United States Patent 5,420,128
Kiyokawa, et. al. May 30, 1995
17.beta.-substituted 4-aza-5.alpha.-androstan-3-one derivatives
Inventors:
Panzeri; Achille (Merate, IT); Nesi; Marcella (Milan, IT); di Salle; Enrico (Milan, IT).
Asignee:
Farmitalia Carlo Erba S.R.L. (Milan, IT).
Appl. No:
098,935
Filed:
Jul. 29, 1993
Foreign Application Priority Data:
Jul. 31, 1992 [GB] 9216329
Intl. Cl.: A61K 31/58
U.S. Cl.: 514/284; 546/ 77; 544/125; 544/361
Field of Search: 514/284; 546/77
Abstract:
A compound of formula (I): ##STR1## wherein R is a hydrogen atom or a C(1) -C(4) alkyl group;
- A is a single bond or a straight or branched C(1) -C(6) alkylene chain;
- R(1) is a hydrogen atom or a C(1) -C(6) alkyl group;
- R(2) is a C(1) -C(6) alkyl group, a C(5) -C(7) cycloalkyl or a C(6) -C(10) cycloalkylalkyl group, aryl or a C(7) -C(10) arylalkyl group, or a C(6) -C(10) heterocyclylalkyl group;
- R(3) is hydrogen, a C(1) -C(4) alkyl group or an aryl or a C(7) -C(10) arylalkyl group;
- Z is a C(1) -C(6) alkyl group, an –OR(5) group wherein R(5) is a C(1) -C(6) alkyl group, ##STR2## group wherein each of R(6) and R(7) is hydrogen, C(1) -C(6) alkyl, C(5) -C(7) cycloalkyl, phenyl or R(6) and R(7) taken together with the nitrogen to which they are linked form a pentatomic or hexatomic saturated heteromonocyclic ring; and the symbol represents a single or a double bond, is a testosterone 68 5.alpha.-reductase inhibitor and is therapeutically useful in benign prostatic hyperplasia, prostatic and breast cancers, seborrhoea, female hirsutism and male pattern baldness.
4 Claims, No Drawings
References Cited:
U.S. Patent Documents
5,155,107 Oct, 1992 Panzeri et al. 546/77
5,302,621 Apr, 1994 Kojima et al. 514/284
Foreign Patent Documents
0155096 Sept, 1985 EP
0200859 Nov, 1986 EP
0271220 Jun, 1998 EP
0484094 May, 1992 EP
Other References
Liang et al. J. Steroid Biochem. vol. 19 No. 1 pp. 385-390 (1983).
Lamb et al. The Prostate vol. 21 pp. 15-34 (1992).
Stinson, Chem. and Eng. News, Jun. 29, 1992 pp. 7 and 8.
Journal of Medicinal Chemistry, vol. 29, No. 11, Nov. 1, 1986, Gary H. Rasmusson, et al., “Azasteroids: Structure-Activity Relationships for Inhibition of 5-.alpha.-Reductase and of Androgen Receptor Binding”, pp. 2298-2315.
Journal of Medicinal Chemistry, vol. 27, No. 12, Dec. 1984, Gary H. Rasmusson, et al., “Azasteroids as Inhibitors of Rat Prostatic 5-.alpha.-Reductase”, pp. 1690-1701.
Primary Examiner: Daus; Donald G.
Attorney, Agent or Firm: Oblon, Spivak, McClelland, Maier & Neustadt
