res., vol. 36(II), No. 12, pp. 1782-1787 (1986).
Primary Examiner: Richter; Johann
Assistant Examiner: Cook; Rebecca
Attorney, Agent or Firm: Corstanje; Brahm J., Suter; David L., Rasser; Jacobus C.
