US4264590A
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Antibacterial peptide
Assignee: Abbott Laboratories
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Filing: 1980-06-09
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Granted: 1981-04-28
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Expires: 2000-06-09
Abstract
Abstract It has been found that dipeptides containing a 3-halo-D-alanine C-terminus are powerful antibacterials and produce a highly useful synergistic effect with antibiotics.
Inventors
- 👤 Daniel I. Chu
- 👤 Jerry R. Martin
- 👤 Alford M. Thomas
- 👤 Norman E. Wideburg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 05:12
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06191; A; A61; A61K; A61K38/00; A61K38/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
77 words
A peptide of the formula ##STR2## wherein the shown aminoacid is in the D-configuration, X is chlorine or fluorine, R o is hydrogen or deuterium, and R is the acyl moiety of a naturally occurring aminoacid in the L-configuration or an α-amino fatty acid wherein the α-amino group may carry a fatty acid acyl group, an aminoloweralkyl acyl group or a loweralkyl group, or the corresponding loweralkyl esters of said peptide, or nontoxic acid addition salts thereof.
Claim 2
Dependent Claim
77 words
A peptide of the formula ##STR2## wherein the shown aminoacid is in the D-configuration, X is chlorine or fluorine, R o is hydrogen or deuterium, and R is the acyl moiety of a naturally occurring aminoacid in the L-configuration or an α-amino fatty acid wherein the α-amino group may carry a fatty acid acyl group, an aminoloweralkyl acyl group or a loweralkyl group, or the corresponding loweralkyl esters of said peptide, or nontoxic acid addition salts thereof.
Claim 3
Dependent Claim
11 words
A peptide according to claim 1 wherein R o is hydrogen.
Claim 4
Dependent Claim
17 words
The peptide of claim 2 wherein X is fluorine and R is the acyl moiety of L-serine.
Claim 5
Dependent Claim
30 words
A peptide of the formula ##STR3## wherein X is fluorine or chlorine and R' is H or an alkyl group of 1-8 carbons, or a nontoxic acid addition salt thereof.
Claim 6
Dependent Claim
30 words
A peptide of the formula ##STR3## wherein X is fluorine or chlorine and R' is H or an alkyl group of 1-8 carbons, or a nontoxic acid addition salt thereof.
Claim 7
Dependent Claim
13 words
The compond of claim 4 wherein X is fluorine and R' is methyl.
Claim 8
Dependent Claim
13 words
The compound of claim 4 wherein X is fluorine and R' is isobutyl.
Claim 9
Dependent Claim
13 words
The compound of claim 4 wherein X is fluorine and R' is isopropyl.
Claim 10
Dependent Claim
13 words
The compound of claim 4 wherein X is chlorine and R' is methyl.
Claim 11
Dependent Claim
13 words
The compound of claim 4 wherein X is chlorine and R' is isobutyl.
Claim 12
Dependent Claim
105 words
An antibacterial composition containing, as the active principle, an antibacterially effective amount of a compound of formula ##STR4## wherein the shown aminoacid is in the D-configuration, X is chlorine or fluorine, R o is hydrogen or deuterium, and R is the acyl moiety of a naturally occurring aminoacid in the L-configuration or an α-amino fatty acid wherein the α-amino group may carry a fatty acid acyl group, or an aminoloweralkyl acyl group or a loweralkyl group, or the corresponding loweralkyl esters of said peptide, or nontoxic acid addition salts thereof, together with between 0-50% by weight thereof of an antibiotic and a pharmaceutically acceptable diluent.
Claim 13
Dependent Claim
105 words
An antibacterial composition containing, as the active principle, an antibacterially effective amount of a compound of formula ##STR4## wherein the shown aminoacid is in the D-configuration, X is chlorine or fluorine, R o is hydrogen or deuterium, and R is the acyl moiety of a naturally occurring aminoacid in the L-configuration or an α-amino fatty acid wherein the α-amino group may carry a fatty acid acyl group, or an aminoloweralkyl acyl group or a loweralkyl group, or the corresponding loweralkyl esters of said peptide, or nontoxic acid addition salts thereof, together with between 0-50% by weight thereof of an antibiotic and a pharmaceutically acceptable diluent.
Claim 14
Dependent Claim
10 words
The composition of claim 10 wherein R o is hydrogen.
Claim 15
Dependent Claim
12 words
The composition of claim 10 in the form of an oral preparation.
Claim 16
Dependent Claim
23 words
The composition of claim 10 wherein said antibiotic is D-cycloserine and is present in an amount of between 12.5 and 50% by weight.
Claim 17
Dependent Claim
17 words
The composition of claim 11 wherein X is fluorine and R is the acyl moiety of L-serine.
Claim 18
Dependent Claim
57 words
An antibacterial composition containing, as the active principle, an antibacterially effective amount of a compound of the formula ##STR5## wherein X is fluorine or chlorine and R' is H or an alkyl group of 1-8 carbons, or a nontoxic acid addition salt thereof, together with 0-50% by weight thereof of an antibiotic, and a pharmaceutically acceptable diluent.
Claim 19
Dependent Claim
57 words
An antibacterial composition containing, as the active principle, an antibacterially effective amount of a compound of the formula ##STR5## wherein X is fluorine or chlorine and R' is H or an alkyl group of 1-8 carbons, or a nontoxic acid addition salt thereof, together with 0-50% by weight thereof of an antibiotic, and a pharmaceutically acceptable diluent.
Claim 20
Dependent Claim
13 words
The composition of claim 15 wherein X is fluorine and R' is methyl.
Claim 21
Dependent Claim
13 words
The composition of claim 15 wherein X is fluorine and R' is isobutyl.
Claim 22
Dependent Claim
13 words
The composition of claim 15 wherein X is chlorine and R' is isobutyl.
Claim 23
Dependent Claim
13 words
The composition of claim 15 wherein X is chlorine and R' is methyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-27 | 1984-10-27 | 1985-04-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-27 | 1988-10-27 | 1989-04-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-27 | 1992-10-27 | 1993-04-28 | $7700.00 | Window Closed / Lapsed |