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US3965099A Expired / Lapsed US ⏱️ 0.0 years remaining

Cephalosporin esters with antibacterial activity

Assignee: GlaxoSmithKline LLC
•
Filing: 1974-06-26
•
Granted: 1976-06-22
•
Expires: 1994-06-26
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Abstract

Abstract Esters of 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid are prepared. These compounds are antibacterial agents.

Inventors

  • 👤 Robert M. DeMarinis
  • 👤 John R. E. Hoover

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-10 01:22
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/36

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 163 words
A compound of the formula ##SPC3## wherein: ##EQU2## n is 0 to 4; R is hydrogen, alkyl having 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, C 1 -C 4 phenalkyl, pyridyl, thienyl, or pyrrolyl; R 1 is hydrogen, methyl or ethyl; R 2 and R 3 are each hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, pyridyl, or thienyl; R 4 and R 5 are each hydrogen or alkyl of 1 to 4 carbon atoms; R 6 is alkyl having 1 to 4 carbon atoms, phenyl, phenalkyl having 1 to 4 carbon atoms, pyridyl, thiadiazolyl, amino or C 1 -C 4 alkylamino; X is NH or oxygen; and each phenyl group is unsubstituted or substituted with one or two substituents selected from the group consisting of alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, hydroxy, amino, NHR 1 , N(R 1 ) 2 , nitro, fluoro, chloro, bromo, or carboxy.
Claim 2
Dependent Claim 163 words
A compound of the formula ##SPC3## wherein: ##EQU2## n is 0 to 4; R is hydrogen, alkyl having 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, C 1 -C 4 phenalkyl, pyridyl, thienyl, or pyrrolyl; R 1 is hydrogen, methyl or ethyl; R 2 and R 3 are each hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, pyridyl, or thienyl; R 4 and R 5 are each hydrogen or alkyl of 1 to 4 carbon atoms; R 6 is alkyl having 1 to 4 carbon atoms, phenyl, phenalkyl having 1 to 4 carbon atoms, pyridyl, thiadiazolyl, amino or C 1 -C 4 alkylamino; X is NH or oxygen; and each phenyl group is unsubstituted or substituted with one or two substituents selected from the group consisting of alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, hydroxy, amino, NHR 1 , N(R 1 ) 2 , nitro, fluoro, chloro, bromo, or carboxy.
Claim 3
Dependent Claim 11 words
A compound as claimed in claim 1 where M is ##EQU3##
Claim 4
Dependent Claim 11 words
A compound as claimed in claim 1 where M is ##EQU4##
Claim 5
Dependent Claim 11 words
A compound as claimed in claim 1 where M is ##EQU5##
Claim 6
Dependent Claim 18 words
A compound as claimed in claim 2 where n is 0 to 1 and R 1 is hydrogen.
Claim 7
Dependent Claim 12 words
A compound as claimed in claim 5 being the compound acetoxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 8
Dependent Claim 12 words
A compound as claimed in claim 5 being the compound pivalyloxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 9
Dependent Claim 12 words
A compound as claimed in claim 5 being the compound p-aminobenzoyloxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 10
Dependent Claim 24 words
A compound as claimed in claim 3 where n is 0 or 1 and R 2 , R 4 and R 5 are hydrogen.
Claim 11
Dependent Claim 12 words
A compound as claimed in claim 9 being the compound glycyloxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 12
Dependent Claim 12 words
A compound as claimed in claim 9 being the compound phenylglycyloxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 13
Dependent Claim 12 words
A compound as claimed in claim 9 being the compound valyloxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 14
Dependent Claim 12 words
A compound as claimed in claim 9 being the compound 2-thienylglycyloxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.
Claim 15
Dependent Claim 12 words
A compound as claimed in claim 1 being the compound 5-indanyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate.

References Cited (Backward Citations)

US3488730A Cited
US3655658A Cited
US3708479A Cited
BE802199A Cited
US3828037A Cited
US3856785A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-22 1979-12-22 1980-06-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-22 1983-12-22 1984-06-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-22 1987-12-22 1988-06-22 $7700.00 Window Closed / Lapsed

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