Patent US4524212A successfully refreshed from Google Patents.
US4524212A
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Acyloxyketone substituted imino and amino acids
Assignee: ER Squibb and Sons LLC
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Filing: 1982-09-27
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Granted: 1985-06-18
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Expires: 2002-09-27
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.
References Cited (Backward Citations)
US4053651A
Cited
US4105776A
Cited
US4192878A
Cited
BE868532A
Cited
US4129566A
Cited
US4154935A
Cited
GB2027025A
Cited
US4316906A
Cited
US4256751A
Cited
US4311697A
Cited
US4217359A
Cited
GB2048863A
Cited
US4329473A
Cited
US4234489A
Cited
US4296113A
Cited
US4310461A
Cited
US4316905A
Cited
US4296033A
Cited
EP0045161A1
Cited
US4337201A
Cited
US4452791A
Cited
US4448772A
Cited
US4444765A
Cited
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) | 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 |