US4546176A
Expired / Lapsed
US
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7-Carboxymethoxyphenylacetamido-3-cephem derivatives and antibacterial preparations containing the same
Assignee: Eisai Co Ltd
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Filing: 1983-10-20
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Granted: 1985-10-08
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Expires: 2003-10-20
Abstract
Abstract 7-Carboxymethoxyphenylacetamido-3-cephem derivatives represented by the formula ##STR1## wherein R 1 means hydroxy, C 1 -C 4 alkanoyloxy or C 1 -C 4 alkoxycarbonyloxy, R 2 is hydrogen or methoxy, R 3 denotes C 1 -C 4 alkanoyloxy, substituted or unsubstituted nitrogen-containing heterocyclic-thio or substituted or unsubstituted pyridinium with a proviso that, when R 3 denotes the substituted or unsubstituted pyridinium, R 3 forms an intramolecular salt with the carboxy at the 4-position of the cephem nucleus, and A is a group of the following formula: ##STR2## in which R 4 and R 5 are individually hydrogen or C 1 -C 4 alkyl, and their pharmaceutically acceptable salts, exhibit excellent anti-bacterial activities against Gram-negative bacteria, particularly, Pseud. aeruginosa, Kleb. pneumoniae, Ser. marcescens and the like.
Inventors
- 👤 Yoshimasa Machida
- 👤 Shigeto Negi
- 👤 Seiichiro Nomoto
- 👤 Takashi Kamiya
- 👤 Kyosuke Kitoh
- 👤 Isao Saito
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 01:43
CPC Classifications
C; C07; C07D; C07D501/00; C07D405/00; C07D405/02; C07D405/12; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/26; C07D501/34; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D501/36; C07D501/38; C07D501/46
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
141 words
A compound of the formula ##STR16## wherein R 1 represents hydroxy, C 1 -C 4 alkanoyloxy or C 1 -C 4 alkoxycarbonyloxy, R 2 represents hydrogen or methoxy, R 3 repesents (1) C 1 -C 4 alkanoyloxy or (2) pyridinium which is unsubstituted or substituted by C 1 -C 4 alkyl, carboxyalkyl, sulfoalkyl, carboxyl, sulfo, amino, N,N-dialkylaminoalkyl, carbamoyl, alkylcarbamoyl, alkoxycarbonyl, cyano, hydroxycarbamoyl, N-hydroxycarbamoylalkyl, carbamoylalkyl, dialkylcarbamoyl, N-hydroxy-N-alkylcarbamoyl, hydroxy, hydroxyalkyl and alkoxycarbonylalkyl with the proviso that, when R 3 denotes the substituted or unsubstituted pyridinium, R 3 forms an intramolecular salt with the carboxy at the 4-position of the cephem nucleus, And A is a group of the formula: ##STR17## in which R 4 and R 5 are individually hydrogen or C 1 -C 4 alkyl, or a pharmaceutically acceptable salt thereof, wherein undefined alkyl and alk are lower alkyl and lower alk.
Claim 2
Dependent Claim
141 words
A compound of the formula ##STR16## wherein R 1 represents hydroxy, C 1 -C 4 alkanoyloxy or C 1 -C 4 alkoxycarbonyloxy, R 2 represents hydrogen or methoxy, R 3 repesents (1) C 1 -C 4 alkanoyloxy or (2) pyridinium which is unsubstituted or substituted by C 1 -C 4 alkyl, carboxyalkyl, sulfoalkyl, carboxyl, sulfo, amino, N,N-dialkylaminoalkyl, carbamoyl, alkylcarbamoyl, alkoxycarbonyl, cyano, hydroxycarbamoyl, N-hydroxycarbamoylalkyl, carbamoylalkyl, dialkylcarbamoyl, N-hydroxy-N-alkylcarbamoyl, hydroxy, hydroxyalkyl and alkoxycarbonylalkyl with the proviso that, when R 3 denotes the substituted or unsubstituted pyridinium, R 3 forms an intramolecular salt with the carboxy at the 4-position of the cephem nucleus, And A is a group of the formula: ##STR17## in which R 4 and R 5 are individually hydrogen or C 1 -C 4 alkyl, or a pharmaceutically acceptable salt thereof, wherein undefined alkyl and alk are lower alkyl and lower alk.
Claim 3
Dependent Claim
60 words
A compound according to claim 1, wherein R 3 represents C 1 -C 4 alkanoyloxy or pyridinium, the said pyridinium being optionally substituted by one or more substituents selected from C 1 -C 4 alkyl, carboxyalkyl, sulfoalkyl, carboxyl, sulfo, amino, N,N-dialkylaminoalkyl, carbamoyl, alkylcarbamoyl, alkoxycarbonyl, cyano, hydroxycarbamoyl, N-hydroxycarbamoylalkyl, carbamoylalkyl, dialkylcarbamoyl, N-hydroxy-N-alkylcarbamoyl, hydroxy, hydroxyalkyl and alkoxycarbonylalkyl, or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
23 words
A compound according to claim 1, wherein R 3 is acetoxy pyridinium, 4-carbamoylpyridinium, 4-(2-sulfoethyl)-pyridinium, 3-carbamoylpyridinium or 4-carboxypyridinium, or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
22 words
A compound according to claim 1, wherein A is a group of the following formula: ##STR18## or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
20 words
A compound according to claim 1, wherein R 1 is hydroxy, acetoxy or ethoxycarbonyloxy, or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
15 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)-acetamido]-3-(4-carbamoylpyridinium)methyl-3-cephem-4-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
15 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-3-[4-(2-sulfoethyl)pyridinium]methyl-3-cephem-4-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
15 words
A compound according to claim 1 which is 7β-[D-2-(carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-3-[4-(2-sulfoethyl)pyridinium]methyl-3-cephem-4-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
15 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-7α-methoxy-3-pyridiniummethyl-3-cephem-4-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
15 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-7α-methoxy-3-(4-carbamoylpyridinium)methyl-3-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
15 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-3-pyridiniummethyl-3-cephem-4-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
15 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-3-(4-carboxypyridinium)methyl-3-cephem-4-carboxylate or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
16 words
A compound according to claim 1, which is 7β-[D-2-(4-carboxymethoxyphenyl)-2-(6,7-dihydroxy-2-methyl-4-oxo-4H-1-benzopyran-3-carboxamido)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
28 words
An antibacterial composition which comprises an antibacterially effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.
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) | 1988-10-07 | 1989-04-08 | 1989-10-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-07 | 1993-04-08 | 1993-10-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-07 | 1997-04-08 | 1997-10-08 | $7700.00 | Window Closed / Lapsed |