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US4039536A Expired / Lapsed US ⏱️ 0.0 years remaining

7-(α-SUBSTITUTED GLYCINAMIDO)-3-SUBSTITUTED METHYL-3-CEPHEM-4-CARBOXYLIC ACIDS AND THEIR DERIVATIVES

Assignee: Astellas Pharma Inc
•
Filing: 1975-03-28
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Granted: 1977-08-02
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Expires: 1995-03-28
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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.

References Cited (Backward Citations)

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FR1438747A Cited
US3592812A Cited
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US3867380A Cited
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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

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