← Back to Patent Explorer
US4894465A Expired / Lapsed US ⏱️ 0.0 years remaining

Intermediates and processes for 6-hydroxymethyl HMG-CoA reductable inhibitors

Assignee: Merck and Co Inc
•
Filing: 1988-02-29
•
Granted: 1990-01-16
•
Expires: 2008-02-29
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract This invention discloses intermediates and processes for the preparation of 6-desmethyl-6-α hydroxymethyl derivatives of lovastatin and analogs thereof at the 8-acyl side chain.

Inventors

  • 👤 Ta J. Lee
  • 👤 William F. Hoffman

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 05:02
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/16; C07D309/28; C07D309/30; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 308 words
A compound of structural formula (H): ##STR28## wherein n is 0 to 3; R 1 and R 2 independently are hydrogen, C 1-5 alkyl, or R 1 and R 2 together with the carbon atom to which they are attached form a carbocyclic ring of 3 to 8 carbon atoms; R 3 and R 4 are independently hydrogen, C 1-3 alkyl, C 3-7 cycloalkyl, C 1-3 alkylthio, phenyl, phenylthio or substituted phenyl in which the substituents are V and W and when n is 2 to 3, each of the R 3 s and R 4 s are independently hydrogen, C 1-3 alkyl, C 3-7 cycloalkyl or only one of the R 3 s or R 4 s on the chain of carbons is phenyl or substituted phenyl; R 5 is hydrogen, tosylate, OT, C 1-5 alkyl or C 1-5 alkyl substituted with tosylate or OT, or C 3-7 cycloalkyl or C 3-7 cycloalkyl; substituted with C 1-3 alkyl, tosylate or OT, C 2-5 alkenyl, phenyl or substituted phenyl in which the substituents are V and W, or R 5 in a group selected from: (a) C 1-5 -alkanoyloxy-C 1-4 -alkyl, (b) ##STR29## in which m is 0 to 3 and R 6 is C 1-5 alkyl; (c) ##STR30## in which R 7 and R 8 are independently C 1-5 alkyl or R 7 and R 8 together with the nitrogen atom to which they are attached form a heterocycle selected from piperidinyl, morpholinyl, pyrrolidinyl, piperazinyl or thiomorpholinyl; (d) ##STR31## in which q is 0 to 2 and R 9 is C 1-5 alkyl or phenyl or substituted phenyl in TO-C 1-3 alkyl which the substituents are V and W; V and W independently are hydrogen, halogen, hydroxy, trifluoromethyl, C 1-3 alkyl, C 1-3 alkyloxy and TO-C 1-3 alkyl; T is tert-butyldimethylsilyl, tert-butyldiphenylsilyl, trimethylsilyl, triethylsilyl, triisopropylsilyl or tetrahydropyranyl.
Claim 2
Dependent Claim 308 words
A compound of structural formula (H): ##STR28## wherein n is 0 to 3; R 1 and R 2 independently are hydrogen, C 1-5 alkyl, or R 1 and R 2 together with the carbon atom to which they are attached form a carbocyclic ring of 3 to 8 carbon atoms; R 3 and R 4 are independently hydrogen, C 1-3 alkyl, C 3-7 cycloalkyl, C 1-3 alkylthio, phenyl, phenylthio or substituted phenyl in which the substituents are V and W and when n is 2 to 3, each of the R 3 s and R 4 s are independently hydrogen, C 1-3 alkyl, C 3-7 cycloalkyl or only one of the R 3 s or R 4 s on the chain of carbons is phenyl or substituted phenyl; R 5 is hydrogen, tosylate, OT, C 1-5 alkyl or C 1-5 alkyl substituted with tosylate or OT, or C 3-7 cycloalkyl or C 3-7 cycloalkyl; substituted with C 1-3 alkyl, tosylate or OT, C 2-5 alkenyl, phenyl or substituted phenyl in which the substituents are V and W, or R 5 in a group selected from: (a) C 1-5 -alkanoyloxy-C 1-4 -alkyl, (b) ##STR29## in which m is 0 to 3 and R 6 is C 1-5 alkyl; (c) ##STR30## in which R 7 and R 8 are independently C 1-5 alkyl or R 7 and R 8 together with the nitrogen atom to which they are attached form a heterocycle selected from piperidinyl, morpholinyl, pyrrolidinyl, piperazinyl or thiomorpholinyl; (d) ##STR31## in which q is 0 to 2 and R 9 is C 1-5 alkyl or phenyl or substituted phenyl in TO-C 1-3 alkyl which the substituents are V and W; V and W independently are hydrogen, halogen, hydroxy, trifluoromethyl, C 1-3 alkyl, C 1-3 alkyloxy and TO-C 1-3 alkyl; T is tert-butyldimethylsilyl, tert-butyldiphenylsilyl, trimethylsilyl, triethylsilyl, triisopropylsilyl or tetrahydropyranyl.
Claim 3
Dependent Claim 30 words
A compound of claim 1 wherein: R 1 is methyl; R 2 is hydrogen or methyl; R 3 s and R 4 s are independently hydrogen or C 1-3 alkyl.
Claim 4
Dependent Claim 31 words
A compound of claim 2 wherein: R 5 is hydrogen, tosylate, OT, C 1-5 alkyl, phenyl or substituted phenyl in which the substituents are V and W; and T is tert-butyldimethylsilyl.
Claim 5
Dependent Claim 34 words
A compound of claim 3 selected from the group wherein: (a) n is 0, R 2 is methyl, R 5 is ethyl; (b) n is 0, R 2 is hydrogen, R 5 is ethyl.

References Cited (Backward Citations)

US4444784A Cited
US4582915A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-01-15 1993-07-17 1994-01-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-01-15 1997-07-17 1998-01-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-01-15 2001-07-17 2002-01-16 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag