US4107304A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oxo-imidazolidine substituted cephalosporins and antibacterial compositions and methods of combatting bacteria employing them
Assignee: Bayer AG
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Filing: 1975-06-27
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Granted: 1978-08-15
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Expires: 1995-06-27
Abstract
Abstract Cephalosporins of the formula ##STR1## their pharmaceutically-acceptable, nontoxic salts, and hydrates thereof are produced, wherein A is hydrogen; unsubstituted or substituted alkyl; aryl; or R 1 --X--, wherein X is --CO-- or --SO 2 --, and R 1 is hydrogen, unsubstituted or substituted alkyl; aryl; thienyl; furyl; amino; alkylamino; dialkylamino; pyrrolidyl; or piperidyl; Or when X is --CO--, R 1 can also be alkoxy; B is phenyl, methylphenyl, chlorophenyl, hydroxyphenyl or the moiety ##STR2## E is hydrogen, hydroxyl or acetoxy; and C is a center of chirality. These compounds are particularly useful for their antimicrobial and, particularly, antibacterial effects.
Inventors
- 👤 Wilfried Schrock
- 👤 Hans-Bodo Konig
- 👤 Michael Preiss
- 👤 Karl Georg Metzger
- 👤 Michael Walkowiak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:15
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
109 words
A compound selected from the group consisting of a cephalosporin derivative of the formula: ##STR87## the nontoxic salts thereof and the hydrates thereof wherein the carbon atom designated * constitutes a center of chirality; E is hydrogen; hydroxy or acetoxy; B is phenyl; methylphenyl; chlorophenyl; hydroxyphenyl; or cyclohexa-1,4-dien-1-yl; and R 1 is phenyl; naphthyl; phenyl or naphthyl substituted by one to five substituents selected from the group consisting of halo, cyano, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and alkylsulfamyl of 1 to 4 carbon atoms; thienyl; furyl; piperidyl; pyrrolidyl; NC--CH 2 --; NC--CH 2 -CH 2 ; or H 3 CO--.
Claim 2
Dependent Claim
109 words
A compound selected from the group consisting of a cephalosporin derivative of the formula: ##STR87## the nontoxic salts thereof and the hydrates thereof wherein the carbon atom designated * constitutes a center of chirality; E is hydrogen; hydroxy or acetoxy; B is phenyl; methylphenyl; chlorophenyl; hydroxyphenyl; or cyclohexa-1,4-dien-1-yl; and R 1 is phenyl; naphthyl; phenyl or naphthyl substituted by one to five substituents selected from the group consisting of halo, cyano, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and alkylsulfamyl of 1 to 4 carbon atoms; thienyl; furyl; piperidyl; pyrrolidyl; NC--CH 2 --; NC--CH 2 -CH 2 ; or H 3 CO--.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein E is acetoxy.
Claim 4
Dependent Claim
45 words
A compound according to claim 1, wherein R 1 is phenyl; naphthyl; or phenyl or naphthyl substituted by one to five substituents selected from the group consisting of halo, cyano, alkyl of 1 to 4 carbon atoms and alkylsulfamyl of 1 to 4 carbon atoms.
Claim 5
Dependent Claim
15 words
A compound according to claim 1, wherein R 1 is thienyl, furyl, piperidyl or pyrrolidyl.
Claim 6
Dependent Claim
15 words
The compound according to claim 1, which is 7-D-α-[2-oxo-3-cyanoacetyl-imidazolidin-1-yl)-carbonyl-amino]-phenylacetamido-3-acetoxymethyl-ceph-3-em-4-carboxylic acid, or the sodium salt thereof.
Claim 7
Dependent Claim
15 words
The compound according to claim 1, which is 7-D-α-[(2-oxo-3-β-cyanopropionyl-imidazolidin-1-yl)-carbonylamino]-phenylacetamido-3-acetamido-3-acetoxymethyl-ceph-3-em-4-carboxylic acid, or the sodium salt thereof.
Claim 8
Dependent Claim
15 words
The compound according to claim 1, which is 7-D-α-[(2-oxo-3-methoxycarbonyl-imidazolidin-1-yl)-carbonylamino]-phenylacetamido-3-acetoxymethyl-ceph-3-em-4-carboxylic acid, or the sodium salt thereof.
Claim 9
Dependent Claim
15 words
The compound according to claim 1, which is 7-{D-α-[(2-oxo-3-benzoyl-imidazolidin-1-yl)-carbonylamino]-phenylacetamido}-3-acetoxymethyl-ceph-3-em-4-carboxylic acid, or the sodium salt thereof.
Claim 10
Dependent Claim
15 words
The compound according to claim 1, which is 7-{D-α-[(2-oxo-3-furoyl-(2)-imidazolidin-1-yl)-carbonylamino]-phenylacetamido}-3-acetoxymethyl-ceph-3-em-4-carboxylic acid, or the sodium salt thereof.
Claim 11
Dependent Claim
15 words
The compound according to claim 1, which is 7-{D-α-[(2-oxo-3-benzoyl-imidazolidin-1-yl)-carbonylamino]-phenylacetamido}-3-methyl-ceph-3-em-4-carboxylic acid, or the sodium salt thereof.
Claim 12
Dependent Claim
10 words
The compound according to claim 1, which is sodium 7-{D-α-[(2-oxo-3-furoyl(3)-imidazolidin-1-yl)-carbonylamino]-phenylacetamido}-3-em-4-carboxylate.
Claim 13
Dependent Claim
9 words
The compound according to claim 1, which is sodium-7-{D-α-[(2-oxo-3-thienyl(2)carbonyl-imidazolidin-1-yl-carbonyamino]-phenylacetamido}-3-acetoxymethyl-ceph-3-em-4-carboxylate.
Claim 14
Dependent Claim
10 words
The compound according to claim 1, which is sodium 7-{D-α-[(2-oxo-3-{4-cyanobenzoyl}-imidazolidin-1-yl)-carbonylamino]-phenylacetamido}-3-acetoxymethyl-ceph-3-em-4-carboxylate.
Claim 15
Dependent Claim
34 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially-effective amount of a compound of claim 1 in combination with a pharmaceutically acceptable nontoxic, inert diluent or carrier.
Claim 16
Dependent Claim
27 words
A method of treating bacterial infections in humans and animals which comprises administering to such human or animal an antibacterially-effective amount of a compound of claim 1.
Claim 17
Dependent Claim
55 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially-effective amount of a compound of claim 1 in combination with an antibacterially-effective amount of a compound selected from the group consisting of Gentamicin, Sisomicin, Kanamicin, Amikacin and Tobramicin, in combination with a pharmaceutically acceptable nontoxic, inert diluent or carrier.
Claim 18
Dependent Claim
43 words
A method of treating bacterial infections in humans and animals which comprises administering an antibacterially-effective amount of a compound of claim 1 in combination with an antibacterially-effective amount of a compound selected from the group consisting of Gentamicin, Sisomicin, Kanamicin, Amikacin and Tobramicin.
Claim 19
Dependent Claim
19 words
An animal feedstuff which comprises an antibacterially-effective amount of a compound of claim 1 in combination with nutritious material.
Claim 20
Dependent Claim
20 words
A growth-promoting composition which comprise an antibacterially-effective amount of a compound of claim 1 in combination with an edible material.
Claim 21
Dependent Claim
22 words
A method of promoting growth in animals which comprises administering to said animal a growth-promoting amount of a compound of claim 1.
References Cited (Backward Citations)
US3687949A
Cited
US3741962A
Cited
US3865819A
Cited
US3860591A
Cited
NL7407815A
Cited
US3966709A
Cited
US3956292A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-08-14 | 1982-02-13 | 1982-08-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-14 | 1986-02-13 | 1986-08-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-14 | 1990-02-13 | 1990-08-15 | $7700.00 | Window Closed / Lapsed |