Patent US4440927A successfully refreshed from Google Patents.
US4440927A
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Process for preparing inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase via a chiral synthon
Assignee: Merck and Co Inc
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Filing: 1982-05-03
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Granted: 1984-04-03
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Expires: 2002-05-03
Abstract
Abstract Totally synthetic analogs of the known inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase, compactin and mevinolin, are prepared from a chiral synthon derived from D-glucose which has the same chirality as the natural products.
Inventors
- 👤 John D. Prugh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 05:51
CPC Classifications
C; C07; C07H; C07H9/00; C07H9/02; C07H9/04; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/14; C07C317/00; C07C321/00; C07C33/00; C07C33/18; C07C33/24; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/16; C07D309/28; C07D309/30; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
158 words
A process for preparing the compound of structural formula: ##STR72## wherein: R 2 and R 3 are independently chloro or C 1-3 alkyl; and R 1 is ##STR73## wherein R 6 is hydrogen, fluoro- or chloro, and R 7 and R 8 are independently hydrogen, chloro or C 1-3 alkyl; which comprises the steps of: (A) treating a compound of structural formula: ##STR74## wherein R 4 is C 1-3 alkyl; R 5 is benzyl, 4-fluorobenzyl, or 4-methoxybenzyl; at 45° to 80° C. for 2-12 hours in the presence of base in a liquid aromatic hydrocarbon; to produce the compound of formula: ##STR75## (B) followed by treatment with palladium hydroxide on carbon catalyst in a C 2-4 alkanol to remove the R 5 group followed by treatment with aqueous acetic acid to produce the compound of structure VI ##STR76## (C) followed by treatment with N-iodosuccinimide and tetra-n-butylammonium iodide in an inert solvent to produce the compound of formula ##STR77##
Claim 2
Dependent Claim
158 words
A process for preparing the compound of structural formula: ##STR72## wherein: R 2 and R 3 are independently chloro or C 1-3 alkyl; and R 1 is ##STR73## wherein R 6 is hydrogen, fluoro- or chloro, and R 7 and R 8 are independently hydrogen, chloro or C 1-3 alkyl; which comprises the steps of: (A) treating a compound of structural formula: ##STR74## wherein R 4 is C 1-3 alkyl; R 5 is benzyl, 4-fluorobenzyl, or 4-methoxybenzyl; at 45° to 80° C. for 2-12 hours in the presence of base in a liquid aromatic hydrocarbon; to produce the compound of formula: ##STR75## (B) followed by treatment with palladium hydroxide on carbon catalyst in a C 2-4 alkanol to remove the R 5 group followed by treatment with aqueous acetic acid to produce the compound of structure VI ##STR76## (C) followed by treatment with N-iodosuccinimide and tetra-n-butylammonium iodide in an inert solvent to produce the compound of formula ##STR77##
Claim 3
Dependent Claim
15 words
The process of claim 1 for the preparation of the compound of structural formula: ##STR78##
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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) | 1987-04-03 | 1987-10-03 | 1988-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-03 | 1991-10-03 | 1992-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-03 | 1995-10-03 | 1996-04-03 | $7700.00 | Window Closed / Lapsed |