US4289696A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polycyclic compounds
Assignee: Beecham Group PLC
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Filing: 1980-02-11
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Granted: 1981-09-15
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Expires: 2000-02-11
Abstract
Abstract The present invention provides a compound of formula (1): ##STR1## wherein G is hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl, R 1 is alkyl or aryl, substituted alkyl or substituted aryl, and R is an organic group such that --CO 2 R is an ester group. The compounds are useful as antibacterial and β-lactamase inhibitory agents.
Inventors
- 👤 Terence C. Smale
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:41
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20; A; A61; A61P; A61P31/00; A61P31/04; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/12; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/568
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
147 words
A compound of the formula: ##STR118## wherein A is chloro, bromo or iodo; R 1 is alkyl of 1 to 6 carbon atoms, unsubstituted or substituted with hydroxy, amino, alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido; phenyl; or phenyl substituted by one or more members selected from the group consisting of halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino, alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido; R is alkyl of 1 to 6 carbon atoms, benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl, p-bromophenacyl, 2,2,2-trichloroethyl, phthalidyl, phthalimidomethyl, α-ethoxycarbonyloxyethyl or alkanoyloxymethyl of 1 to 6 carbon atoms, and G is hydrogen, alkyl or alkenyl, said alkyl and alkenyl being unsubstituted or substituted with hydroxy, oxy, methoxycarbonyl, phenyl or phenyl substituted with alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, nitro or halo.
Claim 2
Dependent Claim
147 words
A compound of the formula: ##STR118## wherein A is chloro, bromo or iodo; R 1 is alkyl of 1 to 6 carbon atoms, unsubstituted or substituted with hydroxy, amino, alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido; phenyl; or phenyl substituted by one or more members selected from the group consisting of halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino, alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido; R is alkyl of 1 to 6 carbon atoms, benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl, p-bromophenacyl, 2,2,2-trichloroethyl, phthalidyl, phthalimidomethyl, α-ethoxycarbonyloxyethyl or alkanoyloxymethyl of 1 to 6 carbon atoms, and G is hydrogen, alkyl or alkenyl, said alkyl and alkenyl being unsubstituted or substituted with hydroxy, oxy, methoxycarbonyl, phenyl or phenyl substituted with alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, nitro or halo.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 wherein G is prop-2-en-1yl, 3-methylbut-2-en-1-yl or pent-2-en-1-yl.
Claim 4
Dependent Claim
12 words
A compound according to claim 1 wherein G is 4-oxopent-2-en-1-yl or 3-methoxy-carbonylprop-2-enyl.
Claim 5
Dependent Claim
20 words
A compound according to claim 1 wherein R 1 is alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido.
Claim 6
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is 2-acetylamidoethyl, phenyl, p-acetamidophenyl, ethyl, propyl, butyl or tertiary alkyl.
Claim 7
Dependent Claim
10 words
A compound according to claim 1 wherein G is hydrogen.
Claim 8
Dependent Claim
28 words
A compound according to claim 1 wherein R is alkyl of 1 to 6 carbon atoms, benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl, p-bromophenacyl, 2,2,2-trichloroethyl, pthalidyl, pthalimidomethyl, α-ethoxycarbonyloxyethyl, pivaloyloxymethyl or acetoxymethyl.
Claim 9
Dependent Claim
10 words
A compound according to claim 1 wherein A is chloro.
Claim 10
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-chloro-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 11
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 12
Dependent Claim
10 words
The compound according to claim 1 which is p-nitrobenzyl 3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 13
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-(2-acetamidoethylsulphinyl)-3-chloro-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 14
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-p-acetamidophenylsulphinyl-3-chloro-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 15
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-chloro-6-(3-methoxycarbonylprop-2-ene-1-yl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 16
Dependent Claim
10 words
The compound according to claim 1 which is p-bromophenacyl 3-chloro-3-ethylsulphinyl-6-(3-methoxycarbonylprop-2-en-1-yl)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 17
Dependent Claim
10 words
The compound according to claim 1 which is phthalidyl 3-chloro-3-ethylsulphinyl-6-(3-methoxycarbonylprop-2-en-1-yl)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 18
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 19
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-chloro-trans-6-(1-hydroxyethyl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]heptane-2-carboxylate.
Claim 20
Dependent Claim
10 words
The compound according to claim 1 which is benzyl 3-chloro-3-ethylsulphinyl-6-(2-hydroxy-2-propyl)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-14 | 1985-03-16 | 1985-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-14 | 1989-03-16 | 1989-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-14 | 1993-03-16 | 1993-09-15 | $7700.00 | Window Closed / Lapsed |