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Certain phosphinic acid derivatives having antibacterial activity

Assignee: Merck and Co Inc
•
Filing: 1990-06-21
•
Granted: 1992-03-24
•
Expires: 2010-06-21
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Abstract

Abstract New 3-(1-aminoalkylphosphinyl)-(2-substituted)propionic acids are described which display antibacterial activity and potentiate carbapenem antibiotics.

Inventors

  • 👤 William H. Parsons
  • 👤 Arthur A. Patchett
  • 👤 William R. Schoen
  • 👤 Masao Taniguchi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 09:52
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/30; C07F9/32; C07F9/3205; C07F9/3241; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/40; C07F9/301; C07F9/302; C07F9/303; C07F9/306; C07F9/3211; C07F9/3217; C07F9/547; C07F9/553; C07F9/576; C07F9/58

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 239 words
A compound of the formula: ##STR53## wherein: R 1 is H, CH 3 ; R 2 is (a) hydrogen, (b) C 1 -C 12 linear or branched alkyl; (c) C 2 -C 12 linear or branched monoalkenyl; or (d) C 7 -C 20 aralkyl, wherein the alkyl chain is linear or branched C 1 -C 8 ; wherein said above values for R 2 can be substituted by a substituent selected from the group consisting of: halo, hydroxy, carboxy, C 1 -C 4 alkoxycarbonyl, C 7 -C 16 arylalkoxycarbonyl, C 3 -C 7 cycloalkyl, C 1 -C 4 alkoxy, C 6 -C 12 aryloxy, amino, mono- or di-C 1 -C 8 alkylamino, thio, C 1 -C 4 alkylthio, C 6 -C 12 arylthio, C 7 -C 16 aralkylthio, or the radical --S--(CH 2 ) n --CH(NH 2 )COOH, where n=1-2; with the proviso that R 2 is at least C 2 alkyl if substituted by one of the above-defined thio groups, and wherein the aryl can be further substituted by C 1 -C 4 linear or branched alkyl, trihalomethyl, nitro, cyano or sulfonamido, halo; R 3 and R 4 are hydrogen, C 1 -C 4 alkyl, aryl selected from the group consisting of phenyl, naphthyl and biphenyl or aralkyl having one to eight carbon atoms in the alkyl portion and an aryl portion selected from the group consisting of phenyl, naphthyl or biphenyl; and including steroisomers and racemates thereof.
Claim 2
Dependent Claim 239 words
A compound of the formula: ##STR53## wherein: R 1 is H, CH 3 ; R 2 is (a) hydrogen, (b) C 1 -C 12 linear or branched alkyl; (c) C 2 -C 12 linear or branched monoalkenyl; or (d) C 7 -C 20 aralkyl, wherein the alkyl chain is linear or branched C 1 -C 8 ; wherein said above values for R 2 can be substituted by a substituent selected from the group consisting of: halo, hydroxy, carboxy, C 1 -C 4 alkoxycarbonyl, C 7 -C 16 arylalkoxycarbonyl, C 3 -C 7 cycloalkyl, C 1 -C 4 alkoxy, C 6 -C 12 aryloxy, amino, mono- or di-C 1 -C 8 alkylamino, thio, C 1 -C 4 alkylthio, C 6 -C 12 arylthio, C 7 -C 16 aralkylthio, or the radical --S--(CH 2 ) n --CH(NH 2 )COOH, where n=1-2; with the proviso that R 2 is at least C 2 alkyl if substituted by one of the above-defined thio groups, and wherein the aryl can be further substituted by C 1 -C 4 linear or branched alkyl, trihalomethyl, nitro, cyano or sulfonamido, halo; R 3 and R 4 are hydrogen, C 1 -C 4 alkyl, aryl selected from the group consisting of phenyl, naphthyl and biphenyl or aralkyl having one to eight carbon atoms in the alkyl portion and an aryl portion selected from the group consisting of phenyl, naphthyl or biphenyl; and including steroisomers and racemates thereof.
Claim 3
Dependent Claim 146 words
The compound of claim 1 wherein: R 1 is methyl; R 2 C 1 -C 10 linear or branched alkyl; C 7 -C 14 aralkyl; wherein both groups can be substituted with halo, amino, mono- or di-C 1 -C 4 linear or branched alkylamino, carboxyl, C 1 -C 4 alkoxycarbonyl, hydroxy, C 1 -C 4 alkoxy, C 5 -C 6 cycloalkyl, C 6 -C 10 aryloxy, thio, C 1 -C 4 linear or branched alkylthio, C 6 -C 10 arylthio, C 7 -C 14 aralkylthio, --S--(CH 2 ) n --CH(NH 2 )CO 2 H, where n=1-2, with the proviso that R 2 or R 5 is at least C 2 alkyl if substituted by one of the above-defined thio groups and wherein the aryl groups can further be substituted by linear or branched C 1 -C 4 alkyl; R 3 and R 4 are hydrogen, benzyl.
Claim 4
Dependent Claim 32 words
The compound of claim 1 in which the stereochemical configurations of the carbon attached to R 1 , and the carbon attached to R 2 , are respectively, D(S), DL(SR) or D(R),DL(RS).
Claim 5
Dependent Claim 24 words
The compound of claim 3 in which the stereochemical configurations of the carbons attached to R 1 and R 2 are D(S), D(R) respectively.
Claim 6
Dependent Claim 27 words
The compound of claim 1 in which the stereochemical configurations of the carbons attached to R 1 and R 2 are L(R) and D(R), L(S), DL(RS), respectively.
Claim 7
Dependent Claim 11 words
The compound of claim 2 which is 1-aminoethyl -(2-carboxypropyl) phosphinic acid.
Claim 8
Dependent Claim 9 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carbomethoxy-propyl)-phosphinic acid.
Claim 9
Dependent Claim 10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-n-butyl) phosphinic acid.
Claim 10
Dependent Claim 10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-5-phenyl-n-pentyl) phosphinic acid.
Claim 11
Dependent Claim 10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-n-nonyl) phosphinic acid.
Claim 12
Dependent Claim 10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-3-chloro-n-propyl) phosphinic acid.
Claim 13
Dependent Claim 10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-3-bromo-n-propyl) phosphinic acid.
Claim 14
Dependent Claim 10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-n-hexyl) phosphinic acid.

References Cited (Backward Citations)

US4147780A Cited
US4160452A Cited
US4256108A Cited
US4265874A Cited
US4539208A Cited
US4374131A Cited
US4416833A Cited
US4715994A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-03-24 1995-09-23 1996-03-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-03-24 1999-09-23 2000-03-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-03-24 2003-09-23 2004-03-24 $7700.00 Window Closed / Lapsed

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