Patent US4524212A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4524212A Expired / Lapsed US ⏱️ 0.0 years remaining

Acyloxyketone substituted imino and amino acids

Assignee: ER Squibb and Sons LLC
•
Filing: 1982-09-27
•
Granted: 1985-06-18
•
Expires: 2002-09-27
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Acyloxyketone substituted imino and amino acids of the formula ##STR1## are disclosed. These compounds are useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.

Inventors

  • 👤 Eric M. Gordon
  • 👤 Jollie D. Godfrey, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 15:23
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/04; C07D319/06; A; A61; A61P; A61P25/00; A61P25/04; A61P9/00; A61P9/12; C07C; C07C59/00; C07C59/40; C07C59/42; C07C59/48; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 261 words
A compound of the formula ##STR234## or a pharmaceutically acceptable salt thereof wherein: X is ##STR235## n is one or two; R 1 is hydrogen, lower alkyl, halo substituted lower alkyl, ##STR236## or --(CH 2 ) m -cycloalkyl; R 2 is lower alkyl, ##STR237## R 3 is lower alkyl, ##STR238## halo substituted lower alkyl, or --(CH 2 ) m -cycloalkyl; R 7 is hydrogen, lower alkyl, halogen, keto, hydroxy, ##STR239## R 8 is keto, halogen, ##STR240## R 9 is keto, ##STR241## R 13 is lower alkyl or 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, hydroxy, phenyl, phenoxy, phenylthio, or phenylmethyl. R 14 is lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo fluoro, trifluoromethyl or hydroxy; m is zero, one, two, three, or four; p is one, two or three provided that p is more than one only if R 13 or R 14 is methyl, methoxy, chloro, or fluoro; R 6 is hydrogen, lower alkyl, benzyl, benzhydryl, or ##STR242## wherein R 17 is hydrogen, lower alkyl, cycloalkyl or phenyl, and R 18 is hydrogen, lower alkyl, lower alkoxy, phenyl, or R 17 and R 18 taken together are --(CH 2 ) 2 --, --(CH 2 ) 3 --, --CH═CH--, or ##STR243## R 15 is hydrogen or lower alkyl of 1 to 4 carbons; R 19 is lower alkyl, benzyl, or phenethyl; and R 20 is hydrogen, lower alkyl, benzyl, or phenethyl.
Claim 2
Dependent Claim 261 words
A compound of the formula ##STR234## or a pharmaceutically acceptable salt thereof wherein: X is ##STR235## n is one or two; R 1 is hydrogen, lower alkyl, halo substituted lower alkyl, ##STR236## or --(CH 2 ) m -cycloalkyl; R 2 is lower alkyl, ##STR237## R 3 is lower alkyl, ##STR238## halo substituted lower alkyl, or --(CH 2 ) m -cycloalkyl; R 7 is hydrogen, lower alkyl, halogen, keto, hydroxy, ##STR239## R 8 is keto, halogen, ##STR240## R 9 is keto, ##STR241## R 13 is lower alkyl or 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, hydroxy, phenyl, phenoxy, phenylthio, or phenylmethyl. R 14 is lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo fluoro, trifluoromethyl or hydroxy; m is zero, one, two, three, or four; p is one, two or three provided that p is more than one only if R 13 or R 14 is methyl, methoxy, chloro, or fluoro; R 6 is hydrogen, lower alkyl, benzyl, benzhydryl, or ##STR242## wherein R 17 is hydrogen, lower alkyl, cycloalkyl or phenyl, and R 18 is hydrogen, lower alkyl, lower alkoxy, phenyl, or R 17 and R 18 taken together are --(CH 2 ) 2 --, --(CH 2 ) 3 --, --CH═CH--, or ##STR243## R 15 is hydrogen or lower alkyl of 1 to 4 carbons; R 19 is lower alkyl, benzyl, or phenethyl; and R 20 is hydrogen, lower alkyl, benzyl, or phenethyl.
Claim 3
Dependent Claim 176 words
A compound of claim 1 wherein: R 6 is hydrogen, straight or branched chain lower alkyl of 1 to 4 carbons, or ##STR244## R 7 is hydrogen, hydroxy, straight or branched chain lower alkyl of 1 to 4 carbons, cyclohexyl, amino, --O-lower alkyl wherein lower alkyl is straight or branched chain of 1 to 4 carbons, ##STR245## 1-naphthyloxy, 2-naphthyloxy, --S-lower alkyl wherein lower alkyl is straight or branched chain of 1 to 4 carbons, ##STR246## 1-naphthylthio, or 2-naphthylthio; R 8 is --O-lower alkyl wherein lower alkyl is straight or branched chain of 1 to 4 carbons, --S-lower alkyl wherein lower alkyl is straight ot branched chain of 1 to 4 carbons, ##STR247## R 9 is phenyl, 2-hydroxyphenyl, or 4-hydroxyphenyl; m is zero, one or two; R 13 is methyl, methoxy, methylthio, chloro, bromo, fluoro, or hydroxy; R 17 is hydrogen, straight or branched chain lower alkyl of 1 to 4 carbons, or cyclohexyl; and R 18 is straight or branched chain lower alkyl of 1 to 4 carbons or phenyl; or an alkali metal salt thereof.
Claim 4
Dependent Claim 54 words
A compound of claim 2 wherein: R 2 is ##STR248## R 3 is ##STR249## n is one; R 1 is hydrogen, straight or branched chain lower alkyl of 1 to 4 carbons, CF 3 , ##STR250## m is zero, one, or two; and R 14 is methyl, methoxy, methylthio, chloro, bromo, fluoro, or hydroxy.
Claim 5
Dependent Claim 55 words
Compound of claim 3 wherein: X is ##STR251## R 7 is hydrogen, cyclohexyl, lower alkoxy of 1 to 4 carbons, ##STR252## m is zero, one or two; R 13 is methyl, methoxy, methylthio, chloro, bromo, fluoro, or hydroxy; and R 6 is hydrogen, --C 2 H 5 , ##STR253## or an alkali metal salt thereof.
Claim 6
Dependent Claim 20 words
A compound of claim 4 wherein R 1 is hydrogen or methyl; R 2 is ##STR254## R 3 is ##STR255##
Claim 7
Dependent Claim 9 words
A compound of claim 5 wherein X is ##STR256##
Claim 8
Dependent Claim 10 words
A compound of claim 6 wherein R 1 is hydrogen.
Claim 9
Dependent Claim 6 words
The compound of claim 7, 1-[(5S)-5-(benzoyloxy)-1,4-dioxo-6-phenylhexyl]-L-proline.
Claim 10
Dependent Claim 10 words
A compound of claim 6 wherein R 1 is methyl.
Claim 11
Dependent Claim 6 words
The compound of claim 9, 1-[(5S,2R)-5-(benzoyloxy)-2-methyl-1,4-dioxo-6-phenylhexyl]-L-proline.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-06-17 1988-12-17 1989-06-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-06-17 1992-12-17 1993-06-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-06-17 1996-12-17 1997-06-18 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag