United States Patent 5,420,128

United States Patent	5,420,128
Kiyokawa, et. al.	May 30, 1995

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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).
Assignee:	Farmitalia Carlo Erba S.R.L. (Milan, IT).
Appl. No.:	098,935
Filed:	Jul. 29, 1993

Foreign Application Priority Data

Intl. Cl.:	A61K 31/58
U.S. Cl.:	514/284; 546/ 77; 544/125; 544/361
Field of Search:	514/284; 546/77

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References Cited

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U.S. Patent Documents

Foreign Patent Documents

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

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Abstract

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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