US4220775A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of 4-aza-17-substituted-5α-androstan-3-ones useful as 5α-reductase inhibitors
Assignee: Merck and Co Inc
•
Filing: 1979-03-15
•
Granted: 1980-09-02
•
Expires: 1999-03-15
Abstract
Abstract A method of preparing a compound of the formula: <IMAGE> (I) <IMAGE> (III) where Formula (I) may also have the structure of partial Formula (III); wherein, A is (1)CH2CH2; (2)CHCH; <IMAGE> <IMAGE> B is <IMAGE> R' is hydrogen or methyl; R'' is hydrogen or beta -methyl; R''' is beta -methyl or hydroxy; Z is (1) oxo; (2) beta -hydrogen and alpha -hydroxy; or alpha -hydrogen or alpha -hydroxyl and (3) (Y)n Q where n=0 or 1, Y is a straight or branched hydrocarbon chain of 1 to 12 carbon atoms and Q is <IMAGE> (a) where R8 is, <IMAGE> (4) <IMAGE> (5) where the dashed bond replaces the 17 alpha hydrogen; (6) cyano; or (7) tetrazolyl;
Inventors
- 👤 Gary H. Rasmusson
- 👤 David B. R. Johnston
- 👤 Donald F. Reinhold
- 👤 Torleif Utne
- 👤 Ronald B. Jobson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 02:40
CPC Classifications
C; C07; C07J; C07J43/00; C07J43/003; C07C; C07C62/00; C07C62/18; C07C62/24; C07J1/00; C07J1/0003; C07J1/0018; C07J1/0022; C07J21/00; C07J3/00; C07J3/005; C07J33/00; C07J33/005; C07J33/007; C07J41/00; C07J41/0005; C07J41/0016; C07J41/0033; C07J41/0066; C07J73/00; C07J73/001; C07J73/005; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/16
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
169 words
A method of preparing the compound of the formula: ##STR27## comprising the steps of (1) treating pregnenolone with iodine and pyridine to form the corresponding 20-pyridinium iodide derivative of pregnenolone; (2) methanolyzing the product of step (1) to form the methyl ester of 17-carboxy androstenol: (3) treating the product of step (2) with aluminum isopropoxide and cyclohexanone to form methyl-4-androsten-3-one-17-carboxylate; (4) hydrolyzing the product of step (3) to form the corresponding 17-acid compound; (5) treating the product of step (4) with an oxalyl chloride: pyridine complex to form the corresponding 17-acid chloride compound; (6) treating the product of step (5) in situ with diethylamine to form 17β-N,N-diethylcarbamoyl-4-androsten-3-one; (7) oxidizing the product of step (6) with sodium periodate and potassium permanganate in a tert-butanol: water solvent system to form the corresponding 5-oxo-3,5-secoandrostan-3-oic acid compound; (8) treating the product of step (7) with methylamine in ethylene glycol to form 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5-androsten-3-one; (9) hydrogenating the product of step (8) by treating it with hydrogen under catalytic conditions to form the final product, 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one.
Claim 2
Independent Claim
169 words
A method of preparing the compound of the formula: ##STR27## comprising the steps of (1) treating pregnenolone with iodine and pyridine to form the corresponding 20-pyridinium iodide derivative of pregnenolone; (2) methanolyzing the product of step (1) to form the methyl ester of 17-carboxy androstenol: (3) treating the product of step (2) with aluminum isopropoxide and cyclohexanone to form methyl-4-androsten-3-one-17-carboxylate; (4) hydrolyzing the product of step (3) to form the corresponding 17-acid compound; (5) treating the product of step (4) with an oxalyl chloride: pyridine complex to form the corresponding 17-acid chloride compound; (6) treating the product of step (5) in situ with diethylamine to form 17β-N,N-diethylcarbamoyl-4-androsten-3-one; (7) oxidizing the product of step (6) with sodium periodate and potassium permanganate in a tert-butanol: water solvent system to form the corresponding 5-oxo-3,5-secoandrostan-3-oic acid compound; (8) treating the product of step (7) with methylamine in ethylene glycol to form 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5-androsten-3-one; (9) hydrogenating the product of step (8) by treating it with hydrogen under catalytic conditions to form the final product, 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one.
Claim 3
Independent Claim
106 words
A method of preparing the compound of the formula: ##STR28## comprising the steps of (1) treating 4-androsten-3-one-17β-carboxylic acid with an oxalyl chloride: pyridine complex to form the corresponding 17-acid chloride; (2) treating the product of step (1) in situ with diethylamine to form 17β-N,N-diethylcarbamoyl-4-androsten-3-one; (3) oxidizing the product of step (2) with sodium periodate and potassium permangenate in a tert-butanol: water solvent system to form the corresponding 5-oxo-3,5-seconandrostan-3-oic acid compound; (4) treating the product of step (3) with methylamine in ethylene glycol to form 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5-androsten-3-one; (5) hydrogenating the product of step (4) by treating it with hydrogen under catalytic conditions to form the final product, 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one.
Claim 4
Independent Claim
106 words
A method of preparing the compound of the formula: ##STR28## comprising the steps of (1) treating 4-androsten-3-one-17β-carboxylic acid with an oxalyl chloride: pyridine complex to form the corresponding 17-acid chloride; (2) treating the product of step (1) in situ with diethylamine to form 17β-N,N-diethylcarbamoyl-4-androsten-3-one; (3) oxidizing the product of step (2) with sodium periodate and potassium permangenate in a tert-butanol: water solvent system to form the corresponding 5-oxo-3,5-seconandrostan-3-oic acid compound; (4) treating the product of step (3) with methylamine in ethylene glycol to form 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5-androsten-3-one; (5) hydrogenating the product of step (4) by treating it with hydrogen under catalytic conditions to form the final product, 17β-N,N-diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one.
References Cited (Backward Citations)
US2227876A
Cited
US2897202A
Cited
US3022312A
Cited
US3285918A
Cited
US3239417A
Cited
US3264301A
Cited
FR1465544A
Cited
BE775919A
Cited
CA970692A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-02 | 1984-03-03 | 1984-09-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-02 | 1988-03-03 | 1988-09-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-02 | 1992-03-03 | 1992-09-02 | $7700.00 | Window Closed / Lapsed |