US5061803A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for making 17-beta alkanoyl 3-oxo-4-aza-5-α-androst-1-enes
Assignee: Merck and Co Inc
•
Filing: 1990-09-24
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Granted: 1991-10-29
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Expires: 2010-09-24
Abstract
Abstract Disclosed is a new process for making 17-beta branched alkanoyl-3-oxo-4-aza-5-α-androst-1-enes, agents for treating benign prostatic hypertrophy (BPH), by reacting methyl 3-oxo-4-aza-5-α-androst-1-ene-17-beta carboxylate with isobutylmagnesium bromide in the novel presence of the hexamethyldisilazane (HMDS). Use of the HMDS results in higher yield and less by-products as opposed to the standard Grignard reaction in the absence of HMDS.
Inventors
- 👤 John M. Williams
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:06
CPC Classifications
C; C07; C07J; C07J73/00; C07J73/001; C07J73/005; A; A61; A61P; A61P13/00; A61P13/02; A61P15/00
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
90 words
A process for making a compound of the following formula: ##STR5## comprising the step of contacting the compound of the formula: ##STR6## with a Grignard reagent of the formula: RMgX, wherein R is C 3 -C 10 alkyl; and X is iodine, bromine, or chlorine; in a dry inert organic solvent at a temperature in the range of -5° to 10° C., in the presence of hexamethyldisilazane, for a sufficient time to form Compound II where in the molar ratio of Δ 1 -azaester: Griganard reagent: HMDS of about 1:3:10.
Claim 2
Dependent Claim
90 words
A process for making a compound of the following formula: ##STR5## comprising the step of contacting the compound of the formula: ##STR6## with a Grignard reagent of the formula: RMgX, wherein R is C 3 -C 10 alkyl; and X is iodine, bromine, or chlorine; in a dry inert organic solvent at a temperature in the range of -5° to 10° C., in the presence of hexamethyldisilazane, for a sufficient time to form Compound II where in the molar ratio of Δ 1 -azaester: Griganard reagent: HMDS of about 1:3:10.
Claim 3
Dependent Claim
9 words
The process of claim 1 wherein R is isobutyl.
Claim 4
Dependent Claim
9 words
The process of claim 1 wherein X is bromine.
Claim 5
Dependent Claim
19 words
The process of claim 1 wherein the solvent is a C 4 -C 6 linear or branched cyclic ether.
Claim 6
Dependent Claim
89 words
A process for making a compound of the following formula: ##STR7## comprising the step of contacting the compound of the formula: ##STR8## with a Grignard reagent of the formula: RMgX, wherein R is C 3 branched alkyl; and X is iodine, bromine or chlorine; in a dry inert organic solvent at a temperature in the range of -5° to 10° C., in the presence of hexamethyldisilazane, for a sufficient time to form Compound 2 where in the molar ratio of Δ 1 -azaester: Grignard reagent: HMDS of about 1:3:10.
Claim 7
Dependent Claim
89 words
A process for making a compound of the following formula: ##STR7## comprising the step of contacting the compound of the formula: ##STR8## with a Grignard reagent of the formula: RMgX, wherein R is C 3 branched alkyl; and X is iodine, bromine or chlorine; in a dry inert organic solvent at a temperature in the range of -5° to 10° C., in the presence of hexamethyldisilazane, for a sufficient time to form Compound 2 where in the molar ratio of Δ 1 -azaester: Grignard reagent: HMDS of about 1:3:10.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1994-10-28 | 1995-04-29 | 1995-10-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-10-28 | 1999-04-29 | 1999-10-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-10-28 | 2003-04-29 | 2003-10-29 | $7700.00 | Window Closed / Lapsed |