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Details for Patent: 5,049,562

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Details for Patent: 5,049,562

Title: 17.beta.-acyl-4-aza-5.alpha.-androst-1-ene-3-ones as 5.alpha.-reductase inhibitors
Abstract:17.beta.-Acyl-4-aza-5.alpha.-androst-1-ene-3-ones of the formula ##STR1## wherein R is selected from hydrogen, methyl and ethyl and R.sup.2 is monocyclic aryl optionally containing 1 or more lower alkyl substituents of from 1-2 carbon atoms and/or 1 or more halo (Cl or Br) substituents; and R', R" and R'" are each selected from hydrogen and methyl and pharmaceutical formulation of the above compounds are active as testosterone 5.alpha.-reductase inhibitors and thus are useful for treatment of acne, seborrhea, female hirsutism, androgenic alopecia, prostatic carcinoma and benign prostatic hypertrophy.
Inventor(s): Rasmusson; Gary H. (Watchung, NJ), Reynolds; Glenn F. (Westfield, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Filing Date:Aug 21, 1989
Application Number:07/396,184
Claims:1. A compound of formula: ##STR8## wherein R is selected from hydrogen, methyl and ethyl; and

R.sup.2 is monocyclic aryl optionally containing 1 or more lower alkyl substituents of from 1-2 carbon atoms and/or 1 or more halo (Cl, F or Br) substituents; and

R', R", R'" are each selected from hydrogen and methyl.

2. A compound of claim 1 having the formula ##STR9## wherein R is hydrogen, methyl or ethyl; and

R.sup.3 is phenyl, phenyl substituted by 1 or 2 lower alkyl substituents of from 1 to 2 carbon atoms, phenyl substituted by 1 or 2 halo (Cl, F or Br) substituents.

3. A compound of claim 2 wherein

R.sup.3 is phenyl, 2-, 3-, or 4-tolyl, xylyl, 2-bromo or 2-chlorophenyl, 2,6-dichloro or 2,6-dibromophenyl.

4. A compound of claim 3 which is

17.beta.-(phenylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-one;

17.beta.-(2-tolylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-one;

17.beta.-(3-tolylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-one;

17.beta.-(4-tolylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-one;

17.beta.-(2-bromophenylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-on e;

17.beta.-(2-chlorophenylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-o ne;

17.beta.-(2,6-dichlorophenylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene -3-one;

17.beta.-(2,6-dibromophenylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene- 3-one;

17.beta.-(xylylcarbonyl)-4-aza-4-methyl-5.alpha.-androst-1-ene-3-one.

5. A compound according to claim 3 which is

17.beta.-(phenylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(2-tolylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(3-tolylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(4-tolylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(2-bromophenylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(2-chlorophenylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(2,6-dichlorophenylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one;

17.beta.-(2,6-dibromophenylcarbonyl)-4-aza-5.alpha.-androst-1-ene-3-one.

6. A compound of claim 5 which is 17.beta.-(phenylcarbonyl)4-aza-5.alpha.-androst-1-ene-3-one.

7. A method of treating the hyperandrogenic condition of acne vulgaris, seborrhea, female hirsutism, and benign prostatic hypertrophy comprising administrating to a patient in need of such treatment of a therapeutically effective amount of a compound of claim 1.

8. A method of inhibiting testosterone 5.alpha.-reductase in a patient in need of such inhibiting treatment comprising administration to such a patient of a therapeutically effective amount of a compound of the claim 1.

9. A pharmaceutical composition for inhibiting testosterone 5.alpha.-reductase which comprises a pharmaceutically acceptable carrier and an effective amount of a compound of claim 1.
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