US5099063A
Expired / Lapsed
US
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Certain phosphinic acid derivatives having antibacterial activity
Assignee: Merck and Co Inc
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Filing: 1990-06-21
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Granted: 1992-03-24
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Expires: 2010-06-21
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 09:39
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)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 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 |