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US5189180A Expired / Lapsed US ⏱️ 0.0 years remaining

Seco-mevinic acid derivatives useful as antihypercholesterolemic agents and new intermediates

Assignee: ER Squibb and Sons LLC
•
Filing: 1991-05-01
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Granted: 1993-02-23
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Expires: 2011-05-01
📄 Original PDF 🌐 Google Patents

Abstract

Abstract Seco-mevinic acid derivatives are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R 1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R 2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR 5 wherein R 5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.

Inventors

  • 👤 Donald S. Karanewsky

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 00:54
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/08; C07C; C07C69/00; C07C69/66; C07C69/67; C07C69/675; C07D309/00; C07D309/16; C07D309/28; C07D309/30; C07D319/00; C07D319/04; C07D319/06; C07D407/00; C07D407/02; C07D407/08; C07D409/00; C07D409/02; C07D409/08; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 13 words
An intermediate of the structure ##STR63## wherein Pro represents a silyl protecting group.
Claim 2
Dependent Claim 13 words
An intermediate of the structure ##STR63## wherein Pro represents a silyl protecting group.
Claim 3
Dependent Claim 246 words
An intermediate of the structure ##STR64## wherein Pro represents a silyl protecting group and Q is ##STR65## wherein R 1 is H, lower alkyl, aryl, lower alkoxy, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; and R 2 is lower alkyl, cycloalkyl or aralkyl; and X is O or NR 5 wherein R 5 is H or alkyl; wherein aryl by itself or as part of another group is a monocyclic or bicyclic aromatic group containing 6 to 10 carbons which may be unsubstituted or substituted with 1 or 2 of lower alkyl, halogen, CF 3 , lower alkoxy, nitro, alkoxy and/or cyano; heteroaryl by itself or as part of another group is a 5- to 10-membered mono or bicyclic ring containing one or two heteroatoms which are N, S or O; aralkyl by itself or as part of another group is a lower alkyl group having an aryl substituent; heteroaralkyl by itself or as part of another group is a heteroaryl linked to an alkylene group; heterocyclic by itself or as part of another group is a 5- to 10-membered monocyclic or bicyclic ring containing 1 or 2 heteroatoms which are N; N and O; or N and S; cycloalkyl by itself or as part of another group is a saturated hydrocarbon containing 3 to 12 carbons which is unsubstituted or substituted with 1 or 2 of halogen, lower alkoxy, lower alkyl, hydroxy, lower alkoxycarbonyl, lower alkanoyl, aroyl, aryl, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, arylthio and/or oxo.
Claim 4
Dependent Claim 246 words
An intermediate of the structure ##STR64## wherein Pro represents a silyl protecting group and Q is ##STR65## wherein R 1 is H, lower alkyl, aryl, lower alkoxy, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; and R 2 is lower alkyl, cycloalkyl or aralkyl; and X is O or NR 5 wherein R 5 is H or alkyl; wherein aryl by itself or as part of another group is a monocyclic or bicyclic aromatic group containing 6 to 10 carbons which may be unsubstituted or substituted with 1 or 2 of lower alkyl, halogen, CF 3 , lower alkoxy, nitro, alkoxy and/or cyano; heteroaryl by itself or as part of another group is a 5- to 10-membered mono or bicyclic ring containing one or two heteroatoms which are N, S or O; aralkyl by itself or as part of another group is a lower alkyl group having an aryl substituent; heteroaralkyl by itself or as part of another group is a heteroaryl linked to an alkylene group; heterocyclic by itself or as part of another group is a 5- to 10-membered monocyclic or bicyclic ring containing 1 or 2 heteroatoms which are N; N and O; or N and S; cycloalkyl by itself or as part of another group is a saturated hydrocarbon containing 3 to 12 carbons which is unsubstituted or substituted with 1 or 2 of halogen, lower alkoxy, lower alkyl, hydroxy, lower alkoxycarbonyl, lower alkanoyl, aroyl, aryl, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, arylthio and/or oxo.
Claim 5
Dependent Claim 245 words
A new intermediate of the structure ##STR66## wherein R 1 is H, lower alkyl, aryl, lower alkoxy, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R 2 is lower alkyl, cycloalkyl or aralkyl; R 5' is CH 2 OH or CO 2 alkyl; and X is O or NR 5 wherein R 5 is H or alkyl, wherein aryl by itself or as part of another group is a monocyclic or bicyclic aromatic group containing 6 to 10 carbons which may be unsubstituted or substituted with 1 or 2 of lower alkyl, halogen, CF 3 , lower alkoxy, nitro, alkoxy and/or cyano; heteroaryl by itself or as part of another group is a 5- to 10-membered mono or bicyclic ring containing one or two heteratoms which are N, S or O; aralkyl by itself or as part of another group is a lower alkyl group having an aryl substituent; heteroaralkyl by itself or as part of another group is a heteroaryl linked to an alkylene group; heterocyclic by itself or as part of another group is a 5- to 10-membered monocyclic or bicyclic ring containing 1 or 2 heteroatoms which are N; N and O; or N and S; cycloalkyl by itself or as part of another group is a saturated hydrocarbon containing 3 to 12 carbons which is unsubstituted or substituted with 1 or 2 of halogen, lower alkoxy, lower alkyl, hydroxy, lower alkoxycarbonyl, lower alkanoyl, aroyl, aryl, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, arylthio and/or oxo.
Claim 6
Dependent Claim 245 words
A new intermediate of the structure ##STR66## wherein R 1 is H, lower alkyl, aryl, lower alkoxy, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R 2 is lower alkyl, cycloalkyl or aralkyl; R 5' is CH 2 OH or CO 2 alkyl; and X is O or NR 5 wherein R 5 is H or alkyl, wherein aryl by itself or as part of another group is a monocyclic or bicyclic aromatic group containing 6 to 10 carbons which may be unsubstituted or substituted with 1 or 2 of lower alkyl, halogen, CF 3 , lower alkoxy, nitro, alkoxy and/or cyano; heteroaryl by itself or as part of another group is a 5- to 10-membered mono or bicyclic ring containing one or two heteratoms which are N, S or O; aralkyl by itself or as part of another group is a lower alkyl group having an aryl substituent; heteroaralkyl by itself or as part of another group is a heteroaryl linked to an alkylene group; heterocyclic by itself or as part of another group is a 5- to 10-membered monocyclic or bicyclic ring containing 1 or 2 heteroatoms which are N; N and O; or N and S; cycloalkyl by itself or as part of another group is a saturated hydrocarbon containing 3 to 12 carbons which is unsubstituted or substituted with 1 or 2 of halogen, lower alkoxy, lower alkyl, hydroxy, lower alkoxycarbonyl, lower alkanoyl, aroyl, aryl, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, arylthio and/or oxo.

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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) 1996-02-23 1996-08-24 1997-02-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-02-23 2000-08-24 2001-02-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-02-23 2004-08-24 2005-02-23 $7700.00 Window Closed / Lapsed

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