Patent US4223038A successfully refreshed from Google Patents.
US4223038A
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Bicyclic β-lactam antibiotics
Assignee: Beecham Group PLC
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Filing: 1978-10-30
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Granted: 1980-09-16
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Expires: 1998-10-30
Abstract
Abstract Compounds of the formula (I): ##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 are produced. 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
2026-11-06 01:33
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: 56
Claim 1
Independent Claim
107 words
A compound of the formula (I): ##STR118## wherein G is hydrogen, R 1 is alkyl of 1 to 6 carbon atoms unsubstituted or substituted by hydroxy, amino or amino protected by by alkanoyl or 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl; phenyl unsubstituted or substituted by one or more halogen alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl, and 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.
Claim 2
Dependent Claim
107 words
A compound of the formula (I): ##STR118## wherein G is hydrogen, R 1 is alkyl of 1 to 6 carbon atoms unsubstituted or substituted by hydroxy, amino or amino protected by by alkanoyl or 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl; phenyl unsubstituted or substituted by one or more halogen alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl, and 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.
Claim 3
Dependent Claim
14 words
A compound according to claim 1, wherein R 1 is 2-acetamidoethyl, phenyl or p-acetamidophenyl.
Claim 4
Dependent Claim
12 words
A compound according to claim 1 wherein R 1 is unbranched alkyl.
Claim 5
Dependent Claim
14 words
A compound according to claim 3 wherein R 1 is ethyl, propyl or butyl.
Claim 6
Dependent Claim
24 words
A compound according to claim 1 wherein R 1 is a tertiary alkyl in which the tertiary centre is α to the sulphur atom.
Claim 7
Dependent Claim
13 words
A compound according to claim 5 wherein R 1 is t-butyl or 1,1-dimethylpropyl.
Claim 8
Dependent Claim
30 words
A compound according to claim 1 wherein R is alkyl of 1 to 6 carbon atoms, benzyl, benzyl substituted by nitro or methoxy, phenacyl, phenacyl substituted by bromo or 2,2,2-trichloroethyl.
Claim 9
Dependent Claim
15 words
A compound according to claim 7 wherein R is benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl or p-bromophenacyl.
Claim 10
Dependent Claim
15 words
A compound according to claim 1 wherein R is phthalidyl, phthalimidomethyl, α-ethoxycarbonyloxyethyl or lower alkanoyloxymethyl.
Claim 11
Dependent Claim
12 words
A compound according to claim 9 wherein R is pivaloyloxymethyl or acetoxymethyl.
Claim 12
Dependent Claim
10 words
A compound according to claim 1 having the stereochemistry: ##STR119##
Claim 13
Dependent Claim
11 words
A compound according to claim 1 having the relative stereochemistry: ##STR120##
Claim 14
Dependent Claim
11 words
A compound according to claim 1 having the relative stereochemistry ##STR121##
Claim 15
Dependent Claim
37 words
A compound selected from the group consisting of: Methyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-phenylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(4'Acetylaminophenyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-t-butylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(2-hydroxyethyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-nitroethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, and 4-Nitrobenzyl 3-(4'-nitrobenzyloxycarbonylaminoethylsulphinyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
Claim 16
Dependent Claim
37 words
A compound selected from the group consisting of: Methyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-phenylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(4'Acetylaminophenyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-t-butylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(2-hydroxyethyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-nitroethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, and 4-Nitrobenzyl 3-(4'-nitrobenzyloxycarbonylaminoethylsulphinyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
Claim 17
Dependent Claim
124 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula: ##STR122## wherein G is hydrogen, R 1 is alkyl of 1 to 6 carbon atoms unsubstituted or substituted by hydroxy, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl of p-nitrobenzyloxycarbonyl; phenyl unsubstituted or substituted by one or more halogen alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl, and 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.
Claim 18
Dependent Claim
124 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula: ##STR122## wherein G is hydrogen, R 1 is alkyl of 1 to 6 carbon atoms unsubstituted or substituted by hydroxy, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl of p-nitrobenzyloxycarbonyl; phenyl unsubstituted or substituted by one or more halogen alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl, and 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.
Claim 19
Dependent Claim
14 words
A composition according to claim 15 wherein R 1 is 2-acetamidoethyl, phenyl or p-acetamidophenyl.
Claim 20
Dependent Claim
12 words
A composition according to claim 15 wherein R 1 is unbranched alkyl.
Claim 21
Dependent Claim
14 words
A composition according to claim 17 wherein R 1 is ethyl, propyl or butyl.
Claim 22
Dependent Claim
24 words
A composition according to claim 15 wherein R 1 is a tertiary alkyl in which the tertiary centre is α to the sulphur atom.
Claim 23
Dependent Claim
13 words
A composition according to claim 19 wherein R 1 is t-butyl or 1,1-dimethylpropyl.
Claim 24
Dependent Claim
30 words
A composition according to claim 15 wherein R is alkyl of 1 to 6 carbon atoms, benzyl, benzyl substituted by nitro or methoxy, phenacyl, phenacyl substituted by bromo or 2,2,2-trichloroethyl.
Claim 25
Dependent Claim
15 words
A composition according to claim 21 wherein R is benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl or p-bromophenacyl.
Claim 26
Dependent Claim
15 words
A composition according to claim 15 wherein R is phthalidyl, phthalimidomethyl, α-ethoxycarbonyloxyethyl or lower alkanoyloxymethyl.
Claim 27
Dependent Claim
12 words
A composition according to claim 23 wherein R is pivaloyloxymethyl or acetoxymethyl.
Claim 28
Dependent Claim
13 words
A composition according to claim 15 wherein the compound has the stereochemistry: ##STR123##
Claim 29
Dependent Claim
14 words
A composition according to claim 15 wherein the compound has the relative stereochemistry: ##STR124##
Claim 30
Dependent Claim
14 words
A composition according to claim 15 wherein the compound has the relative stereochemistry: ##STR125##
Claim 31
Dependent Claim
10 words
A composition according to claim 15 in oral administration form.
Claim 32
Dependent Claim
10 words
A composition according to claim 15 in parenteral administration form.
Claim 33
Dependent Claim
10 words
A composition according to claim 15 in topical application form.
Claim 34
Dependent Claim
10 words
A composition according to claim 15 in rectal administration form.
Claim 35
Dependent Claim
73 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound selected from the group consisting of: Methyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-phenylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(4'Acetylaminophenyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-t-butylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-(2-hydroxyethyl)sulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-nitroethylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, and 4-Nitrobenzyl 3-(4'nitrobenzyloxycarbonylaminoethylsulphinyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, in combination with a pharmaceutically acceptable carrier.
Claim 36
Dependent Claim
73 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound selected from the group consisting of: Methyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-phenylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(4'Acetylaminophenyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-t-butylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-(2-hydroxyethyl)sulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-nitroethylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, and 4-Nitrobenzyl 3-(4'nitrobenzyloxycarbonylaminoethylsulphinyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, in combination with a pharmaceutically acceptable carrier.
Claim 37
Independent Claim
131 words
A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula: ##STR126## wherein G is hydrogen, R 1 is alkyl of 1 to 6 carbon atoms unsubstituted or substituted by hydroxy, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl; phenyl unsubstituted or substituted by one or more halogen alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl, and 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.
Claim 38
Independent Claim
131 words
A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula: ##STR126## wherein G is hydrogen, R 1 is alkyl of 1 to 6 carbon atoms unsubstituted or substituted by hydroxy, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl; phenyl unsubstituted or substituted by one or more halogen alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino or amino protected by alkanoyl of 1 to 6 carbon atoms, benzyloxycarbonyl or p-nitrobenzyloxycarbonyl, and 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.
Claim 39
Dependent Claim
14 words
A method according to claim 33 wherein R 1 is 2-acetamidoethyl, phenyl or p-acetamidophenyl.
Claim 40
Dependent Claim
12 words
A method according to claim 33 wherein R 1 is unbranched alkyl.
Claim 41
Dependent Claim
14 words
A method according to claim 35 wherein R 1 is ethyl, propyl or butyl.
Claim 42
Dependent Claim
24 words
A method according to claim 33 wherein R 1 is a tertiary alkyl in which the tertiary centre is α to the sulphur atom.
Claim 43
Dependent Claim
13 words
A method according to claim 37 wherein R 1 is t-butyl or 1,1-dimethylpropyl.
Claim 44
Dependent Claim
30 words
A method according to claim 33 wherein R is alkyl of 1 to 6 carbon atoms, benzyl, benzyl substituted by nitro or methoxy, phenacyl, phenacyl substituted by bromo, or 2,2,2-trichloroethyl.
Claim 45
Dependent Claim
15 words
A method according to claim 39 wherein R is benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl or p-bromophenacyl.
Claim 46
Dependent Claim
15 words
A method according to claim 33 wherein R is phthalidyl, phthalimidomethyl, α-ethoxycarbonyloxyethyl or lower alkanoyloxymethyl.
Claim 47
Dependent Claim
12 words
A method according to claim 41 wherein R is pivaloyloxymethyl or acetoxymethyl.
Claim 48
Dependent Claim
13 words
A method according to claim 33 wherein the compound has the stereochemistry: ##STR127##
Claim 49
Dependent Claim
14 words
A method according to claim 33 wherein the compound has the relative stereochemistry: ##STR128##
Claim 50
Dependent Claim
14 words
A method according to claim 33 wherein the compound has the relative stereochemistry: ##STR129##
Claim 51
Dependent Claim
11 words
A method according to claim 33 wherein the administration is oral.
Claim 52
Dependent Claim
11 words
A method according to claim 33 wherein the administration is parenteral.
Claim 53
Dependent Claim
13 words
A method according to claim 33 wherein the administration is by topical application.
Claim 54
Dependent Claim
11 words
A method according to claim 33 wherein the administration is rectally.
Claim 55
Independent Claim
74 words
A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound selected from the group consisting of: Methyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-phenylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] -hept-2-ene-2-carboxylate, Benzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(4'Acetylaminophenyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-t-butylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-(2-hydroxyethyl)sulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-nitroethylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, and 4-Nitrobenzyl 3-(4'nitrobenzyloxycarbonylaminoethylsulphinyl)-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate.
Claim 56
Independent Claim
74 words
A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound selected from the group consisting of: Methyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-phenylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-ethylsulphinyl-1-azabicyclo[3,2,0] -hept-2-ene-2-carboxylate, Benzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-(4'Acetylaminophenyl)sulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, Benzyl 3-t-butylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-(2-hydroxyethyl)sulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylsulphinyl-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 3-nitroethylsulphinyl-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate, Benzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo [3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 3-acetylaminoethylsulphinyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, 4-Nitrobenzyl 7-oxo-3-tritylaminoethylsulphinyl-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate, and 4-Nitrobenzyl 3-(4'nitrobenzyloxycarbonylaminoethylsulphinyl)-7-oxo-1-azabicyclo[3,2,0] hept-2-ene-2-carboxylate.
References Cited (Backward Citations)
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Cited
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1983-09-16 | 1984-03-17 | 1984-09-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-16 | 1988-03-17 | 1988-09-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-16 | 1992-03-17 | 1992-09-16 | $7700.00 | Window Closed / Lapsed |