US4715994A
Expired / Lapsed
US
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Novel antibacterial agents and potentiators of carbapenem antibiotics
Assignee: Merck and Co Inc
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Filing: 1986-11-05
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Granted: 1987-12-29
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Expires: 2006-11-05
Abstract
Abstract New 3-(1-aminoalkylphosphinyl)-(2-substituted)propionic acids are described which display antibacterial activity and potentiate carbapenem antibiotics.
Inventors
- 👤 William H. Parsons
- 👤 William R. Schoen
- 👤 Arthur A. Patchett
- 👤 Masao Taniguchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:25
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/30; C07F9/32; C07F9/3205; C07F9/3217; C07F9/301; C07F9/302; C07F9/3211; C07F9/547; C07F9/553; C07F9/576; C07F9/58
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
247 words
A compound of the formula: ##STR53## wherein: R 1 is H, CH 3 ; R 5 is (a) hydrogen, (b) C 1 -C 12 linear or branched alkyl; (c) C 2 -C 12 linear or branched monoalkenyl; (d) C 7 -C 20 aralkyl, wherein the alkyl chain is linear or branched C 1 -C 8 ; (e) heterocyclylalkyl, wherein the alkyl chain is linear or branched C 1 -C 8 and the heterocyclyl ring is 5-6 membered, optionally fused with a benzene ring, fully aromatic, containing 1-2 O, N or S heteroatoms; wherein said above values for R 5 can be substituted by one or more: 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 5 is at least C 2 alkyl if substituted by one of the above-defined thio groups, and wherein the aryl or aromatic heterocyclyl rings can be further substituted by C 1 -C 4 linear or branched alkyl, trihalomethyl, nitro, cyano, halo, or sulfonamido; R 3 and R 4 are hydrogen, C 1 -C 4 alkyl, C 6 -C 12 aryl or C 7 -C 16 aralkyl; and including stereoisomers and racemates thereof.
Claim 2
Dependent Claim
247 words
A compound of the formula: ##STR53## wherein: R 1 is H, CH 3 ; R 5 is (a) hydrogen, (b) C 1 -C 12 linear or branched alkyl; (c) C 2 -C 12 linear or branched monoalkenyl; (d) C 7 -C 20 aralkyl, wherein the alkyl chain is linear or branched C 1 -C 8 ; (e) heterocyclylalkyl, wherein the alkyl chain is linear or branched C 1 -C 8 and the heterocyclyl ring is 5-6 membered, optionally fused with a benzene ring, fully aromatic, containing 1-2 O, N or S heteroatoms; wherein said above values for R 5 can be substituted by one or more: 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 5 is at least C 2 alkyl if substituted by one of the above-defined thio groups, and wherein the aryl or aromatic heterocyclyl rings can be further substituted by C 1 -C 4 linear or branched alkyl, trihalomethyl, nitro, cyano, halo, or sulfonamido; R 3 and R 4 are hydrogen, C 1 -C 4 alkyl, C 6 -C 12 aryl or C 7 -C 16 aralkyl; and including stereoisomers and racemates thereof.
Claim 3
Dependent Claim
164 words
The compound of claim 1 wherein: R 1 is methyl; R 5 is 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, C 1 -C 4 linear or branched alkyl e.g. methyl, ethyl, C 7 -C 14 aralkyl e.g. benzyl.
Claim 4
Dependent Claim
31 words
The compound of claim 1 in which the stereochemical configuration of the carbon atom attached to R 1 is D(S) and the configuration of the double bond is Z or E.
Claim 5
Dependent Claim
29 words
The compound of claim 1 in which the stereochemical configuration of the carbon atom attached to R 1 is L(R) and the configuration of the double bond is Z.
Claim 6
Dependent Claim
10 words
A compound of claim 2 which is 1-aminoethyl-(2-carboxy-2-n-octenyl) phosphinic acid.
Claim 7
Dependent Claim
10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-2-propenyl) phosphinic acid.
Claim 8
Dependent Claim
10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-4-phenyl-2-butenyl) phosphinic acid.
Claim 9
Dependent Claim
10 words
The compound of claim 2 which is 1-(aminoethyl)-(2-carboxy-5-phenyl-2-pentenyl) phosphinic acid.
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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) | 1990-12-28 | 1991-06-29 | 1991-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-28 | 1995-06-29 | 1995-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-28 | 1999-06-29 | 1999-12-29 | $7700.00 | Window Closed / Lapsed |