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EP0155096A2
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EP
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17 Beta-Substituted-4-aza-5-alpha-androstenones and their use as 5-alpha-reductase inhibitors
Assignee: Merck and Co Inc
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Filing: 1985-02-20
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Granted: —
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Expires: 2005-02-20
Abstract
Abstract 17β-N-monosubstituted carbamoyl or 17β-acyl-4-aza-5α--androst-1 -en-3-ones of the formula: in which R is hydrogen, methyl or ethyl; R 2 is a C 1-12 straight or branched alkyl radical or a monocyclic aryl optionally containing one or more methyl or ethyl substituents and/or one or more Cl, F or Br substituents; and in Formula IA R 2 may also be benzyl, phenethyl, 2-pyridyl, 4-pyridyl, 2-pyrrolyl, 2-furyl or thiophenyl; R' is hydrogen or methyl; R" is hydrogen or β-methyl and in Formula IA may also be a-methyl; and R"' is hydrogen, a-methyl or β-methyl and pharmaceutical formulations containing the above compounds are active as testosterone 5a-reductase inhibitors and thus are useful topically for treatment of acne, seborrhoea and female hirsutism, and systemically in the treatment of benign prostatic hypertrophy.
Inventors
- 👤 Gary H. Rasmusson
- 👤 Glenn F. Reynolds
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 21:44
CPC Classifications
C; C07; C07D; C07D213/00; C07C; C07C62/00; C07C62/30; C07C62/38; A; A61; A61P; A61P5/00; C07D221/00; C07D221/02; C07D221/04; C07D221/18; 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: 21
Claim 1
Independent Claim
89 words
A compound of the formula: or in which R is hydrogen, methyl or ethyl; R 2 is a C 1-12 straight or branched alkyl radical or a monocyclic aryl optionally containing one or more methyl or ethyl substituents and/or one or more Cl, F or Br substituents; and in Formula IA R 2 may also be benzyl, phenethyl, 2-pyridyl, 4-pyridyl, 2-pyrrolyl, 2-furyl or thiophenyl; R' is hydrogen or methyl; R" is hydrogen or β-methyl and in Formula IA may also be a-methyl; and R"' is hydrogen, a-methyl or β-methyl.
Claim 2
Dependent Claim
89 words
A compound of the formula: or in which R is hydrogen, methyl or ethyl; R 2 is a C 1-12 straight or branched alkyl radical or a monocyclic aryl optionally containing one or more methyl or ethyl substituents and/or one or more Cl, F or Br substituents; and in Formula IA R 2 may also be benzyl, phenethyl, 2-pyridyl, 4-pyridyl, 2-pyrrolyl, 2-furyl or thiophenyl; R' is hydrogen or methyl; R" is hydrogen or β-methyl and in Formula IA may also be a-methyl; and R"' is hydrogen, a-methyl or β-methyl.
Claim 3
Dependent Claim
30 words
A compound of claim 1 having the formula: or in which R is hydrogen, methyl or ethyl and R is branched chain alkyl or cycloalkyl of from 4-8 carbon atoms.
Claim 4
Dependent Claim
1 words
17β-(N-ethylcarbamoyl)-4-methyl-4-aza-5α-androst-1-en-3-one.
Claim 5
Dependent Claim
1 words
17β-(N-ethylcarbamoyl)-4-methyl-4-aza-5α-androst-1-en-3-one.
Claim 6
Dependent Claim
1 words
17β-(N-ethylcarbamoyl)-4-aza-5α-androst-1-en-3-one.
Claim 7
Dependent Claim
1 words
17β-(N-ethylcarbamoyl)-4-aza-5α-androst-1-en-3-one.
Claim 8
Dependent Claim
1 words
17β-(N-t-butylcarbamoyl)-4-methyl-4-aza-androst-1-en-3-one.
Claim 9
Dependent Claim
1 words
17β-(N-t-butylcarbamoyl)-4-methyl-4-aza-androst-1-en-3-one.
Claim 10
Dependent Claim
1 words
17β-(N-t-butylcarbamoyl)-4-aza-androst-1-en-3-one.
Claim 11
Dependent Claim
1 words
17β-(N-t-butylcarbamoyl)-4-aza-androst-1-en-3-one.
Claim 12
Dependent Claim
1 words
22-Methyl-4-aza-21-nor-5α-chol-1-ene-3,20-dione.
Claim 13
Dependent Claim
1 words
22-Methyl-4-aza-21-nor-5α-chol-1-ene-3,20-dione.
Claim 14
Dependent Claim
1 words
17β-Pyrrolylcarbonyl-4-aza-5α-androst-1-en-3-one.
Claim 15
Dependent Claim
1 words
17β-Pyrrolylcarbonyl-4-aza-5α-androst-1-en-3-one.
Claim 16
Dependent Claim
1 words
4,22-Dimethyl-4-aza-21-nor-5a-chol-1-en-3-one.
Claim 17
Dependent Claim
1 words
4,22-Dimethyl-4-aza-21-nor-5a-chol-1-en-3-one.
Claim 18
Dependent Claim
1 words
4-Methyl-17β-(2-pyrrolylcarbonyl)-4-aza-5α-androst-1-en-3-one.
Claim 19
Dependent Claim
1 words
4-Methyl-17β-(2-pyrrolylcarbonyl)-4-aza-5α-androst-1-en-3-one.
Claim 20
Dependent Claim
36 words
A compound as claimed in any one of claims 1 to 10 for use in treating one or more of the hyperandrogenic conditions of acne vulgaris, seborrhea, female hirsutism, and benign prostatic hypertrophy by parenteral administration.
Claim 21
Dependent Claim
21 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound as claimed in any one of claims 1 to 10.
References Cited (Backward Citations)
No citation records indexed.
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