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US4013653A Expired / Lapsed US ⏱️ 0.0 years remaining

1-oxacephems

Assignee: Queen's University
•
Filing: 1975-07-21
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Granted: 1977-03-22
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Expires: 1995-07-21
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Abstract

Abstract The present invention relates to novel 1-oxacephems of the formula ##STR1## wherein R 9 is hydrogen and R 8 is hydrogen or RCO- wherein R is selected from the group consisting of lower alkyl ##STR2## wherein Ar is a monovalent radical selected from the group consisting of ##STR3## wherein R 1 , R 2 and R 3 are each a member selected from the group consisting of hydrogen, chloro, bromo, iodo, trifluoromethyl, phenyl, lower-alkyl and lower alkoxy, but only one of said R 1 , R 2 and R 3 may represent phenyl; R 4 is hydrogen, amino, carbobenzoxyamino, phenyl, fluoro, chloro, bromo, iodo, carboxyl, SO 3 H, azido, hydroxy, loweralkanoyloxy or loweralkoxy; X is oxygen or sulfur; R 5 and R 6 are hydrogen, phenyl, benzyl, phenethyl or loweralkyl; Z 1 , z 2 and Z 3 are loweralkyl or the Ar- group; R 12 is 2,2,2-trichloroethyl or benzyl; Provided that when R 8 and R 9 are taken together with the nitrogen to which they are attached, they form a phthalimido moiety; R 7 is methyl or hydroxy; and R 1 is hydrogen, loweralkyl, benzyl, benzhydryl, loweralkoxyloweralkyl, loweralkoxybenzyl, phenacyl, trimethylsilyl, 2,2,2-trichloroethyl, or pivaloyloxy.

Inventors

  • 👤 Saul Wolfe

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 08:28
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/535; C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D405/00; C07D405/02; C07D405/06; C07D499/00; C07D499/88; C07D505/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 19 words
The compound of the formula: ##STR59## wherein R 7 is selected from the group consisting of methyl and hydroxyl.
Claim 2
Dependent Claim 19 words
The compound of the formula: ##STR59## wherein R 7 is selected from the group consisting of methyl and hydroxyl.
Claim 3
Dependent Claim 9 words
The compound of claim 1, which is the 3-methyl-4-carboxy-7S-amino-1-oxa,5-aza-6R-bicyclo[4,2,0]oct-3-en-8-one.
Claim 4
Dependent Claim 9 words
The compound of claim 1, which is the 3-hydroxy-4-carboxy-7S-amino-1-oxa,5-aza-6R-bicyclo[4,2,0]oct-3-en-8-one.
Claim 5
Dependent Claim 187 words
The compound of the formula: ##STR60## wherein R 9 is hydrogen and R 8 is hydrogen or RCO- wherein R is selected from the group consisting of ##STR61## wherein Ar is a monovalent radical selected from the group consisting of ##STR62## wherein R 1 , R 2 and R 3 are each a member selected from the group consisting of hydrogen, chloro, bromo, iodo, trifluoromethyl, phenyl, loweralkyl and loweralkoxy, but only one of said R 1 , R 2 and R 3 may represent phenyl; R 4 is hydrogen, amino, carbobenzoxyamino, phenyl, fluoro, chloro, bromo, iodo, carboxyl, SO 3 H, azido, hydroxy, loweralkanoyloxy or loweralkoxy; X is oxygen or sulfur; R 5 and R 6 are hydrogen, phenyl, benzyl, phenethyl or loweralkyl; Z 1 , z 2 and Z 3 are loweralkyl or the Ar- group; R 12 is 2,2,2-trichloroethyl or benzyl; provided that when R 8 and R 9 are taken together with the nitrogen to which they are attached, they form a phthalimido moiety; R 7 is methyl or hydroxy; and R 1 is hydrogen, loweralkyl, benzyl, benzhydryl, loweralkoxyloweralkyl, loweralkoxybenzyl, phenacyl, trimethylsilyl, 2,2,2-trichlorethyl, or pivaloyloxy.
Claim 6
Dependent Claim 187 words
The compound of the formula: ##STR60## wherein R 9 is hydrogen and R 8 is hydrogen or RCO- wherein R is selected from the group consisting of ##STR61## wherein Ar is a monovalent radical selected from the group consisting of ##STR62## wherein R 1 , R 2 and R 3 are each a member selected from the group consisting of hydrogen, chloro, bromo, iodo, trifluoromethyl, phenyl, loweralkyl and loweralkoxy, but only one of said R 1 , R 2 and R 3 may represent phenyl; R 4 is hydrogen, amino, carbobenzoxyamino, phenyl, fluoro, chloro, bromo, iodo, carboxyl, SO 3 H, azido, hydroxy, loweralkanoyloxy or loweralkoxy; X is oxygen or sulfur; R 5 and R 6 are hydrogen, phenyl, benzyl, phenethyl or loweralkyl; Z 1 , z 2 and Z 3 are loweralkyl or the Ar- group; R 12 is 2,2,2-trichloroethyl or benzyl; provided that when R 8 and R 9 are taken together with the nitrogen to which they are attached, they form a phthalimido moiety; R 7 is methyl or hydroxy; and R 1 is hydrogen, loweralkyl, benzyl, benzhydryl, loweralkoxyloweralkyl, loweralkoxybenzyl, phenacyl, trimethylsilyl, 2,2,2-trichlorethyl, or pivaloyloxy.
Claim 7
Dependent Claim 9 words
The compound of claim 4, which is the 3-methyl-4-methoxycarbonyl-7S-phthalimido-1-oxa,5-aza-6R-bicyclo[4,2,0]-oct-3-en-8-one.
Claim 8
Dependent Claim 9 words
The compound of claim 4, which is the 3-hydroxy-4-methoxycarbonyl-7S-phthalimido-1-oxa,5-aza-6R-bicyclo[4,2,0]-oct-3-en-8-one.
Claim 9
Dependent Claim 9 words
The compound of claim 4, which is the 3-methyl-4-benzhydryloxycarbonyl-7S-phthalimido-1-oxa,5-aza-6R-bicyclo[4,2,0]oct-3-en-8-one.
Claim 10
Dependent Claim 9 words
The compound of claim 4, which is the 3-methyl-4-benzhydryloxycarbonyl-7S-trichloroethoxycarbonylamino-1-oxa,5-aza-6R-bicyclo[4,2,0]oct-3-en-8-one.
Claim 11
Dependent Claim 9 words
The compound of claim 4, which is the 3-hydroxy-4-benzhydryloxycarbonyl-7S-trichloroethoxycarbonylamino-1-oxa,5-aza-6R-bicyclo[4,2,0]oct-3-en-8-one.

References Cited (Backward Citations)

DE1914366A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-03-21 1980-09-20 1981-03-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-03-21 1984-09-20 1985-03-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-03-21 1988-09-20 1989-03-22 $7700.00 Window Closed / Lapsed

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