US4039536A
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7-(α-SUBSTITUTED GLYCINAMIDO)-3-SUBSTITUTED METHYL-3-CEPHEM-4-CARBOXYLIC ACIDS AND THEIR DERIVATIVES
Assignee: Astellas Pharma Inc
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Filing: 1975-03-28
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Granted: 1977-08-02
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Expires: 1995-03-28
Abstract
Abstract This invention is concerned with 7-(α-substituted glycinamido)-3-substituted methyl-3-cephem-4-carboxylic acids, derivatives and non-toxic pharmaceutical salts thereof, which possess antibacterial activity, process for preparation thereof, having the following general formula ##STR1## wherein R 1 , R 2 , R 3 and M are as defined hereinafter.
Inventors
- 👤 Tadayoshi Takano
- 👤 Susumu Horibe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:47
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
149 words
Compounds of the formula: ##STR10## wherein R 1 is hydrogen, lower alkyl, phenyl or thienyl; R 2 is phenyl(lower)alkanoyl, phenoxy(lower)alkanoyl or phenylthio(lower)alkanoyl, in which the phenyl moiety may be substituted with one or two halogen atoms, a nitro, carboxy, sulfo, lower alkyl, lower alkoxy, halo(lower)alkyl or phenoxycarbonyl radical; R 3 is a heterocyclic-thio group selected from thiadiazolylthio, oxadiazolylthio, trizolylthio, tetrazolylthio and benzimidazolylthio, in which the heterocyclic moiety may be substituted with lower alkyl, amino(lower)alkyl, in which the amino moiety may have lower alkoxycarbonyl or sulfo(lower)alkyl group, provided that R 1 is hydrogen, lower alkyl or thienyl when R 2 is phenoxy(lower)alkanoyl, in which the phenyl moiety has no substituent and R 3 is lower alkyl substituted; and M is hydrogen or a nontoxic, pharmaceutically acceptable cation; and their lower alkyl, lower alkanoyloxy(lower)alkyl, and phenyl(lower)alkyl esters, wherein the phenyl moiety of the phenyl(lower)alkyl esters may be substituted with lower alkoxy.
Claim 2
Dependent Claim
149 words
Compounds of the formula: ##STR10## wherein R 1 is hydrogen, lower alkyl, phenyl or thienyl; R 2 is phenyl(lower)alkanoyl, phenoxy(lower)alkanoyl or phenylthio(lower)alkanoyl, in which the phenyl moiety may be substituted with one or two halogen atoms, a nitro, carboxy, sulfo, lower alkyl, lower alkoxy, halo(lower)alkyl or phenoxycarbonyl radical; R 3 is a heterocyclic-thio group selected from thiadiazolylthio, oxadiazolylthio, trizolylthio, tetrazolylthio and benzimidazolylthio, in which the heterocyclic moiety may be substituted with lower alkyl, amino(lower)alkyl, in which the amino moiety may have lower alkoxycarbonyl or sulfo(lower)alkyl group, provided that R 1 is hydrogen, lower alkyl or thienyl when R 2 is phenoxy(lower)alkanoyl, in which the phenyl moiety has no substituent and R 3 is lower alkyl substituted; and M is hydrogen or a nontoxic, pharmaceutically acceptable cation; and their lower alkyl, lower alkanoyloxy(lower)alkyl, and phenyl(lower)alkyl esters, wherein the phenyl moiety of the phenyl(lower)alkyl esters may be substituted with lower alkoxy.
Claim 3
Dependent Claim
78 words
Compounds according to claim 1, wherein R 1 is phenyl; R 2 is phenyl(lower)alkanoyl or phenylthio(lower)alkanoyl, in which the phenyl moiety may be substituted with one or two halogen atoms, nitro, carboxy, sulfo, lower alkyl, lower alkoxy, halo(lower)alkyl or phenyoxycarbonyl, or phenoxy(lower)alkanoyl in which the phenyl moiety is substituted with one or two halogen atoms, a nitro, carboxy, sulfo, lower alkyl, lower alkoxy, halo(lower)alkyl or phenoxycarbonyl radical; and R 3 is selected from thiadiazolylthio, oxadiazolylthio, triazolylthio and tetrazolylthio.
Claim 4
Dependent Claim
44 words
Compounds according to claim 1, wherein R 1 is thienyl. R 2 is phenyl(lower)alkanoyl or phenoxy(lower)alkanoyl, in which phenyl moiety may be substituted with one or two halogen atoms, nitro or halo(lower)alkyl, and the R 3 heterocyclic moiety may be substituted with lower alkyl.
Claim 5
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitorophenylacetyl, R 3 is 1-methyl-1H-tetrazol-5-ylthio, M is hydrogen.
Claim 6
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitrophenylacetyl, R 3 is 5-methyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 7
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 5-methyl-1,3,4-oxadiazol-2-ylthio, M is hydrogen.
Claim 8
Dependent Claim
24 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 1-methyl-1H-tetrazol-5-ylthio, M is hydrogen or dicyclohexylammonium.
Claim 9
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 10
Dependent Claim
24 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 5-methyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen or dicyclohexylammonium.
Claim 11
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 3-methyl-1,2,4-triazol-5-ylthio, M is hydrogen.
Claim 12
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2,6-dichlorophenoxyacetyl, R 3 is 1-methyl-1H-tetrazol-5-ylthio, M is hydrogen.
Claim 13
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2,6-dichlorophenoxyacetyl, R 3 is 5-methyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 14
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitrophenoxyacetyl, R 3 is 1-methyl-1H-tetrazol-5-ylthio, M is hydrogen.
Claim 15
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitrophenoxyacetyl, R 3 is 5-aminomethyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 16
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitrophenoxyacetyl, R 3 is 1-(2-t-butoxycarbonylaminoethyl)-1H-tetrazol-5-ylthio, M is hydrogen.
Claim 17
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitrophenoxyacetyl, R 3 is 1-(2-aminoethyl)-1H-tetrazol-5-ylthio, M is hydrogen.
Claim 18
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 4-chloro-2-nitrophenoxyacetyl, R 3 is sulfomethylaminomethyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 19
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is 2-phenoxycarbonylphenoxyacetyl, R 3 is 1-methyl-1H-tetrazol-5-ylthio, M is hydrogen.
Claim 20
Dependent Claim
22 words
A compound according to claim 2, wherein R 1 is phenyl, R 2 is (2-carboxyphenyl)thioacetyl, R 3 is 5-methyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 21
Dependent Claim
24 words
A compound according to claim 3, wherein R 1 is thienyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 1-methyl-1H-tetrazol-5-ylthio, M is hydrogen or dicyclohexylammonium.
Claim 22
Dependent Claim
22 words
A compound according to claim 3, wherein R 1 is thienyl, R 2 is 2-nitrophenoxyacetyl, R 3 is 5-methyl-1,3,4-thiadiazol-2-ylthio, M is hydrogen.
Claim 23
Dependent Claim
22 words
A compound according to claim 3, wherein R 1 is thienyl, R 2 is 2-nitrophenoxyacetyl, R 3 is benzopyrazol-2-ylthio, M is hydrogen.
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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) | 1980-08-01 | 1981-01-31 | 1981-08-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-01 | 1985-01-31 | 1985-08-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-01 | 1989-01-31 | 1989-08-02 | $7700.00 | Window Closed / Lapsed |