US4029806A
Expired / Lapsed
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Nitro-β-lactam antibiotics and processes for their preparation and use
Assignee: Bayer AG
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Filing: 1976-07-22
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Granted: 1977-06-14
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Expires: 1996-07-22
Abstract
Abstract Penicillin and cephalosporin derivatives characterized by the presence of a nitroalkyl, nitrocycloalkyl, nitrophenylalkyl or nitroanilinoalkyl group in the side chain are antibacterial agents. The compounds, of which 6-(2-nitro-3,3-dimethylbutyrylamido)-penicillanic acid, 7-nitroacetamido-3-methyl-ceph-3-em-4-carboxylic acid, and 6-[D-α-(2-nitro-2-methylpropionylamido)phenylacetamido] pencillanic acid are typical embodiments, are prepared by reacting 6-amino-penicillanic acid, 7-amino-cephalosporanic acid (or derivative thereof) or an α-substituted-α-amino-acetamido-penicillanic acid with an appropriate nitrated carboxylic acid or an equivalent nitrated acylating agent.
Inventors
- 👤 Wolfgang Krohn
- 👤 Karl Georg Metzger
- 👤 Michael Preiss
- 👤 Michael Walkowiak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:36
CPC Classifications
C; C07; C07D; C07D499/00; C10; C10M; C10M2219/00; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
53 words
A compound selected from the group consisting of a penicillin of the formula: ##STR32## wherein O 2 N--E is nitroalkyl of 1 to 6 carbon atoms; the carbon atom designated by * constitutes a center of chirality and R 1 is phenyl, hydroxyphenyl or cyclohexa-1,4-dien-1-yl; and the pharmaceutically acceptable salts of said penicillin.
Claim 2
Dependent Claim
53 words
A compound selected from the group consisting of a penicillin of the formula: ##STR32## wherein O 2 N--E is nitroalkyl of 1 to 6 carbon atoms; the carbon atom designated by * constitutes a center of chirality and R 1 is phenyl, hydroxyphenyl or cyclohexa-1,4-dien-1-yl; and the pharmaceutically acceptable salts of said penicillin.
Claim 3
Dependent Claim
17 words
A compound according to claim 1 wherein the configuration about the carbon atom designated * is D.
Claim 4
Dependent Claim
11 words
A compound according to claim 2 wherein R 1 is phenyl.
Claim 5
Dependent Claim
45 words
A compound according to claim 1 which is a salt of said penicillin, said salt being selected from the group consisting of the sodium, potassium, magnesium, calcium, aluminium, di-(lower alkyl)amine, tri-(lower alkyl)amine, procaine, dibenzylamine, N,N'-dibenzylethylenediamine, N-benzyl-β-phenylethylamine, N-methylmorpholine, N-ethyylmorpholine, 1-ephenamine, dehydroabietylamine, N,N'-bis-dehydroabietylethylenediamine and N-(lower alkyl)piperidine salts.
Claim 6
Dependent Claim
15 words
A compound according to claim 1 which is 6-[D-α-(nitroacetamido)-phenylacetamido]-penicillanic acid or the sodium salt thereof.
Claim 7
Dependent Claim
15 words
A compound according to claim 1 which is 6-[D-α-(2-nitro-3,3-dimethylbutyrylamido)phenylacetamido]-penicillanic acid or the sodium salt thereof.
Claim 8
Dependent Claim
15 words
A compound according to claim 1 which is 6-[D-α-(2-nitro-2-methylpropionamido)phenylacetamido]-penicillanic acid or the sodium salt thereof.
Claim 9
Dependent Claim
15 words
A compound according to claim 1 which is 6-[D-α-(3-nitropropionylamido)phenylacetamido]-penicillanic acid or the sodium salt thereof.
Claim 10
Dependent Claim
15 words
A compound according to claim 1 which is 6-[D-α-(2-nitrobutyrylamido)phenylacetamido]-penicillanic acid or the sodium salt thereof.
Claim 11
Dependent Claim
21 words
A pharmaceutical composition comprising an antibacterially effective amount of a compound according to claim 1 in combination with a pharmaceutical carrier.
Claim 12
Dependent Claim
30 words
The method of combatting bacterial infections in an animal or human which comprises administering to said animal or human an antibacterially effective amount of a compound according to claim 1.
Claim 13
Dependent Claim
34 words
A composition for use in promoting growth in animals which comprises at least a growth promoting amount of a compound according to claim 1 in combination with a nutritious carrier or animal drinking water.
Claim 14
Dependent Claim
25 words
The method of promoting growth in an animal which comprises administering to said animal a growth promoting amount of a compound according to claim 1.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-13 | 1980-12-13 | 1981-06-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-13 | 1984-12-13 | 1985-06-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-13 | 1988-12-13 | 1989-06-14 | $7700.00 | Window Closed / Lapsed |