Patent US4011214A successfully refreshed from Google Patents.
US4011214A
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US
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3-(morpholinoalkoxyiminomethyl)cephem compounds
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1974-12-20
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Granted: 1977-03-08
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Expires: 1994-12-20
Abstract
Abstract Novel cephalosporin compounds of the formula ##STR1## wherein R 1 is an acyl group and R 2 is an alkylene group which may be substituted with a lower alkoxyl group, or pharmaceutically acceptable salt thereof, have strong inhibitory actions on broad spectra of gram-positive and gram-negative bacteria and, particularly against Esherichia coli and Klebsiella pneumoniae. Thus, the compounds are useful as therapeutic agent for various bacterial infections of animals including human beings.
Inventors
- 👤 Shinji Terao
- 👤 Mitsuru Shiraishi
- 👤 Toshio Miyawaki
- 👤 Isao Minamida
- 👤 Masayoshi Yamaoka
- 👤 Mitsuo Numata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:50
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/38; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
92 words
A compound of the formula: ##STR11## wherein R 1 is formyl, benzoyl or a group having the formula: ##STR12## wherein R 3 is hydrogen, phenyl, phenoxy, thienyl, tetrazolyl, furyl, pyrazolyl, pyridyloxy, cyclohexenyl, acetyl, cyano, 3-amino-3-carboxypropyl or 3-amino-3-carboxypropyl in which the 3-amino group is protected with isobornyloxycarbonyl, β-methylsulfonylethoxycarbonyl, benzoyl, phathalyl, p-t-butylbenzoyl, phenylacetyl, phenylthiocarbonyl, benzyloxycarbonyl, p-toluenesulfonyl, or p-t-butylbenzenesulfonyl, and R 4 is hydrogen, hydroxyl, sulfo, carboxyl or C 1-2 alkyl, and R 2 is unsubstituted C 1-4 alkylene or substituted C 1-4 alkylene substituted with methoxy or ethoxy, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
92 words
A compound of the formula: ##STR11## wherein R 1 is formyl, benzoyl or a group having the formula: ##STR12## wherein R 3 is hydrogen, phenyl, phenoxy, thienyl, tetrazolyl, furyl, pyrazolyl, pyridyloxy, cyclohexenyl, acetyl, cyano, 3-amino-3-carboxypropyl or 3-amino-3-carboxypropyl in which the 3-amino group is protected with isobornyloxycarbonyl, β-methylsulfonylethoxycarbonyl, benzoyl, phathalyl, p-t-butylbenzoyl, phenylacetyl, phenylthiocarbonyl, benzyloxycarbonyl, p-toluenesulfonyl, or p-t-butylbenzenesulfonyl, and R 4 is hydrogen, hydroxyl, sulfo, carboxyl or C 1-2 alkyl, and R 2 is unsubstituted C 1-4 alkylene or substituted C 1-4 alkylene substituted with methoxy or ethoxy, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
27 words
A compound according to claim 1, wherein R 4 is hydrogen and wherein R 3 is phenyl, phenoxy, thienyl, tetrazolyl, furyl, pyrazolyl, pyridyloxy, cyclohexenyl, acetyl or cyano.
Claim 4
Dependent Claim
15 words
A compound according to claim 2, wherein R 3 is phenyl, thienyl or cyano group.
Claim 5
Dependent Claim
29 words
A compound according to claim 1, wherein R 3 is phenyl, phenoxy, thienyl, tetrazolyl, furyl, pyrazolyl, pyridyloxy, cyclohexenyl or acetyl, and R 4 is hydroxyl, sulfo, carboxyl or alkyl.
Claim 6
Dependent Claim
16 words
A compound according to claim 1, wherein the acyl group is 5-protected or unprotected amino-5-carboxyvaleryl group.
Claim 7
Dependent Claim
19 words
A compound according to claim 1, wherein R 3 is phenyl, phenoxy, pyridyloxy, thienyl, tetrazolyl, furyl, pyrazolyl or cyclohexenyl.
Claim 8
Dependent Claim
14 words
A compound according to claim 6, wherein R 3 is phenyl, phenoxy or pyridyloxy.
Claim 9
Dependent Claim
31 words
A compound according to claim 1, wherein said unsubstituted C 1-4 alkylene group is selected from the group consisting of methylene ethylene, trimethylene, tetramethylene, 1-methylethylene, 2-methylethylene, 1-methylpropylene, 2-methylpropylene, 3-methylpropylene and 1,1-dimethylethylene.
Claim 10
Dependent Claim
32 words
A compound according to claim 6, wherein said unsubstituted C 1-4 alkylene group is selected from the group consisting of methylene, ethylene, trimethylene, tetramethylene, 1-methylene, 2-methylethylene, -methylethylene -methylpropylene, 2-methylpropylene, 3-methylpropylene and 1,1-dimethylethylene.
Claim 11
Dependent Claim
12 words
A compound according to claim 1, wherein said compound is an acid.
Claim 12
Dependent Claim
14 words
A compound according to claim 1, wherein said compound is a pharmaceutically acceptable salt.
Claim 13
Dependent Claim
15 words
A compound according to claim 1 wherein R 4 is hydrogen, hydroxyl, sulfo or carboxyl.
Claim 14
Dependent Claim
44 words
A compound of the formula: ##STR13## wherein R is 3-(p-t-butylbenzoyl)amino-3-carboxypropyl, 3-(p-t-butylbenzenesulfonyl)amino-3-carboxypropyl, phenyl, thienyl or cyano, R 1 is hydrogen, hydroxyl or sulfo and R 2 is unsubstituted C 2-3 alkylene or substituted C 1-4 alkylene substituted with methoxy, or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
44 words
A compound of the formula: ##STR13## wherein R is 3-(p-t-butylbenzoyl)amino-3-carboxypropyl, 3-(p-t-butylbenzenesulfonyl)amino-3-carboxypropyl, phenyl, thienyl or cyano, R 1 is hydrogen, hydroxyl or sulfo and R 2 is unsubstituted C 2-3 alkylene or substituted C 1-4 alkylene substituted with methoxy, or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-[D-5-(p-t-butylbenzoyl)amino-5-carboxyvalerylamido]-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 17
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-[D-5-(p-t-butylbenzenesulfonyl)amino-5-carboxyvalerylamido]-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 18
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-(phenylacetamido)-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 19
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-(2-thienylacetamido)-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 20
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-(D-α-sulfophenylacetamido)-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 21
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-(D-mandelylamido)-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 22
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-cyanoacetamido-3-(2-morpholinoethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 23
Dependent Claim
11 words
A compound claimed in claim 1, which is 7β -(D-mandelylamido)-3-(2-morpholino-1-methylethoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 24
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-(D-mandelylamido)-3-(3-morpholinopropoxy)iminomethyl-3-cephem-4-carboxylic acid.
Claim 25
Dependent Claim
10 words
A compound claimed in claim 1, which is 7β-(D-mandelylamido)-3-[2-morpholino-(1-methoxymethyl)ethoxy]-iminomethyl-cephem-4-carboxylic acid.
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) | 1980-03-07 | 1980-09-06 | 1981-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-07 | 1984-09-06 | 1985-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-07 | 1988-09-06 | 1989-03-08 | $7700.00 | Window Closed / Lapsed |