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US4859681A
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17 α-Acyl-4-aza-5a-androst-1-en-3-ones as 5 alpha-reductase inhibitors
Assignee: Merck and Co Inc
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Filing: 1987-12-03
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Granted: 1989-08-22
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Expires: 2007-12-03
Abstract
Abstract 17 beta -Acyl-4-aza-5 alpha -androst-1-en-3-ones of the formula: <IMAGE> I wherein R is selected from hydrogen, methyl and ethyl and R2 is a monovalent radical selected from straight carbons, or 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, aralkyl selected from benzyl and phenethyl and heterocyclic selected from 2- or 4-pyridyl, 2-pyrrolyl, 2-furyl or thiophenyl; 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 topically for treatment of acne, seborrhea, female hirsutism, and systemically in treatment of benign prostatic hypertrophy.
Inventors
- 👤 Gary H. Rasmusson
- 👤 Glenn F. Reynolds
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 22:38
CPC Classifications
C; C07; C07C; C07C62/00; C07C62/30; C07C62/38; C07J; C07J73/00; C07J73/001; C07J73/005; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/16
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
36 words
A compound of the formula: ##STR8## wherein R is selected from hydrogen, methyl and ethyl and R 2 is branched chain alkyl of from 3-12 carbons, R', R", R'" are each selected from hydrogen and methyl.
Claim 2
Dependent Claim
36 words
A compound of the formula: ##STR8## wherein R is selected from hydrogen, methyl and ethyl and R 2 is branched chain alkyl of from 3-12 carbons, R', R", R'" are each selected from hydrogen and methyl.
Claim 3
Dependent Claim
28 words
A compound of claim 1 having the formula ##STR9## wherein R is hydrogen, methyl or ethyl and R 3 is branched chain alkyl of from 4-8 carbon atoms.
Claim 4
Dependent Claim
10 words
A compound of claim 1 wherein the compound is 22-methyl-4-aza-21-nor-5α-chol-1-ene-3,20-dione.
Claim 5
Dependent Claim
10 words
A compound of claim 1 wherein the compound is 4,22-dimethyl-4-aza-21-nor-5α-chol-1-ene-3,20-dione.
Claim 6
Dependent Claim
10 words
A compound of claim 1 wherein the compound is 23-methyl-4-aza-21-nor-5α-chol-1-ene-3,20-dione.
Claim 7
Dependent Claim
50 words
A method of treating the hyperandrogenic condition of acne vulgaris, seborrhea, female hirsutism, and benign prostatic hypertrophy comprising parenteral administration to a patient in need of such treatment of a therapeutically effective amount of a compound of formula: ##STR10## wherein R and R 2 are defined as in claim 1.
Claim 8
Dependent Claim
34 words
The method of claim 6 where there is employed a compound of the formula: ##STR11## wherein R is hydrogen, methyl or ethyl and R 2 is branched chain alkyl of from 4-8 carbon atoms.
Claim 9
Dependent Claim
60 words
A method of inhibiting testosterone 5α-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 formula: ##STR12## wherein R and R 2 are defined as in claim 1, R' is hydrogen or methyl, R" is hydrogen or β-methyl, R"' is hydrogen, α-methyl or β-methyl.
Claim 10
Dependent Claim
36 words
The compound of claim 8 wherein there is employed a compound of the formula: ##STR13## wherein R is selected from hydrogen, methyl and ethyl and R 3 is branched chain alkyl of from 4-8 carbon atoms.
Claim 11
Dependent Claim
29 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an effective amount of a compound of formula: ##STR14## wherein R and R 2 are defined as in claim 1.
Claim 12
Dependent Claim
34 words
The composition of claim 10 wherein there is employed a compound of the formula: ##STR15## wherein R is hydrogen, methyl or ethyl, and R 3 is branched chain alkyl of from 4-8 carbon atoms.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-08-21 | 1993-02-20 | 1993-08-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-08-21 | 1997-02-20 | 1997-08-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-08-21 | 2001-02-20 | 2001-08-22 | $7700.00 | Window Closed / Lapsed |