US4098888A
Expired / Lapsed
US
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Thiazolylacetamido cephalosporin type compounds
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1975-12-19
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Granted: 1978-07-04
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Expires: 1995-12-19
Abstract
Abstract Novel cephem compounds of the formula; ##STR1## wherein R 1 represents amino or hydroxyl group which may be protected, R 2 represents amino or hydroxyl group or a group convertible into these groups, R 3 represents hydrogen or methoxy group or a group convertible into methoxy group, R 4 represents hydrogen or a residue of a nucleophilic compound and R 8 represents hydrogen or a halogen, or a pharmaceutically acceptable salt or ester thereof, have strong antibiotic properties against a wide variety of microorganisms including gram-positive bacteria as well as gram-negative ones, especially by oral administration and can be used as therapeutic agent for various bacterial infections of animals including human beings.
Inventors
- 👤 Michihiko Ochiai
- 👤 Taiiti Okada
- 👤 Osami Aki
- 👤 Akira Morimoto
- 👤 Kenji Kawakita
- 👤 Yoshihiro Matsushita
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 08:24
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/34; C07D277/38; C07D277/40; C07D277/44; C07D277/46; C07D277/48; C07D277/587
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
149 words
A member selected from the group consisting of (a) a cephem compound of the formula ##STR21## wherein R 1 represents amino, protected amino, hydroxy or protected hydroxy, R 2 represents amino, protected amino, hydroxy, protected hydroxy or the group ##STR22## represents a group of the formula ##STR23## wherein R 5 is hydroxy or protected hydroxy, R 3 represents hydrogen or methoxy, R 4 represents heterocyclic thio wherein heterocyclic is a 5 to 6 membered hetero ring containing 1 to 4 hetero atoms from the group of oxygen, sulfur and nitrogen, said ring being unsubstituted or substituted by lower alkyl, lower alkoxy, halogen, haloalkyl, amino, mercapto, hydroxy, carbamoyl or carboxy, and R 8 represents hydrogen or halogen, (b) a pharmaceutically acceptable salt thereof, and (c) a pharmaceutically acceptable ester of the 4-position carboxyl group selected from the group consisting of alkoxymethyl, α-alkoxyethyl, α-alkoxy-α-substituted methyl, alkylthiomethyl, acyloxymethyl and α-acyloxy-α-substituted methyl esters.
Claim 2
Dependent Claim
149 words
A member selected from the group consisting of (a) a cephem compound of the formula ##STR21## wherein R 1 represents amino, protected amino, hydroxy or protected hydroxy, R 2 represents amino, protected amino, hydroxy, protected hydroxy or the group ##STR22## represents a group of the formula ##STR23## wherein R 5 is hydroxy or protected hydroxy, R 3 represents hydrogen or methoxy, R 4 represents heterocyclic thio wherein heterocyclic is a 5 to 6 membered hetero ring containing 1 to 4 hetero atoms from the group of oxygen, sulfur and nitrogen, said ring being unsubstituted or substituted by lower alkyl, lower alkoxy, halogen, haloalkyl, amino, mercapto, hydroxy, carbamoyl or carboxy, and R 8 represents hydrogen or halogen, (b) a pharmaceutically acceptable salt thereof, and (c) a pharmaceutically acceptable ester of the 4-position carboxyl group selected from the group consisting of alkoxymethyl, α-alkoxyethyl, α-alkoxy-α-substituted methyl, alkylthiomethyl, acyloxymethyl and α-acyloxy-α-substituted methyl esters.
Claim 3
Dependent Claim
24 words
A cephem compound according to claim 1 wherein R 4 represents thiadiazolylthio, triazolylthio or tetrazolylthio, said groups being unsubstituted or substituted by lower alkyl.
Claim 4
Dependent Claim
12 words
A cephem compound according to claim 2 said compound being 7β-[α-hydroxy-α-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 5
Dependent Claim
12 words
A cephem compound according to claim 2 said compound being 7β-[α-(2-aminothiazol-4-yl)-α-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid.
Claim 6
Dependent Claim
24 words
A cephem compound according to claim 1 wherein each of R 1 and R 2 represents amino or hydroxy and R 8 is hydrogen.
Claim 7
Dependent Claim
12 words
A cephem compound according to claim 1 wherein R 3 is hydrogen.
Claim 8
Dependent Claim
24 words
A compound according to claim 1, wherein R 1 is amino, R 2 is hydroxy, R 8 is hydrogen and R 3 is hydrogen.
Claim 9
Dependent Claim
24 words
A compound according to claim 1, wherein R 1 is amino, R 2 is amino, R 8 is hydrogen and R 3 is hydrogen.
Claim 10
Dependent Claim
24 words
A compound according to claim 1, wherein R 1 is hydroxy, R 2 is amino, R 8 is hydrogen and R 3 is hydrogen.
Claim 11
Dependent Claim
27 words
A compound according to claim 1, wherein each of R 1 and R 2 represents amino or hydroxy, R 8 is hydrogen and R 3 is methoxy.
Claim 12
Dependent Claim
29 words
A compound according to claim 33, wherein R 1 is amino or hydroxy, R 8 is hydrogen and the group ##STR24## wherein R 5 represents hydroxy or lower alkoxy.
Claim 13
Dependent Claim
175 words
A pharmaceutical composition which contains a medicinally effective amount of a member of the group consisting of (a) a cephem compound of the formula ##STR25## wherein R 1 represents amino, protected amino, hydroxy or protected hydroxy, R 2 represents amino, protected amino, hydroxy, protected hydroxy or the group ##STR26## represents a group of the formula ##STR27## wherein R 5 is hydroxy or protected hydroxy, R 3 represents hydrogen or methoxy, R 4 represents heterocyclic thio wherein heterocyclic is a 5 to 6 membered hetero ring containing 1 to 4 hetero atoms from the group of oxygen, sulfur and nitrogen, said ring being unsubstituted or substituted by lower alkyl, lower alkoxy, halogen, haloalkyl, amino, mercapto, hydroxy, carbamoyl or carboxy, and R 8 represents hydrogen or halogen, (b) a pharmaceutically acceptable salt thereof, and (c) a pharmaceutically acceptable ester of the 4-position carboxyl group selected from the group consisting of alkoxymethyl, α-alkoxyethyl, α-alkoxy-α-substituted methyl, alkylthiomethyl, acyloxymethyl and α-acyloxy-α-substituted methyl esters together with at least one pharmaceutically acceptable carrier, said composition being administrable in a dosage unit form.
Claim 14
Dependent Claim
175 words
A pharmaceutical composition which contains a medicinally effective amount of a member of the group consisting of (a) a cephem compound of the formula ##STR25## wherein R 1 represents amino, protected amino, hydroxy or protected hydroxy, R 2 represents amino, protected amino, hydroxy, protected hydroxy or the group ##STR26## represents a group of the formula ##STR27## wherein R 5 is hydroxy or protected hydroxy, R 3 represents hydrogen or methoxy, R 4 represents heterocyclic thio wherein heterocyclic is a 5 to 6 membered hetero ring containing 1 to 4 hetero atoms from the group of oxygen, sulfur and nitrogen, said ring being unsubstituted or substituted by lower alkyl, lower alkoxy, halogen, haloalkyl, amino, mercapto, hydroxy, carbamoyl or carboxy, and R 8 represents hydrogen or halogen, (b) a pharmaceutically acceptable salt thereof, and (c) a pharmaceutically acceptable ester of the 4-position carboxyl group selected from the group consisting of alkoxymethyl, α-alkoxyethyl, α-alkoxy-α-substituted methyl, alkylthiomethyl, acyloxymethyl and α-acyloxy-α-substituted methyl esters together with at least one pharmaceutically acceptable carrier, said composition being administrable in a dosage unit form.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-07-03 | 1982-01-02 | 1982-07-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-03 | 1986-01-02 | 1986-07-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-03 | 1990-01-02 | 1990-07-04 | $7700.00 | Window Closed / Lapsed |