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US4555579A Expired / Lapsed US ⏱️ 0.0 years remaining

Dioxolenylmethyl ester prodrugs of phosphinic acid ace inhibitors

Assignee: ER Squibb and Sons LLC
•
Filing: 1983-03-24
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Granted: 1985-11-26
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Expires: 2003-03-24
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Abstract

Abstract Angiotensin converted enzyme inhibitor activity if exhibited by compounds having the formula ##STR1## and salts thereof wherein R 1 is hydrogen, aryl, or heteroaryl; R 2 is hydrogen, amino, alkanoylamino, arylcarbonylamino, or heteroarylcarbonylamino; R 3 is hydrogen, alkyl, or aminoalkyl; R 4 and R 5 are the same or different and each is hydrogen, alkyl, halogen, aryl, arylalkyl, hydroxy, alkoxy, alkylthio, aryloxy, arylthio, or cycloalkyl, or R 4 and R 5 taken together are oxo, ethylenedithio or propylenedithio; one of R 6 and R 7 is ##STR2## and the other is hydrogen, alkyl or arylalkyl; R 8 is hydrogen, alkl or aryl; R 9 is hydrogen or alkyl; n is 0 or an integer of 1 to 8; m is 0 or 1; and A is --(CH 2 ) p --wherein p is 0 or 1, --NH--, or --O--.

Inventors

  • 👤 George C. Rovnyak

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 20:46
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; A; A61; A61P; A61P9/00; A61P9/12; C07F9/553; C07F9/572

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 201 words
A compound having the formula ##STR24## or a salt thereof, wherein R 1 is hydrogen, aryl or heteroaryl; R 2 is hydrogen, amino, alkanoylamino, arylcarbonylamino, or heteroarylcarbonylamino; R 3 is hydrogen, alkyl, or aminoalkyl, R 4 and R 5 are the same or different and each is hydrogen, alkyl, halogen, aryl, arylalkyl, hydroxy, alkoxy, alkylthio, aryloxy, arylthio, or cycloalkyl, or R 4 and R 5 taken together are oxo, ethylenedithio or propylenedithio; R 6 is hydrogen, alkyl or aryl; R 8 is hydrogen, alkyl or aryl; R 9 is hydrogen or alkyl; n is 0 or an integer of 1 to 8; m is 0 or 1; and A is --(CH 2 ) p -- wherein p is 0 or 1, --NH--, or --O--; wherein the term "aryl" refers to phenyl or phenyl substituted with halogen, alkyl, alkoxy, alkylthio, hydroxy, alkanoyl, nitro, amino, dialkylamino, or trifluoromethyl groups; the term "alkyl" refers to groups having 1 to 10 carbon atoms; the term "alkoxy" refers to groups having 1 to 8 carbon atoms; the term "alkanoyl" refers to groups having 2 to 10 carbon atoms; and the term "heteroaryl" refers to pyridyl, furyl, thienyl, pyrimidinyl, quinolyl, indolyl, benzothiophenyl, benzothiazolyl, purinyl, benzoxazolyl, or thiazolyl.
Claim 2
Dependent Claim 201 words
A compound having the formula ##STR24## or a salt thereof, wherein R 1 is hydrogen, aryl or heteroaryl; R 2 is hydrogen, amino, alkanoylamino, arylcarbonylamino, or heteroarylcarbonylamino; R 3 is hydrogen, alkyl, or aminoalkyl, R 4 and R 5 are the same or different and each is hydrogen, alkyl, halogen, aryl, arylalkyl, hydroxy, alkoxy, alkylthio, aryloxy, arylthio, or cycloalkyl, or R 4 and R 5 taken together are oxo, ethylenedithio or propylenedithio; R 6 is hydrogen, alkyl or aryl; R 8 is hydrogen, alkyl or aryl; R 9 is hydrogen or alkyl; n is 0 or an integer of 1 to 8; m is 0 or 1; and A is --(CH 2 ) p -- wherein p is 0 or 1, --NH--, or --O--; wherein the term "aryl" refers to phenyl or phenyl substituted with halogen, alkyl, alkoxy, alkylthio, hydroxy, alkanoyl, nitro, amino, dialkylamino, or trifluoromethyl groups; the term "alkyl" refers to groups having 1 to 10 carbon atoms; the term "alkoxy" refers to groups having 1 to 8 carbon atoms; the term "alkanoyl" refers to groups having 2 to 10 carbon atoms; and the term "heteroaryl" refers to pyridyl, furyl, thienyl, pyrimidinyl, quinolyl, indolyl, benzothiophenyl, benzothiazolyl, purinyl, benzoxazolyl, or thiazolyl.
Claim 3
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 1 is phenyl.
Claim 4
Dependent Claim 14 words
A compound in accordance with claim 1 wherein R 2 is hydrogen or benzoylcarbonylamino.
Claim 5
Dependent Claim 15 words
A compound in accordance with claim 1 wherein n is 2 and m is 1.
Claim 6
Dependent Claim 15 words
A compound in accordance with claim 1 wherein A is --(CH 2 ) p --.
Claim 7
Dependent Claim 36 words
A compound in accordance with claim 1 wherein R 4 and R 5 are the same or different and each is hydrogen, alkyl, cycloalkyl, or phenylthio, or R 4 and R 5 taken together are ethylenedithio.
Claim 8
Dependent Claim 15 words
A compound in accordance with claim 1 wherein R 8 is hydrogen, alkyl or phenyl.
Claim 9
Dependent Claim 67 words
A compound in accordance with claim 1 wherein R 1 is phenyl; R 2 is hydrogen or benzoylamino; n is 2, m is 1; A is --(CH 2 ) p --; R 4 and R 5 are the same or different and each is hydrogen, alkyl, cycloalkyl or phenylthio; or R 4 and R 5 taken together are ethylenedithio; and R 8 is hydrogen, alkyl or phenyl.
Claim 10
Dependent Claim 9 words
The compound in accordance with claim 1, (S)-7-[[[(2-oxo-5-phenyl-1,3-dioxol-4-yl)methoxy](4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid.

References Cited (Backward Citations)

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EP0039086A2 Cited
EP0039477A1 Cited
US4337201A Cited
EP0058427A2 Cited
US4379146A Cited
US4432971A Cited
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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) 1988-11-25 1989-05-27 1989-11-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-11-25 1993-05-27 1993-11-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-11-25 1997-05-27 1997-11-26 $7700.00 Window Closed / Lapsed

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